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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 189 unique cruises and 1,777 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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189 Cruises (1,777 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
$856
Oceanview
$919
Balcony
$1,197
Suite
$1,185
From
US$856
Save 1,260
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
$494
Oceanview
$694
Balcony
$599
Suite
$889
From
US$494
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
$1,073
Oceanview
$1,184
Balcony
$1,389
Suite
$3,899
From
US$1,073
Save 1,039
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: May 2026 to Mar 2027
Visit: USA, Mexico, Belize, Honduras
Princess Standard
Sanctuary Collection
Inside
$444
Oceanview
$789
Balcony
$648
Suite
$834
From
US$444
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
$899
Oceanview
$1,049
Balcony
$1,149
Suite
$1,899
From
US$899
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: 17 October 2026
Visit: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$534
Oceanview
-
Balcony
$829
Suite
$974
From
US$534
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
22 Day Panama Canal & Southern Caribbean: ABC Islands with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 18 October 2026
Visit: USA, Bahamas, Aruba, Colombia (+5 more), Panama, Costa Rica, Cayman Islands, Dominican Republic, Curacao
Fare Saver
Inside
$1,934
Oceanview
$2,024
Balcony
$2,784
Suite
$5,624
From
US$1,934
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
$1,006
Oceanview
$1,079
Balcony
$1,251
Suite
$1,691
From
US$1,006
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
$898
Oceanview
$1,018
Balcony
$1,289
Suite
$3,509
From
US$898
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
$924
Oceanview
-
Balcony
$999
Suite
$1,274
From
US$924
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day 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, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$924
Oceanview
$962
Balcony
$1,174
Suite
$2,874
From
US$924
Save 577
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
$743
Oceanview
$911
Balcony
$940
Suite
$3,395
From
US$743
Save 466
Per Person
View Trip
14 Day Southern Caribbean From New York To Miami with Norwegian Cruise Line
Cruise
 (1)

14 Days (13 Nights) New York to Miami
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Sun
Departure: 24 October 2026
Visit: USA, Bermuda, Puerto Rico, Virgin Islands (+4 more), Curacao, Aruba, Dominican Republic, Bahamas
Inside
$1,479
Oceanview
$1,579
Balcony
$2,889
Suite
$4,719
From
US$1,479
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
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Mexico
Inside
$389
Oceanview
$509
Balcony
$679
Suite
$1,511
From
US$389
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
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,448
From
US$674
Save 571
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
$1,209
Balcony
$1,109
Suite
$1,209
From
US$829
Per Person
View Trip
10 Day Southern Caribbean: ABC Islands with Holland America
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departure: 30 October 2026
Visit: USA, Dominican Republic, Curacao, Aruba, Bahamas
Fare Saver
Inside
$849
Oceanview
$899
Balcony
$1,149
Suite
$2,399
From
US$849
Per Person
View Trip
6 Day Western Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

6 Days (5 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visit: USA, Mexico, Bahamas
Inside
$439
Oceanview
$599
Balcony
$799
Suite
$869
From
US$439
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: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$874
Oceanview
$1,075
Balcony
$1,174
Suite
$3,069
From
US$874
Save 1,909
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$724
Oceanview
-
Balcony
$964
Suite
$1,154
From
US$724
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic (+3 more), Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$729
Oceanview
$789
Balcony
$889
Suite
$1,049
From
US$729
Per Person
View Trip
6 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

6 Days (5 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visit: USA, Cayman Islands, Jamaica
Drinks & WiFi Package
Inside
$358
Oceanview
$428
Balcony
$568
Suite
$2,249
From
US$358
Per Person
View Trip
13 Day Panama Canal Discovery: Costa Rica & Greater Antilles with Holland America
Cruise
 (3)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Nieuw Amsterdam, Oosterdam
Departures: Oct 2026 to Mar 2028
Visit: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Book Early & Have It All Fare Option
Inside
$1,249
Oceanview
$1,299
Balcony
$1,899
Suite
$3,799
From
US$1,249
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: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire (+7 more), Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Bonus Onboard Credit
Inside
$1,962
Oceanview
$2,152
Balcony
$3,017
Suite
$7,235
From
US$1,962
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
$1,824
Oceanview
$2,274
Balcony
$2,634
Suite
$4,164
From
US$1,824
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (1)

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
-
Oceanview
$1,323
Balcony
$1,533
Suite
$4,123
From
US$1,323
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
$796
Oceanview
$1,036
Balcony
$1,446
Suite
$2,980
From
US$796
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
Results: 1-30 of 189

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