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Showing 14cruise vacations: Caribbean,December 2024 - October 2025
2 Sailors , 1 Cabin
Sails Resilient Lady
Showing 14 cruise vacations that match your search
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Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$1,668
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,668
per Cabin
Departing on:
2024Best Rate
Sat, Dec 14 - Sat, Dec 21
from Price$1,668
2025
Sat, Mar 08 - Sat, Mar 15
from Price$2,786
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Sunsets in the Lesser Antilles
San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$1,806
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,806
per Cabin
Departing on:
2025Best Rate
Sat, Jan 04 - Sat, Jan 11
from Price$1,806
2025
Sat, Feb 01 - Sat, Feb 08
from Price$2,926
2025
Sat, Feb 15 - Sat, Feb 22
from Price$2,660
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SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.

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San Juan, St. Vincent, Barbados & More
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Kingstown • San Juan
Sea View cabins from
Price$3,402
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,402
per Cabin
Departing on:
2025
Sat, Jan 11 - Tue, Jan 21
from Price$3,402
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Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,310
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,310
per Cabin
Departing on:
2025
Tue, Jan 21 - Sat, Feb 01
from Price$2,310
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Resilient Valentine's Voyage
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Sea View cabins from
Price$3,206
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,206
per Cabin
Departing on:
2025
Sat, Feb 08 - Sat, Feb 15
from Price$3,206
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San Juan, Barbados & Beyond
San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$2,506
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,506
per Cabin
Departing on:
2025
Sat, Mar 01 - Sat, Mar 08
from Price$2,506
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Puerto Rican Daze & Caribbean Nights
San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan
Insider cabins from
Price$2,182
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,182
per Cabin
Departing on:
2025
Sat, Mar 22 - Tue, Apr 01
from Price$2,182
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Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,824
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,824
per Cabin
Departing on:
2025
Tue, Apr 01 - Sat, Apr 12
from Price$2,824
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San Juan to Spanish Island Nights
San Juan • Santa Cruz de Tenerife • Casablanca • Palma de Mallorca • Valencia • Barcelona
Insider cabins from
Price$2,214
per Cabin
14 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,214
per Cabin
Departing on:
2025
Sat, Apr 12 - Sat, Apr 26
from Price$2,214
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Resilient's Haunted Halloween Soirée
Barcelona • Valencia • Casablanca • Gran Canaria • Miami, Florida
Insider cabins from
Price$3,054
per Cabin
14 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,054
per Cabin
Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from Price$3,054
Average starting price per cabin (incl. taxes & fees)