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Explore 402 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - October 2027
1-4 & 5 nights

70% off 2nd Sailor + Free balcony upgrade ends in…

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Showing 180 cruise vacations that match your search
Showing 180 cruise vacations that match your search
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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$)

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$)

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$)

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

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

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$)

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$)

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$)

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$)
2026
Mon, Nov 23 - Sat, Nov 28
from (US$)

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$)

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
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027
Thu, Feb 11 - Mon, Feb 15
from (US$)

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
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
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)