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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 106 unique cruises and 1,741 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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106 Cruises (1,741 Cruise Departures)
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ships: Icon Of The Seas, Liberty of the Seas, Symphony of the Seas
Departures: May 2026 to Mar 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$604
Oceanview
$723
Balcony
$904
Suite
$1,729
From
US$604
Save 905
Per Person
View Trip
10 Day Miami To Cape Liberty Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) Miami to New York
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 10 May 2027
Visit: USA, Aruba, Curacao, Turks and Caicos Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,132
Oceanview
$1,282
Balcony
$1,481
Suite
$2,191
From
US$1,132
Save 572
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
$713
Oceanview
$722
Balcony
$1,020
Suite
$1,130
From
US$713
Save 917
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: Apr 2026 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Mexico, Belize, Honduras
Princess Standard
Inside
$1,288
Oceanview
-
Balcony
$1,506
Suite
$1,958
From
US$1,288
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: Feb 2026 to Mar 2028
Visit: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,226
Oceanview
$1,661
Balcony
$2,081
Suite
$3,527
From
US$1,226
Save 72
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
$649
Oceanview
$861
Balcony
$1,237
Suite
$1,449
From
US$649
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: May 2026 to Aug 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico
Princess Standard
Inside
$1,022
Oceanview
$1,560
Balcony
$1,660
Suite
$3,879
From
US$1,022
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
Bonus Onboard Credit
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
8 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 17 May 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$970
Oceanview
$1,070
Balcony
$1,198
Suite
$3,098
From
US$970
Save 574
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 (+4 more), Norwegian Escape, Norwegian Getaway, Norwegian Joy, Norwegian Prima
Departures: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$809
Oceanview
$929
Balcony
$1,019
Suite
$1,199
From
US$809
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
Ship: Norwegian Viva
Departures: Apr 2027 to May 2027
Visit: USA, Honduras, Belize, Mexico, Bahamas
Inside
$1,209
Oceanview
$1,349
Balcony
$1,629
Suite
$2,237
From
US$1,209
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
Bonus Onboard Credit
Inside
$559
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$559
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
Inside
$514
Oceanview
$514
Balcony
$749
Suite
$874
From
US$514
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
Departures: Mar 2026 to Oct 2026
Visit: USA, Turks and Caicos Islands, Bahamas
With Love From the World
Inside
$866
Oceanview
$1,031
Balcony
$1,151
Suite
$2,745
From
US$866
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
$1,403
Oceanview
$1,574
Balcony
$1,555
Suite
$4,248
From
US$1,403
Save 822
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departure: 03 May 2026
Visit: USA, Virgin Islands, Saint Martin
Inside
$1,549
Oceanview
$1,749
Balcony
$1,930
Suite
$3,188
From
US$1,549
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: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$759
Oceanview
$879
Balcony
$1,049
Suite
$1,319
From
US$759
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,092
Oceanview
$1,272
Balcony
$1,582
Suite
$2,828
From
US$1,092
Save 59
Per Person
View Trip
15 Day Eastern/Western Caribbean 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, Bahamas, Puerto Rico, Saint Martin, Mexico, Belize, Honduras
Princess Standard
Inside
$1,388
Oceanview
-
Balcony
$1,528
Suite
$2,108
From
US$1,388
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: Brilliant Lady, Resilient Lady (+2 more), Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2027
Visit: USA, Turks and Caicos Islands, Bahamas
With Love From the World
Inside
$645
Oceanview
$745
Balcony
$895
Suite
$2,550
From
US$645
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
$559
Oceanview
$659
Balcony
$759
Suite
$809
From
US$559
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
$779
Oceanview
$1,020
Balcony
$829
Suite
$1,184
From
US$779
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: Apr 2026 to Aug 2026
Visit: USA, Mexico, Belize, Honduras, Bahamas, Puerto Rico, Virgin Islands
Princess Standard
Inside
$1,038
Oceanview
-
Balcony
$1,316
Suite
$1,718
From
US$1,038
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
Bonus Onboard Credit
Inside
$480
Oceanview
$670
Balcony
$670
Suite
$1,541
From
US$480
Per Person
View Trip
7 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2026 to Sep 2026
Visit: USA, Jamaica, Cayman Islands, Bahamas
Exclusive Savings
Inside
$564
Oceanview
$735
Balcony
$869
Suite
$1,133
From
US$564
Save 622
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
$1,274
Oceanview
$1,464
Balcony
$1,537
Suite
$4,382
From
US$1,274
Save 660
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departure: 01 May 2027
Visit: USA, Jamaica, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$742
Oceanview
$791
Balcony
$929
Suite
$1,291
From
US$742
Save 340
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
$695
Oceanview
$793
Balcony
$1,248
Suite
$1,283
From
US$695
Save 433
Per Person
View Trip
10 Day Perfect Day Cococay & South Carib with Royal Caribbean
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departures: Oct 2026 to May 2027
Visit: USA, Aruba, Curacao, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$764
Oceanview
$1,007
Balcony
$1,413
Suite
$2,076
From
US$764
Save 588
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
Bonus Onboard Credit
Exclusive Savings
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Save 59
Per Person
View Trip
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