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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 59 unique cruises and 1,467 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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59 Cruises (1,467 Departures)
59 Cruises (1,467 Departures)
Departures
Duration
5 Days
15 Days
Start & End Cities
Ship Size
Cruise Lines
Price
$300pp
$209,450pp
Countries
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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
$1,142
Oceanview
$1,246
Balcony
$1,425
Suite
$1,960
From (Per Person)
A$1,142
Save 21
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: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,021
Oceanview
$1,170
Balcony
$1,274
Suite
$1,690
From (Per Person)
A$1,021
Save 21
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
$715
Oceanview
$873
Balcony
$1,170
Suite
$2,309
From (Per Person)
A$715
Save 16
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
$1,728
Oceanview
$2,122
Balcony
$2,308
Suite
$5,982
From (Per Person)
A$1,728
Save 1,565
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
$1,109
Balcony
$1,689
Suite
$2,312
From (Per Person)
A$1,047
Save 904
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
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,457
From (Per Person)
A$735
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: Oct 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,319
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 20
Per Person
View Trip
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
$1,683
Oceanview
$1,685
Balcony
$2,053
Suite
$7,020
From (Per Person)
A$1,683
Save 914
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
$1,294
Oceanview
$1,297
Balcony
$1,784
Suite
$6,340
From (Per Person)
A$1,294
Save 667
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
$1,567
Oceanview
$1,874
Balcony
$2,409
Suite
$4,993
From (Per Person)
A$1,567
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
$1,482
Oceanview
$1,551
Balcony
$2,090
Suite
$5,238
From (Per Person)
A$1,482
Save 1,132
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
$666
Oceanview
$800
Balcony
$829
Suite
$843
From (Per Person)
A$666
Save 13
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
$1,512
Oceanview
$1,593
Balcony
$2,187
Suite
$6,319
From (Per Person)
A$1,512
Save 837
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
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,437
From (Per Person)
A$735
Save 15
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
$1,627
Oceanview
$1,825
Balcony
$2,359
Suite
$4,924
From (Per Person)
A$1,627
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
Drinks On Us
Inside
$878
Oceanview
$1,100
Balcony
$1,320
Suite
$3,911
From (Per Person)
A$878
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
Drinks On Us
Inside
$952
Oceanview
$1,099
Balcony
$1,174
Suite
$2,649
From (Per Person)
A$952
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
Ships: Harmony of the Seas, Star Of The Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Mexico, Honduras, Bahamas
Exclusive Savings
Inside
$1,454
Oceanview
$1,544
Balcony
$1,711
Suite
$3,205
From (Per Person)
A$1,454
Save 1,631
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
$2,086
Oceanview
$2,264
Balcony
$2,485
Suite
$4,796
From (Per Person)
A$2,086
Save 1,505
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: Oct 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$549
Oceanview
$578
Balcony
$833
Suite
$1,324
From (Per Person)
A$549
Save 990
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: Harmony of the Seas
Departure: 22 May 2027
Visits: USA, Bahamas, Jamaica, Mexico
Exclusive Savings
Inside
$1,550
Oceanview
$1,826
Balcony
$1,783
Suite
$3,703
From (Per Person)
A$1,550
Save 957
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
$853
Oceanview
$982
Balcony
$1,279
Suite
$2,556
From (Per Person)
A$853
Save 17
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC World Atlantic
Departures: Dec 2027 to Oct 2028
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Mexico
Exclusive Savings
Inside
$2,617
Oceanview
$3,171
Balcony
$3,468
Suite
$6,498
From (Per Person)
A$2,617
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 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
$1,174
Oceanview
$2,010
Balcony
$2,068
Suite
$3,539
From (Per Person)
A$1,174
Save 1,194
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
$1,247
Balcony
$1,723
Suite
$2,569
From (Per Person)
A$1,027
Save 836
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: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,067
Oceanview
$1,171
Balcony
$1,647
Suite
$2,183
From (Per Person)
A$1,067
Save 25
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: Dec 2027 to Oct 2028
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$1,279
Oceanview
$1,556
Balcony
$1,705
Suite
$2,269
From (Per Person)
A$1,279
Per Person
View Trip
8 Day Western 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 +2 more, Norwegian Luna, Norwegian Viva
Departures: Oct 2026 to Feb 2028
Visits: USA, Honduras, Belize, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,096
Oceanview
$1,200
Balcony
$1,409
Suite
$1,691
From (Per Person)
A$1,096
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: Nov 2026 to Oct 2028
Visits: USA, Honduras, Mexico, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$1,934
Oceanview
$2,053
Balcony
$2,647
Suite
$4,587
From (Per Person)
A$1,934
Save 32
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Cruise Lines Exploring The Caribbean & Bahamas

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