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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 52 unique cruises and 1,297 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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52 Cruises (1,297 Departures)
52 Cruises (1,297 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$400pp
$205,420pp
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
Cruise Line: 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
$814
Oceanview
$977
Balcony
$1,275
Suite
$1,425
From (Per Person)
A$814
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
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,538
Oceanview
$1,894
Balcony
$2,429
Suite
$5,062
From (Per Person)
A$1,538
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
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,637
Oceanview
$1,874
Balcony
$2,409
Suite
$5,062
From (Per Person)
A$1,637
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
Visits: USA, Dominican Republic, Bahamas
Inside
$848
Oceanview
$1,063
Balcony
$1,347
Suite
$3,779
From (Per Person)
A$848
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
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$919
Oceanview
$991
Balcony
$1,133
Suite
$3,059
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
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$754
Oceanview
$933
Balcony
$1,200
Suite
$2,536
From (Per Person)
A$754
Save 12
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
Visits: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,229
Oceanview
$1,350
Balcony
$1,684
Suite
$5,267
From (Per Person)
A$1,229
Save 731
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
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,371
Oceanview
$1,420
Balcony
$1,806
Suite
$4,935
From (Per Person)
A$2,165
Save 39
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
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,101
Oceanview
$1,203
Balcony
$1,834
Suite
$2,294
From (Per Person)
A$1,101
Save 1,074
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
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,397
Oceanview
$1,459
Balcony
$1,963
Suite
$4,538
From (Per Person)
A$2,208
Save 48
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
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,703
Oceanview
$1,851
Balcony
$2,168
Suite
$5,475
From (Per Person)
A$1,703
Save 1,312
Per Person
View Trip
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
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,712
Oceanview
$1,712
Balcony
$2,045
Suite
$5,243
From (Per Person)
A$2,740
Save 57
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: Jul 2026 to Apr 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,200
Oceanview
$1,542
Balcony
$1,675
Suite
$1,870
From (Per Person)
A$1,200
Save 22
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: Jul 2026 to Mar 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,274
Oceanview
$1,393
Balcony
$1,616
Suite
$1,765
From (Per Person)
A$1,274
Save 21
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
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$665
Oceanview
$843
Balcony
$1,111
Suite
$2,477
From (Per Person)
A$665
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
Visits: USA, Virgin Islands, Dominican Republic, Haiti
Exclusive Savings
Inside
$2,150
Oceanview
$2,584
Balcony
$2,552
Suite
$4,433
From (Per Person)
A$2,150
Save 1,154
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: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Honduras, Mexico
Exclusive Savings
Inside
$2,161
Oceanview
$2,458
Balcony
$3,052
Suite
$4,587
From (Per Person)
A$2,161
Save 34
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
Ships: Harmony of the Seas, Star Of The Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Mexico, Honduras, Bahamas
Exclusive Savings
Inside
$1,261
Oceanview
$1,419
Balcony
$1,494
Suite
$3,290
From (Per Person)
A$1,261
Save 1,474
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 Oct 2028
Visits: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda
Exclusive Savings
Inside
$1,089
Oceanview
$1,326
Balcony
$1,920
Suite
$2,821
From (Per Person)
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
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,050
Oceanview
$1,156
Balcony
$1,794
Suite
$2,409
From (Per Person)
A$1,050
Save 836
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 2028
Visits: Barbados, Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,165
Oceanview
$2,572
Balcony
$3,780
Suite
$5,632
From (Per Person)
A$2,165
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Enchantment of the Seas, Jewel of the Seas +2 more, Radiance of the Seas, Serenade of the Seas
Departures: Jul 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$607
Oceanview
$689
Balcony
$807
Suite
$1,370
From (Per Person)
A$607
Save 962
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
Visits: USA, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$2,707
Oceanview
$3,586
Balcony
$5,372
Suite
-
From (Per Person)
A$2,707
Save 1,357
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
Visits: USA, Curacao, Bonaire, Aruba, Bahamas
Exclusive Savings
Inside
$1,656
Oceanview
$1,855
Balcony
$3,042
Suite
$3,827
From (Per Person)
A$1,656
Save 994
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Jul 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$982
Oceanview
$1,220
Balcony
$1,517
Suite
$2,309
From (Per Person)
A$982
Save 22
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
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$2,255
Oceanview
$2,405
Balcony
$2,651
Suite
$4,229
From (Per Person)
A$2,255
Save 1,171
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
Visits: USA, Saint Kitts and Nevis, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,489
Oceanview
$1,812
Balcony
$1,766
Suite
$4,115
From (Per Person)
A$1,489
Save 810
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: Aug 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,092
Oceanview
$2,389
Balcony
$2,983
Suite
$4,587
From (Per Person)
A$2,092
Save 35
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 2028
Visits: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Exclusive Savings
Inside
$1,089
Oceanview
$1,326
Balcony
$1,920
Suite
$2,821
From (Per Person)
A$1,089
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: Jul 2026 to Jul 2027
Visits: USA, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,878
Oceanview
$2,142
Balcony
$2,084
Suite
$4,216
From (Per Person)
A$1,878
Save 1,575
Per Person
View Trip
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Cruise Lines Exploring The Caribbean & Bahamas

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