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Puerto Rico Cruises Starting In January 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in January 2027 or 2028, we have 54 unique cruise itineraries and 195 departures available, operated by nine of the world's leading cruise lines departing in January.
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54 Cruises (195 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
$4,138
Balcony
-
Suite
$5,308
From
US$4,138
Save 957
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$481
Save 321
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
$659
Oceanview
$819
Balcony
$1,104
Suite
$1,569
From
US$659
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
$1,129
Balcony
$1,649
Suite
$1,839
From
US$939
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
$2,676
From
US$926
Save 596
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 to Jan 2028
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Princess Standard
Inside
$819
Oceanview
-
Balcony
$924
Suite
$1,499
From
US$819
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
$589
Oceanview
$669
Balcony
$854
Suite
$1,229
From
US$589
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
$1,359
Oceanview
$1,429
Balcony
$1,559
Suite
$2,009
From
US$1,359
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
$889
Oceanview
$939
Balcony
$1,379
Suite
$1,759
From
US$889
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
$1,439
Oceanview
$1,509
Balcony
$1,609
Suite
$2,089
From
US$1,439
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
Departures: Apr 2026 to Jan 2027
Visit: USA, Puerto Rico, Dominican Republic, Bahamas
Limited Time Offer
Inside
$763
Oceanview
$973
Balcony
$1,113
Suite
$3,283
From
US$763
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 Apr 2027
Visit: USA, Saint Martin, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$844
Oceanview
$1,044
Balcony
$1,047
Suite
$2,339
From
US$844
Save 725
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
$1,719
Oceanview
$1,779
Balcony
$1,769
Suite
$2,199
From
US$1,719
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
Inside
$579
Oceanview
$735
Balcony
$756
Suite
$1,229
From
US$579
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
$689
Oceanview
$849
Balcony
$984
Suite
$1,229
From
US$689
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, Wonder of the Seas
Departures: May 2026 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$637
Oceanview
$757
Balcony
$903
Suite
$1,383
From
US$637
Save 531
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
$909
Oceanview
$1,069
Balcony
$1,469
Suite
$1,799
From
US$909
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
$1,529
From
US$709
Save 422
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: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$584
Oceanview
$814
Balcony
$934
Suite
$1,274
From
US$584
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
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$850
Balcony
$1,112
Suite
$3,400
From
US$689
Save 365
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
$5,425
From
US$5,425
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
Visit: Barbados, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda
Princess Standard
Inside
$1,658
Oceanview
$1,978
Balcony
$2,683
Suite
$3,368
From
US$1,658
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
$1,462
From
US$732
Save 435
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
$3,655
From
US$3,655
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visit: Puerto Rico, Aruba, Saint Lucia, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
8 Day A Journey Of Sun-hazed Island Enchantment & Caribbean Treasures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands, USA
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,160
From
US$5,160
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: 23 January 2028
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Bonaire, Curacao
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,519
From
US$1,169
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 Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sky Princess
Departures: Nov 2027 to Mar 2028
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$609
Oceanview
$789
Balcony
$782
Suite
$1,209
From
US$609
Per Person
View Trip
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