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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 145 unique cruises and 1,612 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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145 Cruises (1,612 Departures)
145 Cruises (1,612 Departures)
Departures
Duration
5 Days
72 Days
Start & End Cities
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Price
$300pp
$209,450pp
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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
Inside
$952
Oceanview
$1,099
Balcony
$1,246
Suite
$2,649
From (Per Person)
A$952
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: Nov 2026 to Oct 2028
Visits: USA, Dominican Republic, Virgin Islands, Bahamas
Just Cruise Fare
Exclusive Savings
Inside
$901
Oceanview
$1,170
Balcony
$1,274
Suite
$1,690
From (Per Person)
A$901
Save 18
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
$1,602
Balcony
$1,126
Suite
$1,200
From (Per Person)
A$902
Save 18
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 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
$1,439
Oceanview
$1,552
Balcony
$2,052
Suite
$4,941
From (Per Person)
A$1,439
Save 1,962
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
$636
Oceanview
$814
Balcony
$1,081
Suite
$2,457
From (Per Person)
A$636
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
$878
Oceanview
$1,100
Balcony
$1,320
Suite
$3,911
From (Per Person)
A$878
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
$1,270
Oceanview
$1,627
Balcony
$2,161
Suite
$4,924
From (Per Person)
A$1,270
Save 21
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
$1,487
Oceanview
$1,536
Balcony
$1,993
Suite
$4,872
From (Per Person)
A$1,487
Save 1,063
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
$1,047
Oceanview
$1,109
Balcony
$1,689
Suite
$2,312
From (Per Person)
A$1,047
Save 802
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
Departures: Oct 2026 to Nov 2028
Visits: Martinique, Guadeloupe, Saint Lucia, Saint Vincent, Holland, Colombia, Panama
Exclusive Savings
Balcony
$11,244
Suite
$15,842
From (Per Person)
A$11,244
Save 296
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
$865
Oceanview
$974
Balcony
$1,142
Suite
$1,736
From (Per Person)
A$865
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
$1,685
Oceanview
$2,190
Balcony
$2,903
Suite
$6,982
From (Per Person)
A$1,685
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
$664
Oceanview
$725
Balcony
$739
Suite
$843
From (Per Person)
A$664
Save 13
Per Person
View Trip
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: Oct 2026 to Oct 2028
Visits: USA, Mexico, Honduras, Belize
Just Cruise Fare
Exclusive Savings
Inside
$1,097
Oceanview
$1,202
Balcony
$1,350
Suite
$1,960
From (Per Person)
A$1,097
Save 23
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
$1,659
Oceanview
$1,817
Balcony
$2,183
Suite
$7,382
From (Per Person)
A$1,659
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
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
Exclusive Savings
Inside
$1,230
Oceanview
$1,537
Balcony
$1,844
Suite
-
From (Per Person)
A$1,230
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
$1,330
Oceanview
$1,686
Balcony
$2,221
Suite
$4,993
From (Per Person)
A$1,330
Save 21
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
$755
Oceanview
$844
Balcony
$1,052
Suite
$3,572
From (Per Person)
A$755
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
$1,330
Oceanview
$1,418
Balcony
$1,714
Suite
$5,165
From (Per Person)
A$1,330
Save 699
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
$715
Oceanview
$873
Balcony
$1,170
Suite
$2,309
From (Per Person)
A$715
Save 16
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
Ship: Coral Princess
Departure: 29 October 2026
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
$1,697
Balcony
-
Suite
$3,291
From (Per Person)
A$1,697
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
$1,024
Oceanview
$1,099
Balcony
$1,247
Suite
$1,366
From (Per Person)
A$1,024
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
$6,771
From (Per Person)
A$6,771
Save 128
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
$2,702
Oceanview
$3,552
Balcony
$5,015
Suite
$11,347
From (Per Person)
A$2,702
Save 1,639
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
$1,781
Oceanview
$1,999
Balcony
$2,321
Suite
$5,982
From (Per Person)
A$1,781
Save 1,526
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
$636
Oceanview
$774
Balcony
$1,041
Suite
$2,437
From (Per Person)
A$636
Save 14
Per Person
View Trip
6 Day Western Caribbean Getaway Cruise with Royal Caribbean
Cruise

6 Days (5 Nights) Galveston to Galveston
Operator: Royal Caribbean
Ship: Liberty of the Seas
Departures: Nov 2026 to Apr 2028
Visits: USA, Mexico
Exclusive Savings
Inside
$729
Oceanview
$789
Balcony
$931
Suite
$1,702
From (Per Person)
A$729
Save 744
Per Person
View Trip
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Countries

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Routes

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Country Routes

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Cruise Lines Exploring The Caribbean & Bahamas

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