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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 161 departures available, operated by ten of the world's leading cruise lines departing in November.
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38 Cruises (161 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
$889
Balcony
$1,008
Suite
$2,500
From
US$823
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 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
$429
Oceanview
$549
Balcony
$708
Suite
$1,461
From
US$429
Save 194
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
$2,892
From
US$622
Save 350
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
$1,778
From
US$728
Save 392
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
$690
Oceanview
$734
Balcony
$737
Suite
$2,400
From
US$690
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
$2,436
From
US$746
Save 417
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 & 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
$3,633
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
-
Oceanview
$1,113
Balcony
$1,276
Suite
$3,745
From
US$1,113
Save 632
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
$1,939
Oceanview
-
Balcony
$2,024
Suite
$2,429
From
US$1,939
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
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
$1,908
From
US$840
Save 477
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
$791
Oceanview
$892
Balcony
$1,015
Suite
$2,627
From
US$791
Save 452
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
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
$784
Oceanview
$884
Balcony
$887
Suite
$2,477
From
US$802
Save 505
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
$999
Suite
$1,449
From
US$649
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
$1,078
Oceanview
$1,258
Balcony
$1,498
Suite
$2,826
From
US$1,078
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
$879
Oceanview
-
Balcony
$1,209
Suite
$1,839
From
US$879
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
$1,257
Oceanview
$1,462
Balcony
$2,220
Suite
$4,239
From
US$1,257
Save 686
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
$714
Oceanview
$754
Balcony
$1,219
Suite
$7,504
From
US$714
Save 415
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
$932
Oceanview
$1,048
Balcony
$1,437
Suite
$2,023
From
US$932
Save 504
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
$1,061
Oceanview
$1,231
Balcony
$1,461
Suite
$2,971
From
US$1,061
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
$1,531
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
-
Oceanview
$1,583
Balcony
$1,569
Suite
$3,269
From
US$1,864
Save 612
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
$604
Oceanview
$724
Balcony
$904
Suite
$1,355
From
US$604
Save 703
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
$699
Oceanview
$879
Balcony
$949
Suite
$1,149
From
US$699
Per Person
View Trip
10 Day Caribbean Cruise From Galveston to Galveston with Norwegian Cruise Line
Cruise
 (1)

10 Days (9 Nights) Galveston to Galveston
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Escape
Departure: 04 November 2027
Visit: USA, Mexico, Cayman Islands, Jamaica, Belize
Inside
$1,099
Oceanview
$1,319
Balcony
$1,549
Suite
$1,879
From
US$1,099
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
$1,029
Balcony
$1,079
Suite
$1,179
From
US$699
Per Person
View Trip
Results: 1-30 of 38

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