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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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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
$1,771
Suite
$2,322
From (Per Person)
A$1,067
Save 888
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
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
$1,559
Oceanview
$1,646
Balcony
$1,733
Suite
$4,346
From (Per Person)
A$1,559
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
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
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 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 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
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: 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
$1,267
Oceanview
-
Balcony
$1,496
Suite
$1,941
From (Per Person)
A$1,267
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: Aug 2026 to Mar 2028
Visits: Colombia, Aruba, Curacao, Panama
Exclusive Savings
Inside
$1,464
Oceanview
$1,621
Balcony
$2,195
Suite
$2,297
From (Per Person)
A$1,464
Save 1,647
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
$784
Oceanview
$933
Balcony
$1,171
Suite
$1,305
From (Per Person)
A$784
Save 12
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
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
6 Day Grand Turk & Bimini Beach Club with Virgin Voyages
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departures: Sep 2026 to Oct 2026
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$1,226
Oceanview
$1,299
Balcony
$1,371
Suite
$3,476
From (Per Person)
A$1,226
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: Sep 2026 to Apr 2028
Visits: Panama, Colombia, Aruba, Curacao
Exclusive Savings
Inside
$1,389
Oceanview
$1,545
Balcony
$1,996
Suite
$2,296
From (Per Person)
A$1,389
Save 1,878
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
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: 17 October 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Mexico, Belize, Honduras
Exclusive Savings
Inside
$2,005
Oceanview
-
Balcony
$2,263
Suite
-
From (Per Person)
A$2,005
Per Person
View Trip
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
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
8 Day Tortola, St. Kitts & Puerto Plata 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, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
$1,852
Balcony
$2,731
Suite
$7,498
From (Per Person)
A$1,852
Save 1,238
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
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
11 Day Western Caribbean: Greater Antilles, Belize & Mexico with Holland America
Cruise
 (3)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ships: Eurodam, Rotterdam
Departures: Oct 2026 to Dec 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
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
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
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 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
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
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
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
$2,920
Suite
$6,622
From (Per Person)
A$1,741
Per Person
View Trip
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Caribbean & Bahamas Cruises

Aruba Cruises Bahamas Cruises Barbados Cruises Bermunda Cruises Caribbean Cruises Central America Cruises Jamaica Cruises Mexico Cruises Panama Cruises Puerto Rico Cruises Virgin Islands Cruises

Travel Styles

Festivals & Events Luxury Cruises Short Cruise Breaks Wildlife Cruises

Countries

Aruba Bahamas Barbados Belize Canada Cayman Islands China Curacao Dominican Republic Haiti Honduras Jamaica Martinique Mexico Morocco Puerto Rico Saint Barthelemy Saint Lucia Saint Martin Saint Vincent Singapore Spain Turks and Caicos Islands USA Vietnam Virgin Islands

Cities

Cruises from Barcelona Cruises from Boston Cruises from Bridgetown Cruises from Fort Lauderdale Cruises from Fort-de-France Cruises from Galveston Cruises from La Romana Cruises from Los Angeles Cruises from Miami Cruises from Montreal Cruises from New York Cruises from Orlando Cruises from Quebec City Cruises from San Juan Cruises from San Juan Cruises from San Juan Cruises from Tampa

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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