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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 97 unique cruises and 1,707 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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97 Cruises (1,707 Cruise Departures)
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
$1,379
Oceanview
$1,529
Balcony
$1,829
Suite
$2,463
From
US$1,379
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
$634
Oceanview
$1,088
Balcony
$820
Suite
$1,029
From
US$634
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, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,489
Oceanview
$1,839
Balcony
$2,118
Suite
$3,370
From
US$1,489
Save 64
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
$568
Oceanview
$719
Balcony
$1,608
Suite
$1,578
From
US$568
Save 344
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 Grandiosa
Departures: Feb 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic
Bonus Onboard Credit
Inside
$399
Oceanview
$489
Balcony
$619
Suite
$1,377
From
US$399
Per Person
View Trip
8 Day San Juan, St Kitts & Puerto Plata with Celebrity Cruises
Cruise

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, Dominican Republic
Exclusive Savings
Inside
$1,258
Oceanview
$1,338
Balcony
$1,481
Suite
$3,102
From
US$1,258
Save 666
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
$2,141
From
US$1,132
Save 572
Per Person
View Trip
8 Day St. Thomas & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jan 2026 to May 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$674
Oceanview
$724
Balcony
$1,374
Suite
$2,898
From
US$674
Save 1,744
Per Person
View Trip
6 Day Perfect Day Cococay & East Carib 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
$579
Oceanview
$656
Balcony
$661
Suite
$1,058
From
US$579
Save 576
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
$1,419
Oceanview
$1,749
Balcony
$2,069
Suite
$3,515
From
US$1,419
Save 69
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: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$719
Oceanview
$869
Balcony
$1,109
Suite
$1,249
From
US$719
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
$978
Oceanview
-
Balcony
$1,204
Suite
$1,548
From
US$978
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
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$509
Oceanview
$649
Balcony
$669
Suite
$1,319
From
US$509
Per Person
View Trip
9 Day Perfect Day Cococay & South Carib 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
$1,104
Oceanview
$1,244
Balcony
$1,251
Suite
$2,804
From
US$1,104
Save 817
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
Departure: 02 May 2026
Visit: USA, Mexico, Belize, Honduras, Bahamas, Puerto Rico, Saint Martin
Princess Standard
Inside
$1,298
Oceanview
-
Balcony
$1,829
Suite
-
From
US$1,298
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
$1,361
Oceanview
$1,491
Balcony
$1,551
Suite
$2,911
From
US$1,361
Save 670
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
Departure: 06 May 2027
Visit: USA, Aruba, Bonaire, Curacao, Dominican Republic, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,112
Oceanview
$1,357
Balcony
$2,062
Suite
$2,279
From
US$1,112
Save 545
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
Bonus Onboard Credit
Inside
$808
Oceanview
$988
Balcony
$1,128
Suite
$1,908
From
US$808
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
$481
Oceanview
$581
Balcony
$1,144
Suite
$1,443
From
US$481
Save 306
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
$625
Oceanview
$738
Balcony
$1,060
Suite
$1,120
From
US$625
Save 631
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
$978
Oceanview
$1,140
Balcony
$1,360
Suite
$1,780
From
US$978
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
$1,048
Oceanview
-
Balcony
$1,424
Suite
$1,618
From
US$1,048
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jan 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,424
Oceanview
$1,494
Balcony
$1,704
Suite
$2,822
From
US$1,424
Save 1,063
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
$728
Oceanview
$791
Balcony
$1,132
Suite
$1,223
From
US$728
Save 763
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
$1,040
Oceanview
$1,140
Balcony
$1,340
Suite
$3,452
From
US$1,040
Save 934
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise

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
$709
Oceanview
$1,049
Balcony
$1,149
Suite
$1,359
From
US$709
Per Person
View Trip
8 Day Tortola, St. Maarten & Puerto Plata 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, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$813
Oceanview
$834
Balcony
$1,141
Suite
$2,808
From
US$813
Save 843
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
$1,108
Oceanview
-
Balcony
$1,538
Suite
$1,778
From
US$1,108
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: Apr 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Sanctuary Collection
Inside
$484
Oceanview
$824
Balcony
$595
Suite
$769
From
US$484
Per Person
View Trip
6 Day Western Caribbean Cruise with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departures: May 2026 to Mar 2027
Visit: USA, Bahamas, Dominican Republic
Bonus Onboard Credit
Exclusive Savings
Inside
$496
Oceanview
$598
Balcony
$639
Suite
$1,058
From
US$496
Save 268
Per Person
View Trip
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