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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 211 unique cruises and 1,940 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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211 Cruises (1,940 Departures)
211 Cruises (1,940 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$400pp
$198,630pp
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8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: 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
$1,067
Oceanview
$1,108
Balcony
$1,689
Suite
$2,332
From (Per Person)
A$1,067
Save 951
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
Operator: Princess
Ships: Regal Princess, Star Princess, Sun Princess
Departures: Oct 2026 to Mar 2027
Visits: USA, Mexico, Belize, Honduras
Sanctuary Collection
Exclusive Savings
Inside
$922
Oceanview
$1,170
Balcony
$1,288
Suite
$1,853
From (Per Person)
A$922
Save 21
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic +3 more, Norwegian Escape, Norwegian Getaway, Norwegian Prima
Departures: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,021
Oceanview
$1,244
Balcony
$1,363
Suite
$1,661
From (Per Person)
A$1,021
Save 20
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
Operator: Norwegian Cruise Line
Ship: Norwegian Joy
Departure: 22 October 2027
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,085
Oceanview
$1,159
Balcony
$1,308
Suite
$1,428
From (Per Person)
A$1,085
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,951
Oceanview
$1,387
Balcony
$1,585
Suite
$4,678
From (Per Person)
A$1,387
Per Person
View Trip
7 Day Eastern Caribbean & Bimini Halloween with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 25 October 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
$1,616
Oceanview
$1,702
Balcony
$1,873
Suite
$4,181
From (Per Person)
A$1,616
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ships: MSC Grandiosa, MSC World Atlantic
Departures: Nov 2026 to Nov 2027
Visits: USA, Bahamas, Mexico
Exclusive Savings
Inside
$744
Oceanview
$923
Balcony
$1,190
Suite
$2,507
From (Per Person)
A$744
Save 15
Per Person
View Trip
13 Day Eastern Caribbean Celebration with Cunard
Cruise
 (13)

13 Days (12 Nights) Miami to Miami
Operator: 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
$1,741
Oceanview
$2,118
Balcony
$2,850
Suite
$6,622
From (Per Person)
A$1,741
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: 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
$893
Oceanview
$1,083
Balcony
$1,124
Suite
$1,714
From (Per Person)
A$893
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
Operator: Norwegian Cruise Line
Ships: Norwegian Breakaway, Norwegian Escape, Norwegian Getaway
Departures: Dec 2026 to Mar 2028
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$710
Oceanview
$888
Balcony
$1,097
Suite
$1,231
From (Per Person)
A$710
Save 12
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$814
Oceanview
$1,071
Balcony
$1,378
Suite
$2,309
From (Per Person)
A$814
Save 16
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

16 Days (15 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visits: USA, Cayman Islands, Jamaica, Bonaire, Aruba, Curacao, Dominican Republic
Exclusive Savings
Inside
$2,126
Oceanview
$2,295
Balcony
$2,790
Suite
$11,458
From (Per Person)
A$2,126
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
Operator: 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
$3,057
Oceanview
$3,384
Balcony
-
Suite
-
From (Per Person)
A$3,057
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
Operator: Holland America
Ships: Nieuw Amsterdam, Oosterdam
Departures: Oct 2026 to Mar 2028
Visits: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$1,846
Oceanview
$2,153
Balcony
$3,994
Suite
$6,727
From (Per Person)
A$1,846
Save 30
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Celebrity Cruises
Ship: Celebrity Apex
Departures: Oct 2027 to Apr 2028
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,323
Oceanview
$1,370
Balcony
$1,739
Suite
$4,268
From (Per Person)
A$1,323
Save 1,219
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
Operator: Norwegian Cruise Line
Ship: Norwegian Sun
Departure: 24 October 2026
Visits: USA, Bermuda, Puerto Rico, Virgin Islands +4 more, Curacao, Aruba, Dominican Republic, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$2,392
Oceanview
$2,406
Balcony
$4,133
Suite
$4,848
From (Per Person)
A$2,392
Per Person
View Trip
7 Day Perfect Day Cococay & Grand Turk with Celebrity Cruises
Cruise
 (1)

7 Days (6 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 03 October 2027
Visits: USA, Dominican Republic, Turks and Caicos Islands, Bahamas
Exclusive Savings
Inside
$1,163
Oceanview
$1,219
Balcony
$1,430
Suite
$5,022
From (Per Person)
A$1,163
Save 849
Per Person
View Trip
9 Day Aruba, Bonaire & Curacao Cruise with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2027 to Oct 2027
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,616
Oceanview
$1,736
Balcony
$2,055
Suite
$5,377
From (Per Person)
A$1,616
Save 1,541
Per Person
View Trip
10 Day Eastern Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Operator: Cunard
Ship: Queen Elizabeth
Departure: 27 October 2026
Visits: USA, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Exclusive Savings
Inside
$1,365
Oceanview
$1,781
Balcony
$2,484
Suite
$7,493
From (Per Person)
A$1,365
Per Person
View Trip
8 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departure: 17 October 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,685
Oceanview
-
Balcony
$1,916
Suite
$2,664
From (Per Person)
A$1,685
Per Person
View Trip
13 Day Panama, Colombia & Caribbean Islands with Ponant
Cruise
 (1)

13 Days (12 Nights) Fort-de-France to Colon
Operator: Ponant
Ship: Le Bellot
Departure: 26 October 2026
Visits: Martinique, Guadeloupe, Saint Lucia, Saint Vincent, Holland, Colombia, Panama
Exclusive Savings
Balcony
$10,216
Suite
$15,842
From (Per Person)
A$10,216
Save 264
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 17 October 2026
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,095
Oceanview
$1,146
Balcony
$1,598
Suite
$2,822
From (Per Person)
A$1,095
Save 655
Per Person
View Trip
8 Day Key West, Grand Cayman & Mexico with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Celebrity Cruises
Ships: Celebrity Apex
Departures: Oct 2026 to Apr 2028
Visits: USA, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,152
Oceanview
$1,297
Balcony
$1,548
Suite
$4,336
From (Per Person)
A$1,152
Save 2,442
Per Person
View Trip
6 Day Dominican Republic & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ships: Resilient Lady, Valiant Lady
Departures: Jun 2027 to Oct 2028
Visits: USA, Dominican Republic, Bahamas
Inside
$848
Oceanview
$1,132
Balcony
$1,346
Suite
$3,772
From (Per Person)
A$848
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Operator: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Oct 2026 to Apr 2028
Visits: Panama, Colombia, Aruba, Curacao
Exclusive Savings
Inside
$1,417
Oceanview
$1,500
Balcony
$2,134
Suite
$2,488
From (Per Person)
A$1,417
Save 1,089
Per Person
View Trip
6 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

6 Days (5 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Oct 2027
Visits: USA, Cayman Islands, Jamaica
Exclusive Savings
Inside
$626
Oceanview
$676
Balcony
$824
Suite
$3,364
From (Per Person)
A$626
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,647
Oceanview
$1,884
Balcony
$2,419
Suite
$4,983
From (Per Person)
A$1,647
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Operator: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Oct 2026 to Mar 2028
Visits: Colombia, Aruba, Curacao, Panama
Exclusive Savings
Inside
$1,487
Oceanview
$1,621
Balcony
$2,195
Suite
$2,603
From (Per Person)
A$1,487
Save 1,462
Per Person
View Trip
8 Day Grand Cayman, Mexico & Perfect Day with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 18 October 2026
Visits: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$1,335
Oceanview
$1,480
Balcony
-
Suite
-
From (Per Person)
A$1,480
Save 822
Per Person
View Trip
22 Day Caribbean with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Operator: 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
$2,702
Oceanview
-
Balcony
$5,286
Suite
$10,770
From (Per Person)
A$2,702
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Countries

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Routes

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Country Routes

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Cruise Lines Exploring The Caribbean & Bahamas

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