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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 51 unique cruises and 1,130 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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51 Cruises (1,130 Cruise Departures)
8 Day San Juan, St Kitts & Puerto Plata with Celebrity Cruises
Cruise
 (1)

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, Bahamas
Exclusive Savings
Inside
$1,792
Oceanview
$1,807
Balcony
$2,170
Suite
$4,795
From
A$1,792
Save 1,020
Per Person
View Trip
7 Day Grand Turk, Puerto Plata & Bahamas with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 02 May 2027
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,483
Oceanview
$1,693
Balcony
$2,137
Suite
$4,750
From
A$1,483
Save 791
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
Exclusive Savings
Inside
$757
Oceanview
$935
Balcony
$1,203
Suite
$2,559
From
A$757
Save 14
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
Just Cruise Fare
Exclusive Savings
Inside
$888
Oceanview
$1,112
Balcony
$1,410
Suite
$1,500
From
A$888
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2027 to Oct 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$848
Oceanview
$1,063
Balcony
$1,347
Suite
$3,779
From
A$848
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
Exclusive Savings
Inside
$1,553
Oceanview
$1,910
Balcony
$2,444
Suite
$5,048
From
A$1,553
Save 24
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
Exclusive Savings
Inside
$1,534
Oceanview
$1,890
Balcony
$2,425
Suite
$5,048
From
A$1,534
Save 24
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
Exclusive Savings
Inside
$708
Oceanview
$886
Balcony
$1,153
Suite
$2,490
From
A$708
Save 11
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: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,348
Oceanview
$1,602
Balcony
$1,691
Suite
$1,989
From
A$1,348
Save 22
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
Exclusive Savings
Inside
$1,101
Oceanview
$1,203
Balcony
$1,834
Suite
$2,446
From
A$1,101
Save 903
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: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,393
Oceanview
$1,482
Balcony
$1,631
Suite
$1,779
From
A$1,393
Save 21
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Aug 2027
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,618
Oceanview
$1,675
Balcony
$2,027
Suite
$4,052
From
A$1,618
Save 1,068
Per Person
View Trip
8 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 22 May 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,541
Oceanview
$1,783
Balcony
$1,916
Suite
$4,489
From
A$1,541
Save 820
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

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 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$920
Oceanview
$1,134
Balcony
$1,401
Suite
$3,565
From
A$920
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

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
$1,774
Oceanview
$1,921
Balcony
$2,308
Suite
$5,670
From
A$1,774
Save 1,473
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
Exclusive Savings
Inside
$1,534
Oceanview
$1,738
Balcony
$1,934
Suite
$3,424
From
A$1,534
Save 837
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
Exclusive Savings
Inside
$2,214
Oceanview
$2,447
Balcony
$2,581
Suite
$4,304
From
A$2,214
Save 1,151
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
Exclusive Savings
Inside
$2,170
Oceanview
$2,263
Balcony
$2,484
Suite
$4,845
From
A$2,170
Save 1,622
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
Exclusive Savings
Inside
$1,712
Oceanview
$1,935
Balcony
$3,182
Suite
$3,901
From
A$1,712
Save 994
Per Person
View Trip
12 Day Perfect Day Cococay & East Caribbean 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, Bahamas
Exclusive Savings
Inside
$2,707
Oceanview
$3,529
Balcony
$5,206
Suite
$6,040
From
A$2,707
Save 1,357
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: Jun 2026 to Apr 2028
Visit: USA, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$787
Oceanview
$1,064
Balcony
$1,203
Suite
$2,114
From
A$787
Save 13
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: Star Of The Seas
Departures: Jun 2026 to Jan 2028
Visit: USA, Bahamas, Mexico, Honduras
Exclusive Savings
Inside
$1,834
Oceanview
$2,170
Balcony
$2,243
Suite
$3,270
From
A$1,834
Save 1,644
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: Aug 2026 to Oct 2027
Visit: USA, Curacao, Aruba, Bahamas
Exclusive Savings
Inside
$1,463
Oceanview
$1,684
Balcony
$1,640
Suite
$3,836
From
A$1,463
Save 1,279
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: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$2,296
Oceanview
$2,771
Balcony
$3,365
Suite
$5,959
From
A$2,296
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 02 May 2027
Visit: USA, Saint Kitts and Nevis, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,545
Oceanview
$1,841
Balcony
$1,794
Suite
$4,203
From
A$1,545
Save 837
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
Exclusive Savings
Inside
$1,108
Oceanview
$1,346
Balcony
$1,950
Suite
$2,910
From
A$1,108
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: Apr 2027 to Nov 2027
Visit: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda
Exclusive Savings
Inside
$1,089
Oceanview
$1,326
Balcony
$1,950
Suite
$2,890
From
A$1,089
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Dec 2027
Visit: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,050
Oceanview
$1,156
Balcony
$1,794
Suite
$2,483
From
A$1,050
Save 836
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
Exclusive Savings
Inside
$2,177
Oceanview
$2,768
Balcony
$2,750
Suite
$4,507
From
A$2,177
Save 1,168
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
Exclusive Savings
Inside
$1,029
Oceanview
$1,346
Balcony
$1,950
Suite
$2,910
From
A$1,029
Per Person
View Trip
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