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Caribbean Cruises Starting In October 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in October 2027, 2028 or 2029? Choose from 152 unique cruises and 1,773 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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152 Cruises (1,773 Departures)
152 Cruises (1,773 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$300pp
$191,550pp
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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
Operator: Norwegian Cruise Line
Ships: Norwegian Escape, Norwegian Prima, Norwegian Viva
Departures: Nov 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,053
Oceanview
$1,142
Balcony
$1,246
Suite
$1,857
From (Per Person)
A$1,053
Save 23
Per Person
View Trip
9 Day Southern Caribbean Yacht Harbors with Seabourn
Cruise
 (1)

9 Days (8 Nights) Halifax to Bridgetown
Operator: Seabourn
Ship: Seabourn Venture
Departures: Oct 2027 to Oct 2028
Visits: Canada, Saint Kitts and Nevis, Spain, Saint Lucia, Barbados
Exclusive Savings
Balcony
-
Suite
$6,281
From (Per Person)
A$6,281
Save 117
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: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Mexico, Dominican Republic
Exclusive Savings
Inside
$1,379
Oceanview
$1,726
Balcony
$2,191
Suite
$4,240
From (Per Person)
A$1,379
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
$626
Oceanview
$764
Balcony
$962
Suite
$1,863
From (Per Person)
A$626
Save 14
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
Ships: Enchantment of the Seas, Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Sep 2028
Visits: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,018
Oceanview
$1,102
Balcony
$1,589
Suite
$2,176
From (Per Person)
A$1,018
Save 895
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
$575
Oceanview
$695
Balcony
$754
Suite
$933
From (Per Person)
A$575
Save 13
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
$1,639
Oceanview
$1,746
Balcony
$2,073
Suite
$5,314
From (Per Person)
A$1,639
Save 1,488
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: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Dominican Republic, Mexico
Exclusive Savings
Inside
$1,330
Oceanview
$1,607
Balcony
$2,043
Suite
$4,072
From (Per Person)
A$1,330
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Brilliance of the Seas, Enchantment of the Seas +2 more, Radiance of the Seas, Serenade of the Seas
Departures: Jun 2027 to Sep 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,001
Oceanview
$1,044
Balcony
$1,596
Suite
$2,351
From (Per Person)
A$1,001
Save 693
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ships: Brilliance of the Seas, Enchantment of the Seas, Serenade of the Seas
Departures: May 2027 to Jun 2028
Visits: USA, Mexico, Honduras
Exclusive Savings
Inside
$1,027
Oceanview
$1,075
Balcony
$1,645
Suite
$2,500
From (Per Person)
A$1,027
Save 836
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
Operator: Holland America
Ships: Eurodam, Nieuw Amsterdam
Departures: Dec 2026 to Oct 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,536
Oceanview
$1,843
Balcony
$2,150
Suite
$3,833
From (Per Person)
A$1,536
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
$863
Oceanview
$1,081
Balcony
$1,298
Suite
$3,845
From (Per Person)
A$863
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
Departure: 16 October 2027
Visits: USA, Cayman Islands, Jamaica, Bonaire, Aruba, Curacao, Dominican Republic
Exclusive Savings
Inside
$2,314
Oceanview
$2,552
Balcony
$3,106
Suite
-
From (Per Person)
A$2,314
Per Person
View Trip
8 Day Eastern: St. Maarten & St. Thomas with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Celebrity Cruises
Ship: Celebrity Apex
Departures: Oct 2027 to Mar 2029
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,253
Oceanview
$1,377
Balcony
$1,667
Suite
$4,685
From (Per Person)
A$1,253
Save 1,385
Per Person
View Trip
8 Day Secret treasures of the Lesser Antilles with Ponant
Cruise
 (1)

8 Days (7 Nights) La Romana to Fort-de-France
Operator: Ponant
Ship: Le Bellot
Departure: 25 October 2028
Visits: Dominican Republic, Virgin Islands, Montserrat, Guadeloupe, Dominica, Barbados, Martinique
Exclusive Savings
Balcony
$6,887
Suite
$10,292
From (Per Person)
A$6,887
Save 183
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
$1,158
Oceanview
$1,356
Balcony
$1,354
Suite
$4,488
From (Per Person)
A$1,158
Save 820
Per Person
View Trip
9 Day Aruba & Curacao Holiday with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Ships: Celebrity Beyond, Celebrity Reflection
Departures: Feb 2028 to Dec 2028
Visits: USA, Turks and Caicos Islands, Curacao, Aruba
Exclusive Savings
Inside
$1,511
Oceanview
$1,785
Balcony
$2,074
Suite
$5,581
From (Per Person)
A$1,511
Save 1,526
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
$1,010
Oceanview
$1,069
Balcony
$1,217
Suite
$1,336
From (Per Person)
A$1,010
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 +2 more, Norwegian Escape, Norwegian Getaway
Departures: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$886
Oceanview
$976
Balcony
$1,140
Suite
$1,408
From (Per Person)
A$886
Save 18
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
Departure: 16 October 2027
Visits: USA, Cayman Islands, Jamaica
Exclusive Savings
Inside
$725
Oceanview
$814
Balcony
$1,012
Suite
$3,404
From (Per Person)
A$725
Per Person
View Trip
14 Day Japan & Korea: Tokyo, Hiroshima with Celebrity Cruises
Cruise
 (3)

14 Days (13 Nights) Tokyo to Tokyo
Operator: Celebrity Cruises
Ship: Celebrity Millennium
Departure: 16 October 2028
Visits: Japan, South Korea
Exclusive Savings
Inside
$2,421
Oceanview
$3,270
Balcony
$4,522
Suite
$10,954
From (Per Person)
A$2,421
Save 1,687
Per Person
View Trip
8 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 14 October 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$1,019
Oceanview
$1,145
Balcony
$1,782
Suite
$2,901
From (Per Person)
A$1,019
Save 603
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 2029
Visits: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$895
Oceanview
$988
Balcony
$1,033
Suite
$1,508
From (Per Person)
A$895
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, Norwegian Escape
Departures: Dec 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$902
Oceanview
$1,528
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
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 2027 to Dec 2027
Visits: USA, Bonaire, Aruba, Curacao, Dominican Republic, Jamaica
Exclusive Savings
Inside
$1,589
Oceanview
$1,738
Balcony
$2,094
Suite
$7,293
From (Per Person)
A$1,589
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
Operator: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic
Departures: Dec 2026 to Apr 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$962
Oceanview
$1,395
Balcony
$1,171
Suite
$1,439
From (Per Person)
A$962
Save 22
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: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$636
Oceanview
$774
Balcony
$1,022
Suite
$2,002
From (Per Person)
A$636
Save 16
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
Ships: Celebrity Beyond, Celebrity Xcel
Departures: Nov 2026 to Oct 2027
Visits: USA, Aruba, Bonaire, Curacao
Exclusive Savings
Inside
$1,641
Oceanview
$1,824
Balcony
$1,873
Suite
$5,280
From (Per Person)
A$1,641
Save 1,511
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
$626
Oceanview
$764
Balcony
$982
Suite
$2,031
From (Per Person)
A$626
Save 51
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
Ships: Resilient Lady, Scarlet Lady, Valiant Lady
Departures: Dec 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Inside
$935
Oceanview
$1,082
Balcony
$1,227
Suite
$2,677
From (Per Person)
A$935
Per Person
View Trip
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Caribbean & Bahamas Cruises

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Travel Styles

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Countries

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

Cities

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Routes

Cruises from Barcelona to Miami Cruises from Barcelona to Fort Lauderdale Cruises from Bridgetown to Miami Cruises from Bridgetown to Bridgetown Cruises from Fort Lauderdale to San Juan 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 Los Angeles Cruises from Los Angeles to Miami Cruises from Miami to San Juan Cruises from Miami to Miami Cruises from Miami to Los Angeles Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Montreal to Miami Cruises from Montreal to New York Cruises from New York to Fort Lauderdale Cruises from New York to Miami Cruises from New York to New York Cruises from Orlando to Orlando Cruises from Quebec City to New York Cruises from San Juan to Fort Lauderdale Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Tampa to Tampa Cruises from Tokyo to Tokyo

Country Routes

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

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 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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