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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 73 departures available, operated by four of the world's leading cruise lines departing in October.
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11 Cruises (73 Cruise Departures)
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
Flash Sale
Inside
$328
Oceanview
$398
Balcony
$588
Suite
$2,249
From
US$328
Per Person
View Trip
7 Day Key West, Mexico & Cayman with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Reflection
Departures: Aug 2027 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$812
Oceanview
$876
Balcony
$879
Suite
$1,908
From
US$812
Save 511
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$862
Oceanview
$862
Balcony
$1,144
Suite
$2,322
From
US$880
Save 685
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$699
Oceanview
$865
Balcony
$933
Suite
$2,545
From
US$699
Save 743
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
$677
Oceanview
$809
Balcony
$773
Suite
$2,318
From
US$677
Save 823
Per Person
View Trip
7 Day Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Reflection
Departures: Oct 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$726
Oceanview
$726
Balcony
$729
Suite
$2,100
From
US$726
Save 607
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
$957
Balcony
$1,320
Suite
$2,360
From
US$840
Save 417
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: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$879
Balcony
$979
Suite
$1,149
From
US$699
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
Ships: Norwegian Aqua, Norwegian Epic
Departures: Dec 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$829
Oceanview
$1,449
Balcony
$1,109
Suite
$1,209
From
US$829
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
$1,005
Oceanview
$1,105
Balcony
$1,322
Suite
$4,115
From
US$1,005
Save 868
Per Person
View Trip
Results: 11 results

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