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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 200 unique cruises and 1,902 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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200 Cruises (1,902 Departures)
200 Cruises (1,902 Departures)
Departures
Duration
5 Days
46 Days
Start & End Cities
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Cruise Lines
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Price
$400pp
$203,150pp
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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
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$1,133
Oceanview
-
Balcony
$1,190
Suite
$1,816
From (Per Person)
A$1,133
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
Visits: USA, Bahamas, Aruba, Colombia +5 more, Panama, Costa Rica, Cayman Islands, Dominican Republic, Curacao
Fare Saver
Exclusive Savings
Inside
$2,839
Oceanview
$3,394
Balcony
$4,503
Suite
$9,750
From (Per Person)
A$2,839
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
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,030
Oceanview
$1,189
Balcony
$1,624
Suite
$2,698
From (Per Person)
A$1,146
Save 747
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
Visits: USA, Bahamas, Aruba, Colombia, Panama, Costa Rica, Cayman Islands
Fare Saver
Exclusive Savings
Inside
$1,846
Oceanview
$2,153
Balcony
$3,073
Suite
$6,449
From (Per Person)
A$1,846
Save 49
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
Visits: USA, Aruba, Curacao, Bonaire
Exclusive Savings
Inside
$1,774
Oceanview
$1,921
Balcony
$2,308
Suite
$5,666
From (Per Person)
A$1,774
Save 1,422
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
Visits: USA, Dominican Republic, Curacao, Aruba, Bahamas
Fare Saver
Exclusive Savings
Inside
$1,230
Oceanview
$1,537
Balcony
$1,844
Suite
$4,299
From (Per Person)
A$1,230
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
$1,587
Oceanview
$1,887
Balcony
$2,187
Suite
$5,880
From (Per Person)
A$1,587
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
$1,184
Oceanview
$1,257
Balcony
$1,474
Suite
$4,668
From (Per Person)
A$1,184
Save 1,381
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
Visits: USA, Mexico, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$814
Oceanview
$977
Balcony
$1,275
Suite
$1,425
From (Per Person)
A$814
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
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,206
Oceanview
$1,622
Balcony
$1,764
Suite
$4,666
From (Per Person)
A$1,206
Save 923
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
Visits: USA, Turks and Caicos Islands, Curacao, Bonaire, Aruba
Exclusive Savings
Inside
$1,685
Oceanview
$2,190
Balcony
$3,032
Suite
$7,576
From (Per Person)
A$1,685
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
Visits: USA, Bermuda, Puerto Rico, Virgin Islands +4 more, Curacao, Aruba, Dominican Republic, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$2,540
Oceanview
$2,734
Balcony
$4,103
Suite
$7,215
From (Per Person)
A$2,540
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
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,482
Oceanview
$1,600
Balcony
$1,993
Suite
$4,872
From (Per Person)
A$1,482
Save 1,063
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
Visits: USA, Dominican Republic, Bahamas
Exclusive Savings
Inside
$1,465
Oceanview
$1,698
Balcony
$1,934
Suite
$4,705
From (Per Person)
A$1,465
Save 807
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
Visits: USA, Bahamas, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,220
Oceanview
$1,368
Balcony
$1,377
Suite
$3,817
From (Per Person)
A$1,220
Save 918
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
$1,382
Oceanview
$1,576
Balcony
$1,874
Suite
$2,126
From (Per Person)
A$1,382
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
Visits: USA, Honduras, Belize, Mexico
Sanctuary Collection
Exclusive Savings
Inside
$894
Oceanview
$1,112
Balcony
$1,001
Suite
$1,290
From (Per Person)
A$894
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
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$994
Oceanview
-
Balcony
$1,196
Suite
$1,588
From (Per Person)
A$994
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
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
$2,359
Oceanview
$2,944
Balcony
$3,874
Suite
$9,091
From (Per Person)
A$2,359
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
Visits: USA, Bahamas, Jamaica, Cayman Islands, Honduras, Belize, Mexico
Fare Saver
Exclusive Savings
Inside
$1,389
Oceanview
$1,775
Balcony
$2,003
Suite
$3,072
From (Per Person)
A$1,389
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 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
$1,460
Oceanview
$1,612
Balcony
$1,664
Suite
$1,961
From (Per Person)
A$1,460
Save 1,245
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
$1,190
Oceanview
$1,210
Balcony
$1,627
Suite
$2,033
From (Per Person)
A$1,281
Save 1,198
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
$754
Oceanview
$933
Balcony
$1,200
Suite
$2,536
From (Per Person)
A$754
Save 12
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
$2,279
Oceanview
-
Balcony
$2,307
Suite
$3,748
From (Per Person)
A$2,279
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
$1,645
Suite
$1,840
From (Per Person)
A$1,200
Save 22
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
Visits: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,206
Oceanview
$1,383
Balcony
$1,626
Suite
$4,535
From (Per Person)
A$1,206
Save 1,011
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
Visits: USA, Bahamas, Mexico, Cayman Islands
Exclusive Savings
Inside
$1,162
Oceanview
$1,250
Balcony
$1,425
Suite
$3,870
From (Per Person)
A$1,162
Save 951
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
$2,999
From (Per Person)
A$1,644
Per Person
View Trip
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Caribbean & Bahamas Cruises

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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 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 USA to Brazil Cruises from Barbados to USA Cruises from Canada to USA 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 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 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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