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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 74 departures available, operated by four of the world's leading cruise lines departing in May.
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8 Cruises (74 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
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,645
From
US$595
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
$995
Oceanview
-
Balcony
-
Suite
-
From
US$995
Save 549
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
$1,024
Oceanview
$1,083
Balcony
-
Suite
$11,568
From
US$1,195
Save 390
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
$845
Oceanview
$837
Balcony
$1,058
Suite
$3,117
From
US$845
Save 2,549
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
$625
Oceanview
$886
Balcony
$1,068
Suite
$1,468
From
US$625
Save 566
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
$1,267
Oceanview
$1,414
Balcony
$1,632
Suite
$3,061
From
US$1,267
Save 650
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
$398
Oceanview
$511
Balcony
$969
Suite
$1,087
From
US$398
Save 306
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
$699
Oceanview
$849
Balcony
$979
Suite
$1,219
From
US$699
Per Person
View Trip
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