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Explore 399 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - October 2025
2 Sailors , 1 Cabin
Showing 20 cruise vacations that match your search
Showing 20 cruise vacations that match your search
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DEAL

Grand Turk, Puerto Plata & More

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

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Sailor per night
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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
Sea View cabins from
per Sailor per night
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4 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Sailor per night
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Departing on:
2025Best Rate
Wed, Aug 20 - Sun, Aug 24
from (US$)
2025
Wed, Aug 06 - Sun, Aug 10
from (US$)
2025
Wed, Sep 03 - Sun, Sep 07
from (US$)

Virgin Voyages Comedy Fest from Miami

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

Riviera Maya

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

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Sailor per night
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Departing on:
2025Best Rate
Sun, Oct 05 - Fri, Oct 10
from (US$)
2025
Sun, Sep 07 - Fri, Sep 12
from (US$)
DEAL

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 Sailor per night
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Sailor per night
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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 Sailor per night
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Sailor per night
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Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Sailor per night
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5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Sailor per night
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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
Sea View cabins from
per Sailor per night
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4 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Sailor per night
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Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)
Average starting price per Sailor per night (incl. taxes & fees)