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Caribbean Cruises Starting In May 2027 and 2028

Are you planning a cruise to the Caribbean in May 2027 or 2028? Choose from 59 unique cruises and 1,524 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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59 Cruises (1,524 Departures)
59 Cruises (1,524 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$300pp
$197,370pp
Countries
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6 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$784
Oceanview
$858
Balcony
$947
Suite
$1,067
From (Per Person)
A$784
Save 12
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$784
Oceanview
$962
Balcony
$1,259
Suite
$2,309
From (Per Person)
A$784
Save 16
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,518
Oceanview
$1,874
Balcony
$2,409
Suite
$5,013
From (Per Person)
A$1,518
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2027 to Oct 2028
Visits: USA, Dominican Republic, Bahamas
Drinks On Us
Inside
$848
Oceanview
$1,132
Balcony
$1,346
Suite
$3,772
From (Per Person)
A$848
Per Person
View Trip
8 Day San Juan, St Kitts & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 29 May 2027
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,411
Oceanview
$1,603
Balcony
$1,939
Suite
$5,902
From (Per Person)
A$2,375
Save 40
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic +3 more, Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$976
Oceanview
$1,199
Balcony
$1,318
Suite
$1,676
From (Per Person)
A$976
Save 20
Per Person
View Trip
8 Day Caribbean Cruise From Galveston to Galveston with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Operator: Norwegian Cruise Line
Ships: Norwegian Escape, Norwegian Prima, Norwegian Viva
Departures: Oct 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,202
Oceanview
$1,276
Balcony
$1,529
Suite
$2,050
From (Per Person)
A$1,202
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ships: Brilliant Lady, Resilient Lady +2 more, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Drinks On Us
Inside
$919
Oceanview
$1,132
Balcony
$1,204
Suite
$2,842
From (Per Person)
A$919
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ships: MSC Grandiosa, MSC World Atlantic
Departures: Nov 2026 to Nov 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,507
From (Per Person)
A$735
Save 15
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
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic +2 more, Norwegian Escape, Norwegian Prima
Departures: Oct 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,096
Oceanview
$1,274
Balcony
$1,439
Suite
$1,602
From (Per Person)
A$1,096
Save 19
Per Person
View Trip
8 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 22 May 2027
Visits: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,449
Oceanview
$1,450
Balcony
$1,807
Suite
$6,303
From (Per Person)
A$2,402
Save 40
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,477
From (Per Person)
A$735
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Aug 2027
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,292
Oceanview
$1,514
Balcony
$1,843
Suite
$4,599
From (Per Person)
A$2,150
Save 48
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,468
Oceanview
$1,825
Balcony
$2,359
Suite
$4,983
From (Per Person)
A$1,468
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Oct 2027
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,597
Oceanview
$1,875
Balcony
$2,062
Suite
$5,420
From (Per Person)
A$2,679
Save 54
Per Person
View Trip
7 Day Grand Turk, Puerto Plata & Bahamas with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 02 May 2027
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,134
Oceanview
$1,210
Balcony
$1,390
Suite
$6,348
From (Per Person)
A$1,891
Save 36
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,032
Oceanview
$1,108
Balcony
$1,689
Suite
$2,332
From (Per Person)
A$1,232
Save 857
Per Person
View Trip
8 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ships: Harmony of the Seas, Star Of The Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Mexico, Honduras, Bahamas
Exclusive Savings
Inside
$1,454
Oceanview
$1,556
Balcony
$1,711
Suite
$3,205
From (Per Person)
A$1,759
Save 1,056
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departure: 02 May 2027
Visits: USA, Virgin Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$2,398
Oceanview
$2,818
Balcony
$2,812
Suite
$4,700
From (Per Person)
A$2,948
Save 720
Per Person
View Trip
8 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departure: 22 May 2027
Visits: USA, Bahamas, Jamaica, Mexico
Exclusive Savings
Inside
$1,538
Oceanview
$1,610
Balcony
$1,604
Suite
$3,703
From (Per Person)
A$1,916
Save 572
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Galveston to Galveston
Operator: MSC Cruises
Ship: MSC Seascape
Departures: Sep 2026 to Nov 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$695
Oceanview
$942
Balcony
$1,081
Suite
$2,121
From (Per Person)
A$695
Save 13
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) La Romana to La Romana
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,224
Oceanview
$2,670
Balcony
$3,828
Suite
$5,669
From (Per Person)
A$2,224
Save 65
Per Person
View Trip
10 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

10 Days (9 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2027 to Oct 2027
Visits: USA, Curacao, Bonaire, Aruba, Bahamas
Exclusive Savings
Inside
$1,546
Oceanview
$1,717
Balcony
$2,726
Suite
$3,915
From (Per Person)
A$1,877
Save 593
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Dec 2027
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,022
Oceanview
$1,255
Balcony
$1,756
Suite
$2,370
From (Per Person)
A$1,219
Save 520
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2027 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Virgin Islands
Exclusive Savings
Inside
$2,170
Oceanview
$2,263
Balcony
$2,484
Suite
$4,795
From (Per Person)
A$2,654
Save 888
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC World Atlantic
Departures: Nov 2027 to Nov 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,338
Oceanview
$1,616
Balcony
$1,764
Suite
$2,408
From (Per Person)
A$1,338
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Exclusive Savings
Inside
$1,914
Oceanview
$1,983
Balcony
$2,577
Suite
$4,587
From (Per Person)
A$1,914
Save 35
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Allure of the Seas
Departure: 02 May 2027
Visits: USA, Saint Kitts and Nevis, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,233
Oceanview
$1,594
Balcony
$1,546
Suite
$3,717
From (Per Person)
A$1,467
Save 801
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Operator: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2028
Visits: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Exclusive Savings
Inside
$1,103
Oceanview
$1,340
Balcony
$1,934
Suite
$2,835
From (Per Person)
A$1,103
Save 21
Per Person
View Trip
10 Day Miami To Cape Liberty Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) Miami to New York
Operator: Royal Caribbean
Ship: Independence of the Seas
Departure: 10 May 2027
Visits: USA, Aruba, Curacao, Turks and Caicos Islands
Exclusive Savings
Inside
$1,243
Oceanview
$1,340
Balcony
$2,102
Suite
$4,448
From (Per Person)
A$1,369
Save 438
Per Person
View Trip
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