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Explore 392 cruise vacations

Showing Loading cruise vacations: Caribbean, October 2025 - April 2027

Last chance: 70% off 2nd Sailor + Instant Savings

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Showing 232 cruise vacations that match your search
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★
UP TO $700 OFF

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Cozumel, Mexico
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,806$2,526
per Cabin
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,806$2,526
per Cabin
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$)$1,806Brilliant 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
Sea Terrace cabins from
$2,238$3,262
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$2,238$3,262
per Cabin
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)$2,238
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $700* off
BOOK NOW

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,468$2,008
per Cabin
Loading
5 nights
Scarlet Lady, Resilient Lady, Brilliant Lady & Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,468$2,008
per Cabin
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Departing on:
2026Best Rate
Mon, Sep 14 - Sat, Sep 19
from (US$)$1,468
2025
Fri, Nov 07 - Wed, Nov 12
from (US$)$1,490
2025
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490
★
UP TO $700 OFF

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,856$4,128
per Cabin
Loading
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,856$4,128
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$2,856Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
$1,386$1,972
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,972
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 08 - Sat, Nov 15
from (US$)$1,386
2026
Sat, Mar 21 - Sat, Mar 28
from (US$)$2,538
2027
Sat, Jan 02 - Sat, Jan 09
from (US$)$2,068

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,508$2,014
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,508$2,014
per Cabin
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Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)$1,508

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,252$1,664
per Cabin
Loading
4 nights
Scarlet Lady, Resilient Lady, Brilliant Lady & Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,252$1,664
per Cabin
Loading
Departing on:
2027Best Rate
Thu, Jan 07 - Mon, Jan 11
from (US$)$1,252
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$1,432
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$1,882
★
UP TO $700 OFF

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,888
per Cabin
Loading
7 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,888
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)$1,386
2026
Sat, Mar 28 - Sat, Apr 04
from (US$)$2,528
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)$2,680
★
UP TO $700 OFF

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
$1,932$2,810
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,932$2,810
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Nov 07 - Sat, Nov 14
from (US$)$1,932
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$2,872
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$1,936

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,090$1,396
per Cabin
Loading
5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,090$1,396
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$1,090
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390
2026
Sun, Jan 11 - Fri, Jan 16
from (US$)$1,248
★
UP TO $700 OFF

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$2,972
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,064$2,972
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$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
$1,584$2,232
per Cabin
Loading
5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,584$2,232
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Oct 03 - Thu, Oct 08
from (US$)$1,584
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$2,108
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,590
★
UP TO $700 OFF

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$1,880
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,880
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,768
★
UP TO $700 OFF

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$1,970
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,970
per Cabin
Loading
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386
★
UP TO $700 OFF

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$2,800
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,962$2,800
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$)$1,962Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$)$3,266Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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$1,900
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,386$1,900
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,386
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,468

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
$1,492$2,164
per Cabin
Loading
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,492$2,164
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$1,492
★
UP TO $700 OFF

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
Sea View cabins from
$1,744$2,520
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$1,744$2,520
per Cabin
Loading
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,744
★
UP TO $700 OFF

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,530$3,648
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,530$3,648
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,530Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$)$2,800Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,464$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,464$1,998
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,464
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$1,920
★
UP TO $700 OFF

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
$1,458$2,094
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,458$2,094
per Cabin
Loading
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,458
★
UP TO $700 OFF

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
$2,206$3,192
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,206$3,192
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,206Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,072$2,942
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,072$2,942
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,072
★
UP TO $700 OFF

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
$2,084$3,046
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,084$3,046
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$2,084

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$2,040$2,930
per Cabin
Loading
4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$2,040$2,930
per Cabin
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Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)$2,040
★
UP TO $700 OFF

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
$4,242$6,340
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$4,242$6,340
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$4,242Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
$3,828$5,636
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,828$5,636
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,828
★
UP TO $700 OFF

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
$3,604$5,406
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,604$5,406
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,604

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$3,522$5,136
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,522$5,136
per Cabin
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Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,522
★
UP TO $700 OFF

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
$1,936$2,834
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,936$2,834
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,936
2027
Sat, Feb 06 - Sat, Feb 13
from (US$)$2,222
★
UP TO $700 OFF

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,454$1,930
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,454$1,930
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,454
★
UP TO $700 OFF

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
$4,226$6,248
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$4,226$6,248
per Cabin
Loading
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$)$4,226Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,464$2,006
per Cabin
Loading
7 nights
Resilient Lady & Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,464$2,006
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,464
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,222
2026
Sun, Nov 01 - Sun, Nov 08
from (US$)$2,604
★
UP TO $700 OFF

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
$1,634$2,382
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,634$2,382
per Cabin
Loading
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,634
★
UP TO $700 OFF

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
$1,632$2,366
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,632$2,366
per Cabin
Loading
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,632
★
UP TO $700 OFF

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
$1,782$2,594
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,782$2,594
per Cabin
Loading
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,782

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
$2,552$3,700
per Cabin
Loading
6 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$2,552$3,700
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)$2,552
★
UP TO $700 OFF

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
$1,628$2,340
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,628$2,340
per Cabin
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Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,628
★
UP TO $700 OFF

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
$1,466$2,026
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,466$2,026
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,466
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)$1,618
★
UP TO $700 OFF

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
$3,512$5,148
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,512$5,148
per Cabin
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$)$3,512Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
Sea View cabins from
$2,236$3,276
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$2,236$3,276
per Cabin
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Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)$2,236
★
UP TO $700 OFF

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
$2,900$4,264
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,900$4,264
per Cabin
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Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$)$2,900Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,800$2,562
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,800$2,562
per Cabin
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)$1,800
★
UP TO $700 OFF

Resilient Valentine's Voyage

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,070$2,938
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,070$2,938
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$2,070

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
$1,784$2,602
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,784$2,602
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)$1,784
★
UP TO $700 OFF

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
$1,934$2,826
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,934$2,826
per Cabin
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)$1,934
★
UP TO $700 OFF

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
$2,034$2,990
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,034$2,990
per Cabin
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)$2,034
★
UP TO $700 OFF

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
$3,260$4,776
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,260$4,776
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$)$3,260Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
$1,934$2,824
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,934$2,824
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Dec 05 - Sat, Dec 12
from (US$)$1,934
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)$2,696
2027
Sat, Jan 09 - Sat, Jan 16
from (US$)$2,072

Western Caribbean Cruise

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Insider cabins from
$2,284$3,248
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,284$3,248
per Cabin
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (US$)$2,284
★
UP TO $700 OFF

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
$3,240$4,748
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
$3,240$4,748
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)$3,240

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,566$2,086
per Cabin
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5 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,566$2,086
per Cabin
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Departing on:
2027Best Rate
Sat, Jan 23 - Thu, Jan 28
from (US$)$1,566
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)$2,222
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)$2,478

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,568$2,118
per Cabin
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5 nights
Resilient Lady & Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,568$2,118
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 04 - Sat, Jan 09
from (US$)$1,568
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)$2,226
2026
Sat, Nov 28 - Thu, Dec 03
from (US$)$1,684

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
$2,038$2,902
per Cabin
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6 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,038$2,902
per Cabin
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)$2,038

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,026$2,840
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,026$2,840
per Cabin
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Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)$2,026

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,682$2,316
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,682$2,316
per Cabin
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Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (US$)$1,682

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
Insider cabins from
$2,322$3,420
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,322$3,420
per Cabin
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Departing on:
2026
Sat, Oct 31 - Sat, Nov 07
from (US$)$2,322

Fire & Sunset Soirées

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,434$1,998
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,434$1,998
per Cabin
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Departing on:
2026Best Rate
Thu, Nov 05 - Mon, Nov 09
from (US$)$1,434
2026
Sat, Dec 26 - Wed, Dec 30
from (US$)$1,780

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
Insider cabins from
$2,544$3,656
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,544$3,656
per Cabin
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)$2,544

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
Insider cabins from
$1,758$2,388
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,758$2,388
per Cabin
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Departing on:
2027Best Rate
Sat, Jan 23 - Fri, Jan 29
from (US$)$1,758
2026
Sat, Nov 14 - Fri, Nov 20
from (US$)$1,794
2027
Sat, Mar 13 - Fri, Mar 19
from (US$)$1,888

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
Insider cabins from
$2,738$3,846
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,738$3,846
per Cabin
Loading
Departing on:
2027Best Rate
Mon, Jan 25 - Thu, Feb 04
from (US$)$2,738
2026
Sun, Nov 15 - Wed, Nov 25
from (US$)$3,216
2027
Mon, Feb 22 - Thu, Mar 04
from (US$)$2,956

Captivating Costa Maya & Cozumel Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,896$2,640
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,896$2,640
per Cabin
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Departing on:
2026
Mon, Nov 16 - Sun, Nov 22
from (US$)$1,896

Thanksgiving: St. Isles, Aruba & Curaçao

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Basseterre, St. Kitts and Nevis
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,382$3,484
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,382$3,484
per Cabin
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Departing on:
2026
Fri, Nov 20 - Sat, Nov 28
from (US$)$2,382

Jamaican Waves & Bimini Breeze

  • Miami, Florida
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,678$2,286
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,678$2,286
per Cabin
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Departing on:
2027Best Rate
Mon, Feb 15 - Sat, Feb 20
from (US$)$1,678
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)$1,898

Antiguan Elegance & Sunny St. Isles

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,074$2,974
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,074$2,974
per Cabin
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Departing on:
2026
Sat, Nov 28 - Sat, Dec 05
from (US$)$2,074

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
Insider cabins from
$3,106$4,392
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,106$4,392
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)$3,106
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)$3,214
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)$3,170

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
Insider cabins from
$2,624$3,780
per Cabin
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9 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,624$3,780
per Cabin
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Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
from (US$)$2,624

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Fort-de-France, Martinique
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • San Juan, Puerto Rico
Insider cabins from
$2,844$4,224
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,844$4,224
per Cabin
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Departing on:
2026
Sat, Dec 19 - Sat, Dec 26
from (US$)$2,844

Scarlet Caribbean Holidays

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,006$2,818
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,006$2,818
per Cabin
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Departing on:
2026
Mon, Dec 21 - Sat, Dec 26
from (US$)$2,006

Brilliant Caribbean Holidays

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Miami, Florida
Insider cabins from
$2,232$3,220
per Cabin
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5 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,232$3,220
per Cabin
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Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (US$)$2,232

Valiant New Year's Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Fort-de-France, Martinique
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • San Juan, Puerto Rico
Insider cabins from
$3,752$5,604
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,752$5,604
per Cabin
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Departing on:
2026
Sat, Dec 26 - Sat, Jan 02
from (US$)$3,752

Resilient New Year's Ahoy!

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$4,042$5,970
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$4,042$5,970
per Cabin
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Departing on:
2026
Sun, Dec 27 - Sun, Jan 03
from (US$)$4,042

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
Insider cabins from
$5,354$7,968
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$5,354$7,968
per Cabin
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Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
from (US$)$5,354

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$3,204$4,706
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$3,204$4,706
per Cabin
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Departing on:
2026
Wed, Dec 30 - Mon, Jan 04
from (US$)$3,204

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
Insider cabins from
$2,368$3,376
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,368$3,376
per Cabin
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Departing on:
2027
Fri, Jan 29 - Sat, Feb 06
from (US$)$2,368

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
Insider cabins from
$2,952$4,156
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,952$4,156
per Cabin
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)$2,952

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,424$1,930
per Cabin
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4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,424$1,930
per Cabin
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (US$)$1,424

Lesser Antilles: Valentine's Day

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Insider cabins from
$2,224$3,186
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,224$3,186
per Cabin
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Departing on:
2027
Sat, Feb 13 - Sat, Feb 20
from (US$)$2,224

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,602$3,694
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,602$3,694
per Cabin
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Departing on:
2027
Sun, Feb 14 - Sun, Feb 21
from (US$)$2,602

Saint Isles & The Greater Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,222$3,170
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,222$3,170
per Cabin
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Departing on:
2027
Sat, Feb 20 - Sat, Feb 27
from (US$)$2,222
★
UP TO $700 OFF

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$2,220$3,156
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,220$3,156
per Cabin
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Departing on:
2027
Sat, Mar 06 - Sat, Mar 13
from (US$)$2,220

Barbados, Dominica & St. Isle Spring

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Roseau, Dominica
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
$2,544$3,664
per Cabin
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8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$2,544$3,664
per Cabin
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Departing on:
2027
Fri, Mar 19 - Sat, Mar 27
from (US$)$2,544

Bahamas & Bimini Beach Club

  • Miami, Florida
  • Freeport, Grand Bahama Island, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,644$2,308
per Cabin
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4 nights
Brilliant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,644$2,308
per Cabin
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Departing on:
2027
Mon, Mar 22 - Fri, Mar 26
from (US$)$1,644

Colorful Curaçao, Aruba & Antigua

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea Terrace cabins from
$3,164$4,618
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
$3,164$4,618
per Cabin
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Departing on:
2027
Sat, Mar 27 - Sat, Apr 03
from (US$)$3,164

San Juan to Miami: Dominican Daze

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,578$2,186
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,578$2,186
per Cabin
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Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (US$)$1,578

Grand Cayman & Bimini Beach Club

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$1,688$2,378
per Cabin
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5 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
$1,688$2,378
per Cabin
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Departing on:
2027
Fri, Apr 23 - Wed, Apr 28
from (US$)$1,688
Average starting price per cabin (incl. taxes & fees)