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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 55 unique cruise itineraries and 208 departures available, operated by ten of the world's leading cruise lines departing in January.
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55 Cruises (208 Departures)
55 Cruises (208 Departures)
Departures
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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
Inside
-
Oceanview
$5,744
Balcony
-
Suite
$7,214
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 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 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
$865
Oceanview
$994
Balcony
$1,410
Suite
$1,737
From (Per Person)
A$865
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
$1,689
Oceanview
$1,793
Balcony
$2,508
Suite
$2,835
From (Per Person)
A$1,689
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
$3,075
Oceanview
$3,119
Balcony
$3,194
Suite
$3,521
From (Per Person)
A$3,075
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (2)

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
$855
Oceanview
$1,115
Balcony
$1,169
Suite
$1,706
From (Per Person)
A$855
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
$1,388
Oceanview
$1,687
Balcony
$1,787
Suite
$4,682
From (Per Person)
A$1,388
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
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
$1,674
Oceanview
$1,763
Balcony
$2,478
Suite
$2,701
From (Per Person)
A$1,674
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
$1,053
Oceanview
-
Balcony
$1,251
Suite
$2,063
From (Per Person)
A$1,053
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
$1,808
Oceanview
$2,002
Balcony
$2,818
Suite
$2,999
From (Per Person)
A$1,808
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
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, Aruba, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,523
Oceanview
$2,523
Balcony
$2,821
Suite
$3,075
From (Per Person)
A$2,523
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, Curacao, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,449
Oceanview
$2,523
Balcony
$2,688
Suite
$3,149
From (Per Person)
A$2,449
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
$1,115
Oceanview
$1,189
Balcony
$2,071
Suite
$2,554
From (Per Person)
A$1,115
Save 694
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
$1,170
Oceanview
$1,440
Balcony
$2,413
Suite
-
From (Per Person)
A$1,170
Save 640
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
Inside
-
Oceanview
-
Balcony
-
Suite
$8,820
From (Per Person)
A$8,820
Save 180
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
$1,780
Oceanview
$1,993
Balcony
$2,027
Suite
$4,070
From (Per Person)
A$1,780
Save 957
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: Jun 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 20
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
$1,399
Oceanview
$1,604
Balcony
$1,571
Suite
$3,426
From (Per Person)
A$1,399
Save 1,230
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
$1,144
Oceanview
$1,262
Balcony
$1,380
Suite
$2,345
From (Per Person)
A$1,144
Save 801
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
$1,819
Oceanview
$2,044
Balcony
$2,079
Suite
$4,179
From (Per Person)
A$1,819
Save 976
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
Departures: Mar 2027 to Jan 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Just Cruise Fare
Exclusive Savings
Inside
$2,182
Oceanview
$2,479
Balcony
$2,851
Suite
$3,834
From (Per Person)
A$2,182
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
Departures: Dec 2027 to Feb 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,181
Oceanview
$1,263
Balcony
$1,994
Suite
$2,483
From (Per Person)
A$1,181
Save 726
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
$2,202
From (Per Person)
A$1,113
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Dec 2027 to Mar 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,358
Oceanview
$1,700
Balcony
$2,043
Suite
$5,591
From (Per Person)
A$1,358
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: Jan 2028 to Mar 2028
Visits: Puerto Rico, Aruba, Saint Lucia, Antigua and Barbuda, Saint Martin
Inside
$1,088
Oceanview
$1,288
Balcony
$1,787
Suite
$5,491
From (Per Person)
A$1,088
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: Scarlet Lady
Departure: 02 January 2028
Visits: Puerto Rico, Saint Vincent, Barbados, Dominica, Saint Martin
Inside
$932
Oceanview
$1,104
Balcony
$1,531
Suite
$4,706
From (Per Person)
A$932
Per Person
View Trip
10 Day Eastern Caribbean: U.S. And British Virgin Islands with Holland America
Cruise
 (3)

10 Days (9 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Nieuw Amsterdam
Departures: Jan 2027 to Mar 2027
Visits: USA, Antigua and Barbuda, Virgin Islands, Puerto Rico, Bahamas
Fare Saver
Exclusive Savings
Inside
$1,537
Oceanview
$1,844
Balcony
$2,309
Suite
$4,913
From (Per Person)
A$1,537
Per Person
View Trip
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