Caribbean Cruises Starting In January 2027 and 2028

Are you planning a cruise to the Caribbean in January 2027 or 2028? Choose from 423 unique cruises and 2,634 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.
Filter Results
Departures
Duration
5 Days
122 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$100pp
$134,398pp
Countries
Show More...
Filter Results
423 Cruises (2,634 Cruise Departures)
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Departures: Mar 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
Viking $699 Air Deal
Inside
-
Oceanview
-
Balcony
$3,699
Suite
$5,999
From
US$3,699
Per Person
View Trip
Cruise

13 Days (12 Nights) New York to New York
Cruise Line: Norwegian Cruise Line
Departure: 03 January 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Saint Kitts and Nevis, Virgin Islands
Inside
$1,499
Oceanview
$1,899
Balcony
$2,189
Suite
$2,480
From
US$1,499
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 22 January 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Dominican Republic, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$3,915
From
US$3,915
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$809
Oceanview
$929
Balcony
$1,019
Suite
$1,199
From
US$809
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Celebrity Cruises
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$826
Oceanview
$947
Balcony
$1,064
Suite
$2,566
From
US$826
Save 724
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departure: 15 January 2028
Visit: USA, Bahamas, Cayman Islands, Jamaica, Mexico
Bonus Onboard Credit
Exclusive Savings
Inside
$1,160
Oceanview
$1,300
Balcony
$1,540
Suite
$2,270
From
US$1,160
Save 563
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Departure: 09 January 2028
Visit: Puerto Rico, Saint Martin, Curacao, Saint Lucia, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,447
From
US$1,169
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Departure: 15 January 2028
Visit: USA, Mexico
Exclusive Savings
Inside
$996
Oceanview
$1,096
Balcony
$1,221
Suite
$2,721
From
US$996
Save 620
Per Person
View Trip
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Departures: Jan 2027 to Feb 2027
Visit: USA, Haiti, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$779
Oceanview
$909
Balcony
$1,062
Suite
$1,901
From
US$779
Save 468
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Departures: Nov 2026 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Exclusive Savings
Inside
$1,249
Oceanview
$1,339
Balcony
$1,589
Suite
$2,187
From
US$1,249
Save 54
Per Person
View Trip
Cruise

15 Days (14 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Departure: 22 January 2028
Visit: Martinique, Guadeloupe, Saint Lucia, Barbados (+6 more), Saint Vincent, Grenada, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominica
Bonus Onboard Credit
Inside
$1,892
Oceanview
$2,195
Balcony
$2,641
Suite
$5,066
From
US$1,892
Per Person
View Trip
Cruise

8 Days (7 Nights) New Orleans to New Orleans
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Apr 2027
Visit: USA, Mexico, Cayman Islands, Jamaica
Bonus Onboard Credit
Exclusive Savings
Inside
$564
Oceanview
$640
Balcony
$824
Suite
$1,261
From
US$564
Save 701
Per Person
View Trip
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$4,935
From
US$4,935
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Departures: Nov 2026 to Mar 2027
Visit: USA, Saint Martin, Virgin Islands, Dominican Republic
Bonus Onboard Credit
Exclusive Savings
Inside
$840
Oceanview
$891
Balcony
$1,095
Suite
$2,150
From
US$840
Save 618
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
$1,344
Oceanview
$1,544
Balcony
$1,844
Suite
$5,769
From
US$1,344
Save 802
Per Person
View Trip
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Departures: Jan 2028 to Jan 2028
Visit: Barbados, Saint Vincent, Martinique, Saint Barthelemy, Dominica, Grenada, Saint Lucia
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,080
Balcony
$4,560
Suite
$4,320
From
US$4,080
Save 1,020
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Departures: Dec 2026 to Feb 2027
Visit: Martinique, Saint Vincent, Saint Lucia, Guadeloupe
Inside
-
Oceanview
-
Balcony
$5,060
Suite
$7,560
From
US$5,060
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
$1,405
Oceanview
$1,564
Balcony
$1,580
Suite
$5,253
From
US$1,405
Save 981
Per Person
View Trip
Cruise

10 Days (9 Nights) Tampa to Tampa
Cruise Line: Celebrity Cruises
Departure: 03 January 2027
Visit: USA, Cayman Islands, Jamaica, Honduras, Mexico
Exclusive Savings
Inside
$893
Oceanview
$965
Balcony
$1,349
Suite
$8,928
From
US$893
Save 547
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Departures: Mar 2026 to Feb 2028
Visit: USA, Bahamas, Jamaica, Cayman Islands, Mexico
Inside
$749
Oceanview
$869
Balcony
$1,119
Suite
$1,389
From
US$749
Per Person
View Trip
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,448
From
US$689
Save 568
Per Person
View Trip
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Departures: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Exclusive Savings
Inside
$949
Oceanview
$1,059
Balcony
$1,379
Suite
$1,679
From
US$949
Save 63
Per Person
View Trip
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Departure: 25 January 2028
Visit: Barbados, Saint Vincent, Grenada, Martinique (+5 more), Guadeloupe, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis, Dominica
Bonus Onboard Credit
Exclusive Savings
Inside
$2,057
Oceanview
$2,406
Balcony
$2,843
Suite
$5,433
From
US$2,057
Save 52
Per Person
View Trip
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Jan 2027 to Feb 2027
Visit: Barbados, Martinique, Antigua and Barbuda, Virgin Islands, Dominican Republic, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Inside
$1,448
Oceanview
$1,768
Balcony
$3,006
Suite
$3,831
From
US$1,448
Per Person
View Trip
Cruise
 (3)

22 Days (21 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Rotterdam
Departure: 02 January 2027
Visit: USA, Bahamas, Jamaica, Cayman Islands (+8 more), Belize, Mexico, Saint Martin, Antigua and Barbuda, Dominica, Martinique, Saint Kitts and Nevis, Virgin Islands
Fare Saver
Inside
$2,204
Oceanview
$2,584
Balcony
$3,573
Suite
$5,063
From
US$2,204
Per Person
View Trip
New ReleaseCruise
 (3)

8 Days (7 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Departures: Dec 2026 to Mar 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,854
Balcony
-
Suite
$5,455
From
US$3,854
Save 6,342
Per Person
View Trip
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 20 January 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,640
Suite
$10,640
From
US$6,640
Save 1,660
Per Person
View Trip
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$3,850
From
US$3,850
Per Person
View Trip
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: MSC Cruises
Departure: 30 January 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin, Virgin Islands, Turks and Caicos Islands
Bonus Onboard Credit
Inside
$1,106
Oceanview
$1,396
Balcony
$1,686
Suite
-
From
US$1,106
Per Person
View Trip
Cruise
 (2)

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Departures: Dec 2027 to Mar 2028
Visit: USA, Mexico, Belize
Bonus Onboard Credit
Exclusive Savings
Inside
$817
Oceanview
$887
Balcony
$1,173
Suite
$1,857
From
US$817
Save 534
Per Person
View Trip
Results: 1-30 of 423

No trips found. Try adjusting the search filters.