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Cayman Islands Cruises Starting In December 2026 and 2027

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15 Days
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44 Cruises (184 Cruise Departures)
8 Day Western Caribbean: Greater Antilles & Mexico with Holland America
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 12 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Fare Saver
Inside
$544
Oceanview
$644
Balcony
$944
Suite
$1,699
From
US$544
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
$879
Balcony
$1,049
Suite
$1,319
From
US$759
Per Person
View Trip
9 Day Western Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Explorer of the Seas
Departure: 18 December 2027
Visit: USA, Jamaica, Cayman Islands, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,745
Oceanview
$1,975
Balcony
$2,355
Suite
$3,483
From
US$1,745
Save 816
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 December 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Inside
$1,241
Oceanview
$1,371
Balcony
$1,561
Suite
$2,317
From
US$1,241
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departure: 20 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Dominican Republic
Bonus Onboard Credit
Exclusive Savings
Inside
$2,101
Oceanview
$2,353
Balcony
$2,673
Suite
$3,566
From
US$2,101
Save 51
Per Person
View Trip
8 Day Western Caribbean with Grand Cayman Holiday with Princess
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departure: 19 December 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$1,044
Oceanview
$1,463
Balcony
$1,345
Suite
$1,844
From
US$1,044
Per Person
View Trip
10 Day Western Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Mar 2026 to Dec 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Mexico
Inside
$649
Oceanview
$699
Balcony
$899
Suite
$2,699
From
US$649
Per Person
View Trip
9 Day Perfect Day Cococay Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 31 December 2027
Visit: USA, Bahamas, Cayman Islands, Jamaica, Haiti
Bonus Onboard Credit
Exclusive Savings
Inside
$1,638
Oceanview
$1,867
Balcony
$2,307
Suite
$3,505
From
US$1,638
Save 765
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
Ship: Norwegian Aqua
Departures: Apr 2027 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,269
Oceanview
$1,489
Balcony
$1,769
Suite
$2,355
From
US$1,269
Save 54
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Seaside
Departure: 28 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Inside
$1,513
Oceanview
$1,713
Balcony
$2,043
Suite
-
From
US$1,513
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 Getaway, Norwegian Prima
Departures: Mar 2026 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$749
Oceanview
$869
Balcony
$1,119
Suite
$1,389
From
US$749
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 December 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Inside
$1,536
Oceanview
$1,686
Balcony
$1,946
Suite
$3,021
From
US$1,536
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Explorer of the Seas
Departure: 21 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,085
Oceanview
$1,193
Balcony
$1,758
Suite
$2,313
From
US$1,085
Save 588
Per Person
View Trip
8 Day Western Caribbean Holiday: Greater Antilles with Holland America
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Eurodam, Nieuw Statendam
Departures: Nov 2026 to Feb 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Fare Saver
Inside
$644
Oceanview
$744
Balcony
$994
Suite
$1,499
From
US$644
Per Person
View Trip
Results: 31-44 of 44

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