Caribbean Cruise Deals

Discover amazing cruise deals departing in the next 6 months. Updated weekly with the latest prices from major cruise lines!

⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Quest

14 days, round-trip Eastern Caribbean Voyage

Departure Nov 15, 2025
Duration 14 days
Starting from
$3,399
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⭐ Premium Deals
Celebrity Cruises
Celebrity Silhouette

8 days, round-trip Aruba, Curacao Bonaire

Departure Nov 15, 2025
Duration 8 days
Starting from
$1,204
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

12 days, round-trip Eastern Caribbean St. Lucia

Departure Nov 16, 2025
Duration 12 days
Starting from
$1,599
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Nov 16, 2025
Duration 14 days
Starting from
$1,878
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

21 days, round-trip Southern Eastern Caribbean Abc Islands

Departure Nov 16, 2025
Duration 21 days
Starting from
$2,069
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Wish

4 days, round-trip Very Merrytime Bahamian Cruise From Port Canaveral

Departure Nov 17, 2025
Duration 4 days
Starting from
$2,891
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⭐ Premium Deals
Mystic Cruises
Vasco da Gama-Nicko

16 days, one-way from Las Palmas Gran Canaria to Port Royal Kingston

Departure Nov 17, 2025
Duration 16 days
Starting from
$3,670
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⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, round-trip San Juan the Virgin Islands

Departure Nov 16, 2025
Duration 7 days
Starting from
$2,699
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⭐ Premium Deals
Windstar Cruises
Star Pride

14 days, round-trip Star Collector Lovely Leewards

Departure Nov 16, 2025
Duration 14 days
Starting from
$4,499
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Eurodam

14 days, round-trip Eastern Western Caribbean San Juan Mexico

Departure Nov 16, 2025
Duration 14 days
Starting from
$1,249
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Nov 16, 2025
Duration 5 days
Starting from
$1,090
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Nov 16, 2025
Duration 14 days
Starting from
$1,713
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Nov 16, 2025
Duration 14 days
Starting from
$1,447
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Fantasy

5 days, round-trip Very Merrytime Bahamian Cruise From Port Canaveral

Departure Nov 16, 2025
Duration 5 days
Starting from
$3,606
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Nov 15, 2025
Duration 14 days
Starting from
$1,818
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip San Juan Sunrises Dominican Dreams

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,890
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Nov 15, 2025
Duration 14 days
Starting from
$1,509
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 16, 2025
Duration 7 days
Starting from
$1,451
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 16, 2025
Duration 7 days
Starting from
$1,754
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⭐ Premium Deals
Crystal Cruises
Crystal Serenity

5 days, one-way from San Juan to Bridgetown

Departure Nov 15, 2025
Duration 5 days
Starting from
$2,300
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⭐ Premium Deals
Star Clippers Cruises
Royal Clipper

14 days, one-way from Panama City to St Johns Antigua

Departure Nov 15, 2025
Duration 14 days
Starting from
$4,350
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⭐ Premium Deals
Holland America Cruises
ms Nieuw Statendam

14 days, one-way from Civitavecchia-Rome to Fort Lauderdale

Departure Nov 15, 2025
Duration 14 days
Starting from
$1,444
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Joy

7 days, round-trip Caribbean Great Stirrup Cay Dominican Republic

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,449
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⭐ Premium Deals Bahamas
Celebrity Cruises
Celebrity Apex

7 days, round-trip Key West, Bahamas Grand Turk

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,095
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⭐ Premium Deals
Seabourn Cruises
Seabourn Encore

12 days, one-way from Lisbon to Miami

Departure Nov 20, 2025
Duration 12 days
Starting from
$4,998
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⭐ Premium Deals
MSC Cruises
MSC Grandiosa

15 days, one-way from Marseille to Miami

Departure Nov 20, 2025
Duration 15 days
Starting from
$6,783
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

7 days, one-way from San Juan to Miami

Departure Nov 20, 2025
Duration 7 days
Starting from
$3,690
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

8 days, round-trip Sunny San Juan Isles of Beach Miles

Departure Nov 20, 2025
Duration 8 days
Starting from
$2,064
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

15 days, round-trip An Extended Journey of Soulful Sophistication and Idyllic Island Charm

Departure Nov 20, 2025
Duration 15 days
Starting from
$5,600
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

14 days, one-way from Barcelona to San Juan

Departure Nov 18, 2025
Duration 14 days
Starting from
$4,698
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

26 days, one-way from Barcelona to San Juan

Departure Nov 18, 2025
Duration 26 days
Starting from
$10,098
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⭐ Premium Deals
Hapag-Lloyd Cruises
Hanseatic Inspiration

16 days, one-way from Colon Cristobal Pier to Valparaiso-Santiago

Departure Nov 19, 2025
Duration 16 days
Starting from
$10,678
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⭐ Premium Deals
Cunard Cruises
Queen Mary 2

19 days, one-way from Southampton to New York

Departure Nov 19, 2025
Duration 19 days
Starting from
$2,092
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Mary 2

26 days, round-trip Transatlantic Crossing And Eastern Caribbean

Departure Nov 19, 2025
Duration 26 days
Starting from
$3,229
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⭐ Premium Deals
Oceania Cruises
Oceania Vista

14 days, one-way from Barcelona to Miami

Departure Nov 19, 2025
Duration 14 days
Starting from
$3,799
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⭐ Premium Deals
Costa Cruises
Costa Fascinosa

16 days, one-way from Barcelona to Pointe-a-Pitre

Departure Nov 19, 2025
Duration 16 days
Starting from
$1,920
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⭐ Premium Deals
Seabourn Cruises
Seabourn Sojourn

7 days, round-trip Dominican Republic Delights

Departure Nov 18, 2025
Duration 7 days
Starting from
$3,513
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Splendor

16 days, one-way from Miami to Bridgetown

Departure Nov 17, 2025
Duration 16 days
Starting from
$24,998
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Splendor

30 days, one-way from Miami to Rio de Janeiro

Departure Nov 17, 2025
Duration 30 days
Starting from
$48,598
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

15 days, round-trip An Extended Journey to Enchanting Isles

Departure Nov 17, 2025
Duration 15 days
Starting from
$6,520
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⭐ Premium Deals
Windstar Cruises
Wind Spirit

18 days, one-way from Bridgetown to Puntarenas

Departure Nov 18, 2025
Duration 18 days
Starting from
$8,399
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⭐ Premium Deals
Windstar Cruises
Wind Spirit

11 days, one-way from Bridgetown to Colon

Departure Nov 18, 2025
Duration 11 days
Starting from
$4,599
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⭐ Premium Deals
Seabourn Cruises
Seabourn Sojourn

29 days, one-way from Miami to Los Angeles

Departure Nov 18, 2025
Duration 29 days
Starting from
$11,856
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

21 days, round-trip Caribbean

Departure Nov 18, 2025
Duration 21 days
Starting from
$2,132
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

21 days, round-trip Eastern Southern Caribbean Leeward Abc Islands

Departure Nov 18, 2025
Duration 21 days
Starting from
$1,894
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⭐ Premium Deals
Windstar Cruises
Wind Surf

14 days, one-way from Lisbon to Philipsburg St Maarten

Departure Nov 18, 2025
Duration 14 days
Starting from
$2,899
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

11 days, round-trip Eastern Caribbean Windward Leeward Islands

Departure Nov 18, 2025
Duration 11 days
Starting from
$1,099
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⭐ Premium Deals
Windstar Cruises
Wind Surf

19 days, one-way from Lisbon to Philipsburg St Maarten

Departure Nov 18, 2025
Duration 19 days
Starting from
$4,199
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Dream

5 days, round-trip Very Merrytime Bahamian Cruise From Fort Lauderdale

Departure Nov 17, 2025
Duration 5 days
Starting from
$2,321
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⭐ Premium Deals
Oceania Cruises
Oceania Marina

12 days, one-way from Santa Cruz de Tenerife to Miami

Departure Nov 17, 2025
Duration 12 days
Starting from
$2,399
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About These Deals
Prices shown are starting rates per person and subject to availability. Deals are updated weekly. Click "View Deal" to check current pricing and availability on CruiseMapper. Port Side Left is not responsible for price changes or booking terms.