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Showing 371 cruise vacations that match your search
Showing 371 cruise vacations that match your search
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Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,288CA$1,876
per Sailor
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7 nights
Resilient Lady & Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,288CA$1,876
per Sailor
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Departing on:
2027Best Rate
Sun, Jan 03 - Sun, Jan 10
from (CA$)$1,288
2026
Sat, Jan 31 - Sat, Feb 07
from (CA$)$10,832
Only suites remaining
2026
Sat, Feb 28 - Sat, Mar 07
from (CA$)$1,598

Southern Caribbean Cruise

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Sea Terrace cabins from
CA$2,241CA$3,583
per Sailor
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7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$2,241CA$3,583
per Sailor
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (CA$)$2,241
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OUR MOST INCLUSIVE OFFER
Extra onboard credit on Caribbean sailings
Score up to a $300 bonus when you book select Caribbean sailings in 2026-27!
BOOK YOUR GETAWAY

Southern Caribbean & Aruban Nights

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea Terrace cabins from
CA$3,373CA$5,379
per Sailor
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$3,373CA$5,379
per Sailor
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (CA$)$3,373Brilliant Lady's Inaugural Season

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$794CA$1,127
per Sailor
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4 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$794CA$1,127
per Sailor
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Departing on:
2026Best Rate
Wed, Mar 04 - Sun, Mar 08
from (CA$)$794
2026
Wed, Feb 04 - Sun, Feb 08
from (CA$)$1,021
2026
Wed, Feb 18 - Sun, Feb 22
from (CA$)$965

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,089CA$1,591
per Sailor
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7 nights
Resilient Lady & Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,089CA$1,591
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Mar 07 - Sat, Mar 14
from (CA$)$1,089
2026
Sat, Feb 07 - Sat, Feb 14
from (CA$)$2,010
2026
Sat, Feb 14 - Sat, Feb 21
from (CA$)$1,962

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$849CA$1,211
per Sailor
Loading
5 nights
Scarlet Lady, Resilient Lady & Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$849CA$1,211
per Sailor
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Departing on:
2026Best Rate
Sun, Mar 08 - Fri, Mar 13
from (CA$)$849
2026
Sun, Feb 08 - Fri, Feb 13
from (CA$)$5,769
Only suites remaining
2026
Sun, Feb 22 - Fri, Feb 27
from (CA$)$1,419

Eastern Caribbean Cruise

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • Miami, Florida
Sea View cabins from
CA$1,359CA$2,086
per Sailor
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,359CA$2,086
per Sailor
Loading
Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (CA$)$1,359Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
CA$1,633CA$2,537
per Sailor
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5 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$1,633CA$2,537
per Sailor
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (CA$)$1,633

Valiant Valentine's Voyage

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
CA$1,861CA$2,965
per Sailor
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7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,861CA$2,965
per Sailor
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (CA$)$1,861

Eastern Caribbean Cruise

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
CA$1,400CA$2,159
per Sailor
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,400CA$2,159
per Sailor
Loading
Departing on:
2026
Fri, Feb 20 - Sun, Mar 01
from (CA$)$1,400Brilliant Lady's Inaugural Season

Antigua, Martinique, & Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea Terrace cabins from
CA$2,288CA$3,663
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$2,288CA$3,663
per Sailor
Loading
Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (CA$)$2,288

Grand Turk & Bimini Beach Club

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$920CA$1,329
per Sailor
Loading
5 nights
Scarlet Lady, Resilient Lady, Brilliant Lady & Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$920CA$1,329
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Dec 12 - Thu, Dec 17
from (CA$)$920
2026
Fri, Feb 27 - Wed, Mar 04
from (CA$)$2,487
2026
Fri, Mar 27 - Wed, Apr 01
from (CA$)$1,562

Southern Caribbean Cruise

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
CA$1,388CA$2,168
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,388CA$2,168
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Dec 12 - Sat, Dec 19
from (CA$)$1,388
2026
Sat, Feb 28 - Sat, Mar 07
from (CA$)$4,982
Only suites remaining
2026
Sat, Nov 07 - Sat, Nov 14
from (CA$)$1,488

Southern Caribbean & Aruban Nights

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
CA$1,868CA$2,890
per Sailor
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,868CA$2,890
per Sailor
Loading
Departing on:
2026
Sun, Mar 01 - Thu, Mar 12
from (CA$)$1,868Brilliant Lady's Inaugural Season

Quaint Castries to Elegant Antigua

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea Terrace cabins from
CA$2,003CA$3,195
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$2,003CA$3,195
per Sailor
Loading
Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (CA$)$2,003

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,657CA$2,546
per Sailor
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,657CA$2,546
per Sailor
Loading
Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (CA$)$1,657Brilliant Lady's Inaugural Season

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$992CA$1,417
per Sailor
Loading
5 nights
Scarlet Lady, Resilient Lady & Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$992CA$1,417
per Sailor
Loading
Departing on:
2027Best Rate
Mon, Oct 11 - Sat, Oct 16
from (CA$)$992
2026
Fri, Mar 13 - Wed, Mar 18
from (CA$)$1,064
2026
Fri, Apr 10 - Wed, Apr 15
from (CA$)$1,134

Southern Caribbean & Aruban Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
CA$1,190CA$1,848
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,190CA$1,848
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (CA$)$1,190
2026
Sat, Mar 14 - Sat, Mar 21
from (CA$)$1,288
2027
Sat, Jan 09 - Sat, Jan 16
from (CA$)$1,388

Western Caribbean Cruise

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Insider cabins from
CA$1,104CA$1,636
per Sailor
Loading
6 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,104CA$1,636
per Sailor
Loading
Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (CA$)$1,104

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,131CA$1,671
per Sailor
Loading
8 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,131CA$1,671
per Sailor
Loading
Departing on:
2026Best Rate
Fri, Mar 20 - Sat, Mar 28
from (CA$)$1,131
2026
Sat, Dec 05 - Sun, Dec 13
from (CA$)$1,245
2027
Sat, Mar 27 - Sun, Apr 04
from (CA$)$1,586

Panama Canal & Pacific Wonders

  • Miami, Florida
  • Cartagena, Colombia
  • Colón, Panama
  • Panama Canal (Cruising), Panama
  • Puntarenas, Costa Rica
  • Puerto Quetzal, Guatemala
  • Cabo San Lucas, Mexico
  • Los Angeles, California
Insider cabins from
CA$2,716CA$3,794
per Sailor
Loading
16 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,716CA$3,794
per Sailor
Loading
Departing on:
2027Best Rate
Fri, Mar 26 - Sun, Apr 11
from (CA$)$2,716
2026
Sat, Mar 21 - Mon, Apr 06
from (CA$)$2,716Brilliant Lady's Inaugural Season

Southern Caribbean Cruise

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,388CA$2,084
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,388CA$2,084
per Sailor
Loading
Departing on:
2027Best Rate
Sat, Jan 02 - Sat, Jan 09
from (CA$)$1,388
2026
Sat, Mar 21 - Sat, Mar 28
from (CA$)$1,576

Tortola, Charleston, Newport & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Puerto Plata, Dominican Republic
  • Charleston, South Carolina
  • Newport, Rhode Island
  • New York City, New York
Insider cabins from
CA$1,235CA$1,842
per Sailor
Loading
9 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,235CA$1,842
per Sailor
Loading
Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (CA$)$1,235

The Big Apple to Bermuda

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
CA$992CA$1,374
per Sailor
Loading
5 nights
Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$992CA$1,374
per Sailor
Loading
Departing on:
2026Best Rate
Sun, Sep 27 - Fri, Oct 02
from (CA$)$992
2026
Mon, Apr 06 - Sat, Apr 11
from (CA$)$1,343
2026
Fri, Oct 02 - Wed, Oct 07
from (CA$)$1,207

Brilliant Lady LA MerMaiden

  • Los Angeles, California
  • Santa Barbara, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Insider cabins from
CA$921CA$1,283
per Sailor
Loading
5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$921CA$1,283
per Sailor
Loading
Departing on:
2026
Tue, Apr 07 - Sun, Apr 12
from (CA$)$921Brilliant Lady's Inaugural Season

Virgin Voyages Comedy Fest New York

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Sea View cabins from
CA$1,135CA$1,608
per Sailor
Loading
5 nights
Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,135CA$1,608
per Sailor
Loading
Departing on:
2026
Sat, Apr 11 - Thu, Apr 16
from (CA$)$1,135

California (and Mexico) Dreamin'

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlán, Mexico
  • Los Angeles, California
Insider cabins from
CA$1,276CA$1,932
per Sailor
Loading
6 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,276CA$1,932
per Sailor
Loading
Departing on:
2026
Sun, Apr 12 - Sat, Apr 18
from (CA$)$1,276Brilliant Lady's Inaugural Season

Bermuda Beauty to East Coast Elegance

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • Nassau, Bahamas
  • Charleston, South Carolina
  • New York City, New York
Insider cabins from
CA$1,400CA$1,949
per Sailor
Loading
9 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,400CA$1,949
per Sailor
Loading
Departing on:
2026
Thu, Apr 16 - Sat, Apr 25
from (CA$)$1,400

New York Transatlantic to Spain

  • New York City, New York
  • Ponta Delgada, Azores
  • Funchal, Madeira, Portugal
  • Tangier, Morocco
  • Málaga, Spain
  • Palma de Mallorca, Spain
  • Barcelona
Sea View cabins from
CA$2,776CA$4,342
per Sailor
Loading
14 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,776CA$4,342
per Sailor
Loading
Departing on:
2026
Sat, Apr 25 - Sat, May 09
from (CA$)$2,776

Hollywood Sunsets & Mexican Horizons

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlán, Mexico
  • Puerto Vallarta, Mexico
  • Los Angeles, California
Insider cabins from
CA$1,188CA$1,771
per Sailor
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,188CA$1,771
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Oct 03 - Sat, Oct 10
from (CA$)$1,188
2026
Sun, Apr 26 - Sun, May 03
from (CA$)$1,488Brilliant Lady's Inaugural Season
2026
Sat, Sep 19 - Sat, Sep 26
from (CA$)$1,289

Transatlantic to Spain & Morocco

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Alicante, Spain
  • Barcelona
Insider cabins from
CA$1,976CA$3,120
per Sailor
Loading
14 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,976CA$3,120
per Sailor
Loading
Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (CA$)$1,976

LA Lights & Vancouver Vistas

  • Los Angeles, California
  • Catalina Island, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
CA$1,358CA$1,914
per Sailor
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,358CA$1,914
per Sailor
Loading
Departing on:
2026
Sun, May 03 - Mon, May 11
from (CA$)$1,358Brilliant Lady's Inaugural Season

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$737CA$1,029
per Sailor
Loading
4 nights
Resilient Lady, Scarlet Lady, Brilliant Lady & Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$737CA$1,029
per Sailor
Loading
Departing on:
2026Best Rate
Thu, Oct 22 - Mon, Oct 26
from (CA$)$737
2026
Thu, May 07 - Mon, May 11
from (CA$)$1,363
2026
Thu, May 21 - Mon, May 25
from (CA$)$1,420

Rome, Mykonos & the Amalfi Coast

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$3,338CA$5,331
per Sailor
Loading
7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,338CA$5,331
per Sailor
Loading
Departing on:
2026
Sun, May 10 - Sun, May 17
from (CA$)$3,338

Alaska Awe from Vancouver to Seattle

  • Vancouver, British Columbia
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Juneau, Alaska
  • Icy Strait Point, Alaska
  • Seattle, Washington
Insider cabins from
CA$1,555CA$2,331
per Sailor
Loading
10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,555CA$2,331
per Sailor
Loading
Departing on:
2026
Mon, May 11 - Thu, May 21
from (CA$)$1,555Brilliant Lady's Inaugural Season

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,088CA$3,153
per Sailor
Loading
7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,088CA$3,153
per Sailor
Loading
Departing on:
2027Best Rate
Sun, Aug 01 - Sun, Aug 08
from (CA$)$2,088
2026
Sun, May 17 - Sun, May 24
from (CA$)$2,299
2026
Sun, May 31 - Sun, Jun 07
from (CA$)$2,386

Brilliant Lady Seattle MerMaiden

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
CA$1,488CA$2,192
per Sailor
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,488CA$2,192
per Sailor
Loading
Departing on:
2026
Thu, May 21 - Thu, May 28
from (CA$)$1,488Brilliant Lady's Inaugural Season

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,392CA$3,710
per Sailor
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7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,392CA$3,710
per Sailor
Loading
Departing on:
2026
Sun, May 24 - Sun, May 31
from (CA$)$2,392

Amalfi Coast, Cannes & Ibiza

  • Rome (Civitavecchia)
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
CA$2,329CA$3,727
per Sailor
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6 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,329CA$3,727
per Sailor
Loading
Departing on:
2026
Mon, May 25 - Sun, May 31
from (CA$)$2,329

Seattle, Juneau & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Juneau, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
CA$1,489CA$2,187
per Sailor
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,489CA$2,187
per Sailor
Loading
Departing on:
2026Best Rate
Thu, May 28 - Thu, Jun 04
from (CA$)$1,489Brilliant Lady's Inaugural Season
2026
Thu, Aug 20 - Thu, Aug 27
from (CA$)$1,888Brilliant Lady's Inaugural Season
2027
Thu, May 20 - Thu, May 27
from (CA$)$1,789

Spanish Isles, Rome & Cannes

  • Barcelona
  • Palma de Mallorca, Spain
  • Rome (Civitavecchia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
CA$2,054CA$3,231
per Sailor
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7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,054CA$3,231
per Sailor
Loading
Departing on:
2026
Sun, May 31 - Sun, Jun 07
from (CA$)$2,054

Alaskan Glacier Blues & Coastal Views

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
CA$1,488CA$2,192
per Sailor
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,488CA$2,192
per Sailor
Loading
Departing on:
2026Best Rate
Thu, Jul 30 - Thu, Aug 06
from (CA$)$1,488Brilliant Lady's Inaugural Season
2026
Thu, Jun 04 - Thu, Jun 11
from (CA$)$1,687Brilliant Lady's Inaugural Season
2026
Thu, Jul 02 - Thu, Jul 09
from (CA$)$1,687Brilliant Lady's Inaugural Season

Coastal Gems: Italy, France & Spain

  • Barcelona
  • Provence (Toulon), France
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
CA$2,148CA$3,392
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,148CA$3,392
per Sailor
Loading
Departing on:
2026
Sun, Jun 07 - Sun, Jun 14
from (CA$)$2,148

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,064CA$1,527
per Sailor
Loading
5 nights
Resilient Lady, Scarlet Lady & Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,064CA$1,527
per Sailor
Loading
Departing on:
2027Best Rate
Sat, Sep 18 - Thu, Sep 23
from (CA$)$1,064
2026
Mon, Jun 08 - Sat, Jun 13
from (CA$)$1,470
2026
Sat, Jun 13 - Thu, Jun 18
from (CA$)$1,674

Inside Passage Alaska & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Icy Strait Point, Alaska
  • Haines, Alaska
  • Prince Rupert, British Columbia
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
CA$2,209CA$3,284
per Sailor
Loading
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,209CA$3,284
per Sailor
Loading
Departing on:
2026
Thu, Jun 11 - Tue, Jun 23
from (CA$)$2,209Brilliant Lady's Inaugural Season

Spanish Serenity to French Daydreams

  • Barcelona
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
CA$2,088CA$3,288
per Sailor
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7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,088CA$3,288
per Sailor
Loading
Departing on:
2026
Sun, Jun 14 - Sun, Jun 21
from (CA$)$2,088

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Mykonos, Greece
  • Bodrum, Turkey
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$3,552CA$5,537
per Sailor
Loading
10 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,552CA$5,537
per Sailor
Loading
Departing on:
2026
Sun, Jun 14 - Wed, Jun 24
from (CA$)$3,552

Italian Vistas to Spanish Sunsets

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
CA$2,529CA$4,031
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,529CA$4,031
per Sailor
Loading
Departing on:
2026
Sun, Jun 21 - Sun, Jun 28
from (CA$)$2,529

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$992CA$1,448
per Sailor
Loading
5 nights
Resilient Lady & Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$992CA$1,448
per Sailor
Loading
Departing on:
2026Best Rate
Sat, Nov 28 - Thu, Dec 03
from (CA$)$992
2026
Mon, Jun 22 - Sat, Jun 27
from (CA$)$1,490
2027
Mon, Jan 04 - Sat, Jan 09
from (CA$)$1,062

Alaskan Inside Passage & Canadian Coasts

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Icy Strait Point, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Sitka, Alaska
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
CA$2,170CA$3,300
per Sailor
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,170CA$3,300
per Sailor
Loading
Departing on:
2026
Tue, Jun 23 - Thu, Jul 02
from (CA$)$2,170Brilliant Lady's Inaugural Season

Istanbul Delights & Santorini Dreams

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Chania (Souda Bay), Crete, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$3,123CA$4,783
per Sailor
Loading
11 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,123CA$4,783
per Sailor
Loading
Departing on:
2026
Wed, Jun 24 - Sun, Jul 05
from (CA$)$3,123

Riviera Charms, Rome & Corsica

  • Barcelona
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
CA$1,959CA$3,069
per Sailor
Loading
6 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,959CA$3,069
per Sailor
Loading
Departing on:
2026
Sun, Jun 28 - Sat, Jul 04
from (CA$)$1,959

French Riviera, Italy, Rome & Ibiza

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Florence/Pisa (Livorno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea Terrace cabins from
CA$2,387CA$3,776
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$2,387CA$3,776
per Sailor
Loading
Departing on:
2026
Sat, Jul 04 - Sat, Jul 11
from (CA$)$2,387

French Riviera, Rome, Amalfi & Sicily

  • Barcelona
  • Provence (Marseille), France
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Palermo, Sicily, Italy
  • Barcelona
Sea View cabins from
CA$3,269CA$5,228
per Sailor
Loading
8 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,269CA$5,228
per Sailor
Loading
Departing on:
2026
Sat, Jul 11 - Sun, Jul 19
from (CA$)$3,269

Tuscany, Corsica & Ibiza

  • Barcelona
  • Provence (Toulon), France
  • Florence/Pisa (Livorno), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
CA$2,244CA$3,547
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,244CA$3,547
per Sailor
Loading
Departing on:
2026
Sun, Jul 19 - Sun, Jul 26
from (CA$)$2,244

Rome, Florence, Corsica & Ibiza

  • Barcelona
  • Palma de Mallorca, Spain
  • Cannes, France
  • Rome (Civitavecchia), Italy
  • Florence/Pisa (Livorno), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
CA$2,683CA$4,255
per Sailor
Loading
9 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,683CA$4,255
per Sailor
Loading
Departing on:
2026
Fri, Jul 24 - Sun, Aug 02
from (CA$)$2,683

Moroccan Marvels & Mediterranean Wonders

  • Barcelona
  • Tangier, Morocco
  • Lisbon, Portugal
  • La Coruña, Spain
  • Bilbao, Spain
  • Bordeaux (Le Verdon), France
  • Portsmouth
Sea View cabins from
CA$3,266CA$5,217
per Sailor
Loading
10 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,266CA$5,217
per Sailor
Loading
Departing on:
2026
Sun, Jul 26 - Wed, Aug 05
from (CA$)$3,266

Spanish, French & Italian Classics

  • Barcelona
  • Palma de Mallorca, Spain
  • Provence (Marseille), France
  • Cannes, France
  • Ajaccio, Corsica, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Barcelona
Sea View cabins from
CA$2,385CA$3,771
per Sailor
Loading
8 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,385CA$3,771
per Sailor
Loading
Departing on:
2026
Sun, Aug 02 - Mon, Aug 10
from (CA$)$2,385

Eclipse in the Land of Fire and Ice

  • Portsmouth
  • Dublin (Dun Laoghaire), Ireland
  • Glasgow (Greenock), Scotland
  • Liverpool, United Kingdom
  • Belfast, Northern Ireland
  • Siglufjörður, Iceland
  • Ísafjörður, Iceland
  • Reykjavik, Iceland
  • Edinburgh, Scotland
  • Portsmouth
Insider cabins from
CA$5,328CA$8,294
per Sailor
Loading
15 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$5,328CA$8,294
per Sailor
Loading
Departing on:
2026
Wed, Aug 05 - Thu, Aug 20
from (CA$)$5,328

Total Eclipse of the (Med)

  • Barcelona
  • Palma de Mallorca, Spain
  • Ibiza, Spain
  • Cannes, France
  • Ajaccio, Corsica, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Rome (Civitavecchia)
Insider cabins from
CA$4,605CA$7,468
per Sailor
Loading
12 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$4,605CA$7,468
per Sailor
Loading
Departing on:
2026
Mon, Aug 10 - Sat, Aug 22
from (CA$)$4,605

Virgin Voyages Comedy Fest from the UK

  • Portsmouth
  • Bruges/Zeebruge (Brussels), Belgium
  • Amsterdam, Netherlands
  • Hamburg, Germany
  • Portsmouth
Sea View cabins from
CA$2,387CA$3,679
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,387CA$3,679
per Sailor
Loading
Departing on:
2026
Thu, Aug 20 - Thu, Aug 27
from (CA$)$2,387

Sicily, Naples, Cannes & More

  • Rome (Civitavecchia)
  • Catania, Sicily, Italy
  • Pompeii/Capri (Naples), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Florence/Pisa (Livorno), Italy
  • Rome (Civitavecchia)
Sea View cabins from
CA$2,554CA$4,106
per Sailor
Loading
9 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,554CA$4,106
per Sailor
Loading
Departing on:
2026
Sat, Aug 22 - Mon, Aug 31
from (CA$)$2,554

English Elegance to Idyllic Iceland

  • Portsmouth
  • Amsterdam, Netherlands
  • Edinburgh, Scotland
  • Invergordon, Scotland
  • Akureyri, Iceland
  • Ísafjörður, Iceland
  • Reykjavik
Insider cabins from
CA$3,011CA$4,602
per Sailor
Loading
10 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,011CA$4,602
per Sailor
Loading
Departing on:
2026
Thu, Aug 27 - Sun, Sep 06
from (CA$)$3,011

Rome, Florence, Mykonos & More

  • Rome (Civitavecchia)
  • Florence/Pisa (Livorno), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Chania (Souda Bay), Crete, Greece
  • Santorini, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$4,223CA$6,732
per Sailor
Loading
10 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$4,223CA$6,732
per Sailor
Loading
Departing on:
2026
Mon, Aug 31 - Thu, Sep 10
from (CA$)$4,223

Seattle to Alaska & British Columbia

  • Seattle, Washington
  • Sitka, Alaska
  • Icy Strait Point, Alaska
  • Skagway, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Ketchikan, Alaska
  • Vancouver, British Columbia
Insider cabins from
CA$1,815CA$2,744
per Sailor
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,815CA$2,744
per Sailor
Loading
Departing on:
2026
Thu, Sep 03 - Fri, Sep 11
from (CA$)$1,815Brilliant Lady's Inaugural Season

Iceland, Greenland, Canada & NYC

  • Reykjavik
  • Ísafjörður, Iceland
  • Prince Christian Sound (Cruising), Greenland
  • Qaqortoq, Greenland
  • Nuuk, Greenland
  • St. John's, Newfoundland
  • Halifax, Nova Scotia
  • New York City, New York
Sea View cabins from
CA$4,353CA$6,763
per Sailor
Loading
13 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$4,353CA$6,763
per Sailor
Loading
Departing on:
2026
Sun, Sep 06 - Sat, Sep 19
from (CA$)$4,353

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Bodrum, Turkey
  • Santorini, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$4,161CA$6,559
per Sailor
Loading
10 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$4,161CA$6,559
per Sailor
Loading
Departing on:
2026
Thu, Sep 10 - Sun, Sep 20
from (CA$)$4,161

Vancouver Down the Cali Coast

  • Vancouver, British Columbia
  • Astoria, Oregon
  • San Francisco, California
  • Santa Barbara, California
  • Catalina Island, California
  • San Diego, California
  • Los Angeles, California
Insider cabins from
CA$1,473CA$2,134
per Sailor
Loading
8 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,473CA$2,134
per Sailor
Loading
Departing on:
2026Best Rate
Fri, Sep 11 - Sat, Sep 19
from (CA$)$1,473
2027
Fri, Sep 10 - Sat, Sep 18
from (CA$)$1,701

Fall Foliage in Canada & New England

  • New York City, New York
  • Boston, Massachusetts
  • Portland, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
Insider cabins from
CA$2,030CA$3,053
per Sailor
Loading
8 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,030CA$3,053
per Sailor
Loading
Departing on:
2026
Sat, Sep 19 - Sun, Sep 27
from (CA$)$2,030

Mykonos Moons and Italian Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Rome (Civitavecchia), Italy
  • Barcelona
Sea View cabins from
CA$2,913CA$4,602
per Sailor
Loading
7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$2,913CA$4,602
per Sailor
Loading
Departing on:
2026
Sun, Oct 04 - Sun, Oct 11
from (CA$)$2,913

New York to Bermuda (& Back)

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
CA$1,191CA$1,704
per Sailor
Loading
6 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,191CA$1,704
per Sailor
Loading
Departing on:
2026Best Rate
Wed, Oct 07 - Tue, Oct 13
from (CA$)$1,191
2026
Tue, Oct 13 - Mon, Oct 19
from (CA$)$1,191

Spanish Isles & Transatlantic Miles

  • Barcelona
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Insider cabins from
CA$2,288CA$3,669
per Sailor
Loading
14 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,288CA$3,669
per Sailor
Loading
Departing on:
2026
Sun, Oct 11 - Sun, Oct 25
from (CA$)$2,288

Mexican Riviera Halloween Cruise

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Puerto Vallarta, Mexico
  • Mazatlán, Mexico
  • Los Angeles, California
Insider cabins from
CA$1,089CA$1,605
per Sailor
Loading
7 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,089CA$1,605
per Sailor
Loading
Departing on:
2026
Sat, Oct 17 - Sat, Oct 24
from (CA$)$1,089

NY to San Juan: Bermuda & Caribbean

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • The Beach Club at Bimini, Bahamas
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
CA$1,866CA$2,753
per Sailor
Loading
12 nights
Valiant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,866CA$2,753
per Sailor
Loading
Departing on:
2026
Mon, Oct 19 - Sat, Oct 31
from (CA$)$1,866

SoCal & Ensenada: Halloween Edition

  • Los Angeles, California
  • Catalina Island, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Insider cabins from
CA$920CA$1,318
per Sailor
Loading
5 nights
Brilliant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$920CA$1,318
per Sailor
Loading
Departing on:
2026
Sat, Oct 24 - Thu, Oct 29
from (CA$)$920

Eastern Caribbean & Bimini Halloween

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
CA$1,928CA$3,003
per Sailor
Loading
6 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,928CA$3,003
per Sailor
Loading
Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (CA$)$1,928

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
CA$1,929CA$2,980
per Sailor
Loading
6 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
CA$1,929CA$2,980
per Sailor
Loading
Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (CA$)$1,929

Picturesque Panama Canal Collective

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Puerto Quetzal, Guatemala
  • Puntarenas, Costa Rica
  • Panama City, Panama
  • Panama Canal (Cruising), Panama
  • Cartagena, Colombia
  • Miami, Florida
Insider cabins from
CA$2,643CA$3,747
per Sailor
Loading
17 nights
Brilliant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,643CA$3,747
per Sailor
Loading
Departing on:
2026
Thu, Oct 29 - Sun, Nov 15
from (CA$)$2,643

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,236CA$1,848
per Sailor
Loading
5 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,236CA$1,848
per Sailor
Loading
Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (CA$)$1,236

Valiant's Haunted Halloween Soirée

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Sea View cabins from
CA$1,688CA$2,679
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$1,688CA$2,679
per Sailor
Loading
Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (CA$)$1,688

Fire & Sunset Soirées

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$882CA$1,287
per Sailor
Loading
4 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$882CA$1,287
per Sailor
Loading
Departing on:
2026Best Rate
Thu, Nov 05 - Mon, Nov 09
from (CA$)$882
2026
Sat, Dec 26 - Wed, Dec 30
from (CA$)$1,135

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,473CA$2,228
per Sailor
Loading
8 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,473CA$2,228
per Sailor
Loading
Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (CA$)$1,473

Southern Caribbean Cruise

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • San Juan, Puerto Rico
Insider cabins from
CA$1,190CA$1,703
per Sailor
Loading
6 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,190CA$1,703
per Sailor
Loading
Departing on:
2027Best Rate
Sat, Jan 23 - Fri, Jan 29
from (CA$)$1,190
2026
Sat, Nov 14 - Fri, Nov 20
from (CA$)$1,361
2027
Sat, Mar 13 - Fri, Mar 19
from (CA$)$1,275

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,555CA$2,268
per Sailor
Loading
10 nights
Brilliant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,555CA$2,268
per Sailor
Loading
Departing on:
2027Best Rate
Mon, Jan 25 - Thu, Feb 04
from (CA$)$1,555
2026
Sun, Nov 15 - Wed, Nov 25
from (CA$)$1,555
2027
Mon, Feb 22 - Thu, Mar 04
from (CA$)$1,555

Captivating Costa Maya & Cozumel Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,020CA$1,464
per Sailor
Loading
6 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,020CA$1,464
per Sailor
Loading
Departing on:
2026
Mon, Nov 16 - Sun, Nov 22
from (CA$)$1,020

Thanksgiving: St. Isles, Aruba & Curaçao

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Basseterre, St. Kitts and Nevis
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,472CA$2,296
per Sailor
Loading
8 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,472CA$2,296
per Sailor
Loading
Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (CA$)$1,472

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,134CA$1,630
per Sailor
Loading
5 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,134CA$1,630
per Sailor
Loading
Departing on:
2027Best Rate
Mon, Feb 15 - Sat, Feb 20
from (CA$)$1,134
2026
Mon, Nov 23 - Sat, Nov 28
from (CA$)$1,302

Antiguan Elegance & Sunny St. Isles

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,188CA$1,827
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,188CA$1,827
per Sailor
Loading
Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (CA$)$1,188

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,019CA$1,472
per Sailor
Loading
6 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,019CA$1,472
per Sailor
Loading
Departing on:
2026Best Rate
Sun, Nov 29 - Sat, Dec 05
from (CA$)$1,019
2026
Sun, Dec 13 - Sat, Dec 19
from (CA$)$1,019
2027
Sun, Jan 10 - Sat, Jan 16
from (CA$)$1,104

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,555CA$2,251
per Sailor
Loading
10 nights
Brilliant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,555CA$2,251
per Sailor
Loading
Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (CA$)$1,555
2026
Mon, Nov 30 - Thu, Dec 10
from (CA$)$1,555
2027
Mon, Feb 08 - Thu, Feb 18
from (CA$)$1,555

Eastern Caribbean & Bimini Holiday

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,399CA$2,109
per Sailor
Loading
9 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,399CA$2,109
per Sailor
Loading
Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
from (CA$)$1,399

Eastern Caribbean & Bimini Holiday

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,815CA$2,796
per Sailor
Loading
8 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,815CA$2,796
per Sailor
Loading
Departing on:
2026
Sat, Dec 19 - Sun, Dec 27
from (CA$)$1,815

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Fort-de-France, Martinique
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • San Juan, Puerto Rico
Insider cabins from
CA$1,688CA$2,679
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,688CA$2,679
per Sailor
Loading
Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (CA$)$1,688

Scarlet Caribbean Holidays

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,276CA$1,918
per Sailor
Loading
5 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,276CA$1,918
per Sailor
Loading
Departing on:
2026
Mon, Dec 21 - Sat, Dec 26
from (CA$)$1,276

Grand Turk & Bimini Holiday Cruise

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Insider cabins from
CA$1,420CA$2,180
per Sailor
Loading
5 nights
Brilliant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,420CA$2,180
per Sailor
Loading
Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (CA$)$1,420

Valiant New Year's Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Fort-de-France, Martinique
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • San Juan, Puerto Rico
Insider cabins from
CA$2,487CA$3,995
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,487CA$3,995
per Sailor
Loading
Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (CA$)$2,487

Western Caribbean & Bimini New Year's

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$2,686CA$4,250
per Sailor
Loading
7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,686CA$4,250
per Sailor
Loading
Departing on:
2026
Sun, Dec 27 - Sun, Jan 03
from (CA$)$2,686

Eastern Caribbean & Bimini New Year's

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Tortola, British Virgin Islands
  • St. John's, Antigua
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$2,838CA$4,494
per Sailor
Loading
10 nights
Brilliant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,838CA$4,494
per Sailor
Loading
Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
from (CA$)$2,838

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$2,062CA$3,238
per Sailor
Loading
5 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,062CA$3,238
per Sailor
Loading
Departing on:
2026
Wed, Dec 30 - Mon, Jan 04
from (CA$)$2,062

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • Belize City, Belize
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,358CA$1,977
per Sailor
Loading
8 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,358CA$1,977
per Sailor
Loading
Departing on:
2027Best Rate
Sat, Jan 16 - Sun, Jan 24
from (CA$)$1,358
2027
Sat, Mar 13 - Sun, Mar 21
from (CA$)$1,473

Southern Caribbean & Aruban Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Kralendijk, Bonaire
  • Fort-de-France, Martinique
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,586CA$2,408
per Sailor
Loading
8 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,586CA$2,408
per Sailor
Loading
Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (CA$)$1,586

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,358CA$2,031
per Sailor
Loading
8 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,358CA$2,031
per Sailor
Loading
Departing on:
2027
Sat, Jan 30 - Sun, Feb 07
from (CA$)$1,358

Southern Caribbean & Aruban Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,489CA$2,261
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,489CA$2,261
per Sailor
Loading
Departing on:
2027Best Rate
Sat, Feb 06 - Sat, Feb 13
from (CA$)$1,489
2027
Sat, Mar 27 - Sat, Apr 03
from (CA$)$2,151

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,288CA$1,867
per Sailor
Loading
7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,288CA$1,867
per Sailor
Loading
Departing on:
2027Best Rate
Sun, Feb 28 - Sun, Mar 07
from (CA$)$1,288
2027
Sun, Feb 07 - Sun, Feb 14
from (CA$)$1,339
2027
Sun, Apr 11 - Sun, Apr 18
from (CA$)$1,339

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$965CA$1,377
per Sailor
Loading
4 nights
Scarlet Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$965CA$1,377
per Sailor
Loading
Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (CA$)$965

Lesser Antilles: Valentine's Day

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
CA$1,488CA$2,272
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,488CA$2,272
per Sailor
Loading
Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (CA$)$1,488

Saint Isles & The Greater Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,489CA$2,261
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,489CA$2,261
per Sailor
Loading
Departing on:
2027
Sat, Feb 20 - Sat, Feb 27
from (CA$)$1,489

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
CA$1,488CA$2,251
per Sailor
Loading
7 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,488CA$2,251
per Sailor
Loading
Departing on:
2027
Sat, Mar 06 - Sat, Mar 13
from (CA$)$1,488

Barbados, Dominica & St. Isle Spring

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
CA$1,701CA$2,613
per Sailor
Loading
8 nights
Valiant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,701CA$2,613
per Sailor
Loading
Departing on:
2027
Fri, Mar 19 - Sat, Mar 27
from (CA$)$1,701

Eastern Caribbean Cruise

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Samaná, Dominican Republic
  • Puerto Plata, Dominican Republic
  • Miami, Florida
Insider cabins from
CA$1,190CA$1,820
per Sailor
Loading
6 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,190CA$1,820
per Sailor
Loading
Departing on:
2027
Sun, Mar 21 - Sat, Mar 27
from (CA$)$1,190

Bahamas & Bimini Beach Club

  • Miami, Florida
  • Freeport, Grand Bahama Island, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,127CA$1,682
per Sailor
Loading
4 nights
Brilliant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,127CA$1,682
per Sailor
Loading
Departing on:
2027
Mon, Mar 22 - Fri, Mar 26
from (CA$)$1,127

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Key West, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,339CA$1,952
per Sailor
Loading
7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,339CA$1,952
per Sailor
Loading
Departing on:
2027
Sun, Apr 04 - Sun, Apr 11
from (CA$)$1,339

Eastern Caribbean: San Juan to Miami

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$778CA$1,084
per Sailor
Loading
5 nights
Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$778CA$1,084
per Sailor
Loading
Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (CA$)$778

Grand Cayman & Bimini Beach Club

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
CA$1,135CA$1,697
per Sailor
Loading
5 nights
Resilient Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,135CA$1,697
per Sailor
Loading
Departing on:
2027
Fri, Apr 23 - Wed, Apr 28
from (CA$)$1,135

Transatlantic Miami to Morocco & Spain

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Valencia, Spain
  • Barcelona
Insider cabins from
CA$2,101CA$3,327
per Sailor
Loading
14 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,101CA$3,327
per Sailor
Loading
Departing on:
2027
Sat, Apr 24 - Sat, May 08
from (CA$)$2,101

Coastal Pacific: From LA to Vancouver

  • Los Angeles, California
  • San Diego, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
CA$1,731CA$2,579
per Sailor
Loading
9 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,731CA$2,579
per Sailor
Loading
Departing on:
2027
Sun, May 02 - Tue, May 11
from (CA$)$1,731

Spain & Morocco Transatlantic

  • Miami, Florida
  • Santa Cruz de Tenerife, Spain
  • Tangier, Morocco
  • Málaga, Spain
  • Barcelona
Insider cabins from
CA$2,106CA$3,265
per Sailor
Loading
14 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,106CA$3,265
per Sailor
Loading
Departing on:
2027
Sun, May 02 - Sun, May 16
from (CA$)$2,106

Barcelona to Amalfi, Sicily & Greece

  • Barcelona
  • Ajaccio, Corsica, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,837CA$4,488
per Sailor
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8 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,837CA$4,488
per Sailor
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Departing on:
2027
Sat, May 08 - Sun, May 16
from (CA$)$2,837

Alaska: Vancouver to Seattle

  • Vancouver, British Columbia
  • Inside Passage (Cruising), Alaska
  • Juneau, Alaska
  • Skagway, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Icy Strait Point, Alaska
  • Ketchikan, Alaska
  • Seattle, Washington
Insider cabins from
CA$2,042CA$3,104
per Sailor
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9 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,042CA$3,104
per Sailor
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Departing on:
2027
Tue, May 11 - Thu, May 20
from (CA$)$2,042

French Riviera, Spain & Ibiza Overnight

  • Barcelona
  • Cannes, France
  • Provence (Toulon), France
  • Valencia, Spain
  • Ibiza, Spain
  • Barcelona
Insider cabins from
CA$1,987CA$3,094
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,987CA$3,094
per Sailor
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Departing on:
2027Best Rate
Sun, Oct 03 - Sun, Oct 10
from (CA$)$1,987
2027
Sun, May 16 - Sun, May 23
from (CA$)$2,087
2027
Sun, May 30 - Sun, Jun 06
from (CA$)$2,087

Greek Island Hues & Turkish Views

  • Athens (Piraeus)
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,187CA$3,306
per Sailor
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7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,187CA$3,306
per Sailor
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Departing on:
2027Best Rate
Sun, May 16 - Sun, May 23
from (CA$)$2,187
2027
Sun, Jul 04 - Sun, Jul 11
from (CA$)$2,286
2027
Sun, Aug 22 - Sun, Aug 29
from (CA$)$2,255

Italy, Spain & French Riviera

  • Barcelona
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
CA$2,087CA$3,249
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,087CA$3,249
per Sailor
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Departing on:
2027Best Rate
Sun, May 23 - Sun, May 30
from (CA$)$2,087
2027
Sun, Sep 12 - Sun, Sep 19
from (CA$)$2,087

Greek Isles and the Adriatic

  • Athens (Piraeus)
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea View cabins from
CA$3,435CA$5,378
per Sailor
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11 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$3,435CA$5,378
per Sailor
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Departing on:
2027
Sun, May 30 - Thu, Jun 10
from (CA$)$3,435

Alaska: Fjords & More

  • Seattle, Washington
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Prince Rupert, British Columbia
  • Seattle, Washington
Insider cabins from
CA$1,787CA$2,664
per Sailor
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7 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,787CA$2,664
per Sailor
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Departing on:
2027Best Rate
Thu, Jul 15 - Thu, Jul 22
from (CA$)$1,787
2027
Thu, Jun 03 - Thu, Jun 10
from (CA$)$2,286
2027
Thu, Jun 17 - Thu, Jun 24
from (CA$)$1,788

Western Med: Barcelona to Athens

  • Barcelona
  • Cannes, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Valletta, Malta
  • Chania (Souda Bay), Crete, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,839CA$4,473
per Sailor
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10 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,839CA$4,473
per Sailor
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Departing on:
2027
Sun, Jun 06 - Wed, Jun 16
from (CA$)$2,839

Greece, Turkey and Cairo Overnight

  • Athens (Piraeus)
  • Santorini, Greece
  • Ephesus (Kuşadasi), Turkey
  • Alexandria (Cairo), Egypt
  • Rhodes, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$3,411CA$5,370
per Sailor
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10 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,411CA$5,370
per Sailor
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Departing on:
2027
Thu, Jun 10 - Sun, Jun 20
from (CA$)$3,411

Western Med: Athens to Barcelona

  • Athens (Piraeus)
  • Mykonos, Greece
  • Kotor, Montenegro
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Cannes, France
  • Provence (Marseille), France
  • Barcelona
Insider cabins from
CA$3,122CA$4,925
per Sailor
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11 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,122CA$4,925
per Sailor
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Departing on:
2027
Wed, Jun 16 - Sun, Jun 27
from (CA$)$3,122

Croatia, Montenegro, Greece & Albania

  • Athens (Piraeus)
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Sarandë, Albania
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,088CA$3,244
per Sailor
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7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,088CA$3,244
per Sailor
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Departing on:
2027Best Rate
Sun, Aug 15 - Sun, Aug 22
from (CA$)$2,088
2027
Sun, Jun 20 - Sun, Jun 27
from (CA$)$2,389
2027
Sun, Sep 26 - Sun, Oct 03
from (CA$)$2,188

French Riviera, Spain & Ibiza Overnight

  • Barcelona
  • Nice (Villefranche), France
  • Provence (Toulon), France
  • Valencia, Spain
  • Ibiza, Spain
  • Barcelona
Insider cabins from
CA$2,086CA$3,253
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,086CA$3,253
per Sailor
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Departing on:
2027
Sun, Jun 27 - Sun, Jul 04
from (CA$)$2,086

Italy, Spain & French Riviera

  • Barcelona
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Provence (Marseille), France
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
CA$2,087CA$3,252
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,087CA$3,252
per Sailor
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Departing on:
2027
Sun, Jul 04 - Sun, Jul 11
from (CA$)$2,087

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Insider cabins from
CA$3,484CA$5,432
per Sailor
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10 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,484CA$5,432
per Sailor
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Departing on:
2027
Sun, Jul 11 - Wed, Jul 21
from (CA$)$3,484

Italy, Spain, Malta & French Riviera

  • Barcelona
  • Cannes, France
  • Ajaccio, Corsica, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Valletta, Malta
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
CA$3,271CA$5,201
per Sailor
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10 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,271CA$5,201
per Sailor
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Departing on:
2027
Sun, Jul 18 - Wed, Jul 28
from (CA$)$3,271

Greek Isle Days & Istanbul Nights

  • Athens (Piraeus)
  • Chania (Souda Bay), Crete, Greece
  • Rhodes, Greece
  • Mykonos, Greece
  • Ephesus (Kuşadasi), Turkey
  • Istanbul, Turkey
  • Santorini, Greece
  • Athens (Piraeus)
Insider cabins from
CA$3,607CA$5,624
per Sailor
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11 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,607CA$5,624
per Sailor
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Departing on:
2027
Wed, Jul 21 - Sun, Aug 01
from (CA$)$3,607

Solar Eclipse: Spain, Portugal, Morocco

  • Barcelona
  • Palma de Mallorca, Spain
  • Málaga, Spain
  • Seville (Cádiz), Spain
  • Funchal, Madeira, Portugal
  • Tangier, Morocco
  • Valencia, Spain
  • Barcelona
Sea View cabins from
CA$4,564CA$7,367
per Sailor
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11 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Sea View cabins from
CA$4,564CA$7,367
per Sailor
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Departing on:
2027
Wed, Jul 28 - Sun, Aug 08
from (CA$)$4,564

Western Med: Barcelona to Rome

  • Barcelona
  • Cannes, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Valletta, Malta
  • Rome (Civitavecchia)
Insider cabins from
CA$2,683CA$4,246
per Sailor
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9 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,683CA$4,246
per Sailor
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Departing on:
2027
Sun, Aug 08 - Tue, Aug 17
from (CA$)$2,683

Alaska: Glaciers & More

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Skagway, Alaska
  • Haines, Alaska
  • Juneau, Alaska
  • Icy Strait Point, Alaska
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
CA$2,723CA$4,121
per Sailor
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12 nights
Brilliant Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,723CA$4,121
per Sailor
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Departing on:
2027
Thu, Aug 12 - Tue, Aug 24
from (CA$)$2,723

Alaska: Glaciers & More

  • Seattle, Washington
  • Ketchikan, Alaska
  • Icy Strait Point, Alaska
  • Hubbard Glacier (Cruising), Alaska
  • Sitka, Alaska
  • Victoria, British Columbia
  • Seattle, Washington
Insider cabins from
CA$2,043CA$3,069
per Sailor
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9 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,043CA$3,069
per Sailor
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Departing on:
2027
Tue, Aug 24 - Thu, Sep 02
from (CA$)$2,043

Mediterranean: Athens to Rome

  • Athens (Piraeus)
  • Bodrum, Turkey
  • Santorini, Greece
  • Mykonos, Greece
  • Valletta, Malta
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Rome (Civitavecchia)
Insider cabins from
CA$2,950CA$4,613
per Sailor
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9 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,950CA$4,613
per Sailor
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Departing on:
2027
Sun, Aug 29 - Tue, Sep 07
from (CA$)$2,950

Alaska: Seattle to Vancouver

  • Seattle, Washington
  • Inside Passage (Cruising), Alaska
  • Ketchikan, Alaska
  • Sitka, Alaska
  • Skagway, Alaska
  • Tracy Arm Fjord (Cruising), Alaska
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
CA$1,815CA$2,716
per Sailor
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8 nights
Brilliant Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,815CA$2,716
per Sailor
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Departing on:
2027
Thu, Sep 02 - Fri, Sep 10
from (CA$)$1,815

Italy, Spain & French Riviera

  • Barcelona
  • Provence (Marseille), France
  • Cannes, France
  • Ajaccio, Corsica, France
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Palermo, Sicily, Italy
  • Cagliari, Sardinia, Italy
  • Barcelona
Insider cabins from
CA$3,123CA$4,949
per Sailor
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10 nights
Resilient Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,123CA$4,949
per Sailor
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Departing on:
2027
Thu, Sep 02 - Sun, Sep 12
from (CA$)$3,123

Mediterranean: Rome to Athens

  • Rome (Civitavecchia)
  • Florence/Pisa (Livorno), Italy
  • Pompeii/Capri (Naples), Italy
  • Palermo, Sicily, Italy
  • Valletta, Malta
  • Chania (Souda Bay), Crete, Greece
  • Mykonos, Greece
  • Santorini, Greece
  • Ephesus (Kuşadasi), Turkey
  • Athens (Piraeus)
Insider cabins from
CA$3,763CA$5,979
per Sailor
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12 nights
Scarlet Lady
BOOK NOW
Up to $400 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$3,763CA$5,979
per Sailor
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Departing on:
2027
Tue, Sep 07 - Sun, Sep 19
from (CA$)$3,763

Italy, Spain & French Riviera

  • Barcelona
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Provence (Marseille), France
  • Barcelona
Insider cabins from
CA$1,987CA$3,085
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,987CA$3,085
per Sailor
Loading
Departing on:
2027Best Rate
Sun, Sep 26 - Sun, Oct 03
from (CA$)$1,987
2027
Sun, Oct 17 - Sun, Oct 24
from (CA$)$1,987

Italy, Spain & French Riviera

  • Barcelona
  • Provence (Marseille), France
  • Cannes, France
  • Florence/Pisa (Livorno), Italy
  • Valencia, Spain
  • Palma de Mallorca, Spain
  • Barcelona
Insider cabins from
CA$1,988CA$3,080
per Sailor
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7 nights
Resilient Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,988CA$3,080
per Sailor
Loading
Departing on:
2027
Sun, Oct 10 - Sun, Oct 17
from (CA$)$1,988

Adriatic, Albania and Mykonos Magic

  • Athens (Piraeus)
  • Dubrovnik, Croatia
  • Sarandë, Albania
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
CA$2,187CA$3,396
per Sailor
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7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$2,187CA$3,396
per Sailor
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Departing on:
2027
Sun, Oct 17 - Sun, Oct 24
from (CA$)$2,187

Med Coastal Medley: Athens to Barcelona

  • Athens (Piraeus)
  • Mykonos, Greece
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Barcelona
Insider cabins from
CA$1,987CA$3,089
per Sailor
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7 nights
Scarlet Lady
BOOK NOW
Up to $300 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,987CA$3,089
per Sailor
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Departing on:
2027
Sun, Oct 24 - Sun, Oct 31
from (CA$)$1,987

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
CA$1,134CA$1,619
per Sailor
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5 nights
Valiant Lady
BOOK NOW
Up to $100 in drinks
Getaways for 80% off 2nd Sailor
Insider cabins from
CA$1,134CA$1,619
per Sailor
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Departing on:
2027
Sat, Oct 30 - Thu, Nov 04
from (CA$)$1,134
Average starting price per Sailor (incl. taxes & fees)