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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 77 departures available, operated by four of the world's leading cruise lines departing in May.
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8 Cruises (77 Cruise Departures)
6 Day Grand Cayman & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2026 to Apr 2028
Visit: USA, Cayman Islands, Bahamas
Limited Time Offer
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,795
From
US$595
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
Bonus Onboard Credit
Exclusive Savings
Inside
$949
Oceanview
$980
Balcony
$1,209
Suite
$3,132
From
US$1,372
Save 25
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
Bonus Onboard Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$1,916
Suite
-
From
US$2,913
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,330
Oceanview
$1,441
Balcony
$1,684
Suite
$3,061
From
US$1,330
Save 688
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
Bonus Onboard Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,953
From
US$7,766
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
$660
Oceanview
$871
Balcony
$1,223
Suite
$1,693
From
US$660
Save 541
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: May 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$709
Oceanview
$849
Balcony
$999
Suite
$1,259
From
US$709
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
Exclusive Savings
Inside
$423
Oceanview
$481
Balcony
$1,243
Suite
$1,161
From
US$462
Save 298
Per Person
View Trip
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