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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 12 unique cruise itineraries and 87 departures available, operated by four of the world's leading cruise lines departing in October.
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12 Cruises (87 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
Drinks & WiFi Package
Inside
$378
Oceanview
$448
Balcony
$588
Suite
$2,249
From
US$378
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
$919
Oceanview
$1,015
Balcony
$1,164
Suite
$2,825
From
US$919
Save 1,097
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
$837
Oceanview
$933
Balcony
$957
Suite
$2,010
From
US$837
Save 486
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
$751
Oceanview
$751
Balcony
$774
Suite
$1,912
From
US$751
Save 502
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
$846
Oceanview
$937
Balcony
$1,456
Suite
$2,057
From
US$846
Save 292
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: Aug 2026 to Oct 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$900
Oceanview
$937
Balcony
$1,149
Suite
$3,169
From
US$900
Save 576
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
$952
Oceanview
$1,052
Balcony
$1,470
Suite
$2,810
From
US$952
Save 305
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
$889
Balcony
$1,058
Suite
$3,117
From
US$889
Save 492
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
$702
Oceanview
$870
Balcony
$824
Suite
$2,372
From
US$702
Save 461
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
$1,169
Suite
$1,319
From
US$829
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
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
$1,055
Oceanview
$1,155
Balcony
$1,457
Suite
$4,265
From
US$1,055
Save 554
Per Person
View Trip
Results: 12 results

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