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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 210 unique cruises and 1,989 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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210 Cruises (1,989 Departures)
210 Cruises (1,989 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$400pp
$203,830pp
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22 Day Caribbean with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Operator: Cunard
Ship: Queen Elizabeth
Departure: 15 October 2026
Visits: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia +7 more, Barbados, Saint Martin, Virgin Islands, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Exclusive Savings
Inside
-
Oceanview
$3,157
Balcony
$7,018
Suite
$9,602
From (Per Person)
A$3,157
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
$1,364
Oceanview
$1,467
Balcony
$1,782
Suite
$4,415
From (Per Person)
A$1,364
Save 1,169
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
$1,850
Oceanview
-
Balcony
$2,081
Suite
$2,829
From (Per Person)
A$1,850
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
$1,615
Oceanview
$1,717
Balcony
$1,820
Suite
$5,376
From (Per Person)
A$1,615
Per Person
View Trip
11 Day Caribbean And Antilles with MSC Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Operator: MSC Cruises
Ship: MSC Poesia
Departures: Oct 2026 to Dec 2027
Visits: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Exclusive Savings
Inside
$1,659
Oceanview
$1,817
Balcony
$2,183
Suite
$7,382
From (Per Person)
A$1,659
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
Operator: Holland America
Ship: Rotterdam
Departure: 31 October 2026
Visits: 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
Exclusive Savings
Inside
$2,839
Oceanview
$3,581
Balcony
$4,225
Suite
$6,997
From (Per Person)
A$2,839
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: MSC Cruises
Ship: MSC Grandiosa
Departures: Nov 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic
Exclusive Savings
Inside
$794
Oceanview
$972
Balcony
$1,239
Suite
$2,477
From (Per Person)
A$794
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
$794
Oceanview
$972
Balcony
$1,239
Suite
$2,507
From (Per Person)
A$794
Save 15
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
$1,044
Oceanview
$1,296
Balcony
$1,400
Suite
$2,088
From (Per Person)
A$1,044
Save 21
Per Person
View Trip
8 Day Western Caribbean with Mexico with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Regal Princess, Star Princess
Departures: Sep 2026 to Mar 2027
Visits: USA, Honduras, Belize, Mexico
Sanctuary Collection
Exclusive Savings
Inside
$1,042
Oceanview
$1,153
Balcony
$1,361
Suite
$2,143
From (Per Person)
A$1,042
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
$959
Oceanview
$1,170
Balcony
$1,170
Suite
-
From (Per Person)
A$959
Save 1,192
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
$865
Oceanview
$1,083
Balcony
$1,373
Suite
$3,847
From (Per Person)
A$865
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
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
$3,811
Suite
$7,493
From (Per Person)
A$1,365
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
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic +2 more, Norwegian Escape, Norwegian Prima
Departures: Aug 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,200
Oceanview
$1,274
Balcony
$1,424
Suite
$1,870
From (Per Person)
A$1,200
Save 20
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
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, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,716
Oceanview
$1,983
Balcony
$2,518
Suite
$5,013
From (Per Person)
A$1,716
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
Departures: Sep 2026 to Oct 2026
Visits: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$958
Oceanview
$1,098
Balcony
$1,169
Suite
-
From (Per Person)
A$958
Save 1,622
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
$2,839
Oceanview
$3,384
Balcony
$4,354
Suite
-
From (Per Person)
A$2,839
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
$1,102
Oceanview
$1,305
Balcony
$1,476
Suite
$4,198
From (Per Person)
A$1,249
Save 1,381
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
$2,332
Oceanview
$2,303
Balcony
$2,838
Suite
$5,072
From (Per Person)
A$2,303
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
$1,214
Oceanview
$1,318
Balcony
$1,542
Suite
$1,765
From (Per Person)
A$1,214
Save 21
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
Exclusive Savings
Inside
$1,846
Oceanview
$2,153
Balcony
$3,073
Suite
$6,727
From (Per Person)
A$1,846
Save 30
Per Person
View Trip
11 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (4)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Coral Princess, Enchanted Princess
Departures: Oct 2026 to Mar 2027
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,553
Oceanview
$1,389
Balcony
$2,068
Suite
$3,010
From (Per Person)
A$1,389
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
$666
Oceanview
$715
Balcony
$864
Suite
$2,701
From (Per Person)
A$666
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
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
$1,581
Oceanview
$1,668
Balcony
$2,027
Suite
$5,454
From (Per Person)
A$1,581
Save 1,561
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
$1,706
Oceanview
$1,944
Balcony
$2,478
Suite
$4,983
From (Per Person)
A$1,706
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departure: 03 October 2026
Visits: USA, Honduras, Belize, Mexico, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$2,498
Oceanview
-
Balcony
$3,246
Suite
$3,967
From (Per Person)
A$2,498
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
$1,096
Oceanview
$1,282
Balcony
$1,360
Suite
$5,099
From (Per Person)
A$1,096
Save 838
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 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 Miami Cruises from San Juan to San Juan Cruises from Tampa to Tampa

Country Routes

Cruises from France to Spain 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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