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Caribbean Cruises Starting In May 2027

Are you planning a cruise to the Caribbean in May 2027? Choose from 65 unique cruises and 1,387 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveler reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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65 Cruises (1,387 Cruise Departures)
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico
Inside
$389
Oceanview
$509
Balcony
$679
Suite
$1,511
From
US$389
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,473
From
US$674
Save 571
Per Person
View Trip
8 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 22 May 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,194
Oceanview
$1,403
Balcony
$1,522
Suite
$3,397
From
US$1,194
Save 607
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: May 2027 to Apr 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
Per Person
View Trip
8 Day San Juan, St Kitts & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 29 May 2027
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,334
Oceanview
$1,431
Balcony
$1,636
Suite
$3,238
From
US$1,334
Save 712
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: May 2026 to Oct 2026
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$895
Oceanview
$1,095
Balcony
$1,145
Suite
$2,245
From
US$895
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Inside
$399
Oceanview
$519
Balcony
$729
Suite
$1,461
From
US$399
Per Person
View Trip
7 Day Grand Turk, Puerto Plata & Bahamas with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 02 May 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$919
Oceanview
$1,128
Balcony
$1,296
Suite
$3,074
From
US$919
Save 526
Per Person
View Trip
8 Day Western Caribbean with Mexico From Fort Lauderdale with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Star Princess, Sun Princess
Departures: May 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Sanctuary Collection
Inside
$549
Oceanview
$789
Balcony
$673
Suite
$889
From
US$549
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$749
Oceanview
$872
Balcony
$999
Suite
$3,067
From
US$749
Save 615
Per Person
View Trip
6 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$439
Oceanview
$599
Balcony
$799
Suite
$869
From
US$439
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic (+3 more), Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$729
Oceanview
$789
Balcony
$889
Suite
$1,049
From
US$729
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Aug 2027
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,022
Oceanview
$1,106
Balcony
$1,238
Suite
$2,527
From
US$1,022
Save 717
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Inside
$786
Oceanview
$1,026
Balcony
$1,436
Suite
$2,980
From
US$786
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Oct 2027
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,098
Oceanview
$1,209
Balcony
$1,414
Suite
$3,949
From
US$1,098
Save 1,014
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Dominican Republic
Inside
$776
Oceanview
$1,016
Balcony
$1,396
Suite
$2,960
From
US$776
Per Person
View Trip
15 Day Caribbean East/West Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: May 2026 to Aug 2026
Visit: USA, Mexico, Belize, Honduras, Bahamas, Puerto Rico, Virgin Islands
Princess Standard
Inside
$1,318
Oceanview
-
Balcony
$1,608
Suite
$2,548
From
US$1,318
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Apr 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$645
Oceanview
$795
Balcony
$962
Suite
$2,500
From
US$645
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: May 2026 to Mar 2028
Visit: Colombia, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$943
Oceanview
$1,037
Balcony
$1,337
Suite
$1,437
From
US$943
Save 1,422
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic, Norwegian Prima
Departures: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$879
Balcony
$949
Suite
$1,149
From
US$699
Per Person
View Trip
8 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departure: 22 May 2027
Visit: USA, Bahamas, Jamaica, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$988
Oceanview
$1,149
Balcony
$1,132
Suite
$2,396
From
US$988
Save 580
Per Person
View Trip
10 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

10 Days (9 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2027 to Oct 2027
Visit: USA, Curacao, Bonaire, Aruba, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,156
Oceanview
$1,298
Balcony
$2,224
Suite
$2,486
From
US$1,156
Save 618
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Jewel of the Seas (+2 more), Radiance of the Seas, Serenade of the Seas
Departures: Jun 2026 to Apr 2028
Visit: USA, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$358
Oceanview
$396
Balcony
$515
Suite
$816
From
US$358
Save 539
Per Person
View Trip
6 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ships: Adventure of the Seas, Harmony of the Seas
Departures: Apr 2027 to Feb 2028
Visit: USA, Bahamas, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$609
Oceanview
$714
Balcony
$822
Suite
$1,189
From
US$609
Save 538
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2026 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$958
Oceanview
$1,276
Balcony
$1,404
Suite
$2,505
From
US$958
Save 1,055
Per Person
View Trip
5 Day Eastern Caribbean Getaway with Royal Caribbean
Cruise

5 Days (4 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departures: May 2026 to Mar 2028
Visit: USA, Turks and Caicos Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$414
Oceanview
$454
Balcony
$534
Suite
$844
From
US$414
Save 367
Per Person
View Trip
8 Day Western Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departure: 01 May 2027
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,369
Oceanview
$1,569
Balcony
$1,651
Suite
$2,647
From
US$1,369
Save 674
Per Person
View Trip
5 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

5 Days (4 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departures: May 2026 to Dec 2026
Visit: USA, Turks and Caicos Islands
Exclusive Savings
Inside
$503
Oceanview
$582
Balcony
$815
Suite
$1,132
From
US$503
Save 965
Per Person
View Trip
9 Day Southern Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departures: May 2027 to Dec 2027
Visit: USA, Curacao, Aruba, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,231
Oceanview
$1,391
Balcony
$1,611
Suite
$2,486
From
US$1,231
Save 773
Per Person
View Trip
Results: 1-30 of 65

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