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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 1,300 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 (1,300 Departures)
51 Cruises (1,300 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$400pp
$203,830pp
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
$829
Oceanview
$993
Balcony
$1,290
Suite
$1,410
From (Per Person)
A$829
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
$1,386
Oceanview
$1,445
Balcony
$1,807
Suite
$6,119
From (Per Person)
A$1,386
Save 727
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
$1,761
Oceanview
$1,849
Balcony
$2,186
Suite
$6,162
From (Per Person)
A$1,761
Save 1,000
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
$1,461
Oceanview
$1,461
Balcony
$2,168
Suite
$5,282
From (Per Person)
A$1,461
Save 1,132
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
$1,774
Oceanview
$1,890
Balcony
$2,308
Suite
$5,651
From (Per Person)
A$1,774
Save 1,385
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
$880
Oceanview
$1,103
Balcony
$1,398
Suite
$3,920
From (Per Person)
A$880
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
$1,518
Oceanview
$1,874
Balcony
$2,409
Suite
$4,983
From (Per Person)
A$1,518
Save 24
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: Aug 2026 to Mar 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,274
Oceanview
$1,393
Balcony
$1,661
Suite
$1,765
From (Per Person)
A$1,274
Save 21
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
$1,144
Balcony
$1,834
Suite
$2,319
From (Per Person)
A$1,276
Save 622
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: Aug 2026 to Apr 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,200
Oceanview
$1,453
Balcony
$1,572
Suite
$1,870
From (Per Person)
A$1,200
Save 25
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
$1,558
Oceanview
$1,914
Balcony
$2,449
Suite
$5,062
From (Per Person)
A$1,558
Save 24
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
$1,398
Oceanview
$1,485
Balcony
$2,053
Suite
$6,106
From (Per Person)
A$1,398
Save 726
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
$725
Oceanview
$903
Balcony
$1,170
Suite
$2,477
From (Per Person)
A$725
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
$794
Oceanview
$972
Balcony
$1,239
Suite
$2,507
From (Per Person)
A$794
Save 13
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
$953
Oceanview
$1,028
Balcony
$1,176
Suite
$3,173
From (Per Person)
A$953
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
Ships: Norwegian Aqua, Norwegian Luna, Norwegian Viva
Departures: Oct 2026 to May 2027
Visits: USA, Honduras, Belize, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,424
Oceanview
$1,498
Balcony
$1,721
Suite
$2,391
From (Per Person)
A$1,424
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2028 to Oct 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,214
Oceanview
$2,670
Balcony
$3,858
Suite
$5,660
From (Per Person)
A$2,214
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: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,051
Oceanview
$1,289
Balcony
$1,586
Suite
$2,309
From (Per Person)
A$1,051
Save 23
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
$2,201
Oceanview
$2,845
Balcony
$3,458
Suite
$4,587
From (Per Person)
A$2,201
Save 39
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 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Exclusive Savings
Inside
$1,103
Oceanview
$1,330
Balcony
$1,904
Suite
$2,825
From (Per Person)
A$1,103
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
$593
Oceanview
$660
Balcony
$846
Suite
$1,412
From (Per Person)
A$686
Save 535
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
$2,600
Balcony
$3,808
Suite
$5,660
From (Per Person)
A$2,165
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
$1,601
Oceanview
$1,784
Balcony
$2,928
Suite
$3,921
From (Per Person)
A$1,877
Save 673
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 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, Barbados, Guadeloupe
Exclusive Savings
Inside
$2,234
Oceanview
$2,690
Balcony
$3,838
Suite
$5,679
From (Per Person)
A$2,234
Save 48
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
$2,181
Oceanview
$2,825
Balcony
$3,439
Suite
$4,587
From (Per Person)
A$2,181
Save 35
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
$2,716
Oceanview
$3,586
Balcony
$5,443
Suite
-
From (Per Person)
A$3,196
Save 881
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: Sep 2026 to Oct 2027
Visits: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,578
Oceanview
$1,894
Balcony
$1,887
Suite
$4,024
From (Per Person)
A$1,625
Save 912
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: Aug 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$1,071
Oceanview
$1,388
Balcony
$1,685
Suite
$2,556
From (Per Person)
A$1,071
Save 17
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
$1,103
Oceanview
$1,340
Balcony
$1,934
Suite
$2,835
From (Per Person)
A$1,103
Save 24
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: Aug 2026 to Jul 2027
Visits: USA, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,830
Oceanview
$2,117
Balcony
$2,158
Suite
$4,240
From (Per Person)
A$1,871
Save 1,003
Per Person
View Trip
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Routes

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Country Routes

Cruises from Barbados to Puerto Rico Cruises from Puerto Rico to Barbados Cruises from Puerto Rico to USA Cruises from Dominican Republic to USA Cruises from USA to Puerto Rico Cruises from Barbados to USA Cruises from USA to Dominican Republic Cruises from USA to Barbados

Cruise Lines Exploring The Caribbean & Bahamas

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