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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 38 unique cruise itineraries and 157 departures available, operated by ten of the world's leading cruise lines departing in November.
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38 Cruises (157 Cruise Departures)
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
Inside
$823
Oceanview
$795
Balcony
$995
Suite
$2,500
From
US$795
Per Person
View Trip
6 Day Grand Cayman & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2026 to Mar 2028
Visit: USA, Cayman Islands, Bahamas
Inside
$595
Oceanview
$695
Balcony
$895
Suite
$2,875
From
US$595
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
Departure: 28 November 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$597
Oceanview
$633
Balcony
$927
Suite
$2,816
From
US$597
Save 375
Per Person
View Trip
7 Day Key West, Cayman & Mexico with Celebrity Cruises
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Silhouette
Departures: Nov 2027 to Feb 2028
Visit: USA, Mexico, Cayman Islands
Exclusive Savings
Inside
$664
Oceanview
$709
Balcony
$712
Suite
$2,078
From
US$664
Save 475
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
$372
Oceanview
$477
Balcony
$599
Suite
$1,128
From
US$372
Save 183
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
$988
Suite
$1,753
From
US$728
Save 392
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
Exclusive Savings
Inside
$721
Oceanview
$818
Balcony
$820
Suite
$2,446
From
US$721
Save 442
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
Inside
$774
Oceanview
$954
Balcony
$1,074
Suite
$2,634
From
US$774
Per Person
View Trip
7 Day Cayman, Mexico & Bahamas with Celebrity Cruises
Cruise
 (1)

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
$766
Oceanview
$867
Balcony
$990
Suite
$2,577
From
US$766
Save 477
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 Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2027 to Mar 2028
Visit: USA, Cayman Islands, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$909
Balcony
$1,175
Suite
$1,883
From
US$840
Save 477
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
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
Inside
$973
Oceanview
$1,183
Balcony
$1,323
Suite
$3,423
From
US$973
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
Exclusive Savings
Inside
$868
Oceanview
-
Balcony
$1,232
Suite
$3,438
From
US$893
Save 660
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
$1,819
Oceanview
-
Balcony
$1,804
Suite
$2,129
From
US$1,804
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
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
$541
Oceanview
$614
Balcony
$766
Suite
$1,330
From
US$541
Save 709
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
$1,053
Oceanview
$1,233
Balcony
$1,473
Suite
$2,801
From
US$1,053
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
$1,021
Oceanview
$1,191
Balcony
$1,421
Suite
$5,741
From
US$1,021
Per Person
View Trip
8 Day Western Caribbean Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 22 November 2026
Visit: USA, Mexico, Belize, Cayman Islands
Exclusive Savings
Inside
$619
Oceanview
$669
Balcony
$904
Suite
-
From
US$644
Save 533
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
$869
Oceanview
$1,048
Balcony
$1,168
Suite
$1,579
From
US$869
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
Exclusive Savings
Inside
$1,334
Oceanview
-
Balcony
$2,254
Suite
$4,239
From
US$1,334
Save 931
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
$677
Oceanview
$809
Balcony
$773
Suite
$2,318
From
US$677
Save 823
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
$850
Suite
$1,506
From
US$640
Save 354
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
Exclusive Savings
Inside
$1,256
Oceanview
$1,284
Balcony
$1,344
Suite
$3,298
From
US$1,256
Save 897
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
$699
Balcony
$949
Suite
$1,449
From
US$649
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
$885
Oceanview
$1,016
Balcony
$1,367
Suite
$1,998
From
US$885
Save 504
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 Getaway
Departures: Nov 2026 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$999
Balcony
$1,029
Suite
$1,129
From
US$699
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: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$879
Balcony
$979
Suite
$1,149
From
US$699
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: Nov 2026 to Dec 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Mexico
Bonus Onboard Credit
Value Fare
Inside
$849
Oceanview
$949
Balcony
$1,069
Suite
$3,399
From
US$849
Per Person
View Trip
Results: 1-30 of 38

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