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Cayman Islands Cruises Starting In November 2026 and 2027

If you're looking at joining a cruise to Cayman Islands in November 2026 or 2027, we have 39 unique cruise itineraries and 184 departures available, operated by ten of the world's leading cruise lines departing in November.
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39 Cruises (184 Cruise Departures)
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Galveston to Galveston
Cruise Line: Royal Caribbean
Ship: Liberty of the Seas
Departure: 26 November 2027
Visit: USA, Mexico, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$811
Oceanview
$949
Balcony
$1,312
Suite
$2,155
From
US$1,198
Save 50
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, Scarlet Lady
Departures: Jun 2026 to Mar 2027
Visit: USA, Cayman Islands, Bahamas
Limited Time Offer
Inside
$645
Oceanview
$745
Balcony
$945
Suite
$2,525
From
US$645
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
Limited Time Offer
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,795
From
US$595
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
$919
Oceanview
$1,019
Balcony
$1,219
Suite
$2,820
From
US$1,343
Save 25
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
$708
Balcony
$1,077
Suite
$2,774
From
US$947
Save 25
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
Departure: 28 November 2026
Visit: USA, Bahamas, Cayman Islands
Exclusive Savings
Inside
$556
Oceanview
$666
Balcony
$856
Suite
$1,436
From
US$556
Save 267
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
$629
Oceanview
$766
Balcony
$1,130
Suite
$1,974
From
US$943
Save 50
Per Person
View Trip
7 Day Grand Cayman & Mexico Cruise with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ships: Celebrity Beyond, Celebrity Silhouette
Departures: Nov 2027 to Apr 2028
Visit: USA, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$739
Oceanview
$784
Balcony
$862
Suite
$2,219
From
US$1,052
Save 25
Per Person
View Trip
7 Day Key West, Mexico & Bahamas with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Silhouette
Departure: 21 November 2027
Visit: USA, Bahamas, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$796
Oceanview
$893
Balcony
$970
Suite
$2,339
From
US$1,138
Save 25
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 28 November 2027
Visit: USA, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$728
Oceanview
$809
Balcony
$1,138
Suite
$1,753
From
US$1,070
Save 50
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
Inside
$859
Oceanview
$999
Balcony
$1,189
Suite
$1,949
From
US$859
Per Person
View Trip
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: 21 November 2026
Visit: USA, Jamaica, Cayman Islands, Mexico
Fare Saver
Inside
$649
Oceanview
$749
Balcony
$1,049
Suite
$1,549
From
US$649
Per Person
View Trip
8 Day Bahamas, Mexico & Cayman with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 14 November 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,041
Oceanview
$1,009
Balcony
$1,373
Suite
$4,359
From
US$1,474
Save 25
Per Person
View Trip
7 Day Bahamas, Mexico & Cayman Cruise with Celebrity Cruises
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Xcel
Departure: 15 November 2026
Visit: USA, Bahamas, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,061
Oceanview
$1,149
Balcony
$1,494
Suite
$3,667
From
US$1,536
Save 25
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 Western Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 01 November 2026
Visit: USA, Cayman Islands, Jamaica, Bahamas
Limited Time Offer
Inside
$1,043
Oceanview
$1,253
Balcony
$1,393
Suite
$3,493
From
US$1,043
Per Person
View Trip
8 Day Bahamas, Mexico & Cayman Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Xcel
Departure: 21 November 2026
Visit: USA, Cayman Islands, Mexico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,074
Oceanview
$1,116
Balcony
$1,744
Suite
$4,543
From
US$1,545
Save 25
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
Departures: Nov 2026 to Apr 2028
Visit: USA, Jamaica, Cayman Islands, Bahamas
Limited Time Offer
Inside
$774
Oceanview
$954
Balcony
$1,074
Suite
$2,634
From
US$774
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: 21 November 2027
Visit: USA, Bahamas, Cayman Islands, Jamaica
Inside
$691
Oceanview
$791
Balcony
$971
Suite
$1,701
From
US$691
Per Person
View Trip
9 Day Southern Caribbean with Aruba with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 14 November 2026
Visit: USA, Cayman Islands, Jamaica, Aruba
Princess Standard
Inside
$1,799
Oceanview
-
Balcony
$2,094
Suite
$2,319
From
US$1,799
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: 18 November 2027
Visit: USA, Bahamas, Cayman Islands, Jamaica
Inside
$997
Oceanview
$1,129
Balcony
$1,357
Suite
$2,416
From
US$997
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 21 November 2027
Visit: USA, Bahamas, Cayman Islands, Jamaica
Inside
$1,014
Oceanview
$1,156
Balcony
$1,396
Suite
$2,533
From
US$1,014
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
$798
Oceanview
$848
Balcony
$1,049
Suite
$2,195
From
US$1,125
Save 25
Per Person
View Trip
12 Day Caribbean And Antilles with MSC Cruises
Cruise

12 Days (11 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Seashore
Departure: 22 November 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands
Inside
$1,058
Oceanview
$1,238
Balcony
$1,478
Suite
$2,826
From
US$1,058
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
$841
Oceanview
$942
Balcony
$1,140
Suite
$2,722
From
US$1,203
Save 25
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
$504
Oceanview
$604
Balcony
$991
Suite
$1,629
From
US$524
Save 639
Per Person
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 15 November 2027
Visit: USA, Jamaica, Cayman Islands, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$640
Oceanview
$700
Balcony
$981
Suite
$1,506
From
US$944
Save 50
Per Person
View Trip
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Radiance of the Seas, Serenade of the Seas
Departures: Mar 2027 to Mar 2028
Visit: USA, Mexico, Honduras, Cayman Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$949
Oceanview
$1,048
Balcony
$1,587
Suite
$1,998
From
US$1,385
Save 50
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 (+2 more), Norwegian Getaway, Norwegian Prima
Departures: Apr 2026 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$769
Oceanview
$899
Balcony
$1,119
Suite
$1,229
From
US$769
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: May 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$709
Oceanview
$849
Balcony
$999
Suite
$1,259
From
US$709
Per Person
View Trip
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