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 1,345 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 (1,345 Departures)
57 Cruises (1,345 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$300pp
$197,370pp
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
$1,613
Oceanview
$1,794
Balcony
$2,053
Suite
$7,133
From (Per Person)
A$2,439
Save 41
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
$626
Oceanview
$764
Balcony
$962
Suite
$1,863
From (Per Person)
A$626
Save 47
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
$1,632
Oceanview
$1,670
Balcony
$2,416
Suite
$6,030
From (Per Person)
A$2,477
Save 42
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
$1,849
Oceanview
$1,894
Balcony
$2,354
Suite
$5,982
From (Per Person)
A$2,863
Save 53
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 +2 more, Norwegian Escape, Norwegian Getaway
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$976
Oceanview
$1,110
Balcony
$1,229
Suite
$1,517
From (Per Person)
A$976
Save 18
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: Nov 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,097
Oceanview
$1,171
Balcony
$1,335
Suite
$1,876
From (Per Person)
A$1,097
Save 23
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
$935
Oceanview
$1,082
Balcony
$1,226
Suite
$2,605
From (Per Person)
A$935
Per Person
View Trip
8 Day Perfect Day Cococay & Caribbean 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
$1,622
Oceanview
$1,619
Balcony
$2,428
Suite
$8,337
From (Per Person)
A$2,472
Save 54
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
$1,290
Oceanview
$1,567
Balcony
$2,003
Suite
$4,072
From (Per Person)
A$1,290
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
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
$1,047
Oceanview
$1,115
Balcony
$1,675
Suite
$2,251
From (Per Person)
A$1,220
Save 629
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
$645
Oceanview
$764
Balcony
$982
Suite
$2,111
From (Per Person)
A$645
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
$621
Oceanview
$665
Balcony
$867
Suite
$933
From (Per Person)
A$621
Save 13
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
$1,251
Oceanview
$1,528
Balcony
$1,963
Suite
$4,310
From (Per Person)
A$1,251
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
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Aug 2027
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,370
Oceanview
$1,595
Balcony
$1,983
Suite
$4,898
From (Per Person)
A$2,059
Save 48
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
$863
Oceanview
$1,081
Balcony
$1,298
Suite
$3,845
From (Per Person)
A$863
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, Norwegian Escape
Departures: Dec 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,572
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
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: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$636
Oceanview
$774
Balcony
$1,022
Suite
$2,309
From (Per Person)
A$636
Save 16
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: Jan 2028 to Nov 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,408
Oceanview
$1,685
Balcony
$1,824
Suite
$2,477
From (Per Person)
A$1,408
Per Person
View Trip
8 Day Eastern Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Aura, Norwegian Luna
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$962
Oceanview
$1,289
Balcony
$1,543
Suite
$1,989
From (Per Person)
A$962
Save 22
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
$1,420
Oceanview
$1,848
Balcony
$2,500
Suite
$4,228
From (Per Person)
A$1,596
Save 635
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
$1,328
Oceanview
$1,403
Balcony
$1,404
Suite
$3,665
From (Per Person)
A$1,478
Save 454
Per Person
View Trip
7 Day Perfect Day Cococay & West Caribbean with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Allure of the Seas
Departures: May 2027 to Oct 2027
Visits: USA, Bahamas, Jamaica
Exclusive Savings
Inside
$1,146
Oceanview
$1,305
Balcony
$1,317
Suite
$2,453
From (Per Person)
A$1,377
Save 569
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
$1,027
Oceanview
$1,188
Balcony
$1,723
Suite
$2,500
From (Per Person)
A$1,226
Save 691
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: Nov 2026 to Nov 2028
Visits: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Exclusive Savings
Inside
$1,122
Oceanview
$1,301
Balcony
$1,924
Suite
$2,677
From (Per Person)
A$1,122
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC World America
Departures: Nov 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas
Exclusive Savings
Inside
$764
Oceanview
$863
Balcony
$1,121
Suite
$2,764
From (Per Person)
A$764
Save 61
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: Nov 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$614
Oceanview
$659
Balcony
$731
Suite
$1,409
From (Per Person)
A$614
Save 984
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: Nov 2026 to Jul 2027
Visits: USA, Saint Martin, Virgin Islands, Bahamas
Exclusive Savings
Inside
$1,787
Oceanview
$2,144
Balcony
$2,249
Suite
$4,409
From (Per Person)
A$2,205
Save 1,086
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
$1,230
Oceanview
$1,513
Balcony
$1,896
Suite
$3,999
From (Per Person)
A$1,452
Save 724
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: Nov 2026 to Apr 2028
Visits: USA, Curacao, Aruba, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,700
Oceanview
$2,005
Balcony
$2,105
Suite
$3,927
From (Per Person)
A$2,061
Save 1,465
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: Dec 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$1,686
Oceanview
$1,973
Balcony
$2,538
Suite
$4,587
From (Per Person)
A$1,686
Save 35
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

Luxury Cruises Short Cruise Breaks

Countries

Anguilla Aruba Bahamas Barbados Belize Canada Cayman Islands China Curacao Dominican Republic Honduras Jamaica Japan Martinique Mexico Morocco Puerto Rico Saint Barthelemy Saint Lucia Saint Martin Saint Vincent Singapore South Korea 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 Tampa

Routes

Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Fort Lauderdale to San Juan 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 Fort Lauderdale Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Tampa to Tampa

Country Routes

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