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Explore 399 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - August 2026
2 Sailors , 1 Cabin
Sails Resilient Lady
Showing 47 cruise vacations that match your search
Showing 47 cruise vacations that match your search
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Western Caribbean Charm

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

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
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:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
DEAL

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
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
from (US$)

Costa Mayan Caves & Honduran Waves

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
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$)

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
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, May 16 - Thu, May 21
from (US$)
2026
Sat, May 02 - Thu, May 07
from (US$)
2026
Sat, May 30 - Thu, Jun 04
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
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Thu, May 07 - Mon, May 11
from (US$)
2026
Thu, May 21 - Mon, May 25
from (US$)
2026
Thu, Jun 04 - Mon, Jun 08
from (US$)

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Mon, May 11 - Sat, May 16
from (US$)
2026
Mon, Jul 20 - Sat, Jul 25
from (US$)

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
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026Best Rate
Mon, May 25 - Sat, May 30
from (US$)
2026
Mon, Jul 06 - Sat, Jul 11
from (US$)
2026
Mon, Aug 03 - Sat, Aug 08
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
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jun 13 - Thu, Jun 18
from (US$)
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)
Average starting price per cabin (incl. taxes & fees)