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Explore 399 cruise vacations

Showing Loading cruise vacations: Transatlantic & Repositioning, North America & Caribbean, July 2025 - April 2027
Showing 310 cruise vacations that match your search
Showing 310 cruise vacations that match your search
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DEAL

Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)
DEAL

Grand Turk, Puerto Plata & More

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Sun, Jan 25 - Fri, Jan 30
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)
2025
Sun, Aug 24 - Fri, Aug 29
from (US$)

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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4 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Thu, Sep 24 - Mon, Sep 28
from (US$)
2025
Wed, Aug 06 - Sun, Aug 10
from (US$)
2025
Wed, Aug 20 - Sun, Aug 24
from (US$)
* Port changes in place on select sailings — see full cruise details

Virgin Voyages Comedy Fest from Miami

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Mon, Sep 28 - Sat, Oct 03
from (US$)
2025
Fri, Aug 15 - Wed, Aug 20
from (US$)
2025
Fri, Aug 29 - Wed, Sep 03
from (US$)

Brilliant Lady New York MerMaiden

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
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5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2025
Fri, Sep 05 - Wed, Sep 10
from (US$) Brilliant Lady's Inaugural Season

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady, Resilient Lady & Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 04 - Sat, Jan 09
from (US$)
2025
Sun, Sep 07 - Fri, Sep 12
from (US$)
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)

The Big Apple to Bermuda

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
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per Cabin
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5 nights
Brilliant Lady & Valiant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2026Best Rate
Mon, Apr 06 - Sat, Apr 11
from (US$)
2025
Wed, Sep 10 - Mon, Sep 15
from (US$) Brilliant Lady's Inaugural Season
2026
Sat, Apr 11 - Thu, Apr 16
from (US$)

Fall Colors: Coastal Northeast & Canada

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
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per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Mon, Sep 15 - Tue, Sep 23
from (US$) Brilliant Lady's Inaugural Season

Autumn Leaves: New York to Quebec

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • Quebec City, Quebec
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$) Brilliant Lady's Inaugural Season

Fall Leaves to Miami Scenes

  • Quebec City, Quebec
  • Halifax, Nova Scotia
  • Saint John, New Brunswick
  • Eastport, Maine
  • Boston, Massachusetts
  • Charleston, South Carolina
  • Miami, Florida
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per Cabin
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13 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 03 - Thu, Oct 16
from (US$) Brilliant Lady's Inaugural Season

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
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15 nights
Scarlet Lady
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+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)
DEAL

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
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per Cabin
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14 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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4 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)
DEAL

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)
DEAL

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$) Brilliant Lady's Inaugural Season

One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
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per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
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per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)
DEAL

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season
DEAL

Saint (Isles) & Seas of the Caribbean

  • 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
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Sat, Jan 02 - Sat, Jan 09
from (US$)
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)
DEAL

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)
DEAL

Sunny Miles of Tropical Isles

  • 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
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per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Feb 28 - Sat, Mar 07
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Nov 07 - Sat, Nov 14
from (US$)
DEAL

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)
DEAL

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)
DEAL

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
DEAL

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Sea View cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$) Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$) Brilliant Lady's Inaugural Season

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)
DEAL

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
DEAL

Nicky Jam x Virgin Voyages

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)
DEAL

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sun, Mar 01 - Thu, Mar 12
from (US$) Brilliant Lady's Inaugural Season
2025
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season
DEAL

St. Lucia, St. Maarten, Barbados & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Roseau, Dominica
  • Bridgetown, Barbados
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)
DEAL

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)
DEAL

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Wed, Dec 24 - Sun, Dec 28
from (US$)
2026
Mon, Dec 21 - Sat, Dec 26
from (US$)
* Port changes in place on select sailings — see full cruise details
DEAL

Brilliant New Year's Ahoy!

  • 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
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)
DEAL

Valiant New Year’s Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Wed, Dec 30 - Mon, Jan 04
from (US$)
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)
* Port changes in place on select sailings — see full cruise details
DEAL

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 03 - Sat, Jan 10
from (US$)
2027
Sat, Feb 06 - Sat, Feb 13
from (US$)
DEAL

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$) Brilliant Lady's Inaugural Season
DEAL

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady & Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
2026
Sun, Nov 01 - Sun, Nov 08
from (US$)
DEAL

Virgin Island Views & Saint Isle Blues

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Basseterre, St. Kitts and Nevis
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)
DEAL

St. Kitts, Barbados, Martinique & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
DEAL

Barbados, Antigua, BVI & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
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6 nights
Brilliant Lady
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70% off 2nd Sailor
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)
DEAL

Antigua & the St. Isles

  • 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
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)
DEAL

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
2026
Sun, Dec 06 - Sun, Dec 13
from (US$)
DEAL

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$) Brilliant Lady's Inaugural Season
DEAL

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
DEAL

St. Lucia, Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
DEAL

Brilliant Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$) Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Scarlet Lady
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70% off 2nd Sailor
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)
DEAL

Resilient Valentine's Voyage

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)

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
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)
DEAL

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
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)
DEAL

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
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
DEAL

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
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

Costa Mayan Caves & Honduran Waves

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
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6 nights
Resilient Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (US$)
DEAL

Sunsets in the Lesser Antilles

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (US$)
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)
2027
Sat, Jan 09 - Sat, Jan 16
from (US$)
DEAL

Puerto Rican Nights & St. Croix Delights

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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8 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

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
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16 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 21 - Mon, Apr 06
from (US$) Brilliant Lady's Inaugural Season

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
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9 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (US$)

Brilliant Lady LA MerMaiden

  • Los Angeles, California
  • Santa Barbara, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
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5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Tue, Apr 07 - Sun, Apr 12
from (US$) Brilliant Lady's Inaugural Season

California (and Mexico) Dreamin'

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlàn, Mexico
  • Los Angeles, California
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6 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sun, Apr 12 - Sat, Apr 18
from (US$) Brilliant 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
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9 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Thu, Apr 16 - Sat, Apr 25
from (US$)
DEAL

Puerto Plata, San Juan & Tortola

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Miami, Florida
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7 nights
Scarlet Lady
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70% off 2nd Sailor
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Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)

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
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14 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Apr 25 - Sat, May 09
from (US$)

Hollywood Sunsets & Mexican Horizons

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlàn, Mexico
  • Puerto Vallarta, Mexico
  • Los Angeles, California
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sat, Sep 19 - Sat, Sep 26
from (US$)
2026
Sun, Apr 26 - Sun, May 03
from (US$) Brilliant Lady's Inaugural Season
2026
Sat, Sep 26 - Sat, Oct 03
from (US$)

Transatlantic to Spain & Morocco

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Alicante, Spain
  • Barcelona
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per Cabin
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14 nights
Scarlet Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (US$)

LA Lights & Vancouver Vistas

  • Los Angeles, California
  • Catalina Island, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Sun, May 03 - Mon, May 11
from (US$) Brilliant Lady's Inaugural Season

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
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Mon, May 11 - Thu, May 21
from (US$) Brilliant Lady's Inaugural Season

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
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Thu, May 21 - Thu, May 28
from (US$) Brilliant Lady's Inaugural Season

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
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per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026Best Rate
Thu, Aug 20 - Thu, Aug 27
from (US$) Brilliant Lady's Inaugural Season
2026
Thu, May 28 - Thu, Jun 04
from (US$) Brilliant Lady's Inaugural Season

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
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026Best Rate
Thu, Aug 27 - Thu, Sep 03
from (US$) Brilliant Lady's Inaugural Season
2026
Thu, Jun 04 - Thu, Jun 11
from (US$) Brilliant Lady's Inaugural Season
2026
Thu, Jul 02 - Thu, Jul 09
from (US$) Brilliant Lady's Inaugural Season

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Resilient Lady & Scarlet Lady
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Departing on:
2026Best Rate
Mon, Nov 09 - Sat, Nov 14
from (US$)
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)

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
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Thu, Jun 11 - Tue, Jun 23
from (US$) Brilliant Lady's Inaugural Season

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
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Tue, Jun 23 - Thu, Jul 02
from (US$) Brilliant Lady's Inaugural Season

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
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
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70% off 2nd Sailor
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Departing on:
2026
Thu, Sep 03 - Fri, Sep 11
from (US$) Brilliant 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
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13 nights
Valiant Lady
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Departing on:
2026
Sun, Sep 06 - Sat, Sep 19
from (US$)

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
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per Cabin
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8 nights
Brilliant Lady
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70% off 2nd Sailor
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Departing on:
2026
Fri, Sep 11 - Sat, Sep 19
from (US$)

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
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8 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Sep 19 - Sun, Sep 27
from (US$)

New York to Bermuda (& Back)

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
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6 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026Best Rate
Wed, Oct 07 - Tue, Oct 13
from (US$)
2026
Tue, Oct 13 - Mon, Oct 19
from (US$)

Spanish Isles & Transatlantic Miles

  • Barcelona
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
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per Cabin
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14 nights
Scarlet Lady
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70% off 2nd Sailor
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Departing on:
2026
Sun, Oct 11 - Sun, Oct 25
from (US$)

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
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12 nights
Valiant Lady
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Departing on:
2026
Mon, Oct 19 - Sat, Oct 31
from (US$)

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Scarlet Lady
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Resilient Lady
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70% off 2nd Sailor
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Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)

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
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17 nights
Brilliant Lady
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70% off 2nd Sailor
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Departing on:
2026
Thu, Oct 29 - Sun, Nov 15
from (US$)

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Scarlet Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (US$)
DEAL

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
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)
DEAL

November Nights in the Eastern Caribbean

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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8 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)

Caribbean East: Virgin & Saint Isles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • San Juan, Puerto Rico
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6 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027Best Rate
Sat, Jan 23 - Fri, Jan 29
from (US$)
2026
Sat, Nov 14 - Fri, Nov 20
from (US$)
2027
Sat, Mar 13 - Fri, Mar 19
from (US$)
DEAL

St. Isles & Sun-soaked Seas

  • 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
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10 nights
Brilliant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026Best Rate
Sun, Nov 15 - Wed, Nov 25
from (US$)
2027
Mon, Jan 25 - Thu, Feb 04
from (US$)
2027
Mon, Feb 22 - Thu, Mar 04
from (US$)

Captivating Costa Maya & Cozumel Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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6 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Mon, Nov 16 - Sun, Nov 22
from (US$)
DEAL

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
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8 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Scarlet Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027Best Rate
Mon, Feb 15 - Sat, Feb 20
from (US$)
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)
DEAL

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
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (US$)
DEAL

St. Maarten, Tortola, San Juan & more

  • 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
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10 nights
Brilliant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)
DEAL

Pre-Holiday Caribbean Getaway

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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9 nights
Brilliant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
from (US$)
DEAL

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Fort-de-France, Martinique
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • San Juan, Puerto Rico
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (US$)
DEAL

Resilient Caribbean Holidays

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sun, Dec 20 - Sun, Dec 27
from (US$)

Brilliant Caribbean Holidays

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Miami, Florida
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5 nights
Brilliant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (US$)
DEAL

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
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (US$)
DEAL

Resilient New Year's Ahoy!

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Sun, Dec 27 - Sun, Jan 03
from (US$)
DEAL

Brilliant New Year's Ahoy!

  • 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
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10 nights
Brilliant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
from (US$)
DEAL

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sun, Jan 17 - Sun, Jan 24
from (US$)
DEAL

Puerto Rico to Aruba, Bonaire & More

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Kralendijk, Bonaire
  • Fort-de-France, Martinique
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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8 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (US$)
DEAL

San Juan & St. Isles: Valentine’s Voyage

  • 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
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10 nights
Brilliant Lady
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70% off 2nd Sailor
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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4 nights
Scarlet Lady
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70% off 2nd Sailor
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (US$)
DEAL

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
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7 nights
Valiant Lady
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70% off 2nd Sailor
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Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (US$)
DEAL

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Resilient Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sun, Feb 14 - Sun, Feb 21
from (US$)
DEAL

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
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sat, Feb 20 - Sat, Feb 27
from (US$)
DEAL

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
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sat, Mar 06 - Sat, Mar 13
from (US$)
DEAL

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
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8 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Fri, Mar 19 - Sat, Mar 27
from (US$)
DEAL

Colorful Curaçao, Aruba & Antigua

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
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per Cabin
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7 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sat, Mar 27 - Sat, Apr 03
from (US$)

San Juan to Miami: Dominican Daze

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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5 nights
Valiant Lady
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+ Balcony upgrades
70% off 2nd Sailor
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Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (US$)
Average starting price per cabin (incl. taxes & fees)