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Cayman Islands Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Cayman Islands in October 2026 or 2027, we have 11 unique cruise itineraries and 107 departures available, operated by four of the world's leading cruise lines departing in October.
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11 Cruises (107 Cruise Departures)
7 Day Key West, Mexico & Cayman with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Mar 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$812
Oceanview
$912
Balcony
$942
Suite
$2,117
From
US$953
Save 3,253
Per Person
View Trip
8 Day Key West, Cayman & Mexico with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ships: Celebrity Apex
Departures: Oct 2026 to Nov 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$737
Oceanview
$780
Balcony
$919
Suite
$2,887
From
US$866
Save 635
Per Person
View Trip
6 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

6 Days (5 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visit: USA, Cayman Islands, Jamaica
Bonus Onboard Credit
Drinks, WiFi & Onboard Credit
Inside
$439
Oceanview
$489
Balcony
$629
Suite
$1,769
From
US$439
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Enchantment of the Seas
Departure: 23 October 2027
Visit: USA, Mexico, Honduras, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$734
Oceanview
$824
Balcony
$1,306
Suite
$1,607
From
US$734
Save 404
Per Person
View Trip
10 Day Cape Liberty To Miami Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) New York to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 28 October 2027
Visit: USA, Bermuda, Aruba, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$940
Balcony
$1,320
Suite
$2,360
From
US$840
Save 417
Per Person
View Trip
7 Day Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise
 (2)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Eclipse, Celebrity Reflection
Departures: Apr 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$564
Oceanview
$715
Balcony
$718
Suite
$2,021
From
US$656
Save 368
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
7 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Aug 2026 to Mar 2027
Visit: USA, Mexico, Cayman Islands, Bahamas
Exclusive Savings
Inside
$579
Oceanview
$628
Balcony
$749
Suite
$2,283
From
US$668
Save 462
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
10 Day Aruba, Bonaire & Curacao with Celebrity Cruises
Cruise

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Oct 2026 to Aug 2027
Visit: USA, Cayman Islands, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$890
Oceanview
$1,155
Balcony
$1,307
Suite
$3,376
From
US$1,051
Save 635
Per Person
View Trip
8 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Aqua
Departures: Apr 2027 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,269
Oceanview
$1,489
Balcony
$1,769
Suite
$2,355
From
US$1,269
Save 54
Per Person
View Trip
Results: 11 results

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