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
Princess Cruises
Island Princess

14 days, round-trip Circle Caribbean

Departure Nov 7, 2025
Duration 14 days
Starting from
$1,484
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💎 Mid-Range Deals Caribbean
Holland America Cruises
ms Rotterdam

9 days, round-trip Southern Caribbean Abc Islands

Departure Nov 7, 2025
Duration 9 days
Starting from
$999
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Nov 9, 2025
Duration 14 days
Starting from
$1,657
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⭐ Premium Deals
Marella Cruises
Marella Explorer

14 days, one-way from Malaga to Bridgetown

Departure Nov 9, 2025
Duration 14 days
Starting from
$2,018
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Summit

10 days, round-trip Eastern Caribbean

Departure Nov 10, 2025
Duration 10 days
Starting from
$1,099
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Legend

10 days, round-trip Eastern Caribbean

Departure Nov 10, 2025
Duration 10 days
Starting from
$1,324
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💎 Mid-Range Deals
Carnival Cruise Line Cruises
Carnival Venezia

12 days, one-way from New York to Port Canaveral

Departure Nov 8, 2025
Duration 12 days
Starting from
$699
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

12 days, round-trip Colorful Curaccedilao to the Charming Caymans

Departure Nov 8, 2025
Duration 12 days
Starting from
$3,576
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Nov 8, 2025
Duration 14 days
Starting from
$2,195
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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Quest

14 days, round-trip Eastern Caribbean Voyage

Departure Nov 8, 2025
Duration 14 days
Starting from
$4,579
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⭐ Premium Deals
Crystal Cruises
Crystal Serenity

12 days, one-way from New York to Bridgetown

Departure Nov 8, 2025
Duration 12 days
Starting from
$4,800
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Zuiderdam

14 days, round-trip Western Eastern Caribbean Mexico Bahamas

Departure Nov 8, 2025
Duration 14 days
Starting from
$1,084
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💎 Mid-Range Deals
Carnival Cruise Line Cruises
Carnival Miracle

14 days, one-way from Civitavecchia-Rome to Tampa

Departure Nov 8, 2025
Duration 14 days
Starting from
$923
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Divina

11 days, round-trip Caribbean Bahamas

Departure Nov 9, 2025
Duration 11 days
Starting from
$1,188
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⭐ Premium Deals
Windstar Cruises
Star Pride

14 days, round-trip Star Collector Lovely Leewards

Departure Nov 9, 2025
Duration 14 days
Starting from
$4,499
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⭐ Premium Deals
Oceania Cruises
Oceania Regatta

12 days, one-way from Colon to Los Angeles

Departure Nov 14, 2025
Duration 12 days
Starting from
$2,220
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

12 days, one-way from Fort Lauderdale to Bridgetown

Departure Nov 10, 2025
Duration 12 days
Starting from
$6,350
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⭐ Premium Deals
Crystal Cruises
Crystal Serenity

9 days, one-way from Fort Lauderdale to Bridgetown

Departure Nov 11, 2025
Duration 9 days
Starting from
$3,900
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 2

11 days, one-way from Barcelona to Bridgetown

Departure Nov 11, 2025
Duration 11 days
Starting from
$4,230
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⭐ Premium Deals
Marella Cruises
Marella Discovery 2

14 days, one-way from Malaga to Bridgetown

Departure Nov 13, 2025
Duration 14 days
Starting from
$1,922
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💎 Mid-Range Deals
Norwegian Cruise Line Cruises
Norwegian Epic

10 days, one-way from Lisbon to San Juan

Departure Nov 13, 2025
Duration 10 days
Starting from
$629
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⭐ Premium Deals Caribbean
Princess Cruises
Enchanted Princess

10 days, round-trip Eastern Caribbean with Tortola

Departure Nov 13, 2025
Duration 10 days
Starting from
$1,288
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Adventure Of The Seas

10 days, round-trip Southern Caribbean Cruise

Departure Nov 12, 2025
Duration 10 days
Starting from
$1,516
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⭐ Premium Deals
Viking Cruises
Viking Mars

14 days, round-trip Panama Canal Central America

Departure Nov 12, 2025
Duration 14 days
Starting from
$5,999
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💎 Mid-Range Deals Caribbean
Princess Cruises
Coral Princess

11 days, round-trip Eastern Caribbean with St. Thomas

Departure Nov 13, 2025
Duration 11 days
Starting from
$969
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⭐ 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 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
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 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 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 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
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
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
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
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
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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💎 Mid-Range Deals Caribbean
Cunard Cruises
Queen Elizabeth

9 days, round-trip Western Caribbean

Departure Nov 18, 2025
Duration 9 days
Starting from
$959
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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
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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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

12 days, round-trip Panama Canal with Costa Rica Caribbean Holiday

Departure Nov 17, 2025
Duration 12 days
Starting from
$1,251
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⭐ Premium Deals
Azamara Cruises
Azamara Onward

13 days, one-way from Lisbon to Miami

Departure Nov 17, 2025
Duration 13 days
Starting from
$1,289
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⭐ Premium Deals
Silversea Cruises
Silver Ray

13 days, one-way from Lisbon to Fort Lauderdale

Departure Nov 19, 2025
Duration 13 days
Starting from
$4,950
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💎 Mid-Range Deals Bahamas
MSC Cruises
MSC Divina

10 days, round-trip Caribbean Bahamas

Departure Nov 20, 2025
Duration 10 days
Starting from
$745
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Nov 22, 2025
Duration 14 days
Starting from
$1,458
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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Quest

14 days, round-trip Eastern Caribbean Voyage

Departure Nov 22, 2025
Duration 14 days
Starting from
$4,209
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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.