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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 50 unique cruise itineraries and 220 departures available, operated by nine of the world's leading cruise lines departing in January.
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50 Cruises (220 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
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,949
Balcony
-
Suite
$5,210
From
US$3,949
Save 6,241
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
$301
Oceanview
$321
Balcony
$347
Suite
$1,704
From
US$355
Save 159
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,935
Suite
$5,565
From
US$4,935
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
$2,651
From
US$1,100
Save 422
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: Mar 2026 to Feb 2027
Visit: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$903
Oceanview
$973
Balcony
$1,183
Suite
$3,003
From
US$903
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (6)

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
$699
Oceanview
$879
Balcony
$819
Suite
$1,199
From
US$699
Per Person
View Trip
8 Day St. Kitts, San Juan & Puerto Plata with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departures: Jan 2026 to Apr 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,306
Oceanview
$1,416
Balcony
$1,565
Suite
$3,449
From
US$1,557
Save 829
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

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
$1,339
Oceanview
$1,389
Balcony
$1,589
Suite
$2,245
From
US$1,339
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
$850
Oceanview
-
Balcony
$1,109
Suite
$1,850
From
US$850
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (6)

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
$709
Oceanview
$829
Balcony
$779
Suite
$1,169
From
US$709
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
$1,069
Oceanview
$1,269
Balcony
$1,819
Suite
$2,025
From
US$1,069
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: Jan 2026 to Feb 2026
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$1,009
Oceanview
$2,239
Balcony
$1,120
Suite
$2,653
From
US$1,009
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
$650
Oceanview
$1,049
Balcony
$829
Suite
$1,350
From
US$650
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
$819
Oceanview
$959
Balcony
$1,062
Suite
$1,372
From
US$1,190
Save 50
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 January 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Bonus Onboard Credit
Inside
-
Oceanview
-
Balcony
-
Suite
$1,936
From
US$1,936
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: Jan 2027 to Jan 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Inside
$1,069
Oceanview
$1,319
Balcony
$1,669
Suite
$2,015
From
US$1,069
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

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
$1,199
Oceanview
$1,329
Balcony
$1,569
Suite
$2,215
From
US$1,199
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

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
$1,539
Oceanview
$1,669
Balcony
$1,769
Suite
$2,118
From
US$1,539
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib 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
$971
Oceanview
$1,086
Balcony
$1,070
Suite
$2,339
From
US$971
Save 741
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: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Free Balcony Upgrade
Inside
$597
Oceanview
$853
Balcony
$914
Suite
$1,410
From
US$597
Per Person
View Trip
8 Day Tortola, San Juan & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jan 2026 to Apr 2026
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,021
Oceanview
$1,016
Balcony
$1,475
Suite
$3,477
From
US$1,196
Save 3,542
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day 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: Feb 2026 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$702
Oceanview
$822
Balcony
$954
Suite
$1,442
From
US$702
Save 515
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
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,398
From
US$1,031
Save 50
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico 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 Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$699
Oceanview
$949
Balcony
$760
Suite
$1,199
From
US$699
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 03 January 2027
Visit: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,679
From
US$4,679
Save 7,311
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
Departure: 30 January 2027
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Bahamas
Inside
$952
Oceanview
$1,192
Balcony
$1,432
Suite
$3,800
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
$1,462
From
US$1,091
Save 50
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
Per Person
View Trip
9 Day Caribbean And Antilles with MSC Cruises
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Meraviglia
Departure: 30 January 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin, Virgin Islands
Bonus Onboard Credit
Inside
$598
Oceanview
$818
Balcony
$928
Suite
$2,771
From
US$598
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: Valiant Lady
Departures: Mar 2026 to Apr 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$833
Oceanview
$973
Balcony
$1,113
Suite
$3,493
From
US$833
Per Person
View Trip
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