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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 169 departures available, operated by ten of the world's leading cruise lines departing in November.
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38 Cruises (169 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
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
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
$889
Balcony
$1,008
Suite
$2,500
From
US$823
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
Exclusive Savings
Inside
$689
Oceanview
$734
Balcony
$737
Suite
$2,077
From
US$689
Save 638
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
$746
Oceanview
$843
Balcony
$845
Suite
$2,254
From
US$746
Save 417
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
$841
Oceanview
$921
Balcony
$1,138
Suite
$2,203
From
US$841
Save 279
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
$568
Oceanview
$666
Balcony
$856
Suite
$1,436
From
US$815
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
Departure: 28 November 2027
Visit: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$622
Oceanview
$658
Balcony
$952
Suite
$2,882
From
US$622
Save 350
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
$2,754
From
US$774
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
-
Oceanview
$1,097
Balcony
$1,226
Suite
$3,166
From
US$1,097
Save 703
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
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
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
$1,043
Oceanview
$1,253
Balcony
$1,393
Suite
$3,633
From
US$1,043
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
$1,849
Oceanview
-
Balcony
$1,914
Suite
$2,359
From
US$1,849
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
$524
Oceanview
$613
Balcony
$836
Suite
$1,886
From
US$599
Save 384
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
$1,161
Oceanview
$1,259
Balcony
$1,319
Suite
$3,219
From
US$1,161
Save 720
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
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
$753
Oceanview
$812
Balcony
$1,000
Suite
$1,956
From
US$753
Save 241
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
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
-
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
$1,449
From
US$649
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 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
$754
Oceanview
$834
Balcony
$1,039
Suite
$3,094
From
US$754
Save 439
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
$1,098
Oceanview
$1,228
Balcony
$1,854
Suite
$4,239
From
US$1,098
Save 590
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
$702
Oceanview
$870
Balcony
$824
Suite
$2,372
From
US$702
Save 461
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
$1,045
Oceanview
$1,160
Balcony
$1,587
Suite
$2,448
From
US$1,045
Save 391
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
Ships: Norwegian Aqua, Norwegian Epic
Departures: Dec 2026 to Mar 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$829
Oceanview
$1,449
Balcony
$1,169
Suite
$1,319
From
US$829
Per Person
View Trip
8 Day Western Caribbean with Grand Cayman with Princess
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Nov 2027 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Princess Standard
Inside
$699
Oceanview
$849
Balcony
$854
Suite
$1,370
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 Getaway
Departures: Nov 2026 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$749
Oceanview
$1,089
Balcony
$1,159
Suite
$1,249
From
US$749
Per Person
View Trip
Results: 1-30 of 38

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