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Cayman Islands Cruises Starting In December 2026 and 2027

If you're looking at joining a cruise to Cayman Islands in December 2026 or 2027, we have 48 unique cruise itineraries and 181 departures available, operated by eight of the world's leading cruise lines departing in December.
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48 Cruises (181 Cruise Departures)
8 Day Key West, Grand Cayman & Mexico with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 04 December 2027
Visit: USA, Mexico, Cayman Islands
Exclusive Savings
Inside
$959
Oceanview
$1,034
Balcony
$1,264
Suite
$3,240
From
US$959
Save 553
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
6 Day Grand Cayman & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2026 to Apr 2028
Visit: USA, Cayman Islands, Bahamas
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,645
From
US$595
Per Person
View Trip
8 Day Western Caribbean Holiday with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Reflection
Departure: 21 December 2026
Visit: USA, Mexico, Cayman Islands
Exclusive Savings
Inside
$934
Oceanview
$1,009
Balcony
$1,012
Suite
$3,142
From
US$934
Save 534
Per Person
View Trip
7 Day Key West, Cayman & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Silhouette
Departures: Dec 2027 to Apr 2028
Visit: USA, Cayman Islands, Bahamas
Exclusive Savings
Inside
$656
Oceanview
$763
Balcony
$765
Suite
$2,127
From
US$656
Save 480
Per Person
View Trip
8 Day Grand Cayman & Mexico Holiday with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 26 December 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,289
Oceanview
$1,489
Balcony
$1,889
Suite
$4,657
From
US$1,289
Save 752
Per Person
View Trip
9 Day Western Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) New Orleans to New Orleans
Cruise Line: Royal Caribbean
Ship: Mariner of the Seas
Departure: 31 December 2027
Visit: USA, Mexico, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,457
Oceanview
$1,508
Balcony
$1,758
Suite
$2,668
From
US$1,457
Save 553
Per Person
View Trip
8 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Celebrity Cruises
Ship: Celebrity Constellation
Departures: Dec 2027 to Mar 2028
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$622
Oceanview
$672
Balcony
$952
Suite
$2,565
From
US$622
Save 488
Per Person
View Trip
6 Day Western Caribbean Cruise with Royal Caribbean
Cruise

6 Days (5 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departures: Dec 2026 to Apr 2027
Visit: USA, Cayman Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$708
Oceanview
$768
Balcony
$888
Suite
$1,419
From
US$708
Save 366
Per Person
View Trip
7 Day Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

7 Days (6 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 13 December 2026
Visit: USA, Cayman Islands, Jamaica, Bahamas
Inside
$834
Oceanview
$894
Balcony
$954
Suite
$2,454
From
US$834
Per Person
View Trip
8 Day Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Feb 2027 to Dec 2027
Visit: USA, Cayman Islands, Jamaica, Bahamas
Inside
$833
Oceanview
$1,043
Balcony
$1,253
Suite
$3,073
From
US$833
Per Person
View Trip
8 Day Western Caribbean & Bimini New Year's with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Brilliant Lady
Departure: 28 December 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands
Inside
$1,883
Oceanview
$2,093
Balcony
$2,241
Suite
$4,480
From
US$1,883
Per Person
View Trip
8 Day Western Caribbean & Bimini Holiday with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 20 December 2027
Visit: USA, Cayman Islands, Jamaica, Bahamas
Inside
$1,113
Oceanview
$1,323
Balcony
$1,533
Suite
$3,850
From
US$1,113
Per Person
View Trip
8 Day Western Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Epic
Departure: 13 December 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Inside
$669
Oceanview
-
Balcony
$929
Suite
$1,129
From
US$669
Per Person
View Trip
8 Day Western Caribbean & Bimini New Year's with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 27 December 2026
Visit: USA, Cayman Islands, Jamaica, Bahamas
Inside
$1,743
Oceanview
$1,953
Balcony
$2,233
Suite
$5,803
From
US$1,743
Per Person
View Trip
7 Day Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Nov 2027 to Dec 2027
Visit: USA, Mexico, Cayman Islands, Bahamas
Exclusive Savings
Inside
$791
Oceanview
$892
Balcony
$1,015
Suite
$2,427
From
US$791
Save 452
Per Person
View Trip
8 Day Cayman, Mexico & Bahamas Holiday with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 27 December 2026
Visit: USA, Mexico, Cayman Islands, Bahamas
Exclusive Savings
Inside
$1,564
Oceanview
$1,619
Balcony
$2,224
Suite
$5,138
From
US$1,564
Save 902
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise

11 Days (10 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Nov 2026 to Dec 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands
Inside
$1,041
Oceanview
$1,211
Balcony
$1,441
Suite
$2,971
From
US$1,041
Per Person
View Trip
8 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Xcel
Departures: Dec 2027 to Feb 2028
Visit: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$1,023
Oceanview
$1,101
Balcony
$1,401
Suite
$3,346
From
US$1,023
Save 620
Per Person
View Trip
8 Day Grand Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 06 December 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
-
Oceanview
$976
Balcony
$1,163
Suite
$2,787
From
US$976
Save 631
Per Person
View Trip
9 Day Western Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Serenade of the Seas
Departure: 23 December 2027
Visit: USA, Mexico, Jamaica, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,294
Oceanview
$1,394
Balcony
$2,032
Suite
$3,012
From
US$1,294
Save 476
Per Person
View Trip
8 Day Western Caribbean Holiday Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Freedom of the Seas
Departure: 23 December 2027
Visit: USA, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,332
Oceanview
$1,444
Balcony
$1,836
Suite
$2,716
From
US$1,332
Save 474
Per Person
View Trip
9 Day Western Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 19 December 2027
Visit: USA, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,688
Oceanview
$1,898
Balcony
$2,395
Suite
$3,496
From
US$1,688
Save 635
Per Person
View Trip
9 Day Western Caribbean Holiday Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 20 December 2026
Visit: USA, Mexico, Belize, Cayman Islands
Exclusive Savings
Inside
$966
Oceanview
$1,016
Balcony
$1,228
Suite
$2,908
From
US$966
Save 536
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) New Orleans to New Orleans
Cruise Line: Royal Caribbean
Ship: Mariner of the Seas
Departures: Dec 2026 to Feb 2027
Visit: USA, Mexico, Cayman Islands, Jamaica
Bonus Onboard Credit
Exclusive Savings
Inside
$819
Oceanview
$959
Balcony
$1,320
Suite
$2,073
From
US$819
Save 515
Per Person
View Trip
8 Day Western Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 20 December 2026
Visit: USA, Bahamas, Cayman Islands, Jamaica
Exclusive Savings
Inside
$1,159
Oceanview
$1,409
Balcony
$1,502
Suite
$2,540
From
US$1,159
Save 592
Per Person
View Trip
8 Day Western Caribbean & Perfect Day Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 27 December 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands
Exclusive Savings
Inside
$1,564
Oceanview
$1,864
Balcony
$2,966
Suite
$5,294
From
US$1,564
Save 776
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) New Orleans to New Orleans
Cruise Line: Royal Caribbean
Ship: Mariner of the Seas
Departure: 05 December 2026
Visit: USA, Mexico, Cayman Islands, Jamaica
Exclusive Savings
Inside
$584
Oceanview
$694
Balcony
$936
Suite
$1,756
From
US$584
Save 377
Per Person
View Trip
8 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 06 December 2026
Visit: USA, Bahamas, Cayman Islands, Jamaica
Exclusive Savings
Inside
$635
Oceanview
$775
Balcony
$1,067
Suite
$2,177
From
US$635
Save 381
Per Person
View Trip
7 Day Cayman, Mexico & Bahamas Holiday with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Reflection, Celebrity Silhouette
Departures: Sep 2026 to Dec 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Exclusive Savings
Inside
$682
Oceanview
$838
Balcony
$841
Suite
$2,317
From
US$682
Save 729
Per Person
View Trip
Results: 1-30 of 48

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