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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 559 unique cruises and 2,846 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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559 Cruises (2,846 Departures)
559 Cruises (2,846 Departures)
Departures
Duration
5 Days
141 Days
Start & End Cities
Ship Size
Cruise Lines
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Price
$400pp
$209,450pp
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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 2027 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
$8,129
Suite
$11,461
From (Per Person)
A$8,129
Save 200
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Saint Martin, Barbados, Martinique, Saint Kitts and Nevis, Virgin Islands
Inside
$1,087
Oceanview
$1,685
Balcony
$1,885
Suite
$5,279
From (Per Person)
A$1,087
Per Person
View Trip
8 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departure: 15 January 2028
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Antigua and Barbuda, Saint Martin
Inside
$1,088
Oceanview
$1,686
Balcony
$1,885
Suite
$5,280
From (Per Person)
A$1,088
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (3)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sky Princess
Departure: 02 January 2028
Visits: USA, Bahamas, Puerto Rico, Dominican Republic +4 more, Turks and Caicos Islands, Jamaica, Cayman Islands, Mexico
Exclusive Savings
Inside
$1,946
Oceanview
$2,318
Balcony
$2,360
Suite
$3,718
From (Per Person)
A$1,946
Per Person
View Trip
11 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

11 Days (10 Nights) Philadelphia to Philadelphia
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 13 January 2027
Visits: USA, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,495
Oceanview
$1,629
Balcony
$2,686
Suite
$2,835
From (Per Person)
A$1,495
Per Person
View Trip
10 Day Southern Caribbean Cruise: St.barts, Antigua & Tortola with Azamara Cruises
Cruise
 (6)

10 Days (9 Nights) San Juan to Miami
Operator: Azamara
Ship: Azamara Journey
Departure: 05 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Exclusive Savings
Inside
$2,944
Oceanview
$3,659
Balcony
$4,747
Suite
$13,528
From (Per Person)
A$2,944
Save 45
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: Oct 2026 to Apr 2028
Visits: Panama, Colombia, Aruba, Curacao
Exclusive Savings
Inside
$1,417
Oceanview
$1,500
Balcony
$2,134
Suite
$2,466
From (Per Person)
A$1,417
Save 1,089
Per Person
View Trip
8 Day Southern Caribbean with St. Lucia with Princess
Cruise
 (12)

8 Days (7 Nights) Bridgetown to Bridgetown
Operator: Princess
Ships: Crown Princess, Emerald Princess
Departures: Jan 2027 to Mar 2028
Visits: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$2,066
Oceanview
$2,226
Balcony
$2,357
Suite
$3,595
From (Per Person)
A$2,066
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
$848
Oceanview
$1,132
Balcony
$1,346
Suite
$3,772
From (Per Person)
A$848
Per Person
View Trip
15 Day Eastern Caribbean: Bahamas & San Juan with Holland America
Cruise
 (2)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ship: Nieuw Statendam
Departure: 17 January 2027
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Puerto Rico, Virgin Islands
Fare Saver
Exclusive Savings
Inside
$2,391
Oceanview
$2,757
Balcony
$3,549
Suite
$5,014
From (Per Person)
A$2,391
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Celebration Key with Princess
Cruise
 (7)

15 Days (14 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, Bahamas, Honduras, Mexico
Sanctuary Collection
Exclusive Savings
Inside
$2,278
Oceanview
$2,417
Balcony
$3,096
Suite
$4,413
From (Per Person)
A$2,278
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: 22 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
$2,449
Balcony
$2,777
Suite
$4,101
From (Per Person)
A$2,121
Per Person
View Trip
12 Day Panama Canal & Southern Caribbean with Celebrity Cruises
Cruise
 (1)

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Ship: Celebrity Ascent
Departures: Nov 2027 to Jan 2028
Visits: USA, Aruba, Curacao, Panama, Cayman Islands, Bahamas
Exclusive Savings
Inside
$2,921
Oceanview
$3,656
Balcony
$4,269
Suite
$10,801
From (Per Person)
A$2,921
Save 1,864
Per Person
View Trip
12 Day Panama Canal From Miami To Miami with Norwegian Cruise Line
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Operator: Norwegian Cruise Line
Ship: Norwegian Sun
Departures: Dec 2026 to Mar 2027
Visits: USA, Jamaica, Colombia, Panama, Costa Rica, Belize, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,562
Oceanview
$1,674
Balcony
$2,113
Suite
$2,777
From (Per Person)
A$1,562
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Inside
$1,273
Oceanview
$1,359
Balcony
$1,444
Suite
$4,437
From (Per Person)
A$1,273
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Celebration Key with Princess
Cruise
 (7)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sun Princess
Departure: 22 January 2028
Visits: USA, Bahamas, Virgin Islands, Saint Martin, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Exclusive Savings
Inside
$2,137
Oceanview
$2,420
Balcony
$3,074
Suite
$4,604
From (Per Person)
A$2,137
Per Person
View Trip
22 Day Panama Canal & Southern Caribbean Holiday with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ship: Oosterdam
Departures: Jan 2028 to Mar 2028
Visits: USA, Bahamas, Aruba, Colombia +5 more, Panama, Costa Rica, Cayman Islands, Curacao, Bonaire
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$5,438
Oceanview
$6,894
Balcony
$8,201
Suite
$11,651
From (Per Person)
A$5,438
Per Person
View Trip
11 Day Eastern Caribbean with St. Kitts & Celebration Key with Princess
Cruise
 (2)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Enchanted Princess
Departures: Jan 2027 to Apr 2027
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,468
Oceanview
$1,978
Balcony
$2,012
Suite
$2,705
From (Per Person)
A$1,468
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 Apr 2028
Visits: Colombia, Curacao, Aruba, Panama
Exclusive Savings
Inside
$1,478
Oceanview
$1,621
Balcony
$2,290
Suite
$2,761
From (Per Person)
A$1,478
Save 971
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: 24 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +5 more, Saint Lucia, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Savings
Inside
$1,975
Oceanview
$2,086
Balcony
$4,596
Suite
$6,566
From (Per Person)
A$1,975
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
$1,269
Balcony
$1,457
Suite
$2,408
From (Per Person)
A$1,022
Per Person
View Trip
13 Day Ultimate Southern Caribbean with Celebrity Cruises
Cruise
 (3)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Celebrity Cruises
Ship: Celebrity Eclipse
Departure: 05 January 2028
Visits: USA, Cayman Islands, Aruba, Curacao +4 more, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$2,206
Oceanview
$2,512
Balcony
$2,986
Suite
$8,255
From (Per Person)
A$2,206
Save 1,484
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 +2 more, Norwegian Escape, Norwegian Prima
Departures: Sep 2026 to Sep 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Just Cruise Fare
Exclusive Savings
Inside
$1,126
Oceanview
$1,319
Balcony
$1,572
Suite
$1,796
From (Per Person)
A$1,126
Save 19
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: 02 January 2027
Visits: USA, Bahamas, Jamaica, Cayman Islands +8 more, Belize, Mexico, Saint Martin, Antigua and Barbuda, Dominica, Martinique, Saint Kitts and Nevis, Puerto Rico
Fare Saver
Exclusive Savings
Inside
$3,562
Oceanview
$4,146
Balcony
$5,680
Suite
$8,155
From (Per Person)
A$3,562
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: 03 January 2027
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,256
Oceanview
$2,330
Balcony
$2,479
Suite
$2,925
From (Per Person)
A$2,256
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise
 (3)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sky Princess
Departures: Nov 2027 to Jan 2028
Visits: USA, Bahamas, Jamaica, Cayman Islands +4 more, Mexico, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,945
Oceanview
$2,341
Balcony
$2,382
Suite
$3,648
From (Per Person)
A$1,945
Per Person
View Trip
15 Day Eastern Caribbean Adventurer with Celebration Key with Princess
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Regal Princess
Departure: 17 January 2027
Visits: USA, Bahamas, Dominican Republic, Turks and Caicos Islands, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,935
Oceanview
-
Balcony
$3,738
Suite
$5,321
From (Per Person)
A$1,935
Per Person
View Trip
9 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 29 January 2027
Visits: Puerto Rico, Aruba, Curacao, Bonaire, Martinique, Saint Martin
Inside
$2,269
Oceanview
$2,382
Balcony
$2,611
Suite
$6,486
From (Per Person)
A$2,269
Per Person
View Trip
22 Day Eastern & Western Caribbean: Leeward Islands & Mexico with Holland America
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Holland America
Ships: Eurodam, Rotterdam
Departures: Jan 2027 to Dec 2027
Visits: USA, Saint Martin, Antigua and Barbuda, Dominica +9 more, Martinique, Saint Kitts and Nevis, Puerto Rico, Bahamas, Jamaica, Cayman Islands, Honduras, Belize, Mexico
Fare Saver
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$3,552
Oceanview
$4,136
Balcony
$5,670
Suite
$8,086
From (Per Person)
A$3,552
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
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Caribbean & Bahamas Cruises

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Travel Styles

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Countries

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Cities

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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

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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