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Cayman Islands Cruises Starting In May 2026 and 2027

If you're looking at joining a cruise to Cayman Islands in May 2026 or 2027, we have 8 unique cruise itineraries and 87 departures available, operated by four of the world's leading cruise lines departing in May.
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8 Cruises (87 Cruise Departures)
6 Day Cayman Isles & Bimini Beach Miles with Virgin Voyages
Cruise
 (5)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2026 to Sep 2027
Visit: USA, Cayman Islands, Bahamas
With Love From the World
Inside
$745
Oceanview
$845
Balcony
$995
Suite
$2,795
From
US$745
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
$606
Oceanview
$725
Balcony
$858
Suite
$1,273
From
US$606
Save 596
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$797
Oceanview
$850
Balcony
$1,048
Suite
$2,796
From
US$931
Save 421
Per Person
View Trip
8 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 17 May 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,016
Oceanview
$1,070
Balcony
$1,198
Suite
$3,417
From
US$1,192
Save 426
Per Person
View Trip
8 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 03 May 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$919
Oceanview
$1,019
Balcony
$1,074
Suite
$3,266
From
US$1,074
Save 383
Per Person
View Trip
8 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 22 May 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$1,183
Oceanview
$1,263
Balcony
$1,457
Suite
$3,020
From
US$1,183
Save 600
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
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Tampa to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departure: 02 May 2026
Visit: USA, Cayman Islands, Aruba, Curacao, Panama
Inside
$349
Oceanview
$429
Balcony
$994
Suite
$1,453
From
US$349
Per Person
View Trip
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