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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 213 unique cruises and 1,914 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveller reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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213 Cruises (1,914 Departures)
213 Cruises (1,914 Departures)
Departures
Duration
5 Days
46 Days
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$400pp
$205,420pp
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8 Day Caribbean Cruise From Galveston to Galveston with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Galveston to Galveston
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Escape, Norwegian Viva
Departures: Oct 2026 to Apr 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,246
Oceanview
$1,515
Balcony
$1,662
Suite
$2,109
From (Per Person)
A$1,246
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

16 Days (15 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visits: USA, Cayman Islands, Jamaica, Bonaire, Aruba, Curacao, Dominican Republic
Exclusive Savings
Inside
$1,859
Oceanview
$2,146
Balcony
$2,750
Suite
$11,439
From (Per Person)
A$1,855
Per Person
View Trip
7 Day Eastern Caribbean & Bimini Halloween with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 25 October 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
$1,944
Oceanview
$2,299
Balcony
$2,462
Suite
$4,162
From (Per Person)
A$1,944
Per Person
View Trip
15 Day Circle Caribbean with Princess
Cruise
 (4)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Coral Princess
Departure: 15 October 2026
Visits: USA, Saint Martin, Saint Kitts and Nevis, Martinique +5 more, Dominica, Grenada, Trinidad and Tobago, Aruba, Curacao
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,998
Suite
$4,025
From (Per Person)
A$3,998
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
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,853
Oceanview
$2,164
Balcony
$2,268
Suite
$6,099
From (Per Person)
A$1,853
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
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$804
Oceanview
$982
Balcony
$1,249
Suite
$2,536
From (Per Person)
A$804
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
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,485
Oceanview
$2,006
Balcony
$1,887
Suite
$1,991
From (Per Person)
A$1,485
Save 24
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
Visits: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Exclusive Savings
Inside
$1,263
Oceanview
$1,411
Balcony
$1,609
Suite
$4,244
From (Per Person)
A$1,263
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
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,538
Oceanview
$1,894
Balcony
$2,429
Suite
$5,062
From (Per Person)
A$1,538
Save 24
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
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$994
Oceanview
-
Balcony
$1,024
Suite
$1,687
From (Per Person)
A$994
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: Sep 2026 to Mar 2027
Visits: USA, Honduras, Belize, Mexico
Sanctuary Collection
Exclusive Savings
Inside
$894
Oceanview
$1,132
Balcony
$1,251
Suite
$1,409
From (Per Person)
A$894
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
Ship: Resilient Lady
Departures: Jul 2026 to Oct 2026
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$1,177
Oceanview
$1,251
Balcony
$1,323
Suite
$2,803
From (Per Person)
A$1,177
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: Aug 2026 to Mar 2028
Visits: Colombia, Aruba, Curacao, Panama
Exclusive Savings
Inside
$1,633
Oceanview
$1,789
Balcony
$2,178
Suite
$3,855
From (Per Person)
A$1,633
Save 1,352
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
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,275
Oceanview
$1,317
Balcony
$2,081
Suite
$3,868
From (Per Person)
A$1,275
Save 730
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
Visits: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$2,186
Oceanview
-
Balcony
$2,453
Suite
$3,748
From (Per Person)
A$2,186
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
Visits: USA, Dominican Republic, Curacao, Aruba +5 more, Bahamas, Colombia, Panama, Costa Rica, Jamaica
Fare Saver
Exclusive Savings
Inside
$2,839
Oceanview
$3,384
Balcony
$4,354
Suite
$9,740
From (Per Person)
A$2,839
Per Person
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

7 Days (6 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ships: Brilliance of the Seas, Jewel of the Seas, Serenade of the Seas
Departures: Oct 2026 to Nov 2027
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$878
Oceanview
$880
Balcony
$1,140
Suite
$3,708
From (Per Person)
A$878
Save 533
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: Jul 2026 to Apr 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,200
Oceanview
$1,498
Balcony
$1,646
Suite
$1,870
From (Per Person)
A$1,200
Save 22
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
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$825
Oceanview
$946
Balcony
$1,085
Suite
$1,716
From (Per Person)
A$825
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: Brilliant Lady, Resilient Lady +2 more, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$953
Oceanview
$1,102
Balcony
$1,176
Suite
$3,173
From (Per Person)
A$953
Per Person
View Trip
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: Aug 2026 to Apr 2028
Visits: Panama, Colombia, Aruba, Curacao
Exclusive Savings
Inside
$1,083
Oceanview
$1,358
Balcony
$1,623
Suite
$1,807
From (Per Person)
A$1,340
Save 1,259
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
Visits: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Sint Maarten, Virgin Islands
Exclusive Savings
Inside
$1,686
Oceanview
$2,122
Balcony
$2,795
Suite
$6,626
From (Per Person)
A$1,686
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: Jul 2026 to Mar 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,288
Oceanview
$1,468
Balcony
$1,661
Suite
$1,765
From (Per Person)
A$1,288
Save 21
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: Aug 2026 to Mar 2027
Visits: USA, Mexico, Belize, Honduras
Sanctuary Collection
Exclusive Savings
Inside
$766
Oceanview
$1,192
Balcony
$974
Suite
$1,320
From (Per Person)
A$766
Save 15
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
Visits: USA, Turks and Caicos Islands, Curacao, Bonaire +7 more, Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Exclusive Savings
Inside
$2,709
Oceanview
$3,590
Balcony
$5,293
Suite
$10,778
From (Per Person)
A$2,709
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
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,308
Oceanview
$1,502
Balcony
$1,874
Suite
$2,126
From (Per Person)
A$1,308
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: 17 October 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Mexico, Belize, Honduras
Exclusive Savings
Inside
$1,644
Oceanview
-
Balcony
$2,234
Suite
$2,731
From (Per Person)
A$1,644
Per Person
View Trip
8 Day Key West, Grand 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 Apr 2028
Visits: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,379
Oceanview
$1,420
Balcony
$1,750
Suite
$4,470
From (Per Person)
A$1,507
Save 1,028
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
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,518
Oceanview
$1,874
Balcony
$2,409
Suite
$5,062
From (Per Person)
A$1,518
Save 24
Per Person
View Trip
8 Day Eastern Caribbean Holiday: Amber Cove & Bahamas with Holland America
Cruise
 (3)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Eurodam, Nieuw Amsterdam
Departures: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Fare Saver
Exclusive Savings
Inside
$1,536
Oceanview
$1,843
Balcony
$2,150
Suite
$3,833
From (Per Person)
A$1,536
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Travel Styles

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Countries

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Cities

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Routes

Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to Miami Cruises from Bridgetown to San Juan Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Cartagena to Cartagena Cruises from Colon to Colon Cruises from Fort Lauderdale to Los Angeles Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from La Romana to La Romana Cruises from Lisbon to Miami Cruises from London to Fort Lauderdale Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Los Angeles to Los Angeles Cruises from Miami to San Juan Cruises from Miami to Los Angeles Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Miami to Miami Cruises from Montreal to Miami Cruises from Montreal to New York Cruises from New York to New York Cruises from Orlando to Orlando Cruises from Quebec City to New York Cruises from Rome to Miami Cruises from Rome to Fort Lauderdale Cruises from San Juan to Bridgetown Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Tampa to Tampa

Country Routes

Cruises from Barbados to Puerto Rico Cruises from France to Spain Cruises from Puerto Rico to Barbados Cruises from Puerto Rico to USA Cruises from Chile to USA Cruises from France to Brazil Cruises from Dominican Republic to USA Cruises from USA to Puerto Rico Cruises from Argentina to Brazil Cruises from USA to Brazil Cruises from Argentina to Chile Cruises from Argentina to USA Cruises from Barbados to USA Cruises from Canada to USA Cruises from Chile to Argentina Cruises from England to Spain Cruises from England to USA Cruises from USA to Dominican Republic Cruises from Italy to Brazil Cruises from Italy to Spain Cruises from Italy to USA Cruises from Panama to USA Cruises from Spain to Brazil Cruises from Portugal to Spain Cruises from Portugal to USA Cruises from Spain to USA Cruises from USA to Argentina Cruises from USA to Barbados Cruises from USA to Chile Cruises from USA to Panama Cruises from USA to Peru Cruises from USA to Spain

Cruise Lines Exploring The Caribbean & Bahamas

Azamara Caribbean Cruises Celebrity Caribbean Cruises Crystal Caribbean Cruises Cunard Caribbean Cruises Emerald Caribbean Cruises Explora Journeys Caribbean Cruises Holland America Caribbean Cruises MSC Caribbean Cruises NCL Caribbean Cruises Oceania Caribbean Cruises P&O (UK) Caribbean Cruises Ponant Caribbean Cruises Princess Caribbean Cruises Regent Seven Seas Caribbean Cruises Royal Caribbean Caribbean Cruises Scenic Caribbean Cruises Seabourn Caribbean Cruises Silversea Caribbean Cruises Viking Caribbean Cruises Virgin Voyages Caribbean Cruises

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