Home > Cruises > Caribbean Cruises > Cayman Islands > October

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 10 unique cruise itineraries and 107 departures available, operated by four of the world's leading cruise lines departing in October.
Filter Results
Departures
Duration
6 Days
10 Days
Countries Visited
Start & End Cities
Ship Size
Operators
Price
$300pp
$18,998pp
Countries
Show More...
Filter Results
10 Cruises (107 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
Bonus Onboard Credit
Inside
$424
Oceanview
$474
Balcony
$599
Suite
$1,674
From
US$424
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: Feb 2026 to Oct 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$662
Oceanview
$762
Balcony
$792
Suite
$1,967
From
US$662
Save 3,657
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
Ship: Celebrity Apex
Departures: Oct 2026 to Nov 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$737
Oceanview
$764
Balcony
$920
Suite
$2,519
From
US$737
Save 1,004
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
$522
Oceanview
$573
Balcony
$691
Suite
$2,121
From
US$522
Save 675
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
$727
Oceanview
$863
Balcony
$1,042
Suite
$2,581
From
US$727
Save 753
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
$2,310
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
$1,557
From
US$734
Save 404
Per Person
View Trip
8 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Prima
Departures: Feb 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$1,968
From
US$1,968
Save 141
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
$905
Oceanview
$1,005
Balcony
$1,180
Suite
$3,229
From
US$905
Save 975
Per Person
View Trip
8 Day Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise

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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$2,201
From
US$2,201
Save 159
Per Person
View Trip
Results: 10 results

No results found. Try amending the search filters.




Cruises found! Scroll up to view.

Caribbean & Bahamas Cruises

Aruba Cruises Bahamas Cruises Barbados Cruises Bermunda Cruises Caribbean Cruises Central America Cruises Jamaica Cruises Mexico Cruises Panama Cruises Puerto Rico Cruises Virgin Islands Cruises

Travel Styles

Luxury Cruises

Trip Lengths

10 Day 7 Day

Departure Months

January February March April May June July August September October November December

Cruise Lines Exploring The Caribbean & Bahamas

Azamara Caribbean Cruises Celebrity Caribbean Cruises Cunard Caribbean Cruises Emerald Caribbean Cruises Explora Journeys Caribbean Cruises Holland America Caribbean Cruises MSC Caribbean Cruises NCL Caribbean Cruises Oceania Caribbean Cruises Ponant Caribbean Cruises Princess Caribbean Cruises Regent Seven Seas Caribbean Cruises Royal Caribbean Caribbean Cruises Scenic Caribbean Cruises Seabourn Caribbean Cruises Silversea Caribbean Cruises Viking Caribbean Cruises Virgin Voyages Caribbean Cruises

© 2010-2026. Global Journeys. You're viewing our site in US dollars.

    

About Us | View Your Booking | Operators | Terms & Conditions | Site Map | We're hiring!

Global Journeys Travel Inc. is a Member of the American Society of Travel Advisors (ASTA No: 900374670), CLIA (No. 00046729) & is TICO Accredited (No. 50027921).

Travel Industry Associations