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Puerto Rico Cruises Starting In January 2026, 2027 and 2028

If you're looking at joining a cruise to Puerto Rico in January 2026, 2027 or 2028, we have 56 unique cruise itineraries and 262 departures available, operated by nine of the world's leading cruise lines departing in January.
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56 Cruises (262 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
Black Friday Sale
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,755
Balcony
-
Suite
$5,016
From
US$3,755
Save 6,435
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
$362
Suite
$722
From
US$301
Save 213
Per Person
View Trip
8 Day Eastern Caribbean with St. Thomas From Fort Lauderdale with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Majestic Princess, Regal Princess, Sun Princess
Departures: Nov 2025 to Aug 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Multiple Deals Available
Inside
$279
Oceanview
$349
Balcony
$599
Suite
$799
From
US$279
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: Nov 2025 to Jan 2026
Visit: USA, Puerto Rico, Dominican Republic, Bahamas
Black Friday Deal
Inside
$764
Oceanview
$833
Balcony
$904
Suite
$3,010
From
US$764
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: Nov 2025 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$407
Oceanview
$899
Balcony
$929
Suite
$1,578
From
US$407
Save 665
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
Departures: Jan 2026 to Jan 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Inside
$386
Oceanview
$496
Balcony
$626
Suite
$1,536
From
US$386
Per Person
View Trip
8 Day San Juan Sunrises & Dominican Dreams 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
Black Friday Deal
Inside
$763
Oceanview
$903
Balcony
$1,175
Suite
$2,835
From
US$763
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
Black Friday Sale
Sanctuary Collection
Inside
$874
Oceanview
$974
Balcony
$1,164
Suite
$1,361
From
US$874
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: Nov 2025 to Apr 2026
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$749
Oceanview
$942
Balcony
$1,103
Suite
$2,484
From
US$749
Save 3,817
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: Nov 2025 to Apr 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Exclusive Savings
Inside
$953
Oceanview
$1,009
Balcony
$1,095
Suite
$2,791
From
US$953
Save 1,110
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
$675
Oceanview
$1,074
Balcony
$954
Suite
$1,450
From
US$675
Per Person
View Trip
8 Day Western Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departures: Jan 2026 to Apr 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$868
Oceanview
$968
Balcony
$968
Suite
$2,492
From
US$868
Save 671
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: Nov 2025 to Oct 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$394
Oceanview
$504
Balcony
$714
Suite
$1,424
From
US$394
Per Person
View Trip
7 Day Eastern Caribbean with Turks & Caicos with Princess
Cruise
 (7)

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Majestic Princess
Departure: 11 January 2026
Visit: USA, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Inside
$609
Oceanview
-
Balcony
$789
Suite
$1,259
From
US$609
Per Person
View Trip
8 Day San Juan Sunrises & Dominican Dreams with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Mar 2026 to Jan 2027
Visit: USA, Puerto Rico, Dominican Republic, Bahamas
Black Friday Deal
Inside
$833
Oceanview
$1,113
Balcony
$1,323
Suite
$3,255
From
US$833
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
$875
Oceanview
-
Balcony
$1,234
Suite
$1,950
From
US$875
Per Person
View Trip
9 Day Eastern Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Nov 2025 to Apr 2026
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$730
Oceanview
$880
Balcony
$1,493
Suite
$1,870
From
US$730
Save 1,437
Per Person
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Oasis of the Seas
Departures: Jan 2026 to Mar 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$635
Oceanview
$1,012
Balcony
$885
Suite
$2,637
From
US$635
Save 577
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
$958
Oceanview
$1,028
Balcony
$1,120
Suite
$2,197
From
US$958
Save 775
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
Departures: Dec 2025 to Jan 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$889
Oceanview
$1,020
Balcony
$1,152
Suite
$1,527
From
US$889
Save 897
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
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$4,935
Suite
$5,670
From
US$4,935
Per Person
View Trip
15 Day Caribbean And Antilles with MSC Cruises
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 24 January 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Inside
$914
Oceanview
$1,064
Balcony
$1,394
Suite
$6,062
From
US$914
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
Black Friday Sale
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,224
Balcony
-
Suite
$4,582
From
US$3,224
Save 5,966
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
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
The Exclusive Invitation Offer
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,410
From
US$3,850
Per Person
View Trip
7 Day Caribbean East: Virgin & Saint Isles with Virgin Voyages
Cruise
 (1)

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2027 to Mar 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Black Friday Deal
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,540
From
US$834
Per Person
View Trip
9 Day Eastern Caribbean with St. Thomas with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 11 January 2026
Visit: USA, Sint Maarten, Virgin Islands, Puerto Rico, Turks and Caicos Islands
Princess Standard
Inside
$999
Oceanview
-
Balcony
$1,419
Suite
$2,119
From
US$999
Per Person
View Trip
9 Day Eastern Caribbean with St. Thomas From Fort Lauderdale with Princess
Cruise
 (7)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Majestic Princess
Departures: Nov 2025 to Feb 2026
Visit: USA, Dominican Republic, Puerto Rico, Sint Maarten, Virgin Islands
Princess Standard
Inside
$729
Oceanview
-
Balcony
$1,014
Suite
$1,334
From
US$729
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 17 January 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Martinique, Barbados
Exclusive Savings
Inside
$650
Oceanview
$700
Balcony
$1,063
Suite
$2,094
From
US$650
Save 459
Per Person
View Trip
8 Day Aruban Sights & Antiguan Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Jan 2026 to Feb 2027
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Sint Maarten
Black Friday Deal
Inside
$1,038
Oceanview
$1,043
Balcony
$1,323
Suite
$3,010
From
US$1,038
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departures: Nov 2025 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Dominica, Barbados
Exclusive Savings
Inside
$599
Oceanview
$649
Balcony
$779
Suite
$1,739
From
US$599
Save 559
Per Person
View Trip
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