Home > Cruises > Caribbean Cruises > May

Caribbean Cruises Starting In May 2027 and 2028

Are you planning a cruise to the Caribbean in May 2027 or 2028? Choose from 57 unique cruises and 1,530 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.
Filter Results
57 Cruises (1,530 Departures)
57 Cruises (1,530 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$400pp
$198,630pp
Countries
Show More...
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
$1,346
Oceanview
$1,348
Balcony
$1,800
Suite
$6,261
From (Per Person)
A$1,346
Save 949
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
$1,608
Oceanview
$1,680
Balcony
$2,055
Suite
$5,377
From (Per Person)
A$1,608
Save 1,541
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
$1,716
Oceanview
$1,983
Balcony
$2,518
Suite
$5,013
From (Per Person)
A$1,716
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
$1,706
Oceanview
$1,944
Balcony
$2,478
Suite
$4,983
From (Per Person)
A$1,706
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
Inside
$848
Oceanview
$1,132
Balcony
$1,346
Suite
$3,772
From (Per Person)
A$848
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: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,095
Oceanview
$1,318
Balcony
$1,393
Suite
$1,661
From (Per Person)
A$1,095
Save 20
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
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
$710
Oceanview
$888
Balcony
$1,097
Suite
$1,231
From (Per Person)
A$710
Save 12
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
$1,246
Oceanview
$1,396
Balcony
$1,604
Suite
$2,064
From (Per Person)
A$1,246
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
$794
Oceanview
$972
Balcony
$1,239
Suite
$2,477
From (Per Person)
A$794
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
$784
Oceanview
$962
Balcony
$1,230
Suite
$2,507
From (Per Person)
A$784
Save 15
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
$1,105
Oceanview
$1,316
Balcony
$1,752
Suite
$6,305
From (Per Person)
A$1,105
Save 799
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: Sep 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,126
Oceanview
$1,274
Balcony
$1,483
Suite
$1,826
From (Per Person)
A$1,126
Save 19
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
$1,019
Oceanview
$1,108
Balcony
$1,689
Suite
$2,332
From (Per Person)
A$1,019
Save 951
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
Inside
$919
Oceanview
$1,061
Balcony
$1,204
Suite
$3,056
From (Per Person)
A$919
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: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$913
Oceanview
$1,249
Balcony
$1,556
Suite
$2,309
From (Per Person)
A$913
Save 16
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
$1,539
Oceanview
$1,638
Balcony
$1,933
Suite
$6,325
From (Per Person)
A$1,539
Save 1,112
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
$1,253
Oceanview
$1,360
Balcony
$1,836
Suite
$4,839
From (Per Person)
A$1,253
Save 1,288
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, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$2,300
Oceanview
$2,696
Balcony
$3,359
Suite
$4,587
From (Per Person)
A$2,300
Save 35
Per Person
View Trip
15 Day South Caribbean with MSC Cruises
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Operator: 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
$2,214
Oceanview
$2,600
Balcony
$3,808
Suite
$5,660
From (Per Person)
A$2,214
Per Person
View Trip
9 Day Southern Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Independence of the Seas
Departures: May 2027 to Dec 2027
Visits: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,215
Oceanview
$1,467
Balcony
$1,767
Suite
$3,880
From (Per Person)
A$1,215
Save 1,244
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
$2,413
Oceanview
$2,818
Balcony
$2,771
Suite
$4,700
From (Per Person)
A$2,413
Save 1,276
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) La Romana to La Romana
Operator: 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
$1,103
Oceanview
$1,330
Balcony
$1,904
Suite
$2,825
From (Per Person)
A$1,103
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
$2,290
Oceanview
$2,835
Balcony
$3,429
Suite
$4,587
From (Per Person)
A$2,290
Save 35
Per Person
View Trip
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Enchantment of the Seas, Jewel of the Seas +2 more, Radiance of the Seas, Serenade of the Seas
Departures: Sep 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$593
Oceanview
$618
Balcony
$764
Suite
$1,412
From (Per Person)
A$593
Save 879
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$2,170
Save 1,630
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
$1,601
Oceanview
$1,784
Balcony
$2,848
Suite
$3,969
From (Per Person)
A$1,601
Save 994
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Icon Of The Seas
Departures: Sep 2026 to Jul 2027
Visits: USA, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,415
Oceanview
$1,575
Balcony
$1,909
Suite
$4,115
From (Per Person)
A$1,415
Save 1,574
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
$1,050
Oceanview
$1,255
Balcony
$1,788
Suite
$2,569
From (Per Person)
A$1,050
Save 836
Per Person
View Trip
9 Day Perfect Day Cococay & South Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ships: Allure of the Seas, Legend Of The Seas
Departures: Oct 2026 to Oct 2027
Visits: USA, Curacao, Aruba, Bahamas
Exclusive Savings
Inside
$1,355
Oceanview
$1,688
Balcony
$1,764
Suite
$3,800
From (Per Person)
A$1,355
Save 1,359
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: Star Of The Seas
Departures: Sep 2026 to Jan 2028
Visits: USA, Bahamas, Mexico, Honduras
Exclusive Savings
Inside
$2,100
Oceanview
$2,198
Balcony
$2,329
Suite
$4,270
From (Per Person)
A$2,100
Save 1,593
Per Person
View Trip
Results: 1-30 of 57

No trips found. Try adjusting the search filters.




Cruises found! Scroll up to view.

Caribbean & Bahamas Cruises

Aruba Cruises Bahamas Cruises Barbados Cruises Bermunda Cruises Caribbean Cruises Central America Cruises Jamaica Cruises Mexico Cruises Panama Cruises Puerto Rico Cruises Virgin Islands Cruises

Travel Styles

Festivals & Events Luxury Cruises Short Cruise Breaks Wildlife Cruises

Countries

Aruba Bahamas Barbados Belize Canada Cayman Islands China Curacao Dominican Republic Haiti Honduras Jamaica Martinique Mexico Morocco Puerto Rico Saint Barthelemy Saint Lucia Saint Martin Saint Vincent Singapore Spain Turks and Caicos Islands USA Vietnam Virgin Islands

Cities

Cruises from Bridgetown Cruises from Fort Lauderdale Cruises from Fort-de-France Cruises from Galveston Cruises from La Romana Cruises from Miami Cruises from Orlando Cruises from San Juan Cruises from San Juan Cruises from San Juan Cruises from Tampa

Routes

Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from La Romana to La Romana Cruises from Miami to San Juan Cruises from Miami to Miami Cruises from Miami to Bridgetown Cruises from Orlando to Orlando Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Tampa to Tampa

Country Routes

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

Cruise Lines Exploring The Caribbean & Bahamas

Azamara Caribbean Cruises Celebrity Caribbean Cruises Crystal Caribbean Cruises Cunard Caribbean Cruises Emerald Caribbean Cruises Explora Journeys Caribbean Cruises Holland America Caribbean Cruises MSC Caribbean Cruises NCL Caribbean Cruises Oceania Caribbean Cruises P&O (UK) Caribbean Cruises Ponant Caribbean Cruises Princess Caribbean Cruises Regent Seven Seas Caribbean Cruises Royal Caribbean Caribbean Cruises Scenic Caribbean Cruises Seabourn Caribbean Cruises Silversea Caribbean Cruises Viking Caribbean Cruises Virgin Voyages Caribbean Cruises
© 2010-2026. Global Journeys.
    

Global Journeys | Terms & Conditions

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (ATIA). No. A11351.

Travel Industry Associations