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Showing 35cruise vacations: All Destinations,December 2024 - February 2025
Showing 35 cruise vacations that match your search
Picture of the cruise
Fire & Sunset Soirées: Holiday Edition
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,392
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,392
per Cabin
Departing on:
2024
Wed, Dec 11 - Sun, Dec 15
from Price$1,392
Picture of the cruise
Eastern Caribbean Antilles
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,744
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,744
per Cabin
Departing on:
2025Best Rate
Sat, Jan 25 - Sun, Feb 02
from Price$1,744
2024
Sat, Dec 14 - Sun, Dec 22
from Price$1,904
2025
Sat, Jan 11 - Sun, Jan 19
from Price$2,224
Picture of the promotion

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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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:
2024
Sat, Dec 14 - Sat, Dec 21
from Price$1,668
Picture of the cruise
Dominican Daze
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
2025Best Rate
Fri, Jan 31 - Wed, Feb 05
from Price$1,490
2024
Sun, Dec 15 - Fri, Dec 20
from Price$1,870
2025
Fri, Jan 03 - Wed, Jan 08
from Price$2,252
Picture of the cruise
Resilient Caribbean Holidays
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Sea View cabins from
Price$2,926
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$2,926
per Cabin
Departing on:
2024
Sat, Dec 21 - Sat, Dec 28
from Price$2,926
Picture of the cruise
Fire & Sunset Soirées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,192
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,192
per Cabin
Departing on:
2025Best Rate
Wed, Feb 05 - Sun, Feb 09
from Price$1,192
2024
Thu, Dec 26 - Mon, Dec 30
from Price$10,678
Only suites remaining
2025
Wed, Jan 08 - Sun, Jan 12
from Price$2,800
Picture of the cruise
Scarlet New Year's Ahoy!
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$4,464
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$4,464
per Cabin
Departing on:
2024
Sat, Dec 28 - Sun, Jan 05
from Price$4,464
Picture of the cruise
Valiant New Year's Ahoy!
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Sea View cabins from
Price$3,202
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,202
per Cabin
Departing on:
2024
Mon, Dec 30 - Fri, Jan 03
from Price$3,202
Picture of the cruise
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
Picture of the cruise
Western Caribbean Charm
Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,428
per Cabin
6 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,428
per Cabin
Departing on:
2025Best Rate
Sun, Feb 16 - Sat, Feb 22
from Price$1,428
2025
Sun, Jan 05 - Sat, Jan 11
from Price$6,340
Only suites remaining
2025
Sun, Jan 19 - Sat, Jan 25
from Price$2,640
Picture of the cruise
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
Picture of the cruise
Riviera Maya
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,492
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,492
per Cabin
Departing on:
2025Best Rate
Sun, Jan 12 - Fri, Jan 17
from Price$1,492
2025
Sun, Jan 26 - Fri, Jan 31
from Price$1,990
2025
Sun, Feb 09 - Fri, Feb 14
from Price$1,492
Picture of the cruise
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
Picture of the cruise
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
Picture of the cruise
Scarlet Valentine's Voyage
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,320
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,320
per Cabin
Departing on:
2025
Sat, Feb 08 - Sun, Feb 16
from Price$2,320
Picture of the cruise
Valiant Valentine's Voyage
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Sea View cabins from
Price$1,690
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$1,690
per Cabin
Departing on:
2025
Fri, Feb 14 - Wed, Feb 19
from Price$1,690
Average starting price per cabin (incl. taxes & fees)