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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
Inside
$745
Oceanview
$845
Balcony
$995
Suite
$2,875
From
US$745
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
$841
Oceanview
$1,805
Balcony
$1,358
Suite
$3,023
From
US$841
Save 577
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
$1,406
Suite
$3,020
From
US$1,183
Save 600
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
Bonus Onboard Credit
Exclusive Savings
Inside
$631
Oceanview
$760
Balcony
$853
Suite
$1,083
From
US$631
Save 618
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
$727
Oceanview
$863
Balcony
$1,042
Suite
$2,581
From
US$727
Save 753
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
$898
Oceanview
$993
Balcony
$1,159
Suite
$3,361
From
US$898
Save 605
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
$501
Oceanview
$611
Balcony
$1,163
Suite
$1,573
From
US$501
Save 314
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise

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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$2,201
From
US$2,201
Save 159
Per Person
View Trip
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