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Caribbean Cruises Starting In October 2026, 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in October 2026, 2027, 2028 or 2029? Choose from 191 unique cruises and 1,753 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveler reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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191 Cruises (1,753 Cruise Departures)
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Jun 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$777
Oceanview
$787
Balcony
$1,061
Suite
$1,208
From
US$777
Save 1,050
Per Person
View Trip
8 Day Western Caribbean with Mexico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Star Princess
Departures: Jul 2026 to Mar 2027
Visit: USA, Honduras, Belize, Mexico
Princess Standard
Sanctuary Collection
Inside
$539
Oceanview
$699
Balcony
$614
Suite
$789
From
US$539
Per Person
View Trip
22 Day Western & Eastern Caribbean: Mexico & Leeward Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 31 October 2026
Visit: USA, Bahamas, Jamaica, Cayman Islands (+9 more), Honduras, Belize, Mexico, Saint Martin, Antigua and Barbuda, Dominica, Saint Lucia, Saint Kitts and Nevis, Virgin Islands
Fare Saver
Inside
$2,164
Oceanview
$2,574
Balcony
$3,064
Suite
$4,464
From
US$2,164
Per Person
View Trip
6 Day Dominican Republic & 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 2027 to Oct 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,650
From
US$595
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Dec 2027
Visit: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Inside
$798
Oceanview
$918
Balcony
$1,289
Suite
$4,669
From
US$798
Per Person
View Trip
22 Day Southern Caribbean & Panama Canal: ABC Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba (+5 more), Bahamas, Colombia, Panama, Costa Rica, Jamaica
Fare Saver
Inside
$2,129
Oceanview
$2,309
Balcony
$2,989
Suite
$5,729
From
US$2,129
Per Person
View Trip
8 Day Tortola, St. Maarten & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$817
Oceanview
$1,091
Balcony
$1,299
Suite
$2,999
From
US$817
Save 631
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Inside
$786
Oceanview
$1,026
Balcony
$1,436
Suite
$2,980
From
US$786
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
$969
Suite
$1,129
From
US$699
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 03 October 2027
Visit: USA, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$693
Oceanview
$861
Balcony
$890
Suite
$3,185
From
US$693
Save 516
Per Person
View Trip
13 Day Eastern Caribbean Celebration with Cunard
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departures: Oct 2026 to Nov 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Cunard Fare
Value Fare
Inside
$739
Oceanview
$919
Balcony
$969
Suite
$3,579
From
US$739
Per Person
View Trip
11 Day Western Caribbean: Greater Antilles, Belize & Mexico with Holland America
Cruise
 (3)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Honduras, Belize, Mexico
Fare Saver
Inside
$1,049
Oceanview
$1,249
Balcony
$1,399
Suite
$1,999
From
US$1,049
Per Person
View Trip
8 Day Tortola, St. Kitts & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Aug 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$840
Oceanview
$928
Balcony
$1,174
Suite
$3,240
From
US$840
Save 745
Per Person
View Trip
7 Day Eastern Caribbean & Bimini Halloween with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 25 October 2026
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
-
Oceanview
$1,554
Balcony
$1,734
Suite
$2,814
From
US$1,554
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$584
Oceanview
$644
Balcony
$694
Suite
$1,149
From
US$584
Per Person
View Trip
22 Day Caribbean with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 15 October 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+7 more), Barbados, Saint Martin, Virgin Islands, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Cunard Fare
Value Fare
Inside
$1,579
Oceanview
$1,749
Balcony
$2,099
Suite
$6,279
From
US$1,579
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 03 October 2026
Visit: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,648
Oceanview
-
Balcony
$2,358
Suite
$2,728
From
US$1,648
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$604
Oceanview
$757
Balcony
$1,093
Suite
$1,722
From
US$1,005
Save 50
Per Person
View Trip
8 Day Western Caribbean with Mexico From Fort Lauderdale with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Star Princess, Sun Princess
Departures: Jun 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Sanctuary Collection
Inside
$574
Oceanview
$804
Balcony
$601
Suite
$859
From
US$574
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico, Dominican Republic
Inside
$776
Oceanview
$1,016
Balcony
$1,396
Suite
$2,960
From
US$776
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,113
Oceanview
$1,323
Balcony
$1,533
Suite
$4,123
From
US$1,113
Per Person
View Trip
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ships: Resilient Lady, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2028
Visit: USA, Turks and Caicos Islands, Bahamas
Inside
$645
Oceanview
$795
Balcony
$984
Suite
$2,500
From
US$645
Per Person
View Trip
7 Day Perfect Day Cococay & Caribbean with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 31 October 2027
Visit: USA, Dominican Republic, Bahamas
Exclusive Savings
Inside
$834
Oceanview
$1,004
Balcony
$1,105
Suite
$2,922
From
US$834
Save 611
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departures: Oct 2027 to Apr 2028
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$836
Oceanview
$938
Balcony
$1,121
Suite
$2,921
From
US$836
Save 773
Per Person
View Trip
6 Day Western Caribbean Cruise From Miami To Miami with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Joy
Departure: 22 October 2027
Visit: USA, Mexico, Bahamas
Inside
$779
Oceanview
$909
Balcony
$1,109
Suite
$1,279
From
US$779
Per Person
View Trip
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 10 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,049
Oceanview
-
Balcony
$1,054
Suite
$1,499
From
US$1,049
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Oct 2027
Visit: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,023
Oceanview
$1,134
Balcony
$1,339
Suite
$3,362
From
US$1,023
Save 1,073
Per Person
View Trip
10 Day Eastern Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Cunard Fare
Value Fare
Inside
$649
Oceanview
$739
Balcony
$789
Suite
$2,719
From
US$649
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Jun 2026 to Mar 2028
Visit: Colombia, Aruba, Curacao, Panama
Bonus Onboard Credit
Exclusive Savings
Inside
$848
Oceanview
$884
Balcony
$1,230
Suite
$1,287
From
US$848
Save 1,357
Per Person
View Trip
11 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (4)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Coral Princess, Enchanted Princess
Departures: Oct 2026 to Mar 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Princess Standard
Inside
$879
Oceanview
$1,154
Balcony
$1,319
Suite
$1,769
From
US$879
Per Person
View Trip
Results: 1-30 of 191

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