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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 85 unique cruises and 1,559 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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85 Cruises (1,559 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
Bonus Onboard Credit
Exclusive Savings
Inside
$839
Oceanview
$949
Balcony
$1,175
Suite
$1,215
From
US$839
Save 1,507
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
$1,221
Oceanview
$1,126
Balcony
$1,195
Suite
$2,145
From
US$1,126
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
$809
Balcony
$979
Suite
$1,079
From
US$729
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
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,875
From
US$595
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
Inside
$449
Oceanview
$509
Balcony
$559
Suite
$629
From
US$449
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
$357
Oceanview
$364
Balcony
$566
Suite
$1,087
From
US$357
Save 288
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
Inside
$699
Oceanview
$849
Balcony
$979
Suite
$1,219
From
US$699
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
$836
Oceanview
$1,076
Balcony
$1,456
Suite
$2,960
From
US$836
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
$469
Oceanview
$749
Balcony
$524
Suite
$869
From
US$469
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
$846
Oceanview
$1,086
Balcony
$1,496
Suite
$2,980
From
US$846
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
Exclusive Savings
Inside
$1,118
Oceanview
-
Balcony
-
Suite
-
From
US$1,118
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
$529
Oceanview
$579
Balcony
$799
Suite
$899
From
US$529
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
$866
Oceanview
$997
Balcony
$1,341
Suite
$1,426
From
US$866
Save 1,118
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
Inside
$645
Oceanview
$745
Balcony
$895
Suite
$2,500
From
US$645
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
Inside
$419
Oceanview
$539
Balcony
$620
Suite
$1,511
From
US$419
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
$419
Oceanview
$539
Balcony
$621
Suite
$1,461
From
US$419
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
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,473
From
US$689
Save 568
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
Inside
$899
Oceanview
$899
Balcony
$1,109
Suite
$1,579
From
US$899
Per Person
View Trip
12 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

12 Days (11 Nights) Baltimore to Baltimore
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 10 May 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,514
Oceanview
$1,739
Balcony
$3,034
Suite
-
From
US$1,514
Save 723
Per Person
View Trip
9 Day Perfect Day Cococay & South Caribbean 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 Oct 2027
Visit: USA, Curacao, Aruba, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$988
Oceanview
$1,242
Balcony
$1,250
Suite
$2,954
From
US$988
Save 871
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
$849
Oceanview
$989
Balcony
$1,917
Suite
-
From
US$1,305
Save 50
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
$2,346
From
US$1,231
Save 773
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Inside
$1,171
Oceanview
$1,581
Balcony
$1,901
Suite
$3,591
From
US$1,171
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Barbados, Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin, Antigua and Barbuda
Inside
$1,448
Oceanview
$1,748
Balcony
$2,738
Suite
$3,898
From
US$1,448
Per Person
View Trip
8 Day Eastern 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 Aura, Norwegian Luna
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$859
Oceanview
$1,009
Balcony
$1,339
Suite
$1,679
From
US$859
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos From Orlando with Princess
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departure: 11 May 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$799
Oceanview
-
Balcony
-
Suite
-
From
US$799
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departure: 02 May 2026
Visit: USA, Mexico, Honduras
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,330
From
US$4,330
Save 2,464
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,440
Oceanview
$1,560
Balcony
$1,680
Suite
$3,185
From
US$1,440
Save 1,028
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: MSC Cruises
Ship: MSC Seascape
Departures: May 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Inside
$379
Oceanview
$485
Balcony
$565
Suite
$1,195
From
US$379
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
Results: 1-30 of 85

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