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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 99 departures available, operated by four of the world's leading cruise lines departing in October.
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11 Cruises (99 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
$419
Oceanview
$489
Balcony
$639
Suite
$1,769
From
US$419
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
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Apr 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$887
Oceanview
$987
Balcony
$1,092
Suite
$2,336
From
US$887
Save 645
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
Bonus Onboard Credit
Exclusive Savings
Inside
$839
Oceanview
$910
Balcony
$1,178
Suite
$3,490
From
US$839
Save 836
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
Bonus Onboard Credit
Exclusive Savings
Inside
$897
Oceanview
$952
Balcony
$1,199
Suite
$3,350
From
US$897
Save 639
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
Bonus Onboard Credit
Exclusive Savings
Inside
$669
Oceanview
$741
Balcony
$871
Suite
$2,514
From
US$669
Save 607
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
Bonus Onboard Credit
Exclusive Savings
Inside
$790
Oceanview
$865
Balcony
$943
Suite
$2,425
From
US$790
Save 430
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
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 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
Exclusive Savings
Inside
$849
Oceanview
$1,509
Balcony
$1,259
Suite
$1,359
From
US$849
Save 54
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,055
Oceanview
$1,155
Balcony
$1,330
Suite
$4,189
From
US$1,055
Save 647
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
$999
Balcony
$1,049
Suite
$1,319
From
US$759
Per Person
View Trip
Results: 11 results

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