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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 191 unique cruises and 1,838 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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191 Cruises (1,838 Departures)
191 Cruises (1,838 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$300pp
$209,450pp
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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
$3,291
Oceanview
$1,685
Balcony
-
Suite
-
From (Per Person)
A$1,685
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
$1,441
Oceanview
$1,530
Balcony
$2,005
Suite
$7,233
From (Per Person)
A$1,441
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
$1,205
Oceanview
$1,204
Balcony
$1,444
Suite
$5,065
From (Per Person)
A$1,204
Save 850
Per Person
View Trip
10 Day Southern Caribbean: ABC Islands with Holland America
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Operator: 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
$2,230
Suite
-
From (Per Person)
A$1,230
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
$1,568
Oceanview
$1,941
Balcony
$2,062
Suite
$5,420
From (Per Person)
A$1,568
Save 1,645
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
-
Suite
-
From (Per Person)
A$2,839
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
$1,664
Oceanview
$833
Balcony
-
Suite
-
From (Per Person)
A$833
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
$1,349
Oceanview
$1,352
Balcony
$1,746
Suite
$4,310
From (Per Person)
A$1,349
Save 1,204
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
Drinks On Us
Inside
-
Oceanview
$2,117
Balcony
$2,205
Suite
-
From (Per Person)
A$2,117
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: 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
$1,032
Oceanview
$1,109
Balcony
$1,689
Suite
$2,332
From (Per Person)
A$1,032
Save 951
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: Brilliant Lady, Resilient Lady +2 more, Scarlet Lady, Valiant Lady
Departures: Nov 2026 to Oct 2028
Visits: USA, Turks and Caicos Islands, Bahamas
Drinks On Us
Inside
$952
Oceanview
$1,100
Balcony
$1,174
Suite
$2,797
From (Per Person)
A$952
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
-
Balcony
$5,205
Suite
-
From (Per Person)
A$2,839
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
$2,413
Oceanview
$2,661
Balcony
$3,235
Suite
-
From (Per Person)
A$2,413
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
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,457
From (Per Person)
A$735
Per Person
View Trip
8 Day Tortola, St. Maarten & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 25 October 2026
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
-
Oceanview
$1,446
Balcony
-
Suite
-
From (Per Person)
A$1,446
Save 1,023
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
$4,432
Oceanview
$2,270
Balcony
-
Suite
-
From (Per Person)
A$2,270
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
$2,813
Oceanview
$1,408
Balcony
-
Suite
-
From (Per Person)
A$1,408
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: 10 October 2026
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands
Exclusive Savings
Inside
$2,941
Oceanview
$1,472
Balcony
-
Suite
-
From (Per Person)
A$1,472
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
Fare Saver
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$1,536
Oceanview
$1,843
Balcony
$2,150
Suite
$3,833
From (Per Person)
A$1,536
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
$1,332
Oceanview
$1,358
Balcony
$1,806
Suite
$4,379
From (Per Person)
A$1,332
Save 1,430
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
Drinks On Us
Inside
-
Oceanview
$1,746
Balcony
$1,953
Suite
-
From (Per Person)
A$1,746
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
$1,038
Oceanview
$1,455
Balcony
$1,231
Suite
$1,470
From (Per Person)
A$1,038
Save 21
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
$1,627
Oceanview
$1,825
Balcony
$2,359
Suite
$4,943
From (Per Person)
A$1,627
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
$1,567
Oceanview
$1,874
Balcony
$2,409
Suite
$4,993
From (Per Person)
A$1,567
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
$2,562
Oceanview
$3,411
Balcony
$4,768
Suite
$10,785
From (Per Person)
A$2,562
Save 1,779
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
$829
Balcony
$888
Suite
$1,008
From (Per Person)
A$784
Save 12
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
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$1,389
Oceanview
$1,775
Balcony
$2,003
Suite
$3,072
From (Per Person)
A$1,389
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
$735
Oceanview
$913
Balcony
$1,180
Suite
$2,487
From (Per Person)
A$735
Save 15
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: Oct 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$1,095
Oceanview
$1,170
Balcony
$1,274
Suite
$1,690
From (Per Person)
A$1,095
Save 20
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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Routes

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Country Routes

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 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 Panama Cruises from USA to Argentina Cruises from Chile to Argentina Cruises from USA to Barbados Cruises from Canada to Japan Cruises from USA to Japan Cruises from USA to Peru

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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