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 491 unique cruises and 2,644 departures operated by Caribbean's leading cruise lines. Easily compare prices, itineraries, inclusions and traveler reviews to find the Caribbean cruise that best matches your travel style, budget and dates.
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491 Cruises (2,644 Cruise Departures)
Cruise
 (1)

8 Days (7 Nights) Colon to Colon
Cruise Line: Royal Caribbean
Departures: Jun 2026 to Apr 2028
Visit: Panama, Colombia, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$777
Oceanview
$787
Balcony
$1,061
Suite
$1,208
From
US$777
Save 1,050
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departures: Jul 2026 to Mar 2027
Visit: USA, Honduras, Belize, Mexico
Princess Standard
Sanctuary Collection
Inside
$539
Oceanview
$699
Balcony
$614
Suite
$789
From
US$539
Per Person
View Trip
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Departures: Nov 2026 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Viking $799 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Save 750
Per Person
View Trip
Cruise
 (2)

6 Days (5 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Departures: Jun 2027 to Oct 2028
Visit: USA, Dominican Republic, Bahamas
Inside
$595
Oceanview
$745
Balcony
$945
Suite
$2,650
From
US$595
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Miami to Miami
Cruise Line: Princess
Departures: Jan 2028
Visit: USA, Belize, Honduras, Mexico (+4 more), Bahamas, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$1,223
Oceanview
-
Balcony
$1,663
Suite
$2,453
From
US$1,223
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Departure: 16 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Barbados, Saint Lucia, Saint Kitts and Nevis, Dominica, Grenada
Princess Standard
Inside
$1,463
Oceanview
$1,933
Balcony
$2,383
Suite
$3,213
From
US$1,463
Per Person
View Trip
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 31 January 2028
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, Puerto Rico
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,640
Suite
$11,800
From
US$6,640
Save 1,660
Per Person
View Trip
Cruise
 (3)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 02 January 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands, Belize, Mexico
Fare Saver
Inside
$1,149
Oceanview
$1,449
Balcony
$1,749
Suite
$2,499
From
US$1,149
Per Person
View Trip
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departures: Dec 2026 to Mar 2027
Visit: USA, Jamaica, Colombia, Panama, Costa Rica, Belize, Mexico
Inside
$1,599
Oceanview
$1,659
Balcony
$2,129
Suite
$3,309
From
US$1,599
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Nov 2026 to Jan 2027
Visit: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Martinique, Saint Kitts and Nevis
Inside
$1,113
Oceanview
$1,323
Balcony
$1,253
Suite
$2,863
From
US$1,113
Per Person
View Trip
Cruise
 (1)

7 Days (6 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Departure: 14 January 2028
Visit: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,593
Oceanview
$2,043
Balcony
$2,323
Suite
$3,208
From
US$1,593
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Departures: Jan 2028
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$674
Oceanview
-
Balcony
$864
Suite
$1,279
From
US$674
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Departures: Dec 2026 to Jan 2027
Visit: Martinique, Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Guadeloupe
Inside
-
Oceanview
-
Balcony
$6,010
Suite
$8,870
From
US$6,010
Per Person
View Trip
Cruise
 (1)

13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Silversea
Ship: Silver Nova
Departure: 06 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+5 more), Saint Kitts and Nevis, Aruba, Curacao, Bonaire, Barbados
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,900
Suite
$13,600
From
US$6,900
Save 4,600
Per Person
View Trip
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 09 January 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,640
Suite
$11,800
From
US$6,640
Save 1,660
Per Person
View Trip
Cruise
 (3)

10 Days (9 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Departure: 05 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Inside
$2,779
Oceanview
$3,449
Balcony
$4,119
Suite
$6,349
From
US$2,779
Per Person
View Trip
Cruise
 (11)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Departures: Jan 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Princess Standard
Inside
$674
Oceanview
$724
Balcony
$1,154
Suite
$1,329
From
US$674
Per Person
View Trip
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Departures: Nov 2027 to Apr 2028
Visit: USA, Turks and Caicos Islands, Dominican Republic, Bahamas
Inside
$833
Oceanview
$1,043
Balcony
$1,253
Suite
$3,500
From
US$833
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 03 January 2027
Visit: USA, Bahamas, Turks and Caicos Islands, Aruba, Bonaire, Curacao
Princess Standard
Inside
$3,003
Oceanview
-
Balcony
$4,323
Suite
$5,883
From
US$3,003
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Departures: Nov 2026 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Mexico
Inside
$786
Oceanview
$1,026
Balcony
$1,436
Suite
$2,980
From
US$786
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Departures: Dec 2026 to Jan 2028
Visit: USA, Bahamas, Aruba, Colombia (+5 more), Panama, Costa Rica, Cayman Islands, Bonaire, Curacao
Fare Saver
Book Early & Have It All Fare Option
Inside
$2,504
Oceanview
$2,904
Balcony
$3,764
Suite
$7,404
From
US$2,504
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Jun 2026 to Apr 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$699
Oceanview
$879
Balcony
$969
Suite
$1,129
From
US$699
Per Person
View Trip
Cruise
 (11)

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Departure: 15 January 2027
Visit: Barbados, Puerto Rico, Saint Martin, Martinique, Grenada, Saint Lucia
Princess Standard
Inside
$1,224
Oceanview
$1,474
Balcony
$1,824
Suite
$2,399
From
US$1,224
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Antigua and Barbuda, Saint Martin
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Cartagena to Cartagena
Cruise Line: Royal Caribbean
Departure: 31 January 2027
Visit: Colombia, Curacao, Aruba, Bonaire, Panama
Exclusive Savings
Inside
$1,202
Oceanview
$1,202
Balcony
$1,964
Suite
$1,975
From
US$1,202
Save 635
Per Person
View Trip
Cruise
 (2)

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departures: Jan 2027 to Mar 2027
Visit: USA, Antigua and Barbuda, Saint Lucia, Barbados, Saint Vincent, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,146
Oceanview
$1,497
Balcony
$1,532
Suite
$5,346
From
US$1,146
Save 808
Per Person
View Trip
Cruise
 (1)

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Departure: 31 January 2027
Visit: USA, Bahamas, Turks and Caicos Islands, Aruba, Curacao, Bonaire
Princess Standard
Inside
$3,393
Oceanview
-
Balcony
$4,113
Suite
$5,623
From
US$3,393
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Departures: Dec 2027 to Mar 2028
Visit: USA, Belize, Honduras, Mexico, Bahamas
Princess Standard
Inside
$624
Oceanview
-
Balcony
$724
Suite
$999
From
US$624
Per Person
View Trip
Cruise
 (2)

13 Days (12 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Departure: 05 January 2028
Visit: USA, Cayman Islands, Aruba, Curacao (+4 more), Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,294
Oceanview
$1,494
Balcony
$1,794
Suite
$5,827
From
US$1,294
Save 852
Per Person
View Trip
Cruise
 (2)

9 Days (8 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Nov 2027 to Mar 2028
Visit: USA, Cayman Islands, Mexico, Honduras
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$909
Balcony
$1,175
Suite
$1,933
From
US$840
Save 477
Per Person
View Trip
Results: 1-30 of 491

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Routes

Cruises from Barcelona to Fort Lauderdale Cruises from Barcelona to London Cruises from Barcelona to Rome Cruises from Barcelona to Barcelona Cruises from Barcelona to Miami 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 Barcelona Cruises from Fort Lauderdale to Fort Lauderdale Cruises from Fort-de-France to Fort-de-France Cruises from Galveston to Galveston Cruises from Genoa to Genoa Cruises from Hamburg to London Cruises from Hamburg to Hamburg Cruises from Jacksonville to Jacksonville Cruises from La Romana to La Romana Cruises from London to Barcelona Cruises from London to Fort Lauderdale Cruises from London to Rome Cruises from London to London Cruises from London to New York Cruises from Los Angeles to Miami Cruises from Marseille to Marseille Cruises from Miami to San Juan Cruises from Miami to Rome Cruises from Miami to Bridgetown Cruises from Miami to Panama City Cruises from Miami to Barcelona 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 Rome to London Cruises from Rome to Miami Cruises from Rome to Barcelona Cruises from Rome to Fort Lauderdale Cruises from Rome to Rome Cruises from San Juan to Miami Cruises from San Juan to San Juan Cruises from Singapore to Hong Kong Cruises from Tampa to Tampa