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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 57 unique cruise itineraries and 194 departures available, operated by ten of the world's leading cruise lines departing in January.
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57 Cruises (194 Cruise Departures)
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
Visit: Puerto Rico, Virgin Islands
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$3,638
Balcony
-
Suite
$4,808
From
US$3,638
Save 1,457
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
Visit: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$481
Oceanview
$501
Balcony
$527
Suite
$1,963
From
US$571
Save 231
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
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic
Inside
$899
Oceanview
$999
Balcony
$1,419
Suite
$1,699
From
US$899
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
Visit: Puerto Rico, Curacao, Aruba, Virgin Islands
Inside
$1,489
Oceanview
$1,489
Balcony
$1,689
Suite
$1,949
From
US$1,489
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
Visit: Puerto Rico, Virgin Islands, Aruba, Curacao
Inside
$1,839
Oceanview
$1,889
Balcony
$1,959
Suite
$2,249
From
US$1,839
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
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$574
Oceanview
$744
Balcony
$1,134
Suite
$1,559
From
US$574
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
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$724
Oceanview
-
Balcony
$864
Suite
$1,329
From
US$724
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
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Inside
$859
Oceanview
$929
Balcony
$1,319
Suite
$1,659
From
US$859
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
Visit: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$973
Oceanview
$1,183
Balcony
$1,323
Suite
$3,283
From
US$973
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
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$926
Oceanview
$1,026
Balcony
$1,151
Suite
$3,066
From
US$951
Save 571
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
Visit: Puerto Rico, Bonaire, Curacao, Virgin Islands
Inside
$1,419
Oceanview
$1,479
Balcony
$1,599
Suite
$1,959
From
US$1,419
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
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Princess Premier
Inside
$529
Oceanview
$704
Balcony
$691
Suite
$1,069
From
US$529
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
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$524
Oceanview
$644
Balcony
$794
Suite
$1,189
From
US$524
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
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic
Inside
$939
Oceanview
$1,119
Balcony
$1,599
Suite
$1,789
From
US$939
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
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$574
Oceanview
$674
Balcony
$884
Suite
$1,059
From
US$574
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
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,920
From
US$5,920
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
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,159
Oceanview
$1,319
Balcony
$1,359
Suite
$2,694
From
US$1,159
Save 589
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
Visit: Puerto Rico, Bonaire, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$709
Oceanview
$759
Balcony
$1,409
Suite
$1,604
From
US$709
Save 422
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
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$532
Oceanview
$674
Balcony
$845
Suite
$1,508
From
US$532
Save 526
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
Visit: USA, Saint Martin, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$759
Oceanview
$1,094
Balcony
$1,106
Suite
$2,205
From
US$759
Save 798
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
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,132
Oceanview
$1,283
Balcony
$1,322
Suite
$2,616
From
US$1,132
Save 576
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
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$670
Oceanview
$829
Balcony
$1,182
Suite
$4,183
From
US$670
Save 356
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 Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$567
Oceanview
$763
Balcony
$897
Suite
$1,314
From
US$567
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
Visit: USA, Antigua and Barbuda, Virgin Islands, Puerto Rico, Bahamas
Fare Saver
Inside
$999
Oceanview
$1,199
Balcony
$1,499
Suite
$2,999
From
US$999
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 Viva
Departure: 16 January 2028
Visit: Puerto Rico, Aruba, Barbados, Saint Martin, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 23 January 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Turks and Caicos Islands
Princess Standard
Inside
$1,064
Oceanview
-
Balcony
$1,994
Suite
$2,699
From
US$1,064
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
Visit: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,020
From
US$4,020
Per Person
View Trip
9 Day St. Maarten, San Juan & St. Thomas with Celebrity Cruises
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 15 January 2028
Visit: USA, Virgin Islands, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,229
Oceanview
$1,329
Balcony
$1,529
Suite
$4,249
From
US$1,254
Save 710
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
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Inside
$952
Oceanview
$1,192
Balcony
$1,432
Suite
$3,920
From
US$952
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
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$732
Oceanview
$792
Balcony
$1,332
Suite
$1,537
From
US$732
Save 435
Per Person
View Trip
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