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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 76 departures available, operated by four of the world's leading cruise lines departing in October.
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11 Cruises (76 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
$358
Oceanview
$428
Balcony
$609
Suite
$2,249
From
US$358
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
$909
Balcony
$912
Suite
$1,958
From
US$837
Save 486
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: May 2026 to Oct 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$830
Oceanview
$855
Balcony
$1,058
Suite
$3,206
From
US$887
Save 1,082
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
$987
Oceanview
$987
Balcony
$1,269
Suite
$3,049
From
US$987
Save 580
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
$847
Oceanview
$851
Balcony
$903
Suite
$2,192
From
US$847
Save 482
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
$784
Oceanview
$884
Balcony
$887
Suite
$2,477
From
US$802
Save 505
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
$2,385
From
US$840
Save 417
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
$1,632
From
US$734
Save 404
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
$1,209
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
$879
Balcony
$949
Suite
$1,149
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 849
Per Person
View Trip
Results: 11 results

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