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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 44 unique cruise itineraries and 185 departures available, operated by eight of the world's leading cruise lines departing in December.
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44 Cruises (185 Cruise Departures)
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
$812
Oceanview
$855
Balcony
$1,069
Suite
$3,232
From
US$812
Save 840
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
$658
Oceanview
$719
Balcony
$788
Suite
$1,259
From
US$658
Save 426
Per Person
View Trip
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
Bonus Onboard Credit
Exclusive Savings
Inside
$909
Oceanview
$1,009
Balcony
$1,209
Suite
$2,909
From
US$909
Save 443
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,339
Oceanview
$1,539
Balcony
$2,014
Suite
$4,947
From
US$1,339
Save 702
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
Bonus Onboard Credit
Exclusive Savings
Inside
$990
Oceanview
$1,162
Balcony
$1,240
Suite
$3,787
From
US$990
Save 487
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: Nov 2027 to Mar 2028
Visit: USA, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$672
Oceanview
$722
Balcony
$1,077
Suite
$2,802
From
US$672
Save 438
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
$1,547
Oceanview
$1,597
Balcony
$1,967
Suite
$2,512
From
US$1,547
Save 752
Per Person
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ship: Liberty of the Seas
Departures: Nov 2027 to Jan 2028
Visit: USA, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$568
Oceanview
$688
Balcony
$869
Suite
$1,669
From
US$568
Save 488
Per Person
View Trip
7 Day Perfect Day Cococay & West Carib with Royal Caribbean
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 18 December 2027
Visit: USA, Bahamas, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$717
Oceanview
$798
Balcony
$957
Suite
$1,383
From
US$717
Save 384
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
Bonus Onboard Credit
Exclusive Savings
Inside
$763
Oceanview
$813
Balcony
$913
Suite
$2,152
From
US$763
Save 430
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
Bonus Onboard Credit
Exclusive Savings
Inside
$865
Oceanview
$965
Balcony
$1,140
Suite
$2,615
From
US$865
Save 402
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
$879
Oceanview
$966
Balcony
$1,248
Suite
$1,822
From
US$879
Save 536
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
With Love From the World
Inside
$714
Oceanview
$894
Balcony
$1,074
Suite
$2,574
From
US$714
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
Bonus Onboard Credit
Exclusive Savings
Inside
$765
Oceanview
$813
Balcony
$891
Suite
$2,893
From
US$765
Save 532
Per Person
View Trip
8 Day Western Carib & 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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,544
Oceanview
$1,574
Balcony
$2,360
Suite
$4,660
From
US$1,544
Save 768
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
Bonus Onboard Credit
Exclusive Savings
Inside
$675
Oceanview
$775
Balcony
$997
Suite
$1,367
From
US$675
Save 398
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
Bonus Onboard Credit
Inside
$888
Oceanview
$1,048
Balcony
$1,248
Suite
$2,684
From
US$888
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
Departures: Dec 2026 to Apr 2027
Visit: USA, Bahamas, Mexico, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$829
Oceanview
$942
Balcony
$1,185
Suite
$3,333
From
US$829
Save 710
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,285
Oceanview
$1,343
Balcony
$1,644
Suite
$3,044
From
US$1,285
Save 673
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
With Love From the World
Inside
$1,883
Oceanview
$2,093
Balcony
$2,373
Suite
$5,523
From
US$1,883
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,159
Oceanview
$1,359
Balcony
$1,582
Suite
$2,191
From
US$1,159
Save 592
Per Person
View Trip
8 Day Bahamas, Mexico & Cayman with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Xcel
Departures: Dec 2026 to Mar 2027
Visit: USA, Bahamas, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,028
Oceanview
$1,387
Balcony
$1,558
Suite
$4,225
From
US$1,028
Save 803
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: Nov 2026 to Apr 2027
Visit: USA, Mexico, Cayman Islands, Jamaica
Bonus Onboard Credit
Exclusive Savings
Inside
$564
Oceanview
$640
Balcony
$824
Suite
$1,227
From
US$631
Save 701
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,722
Oceanview
$1,893
Balcony
$2,675
Suite
$6,820
From
US$1,722
Save 916
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
Ship: Celebrity Silhouette
Departure: 13 December 2026
Visit: USA, Bahamas, Mexico, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$634
Oceanview
$704
Balcony
$879
Suite
$2,892
From
US$634
Save 259
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departures: Nov 2026 to Dec 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands
Bonus Onboard Credit
Inside
$789
Oceanview
$1,139
Balcony
$1,119
Suite
$1,569
From
US$789
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
$1,220
Oceanview
$1,332
Balcony
$1,630
Suite
$2,194
From
US$1,220
Save 586
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,071
Oceanview
$1,151
Balcony
$1,526
Suite
$3,500
From
US$1,071
Save 570
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
Bonus Onboard Credit
Exclusive Savings
Inside
$631
Oceanview
$781
Balcony
$953
Suite
$1,486
From
US$631
Save 397
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
Results: 1-30 of 44

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