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Caribbean Cruises Starting In January 2027, 2028 and 2029

Are you planning a cruise to the Caribbean in January 2027, 2028 or 2029? Choose from 561 unique cruises and 2,898 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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561 Cruises (2,898 Departures)
561 Cruises (2,898 Departures)
Departures
Duration
5 Days
141 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$400pp
$203,830pp
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11 Day West Indies Explorer with Viking Cruises
Cruise
 (1)

11 Days (10 Nights) San Juan to San Juan
Operator: Viking
Ships: Viking Sea, Viking Sky
Departures: Nov 2026 to Jan 2029
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia +4 more, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Savings
Balcony
$6,610
Suite
$9,354
From (Per Person)
A$6,610
Save 1,385
Per Person
View Trip
11 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Brilliant Lady
Departures: Nov 2026 to Feb 2027
Visits: USA, Saint Martin, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Bahamas
Inside
$1,582
Oceanview
$1,728
Balcony
$2,163
Suite
$5,938
From (Per Person)
A$1,582
Per Person
View Trip
9 Day St. Maarten, San Juan & St. Thomas with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 15 January 2028
Visits: USA, Virgin Islands, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,888
Oceanview
$2,027
Balcony
$2,296
Suite
$6,048
From (Per Person)
A$1,888
Save 1,200
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sun Princess
Departure: 03 January 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$1,022
Oceanview
$1,170
Balcony
$1,418
Suite
$2,400
From (Per Person)
A$1,022
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 Getaway
Departures: Nov 2026 to Feb 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,244
Oceanview
$1,499
Balcony
$1,572
Suite
$1,811
From (Per Person)
A$1,244
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 17 January 2027
Visits: Puerto Rico, Bonaire, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,107
Oceanview
$2,226
Balcony
$2,479
Suite
$2,747
From (Per Person)
A$2,107
Per Person
View Trip
8 Day Western Caribbean with Mexico From Fort Lauderdale with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ships: Regal Princess, Star Princess, Sun Princess
Departures: Oct 2026 to Mar 2027
Visits: USA, Mexico, Belize, Honduras
Sanctuary Collection
Exclusive Savings
Inside
$972
Oceanview
$1,190
Balcony
$1,288
Suite
$1,982
From (Per Person)
A$972
Save 20
Per Person
View Trip
9 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (2)

9 Days (8 Nights) Tampa to Tampa
Operator: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2027 to Mar 2028
Visits: USA, Cayman Islands, Mexico, Honduras
Exclusive Savings
Inside
$1,329
Oceanview
$1,423
Balcony
$1,629
Suite
$2,879
From (Per Person)
A$1,329
Save 786
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise
 (3)

8 Days (7 Nights) Marigot to Bridgetown
Operator: Emerald Cruises
Ships: Emerald Azzurra
Departures: Dec 2026 to Mar 2027
Visits: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis +4 more, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Exclusive Savings
Oceanview
$6,770
Suite
$7,314
From (Per Person)
A$6,770
Save 4,636
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Kitts with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Jan 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$1,090
Oceanview
$1,193
Balcony
$1,625
Suite
$2,278
From (Per Person)
A$1,090
Per Person
View Trip
8 Day Western Caribbean with Mexico & Celebration Key with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sun Princess
Departures: Dec 2027 to Feb 2028
Visits: USA, Belize, Honduras, Mexico, Bahamas
Sanctuary Collection
Exclusive Savings
Inside
$1,161
Oceanview
$1,389
Balcony
$1,527
Suite
$2,280
From (Per Person)
A$1,161
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visits: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$1,310
Oceanview
$1,413
Balcony
$1,515
Suite
$5,376
From (Per Person)
A$1,310
Per Person
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (12)

15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visits: Puerto Rico, Saint Martin, Martinique, Grenada +4 more, Saint Lucia, Barbados, Virgin Islands, Antigua and Barbuda
Exclusive Savings
Inside
$2,636
Oceanview
$2,867
Balcony
$5,547
Suite
$7,586
From (Per Person)
A$2,636
Per Person
View Trip
8 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departure: 03 January 2027
Visits: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,209
Oceanview
$1,311
Balcony
$1,413
Suite
$4,157
From (Per Person)
A$1,209
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 Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Operator: Royal Caribbean
Ship: Grandeur of the Seas
Departures: Jan 2028 to Apr 2028
Visits: Panama, Colombia, Curacao, Aruba
Exclusive Savings
Inside
$1,429
Oceanview
$1,592
Balcony
$2,134
Suite
$2,371
From (Per Person)
A$1,527
Save 926
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: Jan 2027 to Apr 2028
Visits: Colombia, Curacao, Aruba, Panama
Exclusive Savings
Inside
$1,517
Oceanview
$1,623
Balcony
$2,197
Suite
$2,578
From (Per Person)
A$1,517
Save 1,088
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: Jan 2028 to Mar 2028
Visits: Colombia, Curacao, Aruba, Panama
Exclusive Savings
Inside
$1,580
Oceanview
$1,758
Balcony
$2,420
Suite
$2,708
From (Per Person)
A$1,580
Save 970
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 31 January 2027
Visits: Puerto Rico, Curacao, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,032
Oceanview
$2,226
Balcony
$2,479
Suite
$2,703
From (Per Person)
A$2,032
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
Departure: 14 January 2027
Visits: USA, Curacao, Aruba, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,708
Oceanview
$1,758
Balcony
$2,094
Suite
$7,085
From (Per Person)
A$1,708
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
$1,067
Oceanview
$1,108
Balcony
$1,744
Suite
$2,322
From (Per Person)
A$1,067
Save 888
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
Ship: Rotterdam
Departure: 02 January 2027
Visits: USA, Bahamas, Jamaica, Cayman Islands, Belize, Mexico
Fare Saver
Exclusive Savings
Inside
$1,775
Oceanview
$2,082
Balcony
$2,617
Suite
$3,924
From (Per Person)
A$1,775
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Operator: Princess
Ship: Regal Princess
Departures: Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic, Bahamas, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$1,686
Oceanview
-
Balcony
$2,330
Suite
$3,736
From (Per Person)
A$1,686
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Operator: Princess
Ship: Regal Princess
Departures: Jan 2028
Visits: USA, Belize, Honduras, Mexico +4 more, Bahamas, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,687
Oceanview
-
Balcony
$2,206
Suite
$3,469
From (Per Person)
A$1,687
Per Person
View Trip
6 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (12)

6 Days (5 Nights) San Juan to Bridgetown
Operator: Princess
Ship: Crown Princess
Departure: 03 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$1,307
Oceanview
$1,328
Balcony
$1,525
Suite
$2,733
From (Per Person)
A$1,307
Per Person
View Trip
8 Day Southern Caribbean with Barbados and St. Lucia with Princess
Cruise
 (12)

8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,021
Oceanview
$1,110
Balcony
$1,585
Suite
$1,981
From (Per Person)
A$1,021
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
Departure: 23 January 2027
Visits: Panama, Colombia, Curacao, Aruba
Exclusive Savings
Inside
$1,854
Oceanview
$2,084
Balcony
-
Suite
-
From (Per Person)
A$1,854
Save 1,029
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 15 January 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Antigua and Barbuda, Saint Martin
Just Cruise Fare
Exclusive Savings
Inside
$2,121
Oceanview
$2,419
Balcony
$2,777
Suite
$4,131
From (Per Person)
A$2,121
Per Person
View Trip
8 Day A Journey from Dominican Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 09 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
View Trip
13 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

13 Days (12 Nights) Philadelphia to Philadelphia
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 15 January 2028
Visits: USA, Saint Martin, Saint Lucia, Barbados, Antigua and Barbuda, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$2,101
Oceanview
$2,459
Balcony
$3,084
Suite
$3,650
From (Per Person)
A$2,101
Per Person
View Trip
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Countries

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Routes

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 London Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from Jacksonville to Jacksonville Cruises from La Romana to La Romana Cruises from London to Fort Lauderdale Cruises from London to London Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Miami to San Juan Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Miami to Miami Cruises from Miami to London Cruises from New Orleans to New Orleans Cruises from New York to New York Cruises from New York to London Cruises from Orlando to Orlando Cruises from Panama City to Miami Cruises from Philadelphia to Philadelphia Cruises from Philipsburg to Bridgetown Cruises from Pointe-A-Pitre to Pointe-A-Pitre Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa

Country Routes

Cruises from Australia to England Cruises from Puerto Rico to USA Cruises from Chile to USA Cruises from Singapore to China Cruises from Dominican Republic to USA Cruises from Brazil to Spain 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 Australia to USA Cruises from Barbados to USA Cruises from Brazil to Argentina Cruises from Canada to USA Cruises from Chile to Argentina Cruises from England to Spain Cruises from England to USA Cruises from Saint Martin to Barbados Cruises from USA to Dominican Republic Cruises from Panama to USA Cruises from Spain to Brazil Cruises from Barbados to Saint Martin Cruises from Spain to USA Cruises from USA to Argentina Cruises from USA to Barbados Cruises from USA to Canada Cruises from USA to Chile Cruises from USA to England Cruises from Spain to England Cruises from USA to Panama Cruises from USA to Peru Cruises from USA to Spain

Cruise Lines Exploring The Caribbean & Bahamas

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