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Puerto Rico Cruises Starting In January 2027, 2028 and 2029

If you're looking at joining a cruise to Puerto Rico in January 2027, 2028 or 2029, we have 54 unique cruise itineraries and 213 departures available, operated by ten of the world's leading cruise lines departing in January.
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54 Cruises (213 Departures)
54 Cruises (213 Departures)
Departures
Duration
5 Days
12 Days
Countries Visited
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$800pp
$28,480pp
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6 Day Beaches of the Virgin Islands with Emerald Cruises
New ReleaseCruise

6 Days (5 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Feb 2028
Visits: Puerto Rico, Virgin Islands
Exclusive Savings
Oceanview
$5,744
Suite
$8,194
From (Per Person)
A$5,744
Save 2,101
Per Person
View Trip
5 Day San Juan To Ft. Lauderdale with Celebrity Cruises
Cruise

5 Days (4 Nights) San Juan to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 02 January 2028
Visits: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$822
Oceanview
$853
Balcony
$955
Suite
$3,986
From (Per Person)
A$822
Save 455
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
Cruise Line: Princess
Ship: Sun Princess
Departure: 03 January 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$895
Oceanview
$1,044
Balcony
$1,390
Suite
$1,945
From (Per Person)
A$895
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departures: Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$974
Oceanview
-
Balcony
$1,182
Suite
$1,983
From (Per Person)
A$974
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Jan 2027 to Mar 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$925
Oceanview
$1,143
Balcony
$1,786
Suite
$2,618
From (Per Person)
A$925
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (3)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Dec 2027 to Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$815
Oceanview
$1,062
Balcony
$1,112
Suite
$1,647
From (Per Person)
A$815
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 03 January 2027
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$3,119
Oceanview
$3,164
Balcony
$3,194
Suite
$3,492
From (Per Person)
A$3,119
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 03 January 2027
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$1,659
Oceanview
$1,689
Balcony
$2,478
Suite
$2,686
From (Per Person)
A$1,659
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departure: 22 January 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,545
Oceanview
$1,683
Balcony
$1,962
Suite
$4,841
From (Per Person)
A$1,545
Save 873
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 17 January 2027
Visits: Puerto Rico, Bonaire, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,449
Oceanview
$2,523
Balcony
$2,688
Suite
$3,104
From (Per Person)
A$2,449
Per Person
View Trip
8 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 03 January 2027
Visits: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,335
Oceanview
$1,646
Balcony
$1,750
Suite
$4,339
From (Per Person)
A$1,335
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 13 January 2027
Visits: USA, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,644
Oceanview
$1,719
Balcony
$2,463
Suite
$2,671
From (Per Person)
A$1,644
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departures: Dec 2026 to Jan 2027
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$925
Oceanview
$1,063
Balcony
$1,291
Suite
$1,945
From (Per Person)
A$925
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Pearl
Departures: Nov 2026 to Feb 2028
Visits: USA, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,734
Oceanview
$1,927
Balcony
$2,818
Suite
$2,969
From (Per Person)
A$1,734
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 31 January 2027
Visits: Puerto Rico, Curacao, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,464
Oceanview
$2,523
Balcony
$2,821
Suite
$2,896
From (Per Person)
A$2,464
Per Person
View Trip
8 Day Perfect Day Cococay & Caribbean Holid with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Independence of the Seas
Departures: Nov 2026 to Apr 2027
Visits: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,309
Oceanview
$1,363
Balcony
$1,609
Suite
$3,870
From (Per Person)
A$1,309
Save 537
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departure: 29 January 2028
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,953
Oceanview
$2,166
Balcony
$2,275
Suite
$6,395
From (Per Person)
A$1,953
Save 784
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departure: 15 January 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,992
Oceanview
$2,217
Balcony
$2,326
Suite
$6,556
From (Per Person)
A$1,992
Save 803
Per Person
View Trip
10 Day A Journey from From Hidden Shores to Timeless Elegance with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Suite
$8,820
From (Per Person)
A$8,820
Save 180
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Jul 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$982
Oceanview
$1,220
Balcony
$1,517
Suite
$2,309
From (Per Person)
A$982
Save 22
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,596
Oceanview
$1,788
Balcony
$1,762
Suite
$5,470
From (Per Person)
A$1,596
Save 1,037
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 03 January 2028
Visits: Puerto Rico, Bonaire, Curacao, Aruba
Exclusive Savings
Inside
$1,288
Oceanview
$1,362
Balcony
$2,318
Suite
$4,242
From (Per Person)
A$1,288
Save 521
Per Person
View Trip
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departure: 24 January 2027
Visits: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,376
Oceanview
$1,525
Balcony
$2,029
Suite
-
From (Per Person)
A$1,376
Save 482
Per Person
View Trip
8 Day A Journey into Dominican Charm & Caribbean Splendour with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 30 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 30 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,003
Oceanview
$1,024
Balcony
$1,860
Suite
$3,565
From (Per Person)
A$1,003
Save 528
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visits: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Inside
$1,129
Oceanview
$1,337
Balcony
$1,853
Suite
$5,695
From (Per Person)
A$1,129
Per Person
View Trip
7 Day Southern Caribbean with Puerto Rico with Princess
Cruise
 (1)

7 Days (6 Nights) Bridgetown to Bridgetown
Cruise Line: Princess
Ship: Emerald Princess
Departure: 14 January 2028
Visits: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda
Exclusive Savings
Inside
$2,220
Oceanview
$2,845
Balcony
$3,289
Suite
$4,656
From (Per Person)
A$2,220
Per Person
View Trip
7 Day Southern Caribbean Cruise with Virgin Voyages
Cruise
 (2)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: 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
$1,234
Oceanview
$1,500
Balcony
$1,767
Suite
$5,050
From (Per Person)
A$1,234
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visits: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$1,440
Oceanview
$1,751
Balcony
$2,062
Suite
$5,477
From (Per Person)
A$1,440
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Sun Princess
Departures: Apr 2027 to Jan 2028
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,113
Oceanview
$1,371
Balcony
$1,668
Suite
$2,132
From (Per Person)
A$1,113
Per Person
View Trip
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