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Jamaica Cruises Starting In May 2026 and 2027

If you're looking at joining a cruise to Jamaica in May 2026 or 2027, we have 6 unique cruise itineraries and 83 departures available, operated by two of the world's leading cruise lines departing in May.
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6 Cruises (83 Cruise Departures)
6 Day Western Caribbean Getaway with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departure: 01 May 2027
Visit: USA, Jamaica, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$742
Oceanview
$791
Balcony
$929
Suite
$1,291
From
US$742
Save 340
Per Person
View Trip
7 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Mar 2026 to Jun 2026
Visit: USA, Bahamas, Jamaica
Exclusive Savings
Inside
$791
Oceanview
$865
Balcony
$1,254
Suite
$1,529
From
US$791
Save 560
Per Person
View Trip
6 Day Perfect Day Cococay & West Carib with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departures: May 2027 to Oct 2027
Visit: USA, Jamaica, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$770
Oceanview
$819
Balcony
$998
Suite
$1,349
From
US$770
Save 429
Per Person
View Trip
7 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: May 2026 to Sep 2026
Visit: USA, Jamaica, Cayman Islands, Bahamas
Exclusive Savings
Inside
$564
Oceanview
$735
Balcony
$869
Suite
$1,133
From
US$564
Save 622
Per Person
View Trip
8 Day Perfect Day Cococay & West Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: May 2027 to Jul 2027
Visit: USA, Bahamas, Jamaica, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$956
Oceanview
$1,106
Balcony
$1,223
Suite
$2,299
From
US$956
Save 665
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: Mar 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$759
Oceanview
$879
Balcony
$1,049
Suite
$1,319
From
US$759
Per Person
View Trip
Results: 6 results

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