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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 87 unique cruises and 1,621 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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87 Cruises (1,621 Cruise Departures)
8 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$1,131
Oceanview
$1,381
Balcony
$1,593
Suite
$2,852
From
US$1,131
Save 1,025
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
Inside
$749
Oceanview
$775
Balcony
$779
Suite
$1,329
From
US$749
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise

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
$1,092
Oceanview
$1,215
Balcony
$1,415
Suite
$3,535
From
US$1,092
Save 954
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
$1,205
Oceanview
$1,298
Balcony
$2,224
Suite
$2,411
From
US$1,205
Save 639
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
Inside
$719
Oceanview
$809
Balcony
$949
Suite
$1,079
From
US$719
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
Departures: May 2027 to Jul 2027
Visit: USA, Bahamas, Jamaica, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$818
Oceanview
$968
Balcony
$1,085
Suite
$2,111
From
US$818
Save 665
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
$1,236
Oceanview
$1,451
Balcony
$1,444
Suite
$4,454
From
US$1,236
Save 730
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
$783
Oceanview
$846
Balcony
$1,415
Suite
-
From
US$783
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
$1,398
From
US$689
Save 568
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$724
Oceanview
$934
Balcony
$1,064
Suite
$2,076
From
US$724
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 481
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Nov 2026 to Nov 2027
Visit: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Inside
$559
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$559
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Apr 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,226
Oceanview
$1,609
Balcony
$1,746
Suite
$2,705
From
US$1,226
Save 1,110
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
$479
Oceanview
$529
Balcony
$579
Suite
$629
From
US$479
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, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Inside
$1,161
Oceanview
$1,651
Balcony
$1,891
Suite
$3,591
From
US$1,161
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
$567
Oceanview
$657
Balcony
$699
Suite
$1,080
From
US$567
Save 538
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
$1,326
Suite
$1,331
From
US$866
Save 1,114
Per Person
View Trip
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
$748
Oceanview
$762
Balcony
$1,289
Suite
$1,080
From
US$748
Save 934
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
$645
Oceanview
$695
Balcony
$895
Suite
$2,550
From
US$645
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
$1,133
Balcony
$2,209
Suite
$1,585
From
US$1,118
Save 615
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
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
$1,269
Oceanview
$1,145
Balcony
$1,145
Suite
$2,295
From
US$1,145
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
$569
Oceanview
$629
Balcony
$779
Suite
$929
From
US$569
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
$906
Oceanview
$1,146
Balcony
$1,556
Suite
$2,980
From
US$906
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
$398
Oceanview
$501
Balcony
$969
Suite
$1,012
From
US$398
Save 306
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Mexico
Inside
$738
Oceanview
$908
Balcony
$1,052
Suite
$2,311
From
US$738
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
Inside
$549
Oceanview
-
Balcony
$714
Suite
$949
From
US$549
Per Person
View Trip
8 Day Eastern Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departure: 02 May 2027
Visit: USA, Virgin Islands, Dominican Republic, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$1,343
Oceanview
$1,603
Balcony
$1,666
Suite
$2,872
From
US$1,343
Save 683
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise

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
$799
Oceanview
$872
Balcony
$1,058
Suite
$2,277
From
US$824
Save 1,811
Per Person
View Trip
7 Day Grand Turk, Puerto Plata & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Aug 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,026
Oceanview
$1,146
Balcony
$1,196
Suite
$2,478
From
US$1,026
Save 617
Per Person
View Trip
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