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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 212 departures available, operated by eleven of the world's leading cruise lines departing in January.
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55 Cruises (212 Departures)
55 Cruises (212 Departures)
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5 Days
15 Days
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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
$3,004
From (Per Person)
A$822
Save 455
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
$2,449
Balcony
$2,747
Suite
$2,821
From (Per Person)
A$2,449
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 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
$2,333
From (Per Person)
A$895
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
$855
Oceanview
$1,097
Balcony
$1,149
Suite
$1,647
From (Per Person)
A$855
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
$974
Oceanview
$1,093
Balcony
$1,291
Suite
$1,945
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
$974
Oceanview
$1,172
Balcony
$1,806
Suite
$2,548
From (Per Person)
A$974
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 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
$1,129
Oceanview
$1,233
Balcony
$1,335
Suite
$4,339
From (Per Person)
A$1,129
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 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
$3,001
Oceanview
$3,045
Balcony
$3,075
Suite
$3,342
From (Per Person)
A$3,001
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
$1,704
Oceanview
$1,912
Balcony
$2,686
Suite
$2,821
From (Per Person)
A$1,704
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
$2,732
Suite
$3,045
From (Per Person)
A$2,449
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
$894
Oceanview
-
Balcony
$1,112
Suite
$1,805
From (Per Person)
A$894
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 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
$1,461
Oceanview
$1,578
Balcony
$1,528
Suite
$3,426
From (Per Person)
A$1,461
Save 1,184
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
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: Aug 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,061
Oceanview
$1,319
Balcony
$1,616
Suite
$2,309
From (Per Person)
A$1,061
Save 24
Per Person
View Trip
15 Day Festive Crossing with Oceania Cruises
Cruise

15 Days (14 Nights) Lisbon to Miami
Cruise Line: Oceania
Ship: Oceania Aurelia
Departure: 04 January 2028
Visits: Portugal, Spain, Puerto Rico, USA
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,517
Suite
$7,458
From (Per Person)
A$6,517
Save 2,183
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 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
$1,143
Oceanview
$1,190
Balcony
$1,450
Suite
$3,060
From (Per Person)
A$1,242
Save 720
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
$1,164
Oceanview
$1,843
Balcony
$2,723
Suite
-
From (Per Person)
A$1,224
Save 447
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
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 & 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
$1,128
Oceanview
$1,336
Balcony
$1,853
Suite
$5,695
From (Per Person)
A$1,128
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: 15 January 2028
Visits: Puerto Rico, Virgin Islands, Dominica, Antigua and Barbuda, Saint Martin
Exclusive Savings
Inside
$1,212
Oceanview
$1,307
Balcony
$2,356
Suite
$2,685
From (Per Person)
A$1,212
Save 707
Per Person
View Trip
8 Day A Journey from Dominican Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 09 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
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
$1,409
Oceanview
$1,763
Balcony
$2,119
Suite
$5,799
From (Per Person)
A$1,409
Per Person
View Trip
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