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Explore 401 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - May 2026
2 Sailors , 1 Cabin
Showing 19 cruise vacations that match your search
Showing 19 cruise vacations that match your search
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DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
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$)
DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
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$)
DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)
DEAL

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

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

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
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)
Average starting price per cabin (incl. taxes & fees)