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Explore 387 cruise vacations

Showing Loading cruise vacations: All Destinations, November 2025 - October 2026
Showing 202 cruise vacations that match your search
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Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$3,336$5,232
per Cabin
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$3,336$5,232
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$3,336Brilliant Lady's Inaugural Season

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
$1,944$3,042
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,944$3,042
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 08 - Sat, Nov 15
from (US$)$1,944
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)$2,410

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,192$1,728
per Cabin
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4 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,192$1,728
per Cabin
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Departing on:
2026Best Rate
Wed, Jan 07 - Sun, Jan 11
from (US$)$1,192
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$4,312
Only suites remaining
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$3,992
Only suites remaining

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
Insider cabins from
$1,806$2,838
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,806$2,838
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Feb 28 - Sat, Mar 07
from (US$)$1,806
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$2,876

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$990$1,302
per Cabin
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5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$990$1,302
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$990
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390
2026
Sun, Jan 11 - Fri, Jan 16
from (US$)$1,290

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
$2,064$3,188
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,064$3,188
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$2,064Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,490$2,232
per Cabin
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5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,490$2,232
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Oct 03 - Thu, Oct 08
from (US$)$1,490
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$4,990
Only suites remaining
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,590

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
$1,386$2,110
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,110
per Cabin
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Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386

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
Insider cabins from
$1,962$3,000
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,962$3,000
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$)$1,962Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$)$3,042Brilliant Lady's Inaugural Season

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$2,022
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,022
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,386
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,806

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
Sea Terrace cabins from
$2,008$3,184
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
$2,008$3,184
per Cabin
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Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$2,008

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,390$2,008
per Cabin
Loading
5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,390$2,008
per Cabin
Loading
Departing on:
2026Best Rate
Mon, Sep 14 - Sat, Sep 19
from (US$)$1,390
2025
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490
2026
Fri, Jan 02 - Wed, Jan 07
from (US$)$1,490

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
$1,584$2,440
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,584$2,440
per Cabin
Loading
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,584

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,666
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)$1,806

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,532$3,918
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$2,532$3,918
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,532Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$)$2,948Brilliant Lady's Inaugural Season

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,386
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$1,806

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
Insider cabins from
$1,412$2,170
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,412$2,170
per Cabin
Loading
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,412

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Sea View cabins from
$2,544$3,992
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,544$3,992
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,544Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,946$2,942
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$2,942
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$1,946

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
$1,946$3,046
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$3,046
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$1,946

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,912$2,930
per Cabin
Loading
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea Terrace cabins from
$1,912$2,930
per Cabin
Loading
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)$1,912

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
$3,942$6,340
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,942$6,340
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$3,942Brilliant Lady's Inaugural Season

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
$3,616$5,712
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,616$5,712
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,616

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
$3,346$5,406
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,346$5,406
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,346

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$3,290$5,136
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$3,290$5,136
per Cabin
Loading
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,290

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
$1,806$2,834
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,806$2,834
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,806

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,930
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,930
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,386

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$3,996$6,348
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$3,996$6,348
per Cabin
Loading
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$)$3,996Brilliant Lady's Inaugural Season

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$2,006
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,006
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,386
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,086

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
Insider cabins from
$1,526$2,382
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,382
per Cabin
Loading
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,526

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
Insider cabins from
$1,526$2,366
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,366
per Cabin
Loading
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,526

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
Insider cabins from
$1,666$2,594
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,666$2,594
per Cabin
Loading
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,666

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Sea View cabins from
$2,388$3,700
per Cabin
Loading
6 nights
Brilliant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,388$3,700
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)$2,388

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
Insider cabins from
$1,526$2,340
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,340
per Cabin
Loading
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,526

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$2,026
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,026
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,386
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$1,806

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
$4,100$6,516
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$4,100$6,516
per Cabin
Loading
Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$)$4,100Brilliant Lady's Inaugural Season

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
Insider cabins from
$1,666$2,576
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,666$2,576
per Cabin
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$1,666

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
Insider cabins from
$2,704$4,264
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,704$4,264
per Cabin
Loading
Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$)$2,704Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,890$2,894
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,890$2,894
per Cabin
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)$1,890

Resilient Valentine's Voyage

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,946$2,938
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$2,938
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$1,946

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
Insider cabins from
$1,666$2,602
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,666$2,602
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$1,666

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
Insider cabins from
$1,806$2,826
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,806$2,826
per Cabin
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)$1,806

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
Insider cabins from
$1,944$3,066
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,944$3,066
per Cabin
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$1,944

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
Sea View cabins from
$3,042$4,776
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,042$4,776
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$)$3,042Brilliant Lady's Inaugural Season

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
Insider cabins from
$2,340$3,738
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,340$3,738
per Cabin
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Departing on:
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)$2,340

Western Caribbean Cruise

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Sea View cabins from
$2,268$3,452
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,268$3,452
per Cabin
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (US$)$2,268

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
Sea View cabins from
$3,024$4,748
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,024$4,748
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)$3,024

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
$6,368$9,736
per Cabin
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16 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$6,368$9,736
per Cabin
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Departing on:
2026
Sat, Mar 21 - Mon, Apr 06
from (US$)$6,368Brilliant Lady's Inaugural Season

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,366$3,660
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,366$3,660
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)$2,366
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)$2,506

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
$1,784$2,700
per Cabin
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9 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,784$2,700
per Cabin
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Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (US$)$1,784

The Big Apple to Bermuda

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
$1,690$2,466
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,690$2,466
per Cabin
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Departing on:
2026Best Rate
Sun, Sep 27 - Fri, Oct 02
from (US$)$1,690
2026
Mon, Apr 06 - Sat, Apr 11
from (US$)$2,190
2026
Fri, Oct 02 - Wed, Oct 07
from (US$)$1,690

Brilliant Lady LA MerMaiden

  • Los Angeles, California
  • Santa Barbara, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Sea View cabins from
$2,540$3,938
per Cabin
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5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$2,540$3,938
per Cabin
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Departing on:
2026
Tue, Apr 07 - Sun, Apr 12
from (US$)$2,540Brilliant 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
$1,890$2,812
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,890$2,812
per Cabin
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Departing on:
2026
Sat, Apr 11 - Thu, Apr 16
from (US$)$1,890

California (and Mexico) Dreamin'

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlán, Mexico
  • Los Angeles, California
Insider cabins from
$2,644$4,126
per Cabin
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6 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,644$4,126
per Cabin
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Departing on:
2026
Sun, Apr 12 - Sat, Apr 18
from (US$)$2,644Brilliant 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
$2,170$3,188
per Cabin
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9 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,170$3,188
per Cabin
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Departing on:
2026
Thu, Apr 16 - Sat, Apr 25
from (US$)$2,170

Hollywood Sunsets & Mexican Horizons

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Mazatlán, Mexico
  • Puerto Vallarta, Mexico
  • Los Angeles, California
Insider cabins from
$1,946$2,916
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$2,916
per Cabin
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Departing on:
2026Best Rate
Sat, Sep 26 - Sat, Oct 03
from (US$)$1,946
2026
Sun, Apr 26 - Sun, May 03
from (US$)$3,206Brilliant Lady's Inaugural Season
2026
Sat, Sep 19 - Sat, Sep 26
from (US$)$2,086

Transatlantic to Spain & Morocco

  • Miami, Florida
  • Las Palmas de Gran Canaria, Spain
  • Casablanca, Morocco
  • Alicante, Spain
  • Barcelona
Insider cabins from
$4,006$6,472
per Cabin
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14 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$4,006$6,472
per Cabin
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Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (US$)$4,006

LA Lights & Vancouver Vistas

  • Los Angeles, California
  • Catalina Island, California
  • San Francisco, California
  • Astoria, Oregon
  • Victoria, British Columbia
  • Vancouver, British Columbia
Insider cabins from
$2,224$3,344
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,224$3,344
per Cabin
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Departing on:
2026
Sun, May 03 - Mon, May 11
from (US$)$2,224Brilliant Lady's Inaugural Season

Rome, Mykonos & the Amalfi Coast

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Amalfi Coast (Salerno), Italy
  • Catania, Sicily, Italy
  • Mykonos, Greece
  • Athens (Piraeus)
RockStar Quarters suites from
$9,050
per Cabin
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7 nights
Scarlet Lady
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+ up to $300 free drinks
80% off second Sailor
RockStar Quarters suites from
$9,050
per Cabin
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Departing on:
2026
Sun, May 10 - Sun, May 17
from (US$)$9,050
Only suites remaining

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
$3,924$6,158
per Cabin
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10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$3,924$6,158
per Cabin
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Departing on:
2026
Mon, May 11 - Thu, May 21
from (US$)$3,924Brilliant Lady's Inaugural Season

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,020$4,688
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,020$4,688
per Cabin
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Departing on:
2026Best Rate
Sun, May 31 - Sun, Jun 07
from (US$)$3,020
2026
Sun, May 17 - Sun, May 24
from (US$)$3,220
2026
Sun, Jun 07 - Sun, Jun 14
from (US$)$3,486

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
$3,356$5,204
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,356$5,204
per Cabin
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Departing on:
2026
Thu, May 21 - Thu, May 28
from (US$)$3,356Brilliant Lady's Inaugural Season

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
$3,348$5,278
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,348$5,278
per Cabin
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Departing on:
2026
Sun, May 24 - Sun, May 31
from (US$)$3,348

Amalfi Coast, Cannes & Ibiza

  • Rome (Civitavecchia)
  • Amalfi Coast (Salerno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,266$5,226
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,266$5,226
per Cabin
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Departing on:
2026
Mon, May 25 - Sun, May 31
from (US$)$3,266

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
$3,158$4,858
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,158$4,858
per Cabin
Loading
Departing on:
2026Best Rate
Thu, Aug 20 - Thu, Aug 27
from (US$)$3,158Brilliant Lady's Inaugural Season
2026
Thu, May 28 - Thu, Jun 04
from (US$)$3,346Brilliant Lady's Inaugural Season

Spanish Isles, Rome & Cannes

  • Barcelona
  • Palma de Mallorca, Spain
  • Rome (Civitavecchia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,346$5,306
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,346$5,306
per Cabin
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Departing on:
2026
Sun, May 31 - Sun, Jun 07
from (US$)$3,346

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
$2,506$3,790
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,506$3,790
per Cabin
Loading
Departing on:
2026Best Rate
Thu, Jul 23 - Thu, Jul 30
from (US$)$2,506Brilliant Lady's Inaugural Season
2026
Thu, Jun 04 - Thu, Jun 11
from (US$)$3,066Brilliant Lady's Inaugural Season
2026
Thu, Jul 02 - Thu, Jul 09
from (US$)$3,356Brilliant 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
$2,880$4,536
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,880$4,536
per Cabin
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Departing on:
2026
Sun, Jun 07 - Sun, Jun 14
from (US$)$2,880

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$2,090$3,150
per Cabin
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5 nights
Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$2,090$3,150
per Cabin
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Departing on:
2026Best Rate
Mon, Jun 08 - Sat, Jun 13
from (US$)$2,090
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)$2,348

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
$5,496$8,626
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$5,496$8,626
per Cabin
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Departing on:
2026
Thu, Jun 11 - Tue, Jun 23
from (US$)$5,496Brilliant Lady's Inaugural Season

Spanish Serenity to French Daydreams

  • Barcelona
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$2,948$4,644
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,948$4,644
per Cabin
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Departing on:
2026
Sun, Jun 14 - Sun, Jun 21
from (US$)$2,948

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea View cabins from
$5,636$8,994
per Cabin
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10 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$5,636$8,994
per Cabin
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Departing on:
2026Best Rate
Sun, Jun 14 - Wed, Jun 24
from (US$)$5,636
2026
Thu, Sep 10 - Sun, Sep 20
from (US$)$5,826

Italian Vistas to Spanish Sunsets

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$3,080$4,876
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,080$4,876
per Cabin
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Departing on:
2026
Sun, Jun 21 - Sun, Jun 28
from (US$)$3,080

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,972$2,976
per Cabin
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5 nights
Resilient Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,972$2,976
per Cabin
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Departing on:
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)$1,972

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
$4,122$6,454
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$4,122$6,454
per Cabin
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Departing on:
2026
Tue, Jun 23 - Thu, Jul 02
from (US$)$4,122Brilliant Lady's Inaugural Season

Istanbul Delights & Santorini Dreams

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Chania (Souda Bay), Crete, Greece
  • Santorini, Greece
  • Athens (Piraeus)
Sea View cabins from
$5,054$7,948
per Cabin
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11 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$5,054$7,948
per Cabin
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Departing on:
2026
Wed, Jun 24 - Sun, Jul 05
from (US$)$5,054

Riviera Charms, Rome & Corsica

  • Barcelona
  • Nice (Villefranche), France
  • Rome (Civitavecchia), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,042$4,794
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,042$4,794
per Cabin
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Departing on:
2026
Sun, Jun 28 - Sat, Jul 04
from (US$)$3,042

French Riviera, Italy, Rome & Ibiza

  • Barcelona
  • Rome (Civitavecchia), Italy
  • Florence/Pisa (Livorno), Italy
  • Cannes, France
  • Ibiza, Spain
  • Barcelona
Sea View cabins from
$3,414$5,406
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,414$5,406
per Cabin
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Departing on:
2026
Sat, Jul 04 - Sat, Jul 11
from (US$)$3,414

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
$4,432$7,078
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$4,432$7,078
per Cabin
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Departing on:
2026
Sat, Jul 11 - Sun, Jul 19
from (US$)$4,432

Tuscany, Corsica & Ibiza

  • Barcelona
  • Provence (Toulon), France
  • Florence/Pisa (Livorno), Italy
  • Ajaccio, Corsica, France
  • Ibiza, Spain
  • Barcelona
Insider cabins from
$2,282$3,532
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,282$3,532
per Cabin
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Departing on:
2026
Sun, Jul 19 - Sun, Jul 26
from (US$)$2,282

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
$4,122$6,566
per Cabin
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9 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$4,122$6,566
per Cabin
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Departing on:
2026
Fri, Jul 24 - Sun, Aug 02
from (US$)$4,122

Moroccan Marvels & Mediterranean Wonders

  • Barcelona
  • Tangier, Morocco
  • Lisbon, Portugal
  • La Coruña, Spain
  • Bilbao, Spain
  • Bordeaux (Le Verdon), France
  • Portsmouth
Insider cabins from
$3,380$5,316
per Cabin
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10 nights
Valiant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$3,380$5,316
per Cabin
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Departing on:
2026
Sun, Jul 26 - Wed, Aug 05
from (US$)$3,380

Spanish, French & Italian Classics

  • Barcelona
  • Palma de Mallorca, Spain
  • Provence (Marseille), France
  • Cannes, France
  • Ajaccio, Corsica, France
  • Tuscany/Cinque Terre (La Spezia), Italy
  • Barcelona
Insider cabins from
$3,062$4,818
per Cabin
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8 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,062$4,818
per Cabin
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Departing on:
2026
Sun, Aug 02 - Mon, Aug 10
from (US$)$3,062

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
$8,322$13,132
per Cabin
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15 nights
Valiant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$8,322$13,132
per Cabin
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Departing on:
2026
Wed, Aug 05 - Thu, Aug 20
from (US$)$8,322

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
$6,862$11,148
per Cabin
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12 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$6,862$11,148
per Cabin
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Departing on:
2026
Mon, Aug 10 - Sat, Aug 22
from (US$)$6,862

Virgin Voyages Comedy Fest from the UK

  • Portsmouth
  • Bruges/Zeebruge (Brussels), Belgium
  • Amsterdam, Netherlands
  • Hamburg, Germany
  • Portsmouth
Sea View cabins from
$3,354$5,222
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$3,354$5,222
per Cabin
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Departing on:
2026
Thu, Aug 20 - Thu, Aug 27
from (US$)$3,354

Sicily, Naples, Cannes & More

  • Rome (Civitavecchia)
  • Catania, Sicily, Italy
  • Pompeii/Capri (Naples), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Florence/Pisa (Livorno), Italy
  • Rome (Civitavecchia)
Insider cabins from
$3,008$4,802
per Cabin
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9 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,008$4,802
per Cabin
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Departing on:
2026
Sat, Aug 22 - Mon, Aug 31
from (US$)$3,008

English Elegance to Idyllic Iceland

  • Portsmouth
  • Amsterdam, Netherlands
  • Edinburgh, Scotland
  • Invergordon, Scotland
  • Akureyri, Iceland
  • Ísafjörður, Iceland
  • Reykjavik
Insider cabins from
$3,980$6,022
per Cabin
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10 nights
Valiant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$3,980$6,022
per Cabin
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Departing on:
2026
Thu, Aug 27 - Sun, Sep 06
from (US$)$3,980

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)
Insider cabins from
$5,060$8,122
per Cabin
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10 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$5,060$8,122
per Cabin
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Departing on:
2026
Mon, Aug 31 - Thu, Sep 10
from (US$)$5,060

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
$2,864$4,348
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,864$4,348
per Cabin
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Departing on:
2026
Thu, Sep 03 - Fri, Sep 11
from (US$)$2,864Brilliant 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
Insider cabins from
$4,854$7,604
per Cabin
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13 nights
Valiant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$4,854$7,604
per Cabin
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Departing on:
2026
Sun, Sep 06 - Sat, Sep 19
from (US$)$4,854

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
$2,690$4,102
per Cabin
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8 nights
Brilliant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,690$4,102
per Cabin
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Departing on:
2026
Fri, Sep 11 - Sat, Sep 19
from (US$)$2,690

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
$2,544$3,788
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,544$3,788
per Cabin
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Departing on:
2026
Sat, Sep 19 - Sun, Sep 27
from (US$)$2,544

Mykonos Moons and Italian Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Amalfi Coast (Salerno), Italy
  • Rome (Civitavecchia), Italy
  • Barcelona
Insider cabins from
$3,482$5,502
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,482$5,502
per Cabin
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Departing on:
2026
Sun, Oct 04 - Sun, Oct 11
from (US$)$3,482

New York to Bermuda (& Back)

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
$2,028$3,030
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,028$3,030
per Cabin
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Departing on:
2026Best Rate
Wed, Oct 07 - Tue, Oct 13
from (US$)$2,028
2026
Tue, Oct 13 - Mon, Oct 19
from (US$)$2,252

Spanish Isles & Transatlantic Miles

  • Barcelona
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Insider cabins from
$3,340$5,380
per Cabin
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14 nights
Scarlet Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$3,340$5,380
per Cabin
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Departing on:
2026
Sun, Oct 11 - Sun, Oct 25
from (US$)$3,340

Mexican Riviera Halloween Cruise

  • Los Angeles, California
  • Cabo San Lucas, Mexico
  • Puerto Vallarta, Mexico
  • Mazatlán, Mexico
  • Los Angeles, California
Insider cabins from
$1,946$2,964
per Cabin
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7 nights
Brilliant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$2,964
per Cabin
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Departing on:
2026
Sat, Oct 17 - Sat, Oct 24
from (US$)$1,946

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
Insider cabins from
$2,376$3,492
per Cabin
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12 nights
Valiant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$2,376$3,492
per Cabin
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Departing on:
2026
Mon, Oct 19 - Sat, Oct 31
from (US$)$2,376

SoCal & Ensenada: Halloween Edition

  • Los Angeles, California
  • Catalina Island, California
  • San Diego, California
  • Ensenada, Mexico
  • Los Angeles, California
Sea View cabins from
$1,490$2,170
per Cabin
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5 nights
Brilliant Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,490$2,170
per Cabin
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Departing on:
2026
Sat, Oct 24 - Thu, Oct 29
from (US$)$1,490

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
Insider cabins from
$1,960$2,978
per Cabin
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6 nights
Scarlet Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,960$2,978
per Cabin
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)$1,960

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,908$2,840
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,908$2,840
per Cabin
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Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)$1,908

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
$5,732$8,518
per Cabin
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17 nights
Brilliant Lady
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$5,732$8,518
per Cabin
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Departing on:
2026
Thu, Oct 29 - Sun, Nov 15
from (US$)$5,732

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,590$2,316
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$1,590$2,316
per Cabin
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Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (US$)$1,590

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 Terrace cabins from
$2,876$4,604
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
$2,876$4,604
per Cabin
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)$2,876
Average starting price per cabin (incl. taxes & fees)