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

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Showing 247 cruise vacations that match your search
Showing 247 cruise vacations that match your search
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Grand Cayman, Costa Maya & More

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

Grand Turk, Puerto Plata & More

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

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Sun, Sep 21 - Fri, Sep 26
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)
2025
Sun, Aug 24 - Fri, Aug 29
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Fri, Oct 10 - Wed, Oct 15
from (US$)
2025
Fri, Aug 01 - Wed, Aug 06
from (US$)
2025
Fri, Aug 15 - Wed, Aug 20
from (US$)

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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4 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Thu, Oct 21 - Mon, Oct 25
from (US$)
2025
Wed, Aug 06 - Sun, Aug 10
from (US$)
2025
Wed, Aug 20 - Sun, Aug 24
from (US$)
* Port changes in place on select sailings — see full cruise details

Virgin Voyages Comedy Fest from Miami

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

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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5 nights
Valiant Lady, Resilient Lady & Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Sun, Sep 07 - Fri, Sep 12
from (US$)
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)

Brilliant Lady Miami MerMaiden

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

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025Best Rate
Sun, Oct 19 - Fri, Oct 24
from (US$)
2027
Sat, Oct 30 - Thu, Nov 04
from (US$)

Dominican Daze: Halloween Edition

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

Valiant's Haunted Halloween Soirée

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

Honduras, Mexico & Bahamas

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

Western Caribbean: From Miami to Bimini

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

Western Caribbean Charm

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

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
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Scarlet Lady, Resilient Lady & Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Sep 19 - Thu, Sep 24
from (US$)
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)

Cayman Coves & Jamaican Waterfalls

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

San Juan, Samaná & Bimini

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

Resilient Caribbean Holidays

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

Scarlet Caribbean Holidays

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

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
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sun, Dec 27 - Sun, Jan 03
from (US$)
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

Scarlet New Year's Ahoy!

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

Cozumel, Grand Cayman & Bimini

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

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady & Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sun, Dec 13 - Sun, Dec 20
from (US$)
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)

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
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
2026
Sun, Dec 06 - Sun, Dec 13
from (US$)

Cayman Coves & Jamaican Waterfalls

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

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)

Resilient Valentine's Voyage

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

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

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
Insider cabins from
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Resilient Lady, Scarlet Lady & Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Sat, Sep 18 - Thu, Sep 23
from (US$)
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)
2026
Sat, Jun 13 - Thu, Jun 18
from (US$)

NY to San Juan: Bermuda & Caribbean

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • The Beach Club at Bimini, Bahamas
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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12 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Mon, Oct 19 - Sat, Oct 31
from (US$)

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)

Mexico & Bimini: Halloween Edition

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

Scarlet's Haunted Halloween Soirée

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

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
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)

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

Captivating Costa Maya & Cozumel Charm

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

Jamaican Waves & Bimini Breeze

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

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
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)

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
per Cabin
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9 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Mon, Dec 14 - Wed, Dec 23
from (US$)

Resilient Caribbean Holidays

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

Brilliant Caribbean Holidays

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

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
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Mon, Dec 28 - Thu, Jan 07
from (US$)

Cayman Isles & Jamaican Miles

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

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
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)

Key West & Bimini: Valentine’s Voyage

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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4 nights
Scarlet Lady
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+ free drinks
70% off 2nd Sailor + Balcony upgrades
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per Cabin
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (US$)

PR, DR & Bimini: Valentine’s Voyage

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

San Juan to Miami: Dominican Daze

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