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Caribbean Cruises Starting In May 2026 and 2027

Are you planning a cruise to the Caribbean in May 2026 or 2027? Choose from 88 unique cruises and 1,627 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveller reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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88 Cruises (1,627 Cruise Departures)
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: May 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Exclusive Savings
Inside
$1,232
Oceanview
$1,248
Balcony
$1,629
Suite
$1,819
From
A$1,232
Save 1,423
Per Person
View Trip
8 Day Eastern Caribbean with St. Thomas From Fort Lauderdale with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: May 2026 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Princess Standard
Exclusive Savings
Inside
$796
Oceanview
-
Balcony
$1,021
Suite
$1,331
From
A$796
Save 12
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
Limited Time Offer
Inside
$1,316
Oceanview
$1,752
Balcony
$1,938
Suite
$3,728
From
A$1,316
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (4)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Coral Princess, Regal Princess
Departures: May 2026 to Dec 2026
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Princess Standard
Exclusive Savings
Inside
$1,123
Oceanview
$1,157
Balcony
$1,254
Suite
$2,034
From
A$1,123
Save 22
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise
 (1)

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Grandeur of the Seas (+3 more), Jewel of the Seas, Radiance of the Seas, Serenade of the Seas
Departures: Apr 2026 to Apr 2028
Visit: USA, Mexico
Exclusive Savings
Inside
$632
Oceanview
$693
Balcony
$824
Suite
$1,412
From
A$632
Save 1,175
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: May 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,349
Oceanview
$1,571
Balcony
$1,766
Suite
$2,183
From
A$1,349
Save 23
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, Mexico
Easter Flash Sale
Exclusive Savings
Inside
$797
Oceanview
$965
Balcony
$1,223
Suite
$2,559
From
A$797
Save 15
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Tampa to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departure: 02 May 2026
Visit: USA, Cayman Islands, Aruba, Curacao, Panama
Exclusive Savings
Inside
$1,129
Oceanview
$1,254
Balcony
$1,509
Suite
$1,995
From
A$1,129
Save 179
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
Exclusive Savings
Inside
$1,672
Oceanview
$2,029
Balcony
$2,563
Suite
$5,048
From
A$1,672
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
Ships: Resilient Lady, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Apr 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Limited Time Offer
Inside
$925
Oceanview
$1,083
Balcony
$1,392
Suite
$3,974
From
A$925
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: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,379
Oceanview
$1,512
Balcony
$1,721
Suite
$1,914
From
A$1,379
Save 21
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
Exclusive Savings
Inside
$1,353
Oceanview
$1,521
Balcony
$1,791
Suite
$2,090
From
A$1,353
Save 1,405
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
Exclusive Savings
Inside
$1,119
Oceanview
$1,224
Balcony
$1,877
Suite
$2,396
From
A$1,119
Save 927
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
Just Cruise Fare
Exclusive Savings
Inside
$1,067
Oceanview
$1,156
Balcony
$1,381
Suite
$1,604
From
A$1,067
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
Exclusive Savings
Inside
$736
Oceanview
$1,122
Balcony
$1,064
Suite
$1,469
From
A$736
Save 13
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: Apr 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Easter Flash Sale
Exclusive Savings
Inside
$609
Oceanview
$718
Balcony
$827
Suite
$2,490
From
A$609
Save 11
Per Person
View Trip
6 Day Western Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Escape
Departure: 19 May 2026
Visit: USA, Bahamas, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$933
Oceanview
$1,009
Balcony
$1,083
Suite
$1,157
From
A$933
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
Exclusive Savings
Inside
$1,633
Oceanview
$1,989
Balcony
$2,524
Suite
$5,048
From
A$1,633
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
Ship: Rhapsody of the Seas
Departure: 02 May 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Dominica
Senior Discount
Exclusive Savings
Inside
$1,606
Oceanview
$1,624
Balcony
$2,289
Suite
$2,712
From
A$1,606
Save 986
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Apr 2027 to Apr 2028
Visit: USA, Dominican Republic, Bahamas
Limited Time Offer
Inside
$927
Oceanview
$1,161
Balcony
$1,472
Suite
$4,479
From
A$927
Per Person
View Trip
9 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 02 May 2026
Visit: USA, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,404
Oceanview
$2,365
Balcony
$2,261
Suite
$6,406
From
A$1,404
Save 763
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 Nov 2027
Visit: Martinique, Antigua and Barbuda, Dominican Republic, Barbados
Exclusive Savings
Inside
$1,108
Oceanview
$1,346
Balcony
$1,950
Suite
$2,910
From
A$1,108
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Dec 2027
Visit: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,075
Oceanview
$1,198
Balcony
$1,793
Suite
$2,434
From
A$1,075
Save 876
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Easter Flash Sale
Exclusive Savings
Inside
$846
Oceanview
$1,074
Balcony
$1,262
Suite
$2,727
From
A$846
Per Person
View Trip
9 Day Southern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departure: 15 May 2026
Visit: USA, Curacao, Aruba, Bahamas
Exclusive Savings
Inside
$1,578
Oceanview
$1,755
Balcony
$2,897
Suite
$3,884
From
A$1,578
Save 888
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Apr 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas
Easter Flash Sale
Exclusive Savings
Inside
$1,094
Oceanview
$1,381
Balcony
$1,658
Suite
$2,381
From
A$1,094
Save 17
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departures: May 2026 to Jul 2026
Visit: USA, Saint Kitts and Nevis, Sint Maarten, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,929
Oceanview
$2,231
Balcony
$2,198
Suite
$6,732
From
A$1,929
Save 1,243
Per Person
View Trip
6 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Freedom of the Seas, Independence of the Seas
Departures: May 2026 to Dec 2027
Visit: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$889
Oceanview
$972
Balcony
$1,140
Suite
$1,803
From
A$889
Save 508
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Sep 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Exclusive Savings
Inside
$795
Oceanview
$773
Balcony
$1,162
Suite
$1,488
From
A$773
Per Person
View Trip
8 Day Western Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Luna, Norwegian Viva
Departures: Oct 2026 to May 2027
Visit: USA, Honduras, Belize, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,766
Oceanview
$1,766
Balcony
$2,094
Suite
$2,808
From
A$1,766
Per Person
View Trip
Results: 1-30 of 88

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