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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 56 unique cruise itineraries and 200 departures available, operated by eleven of the world's leading cruise lines departing in January.
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56 Cruises (200 Departures)
56 Cruises (200 Departures)
Departures
Duration
5 Days
15 Days
Countries Visited
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$700pp
$28,620pp
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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
Operator: Emerald Cruises
Ship: Emerald Kaia
Departures: Jan 2028 to Feb 2028
Visits: Puerto Rico, Virgin Islands
Exclusive Savings
Oceanview
$5,744
Balcony
$7,214
Suite
$11,012
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
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 02 January 2028
Visits: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$744
Oceanview
$774
Balcony
$778
Suite
$2,652
From (Per Person)
A$744
Save 533
Per Person
View Trip
8 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departure: 03 January 2027
Visits: USA, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,287
Oceanview
$1,387
Balcony
$1,487
Suite
$3,581
From (Per Person)
A$1,287
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Operator: Celebrity Cruises
Ship: Celebrity Apex
Departure: 22 January 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,389
Oceanview
$1,528
Balcony
$1,708
Suite
$4,237
From (Per Person)
A$1,389
Save 1,029
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 03 January 2027
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,107
Oceanview
$2,212
Balcony
$2,479
Suite
$2,703
From (Per Person)
A$2,107
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
Operator: 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
$1,495
Oceanview
$1,645
Balcony
$2,701
Suite
$2,850
From (Per Person)
A$1,495
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 17 January 2027
Visits: Puerto Rico, Bonaire, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,003
Oceanview
$2,107
Balcony
$2,151
Suite
$2,658
From (Per Person)
A$2,003
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (3)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sky Princess
Departures: Dec 2027 to Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$893
Oceanview
$1,147
Balcony
$1,174
Suite
$1,586
From (Per Person)
A$893
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
Operator: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 13 January 2027
Visits: USA, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$1,465
Oceanview
$1,600
Balcony
$2,686
Suite
$2,835
From (Per Person)
A$1,465
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
Operator: Princess
Ship: Sun Princess
Departure: 03 January 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$1,022
Oceanview
$1,269
Balcony
$1,457
Suite
$2,408
From (Per Person)
A$1,022
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
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 31 January 2027
Visits: Puerto Rico, Curacao, Saint Martin, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$1,958
Oceanview
$2,062
Balcony
$2,107
Suite
$2,494
From (Per Person)
A$1,958
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: MSC Cruises
Ships: MSC Seaside, MSC World America
Departures: Sep 2026 to Oct 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$814
Oceanview
$1,041
Balcony
$1,338
Suite
$2,309
From (Per Person)
A$814
Save 16
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: 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
$972
Oceanview
$1,289
Balcony
$1,982
Suite
$2,378
From (Per Person)
A$972
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
Operator: Princess
Ship: Sun Princess
Departures: Dec 2026 to Jan 2027
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$1,014
Oceanview
$1,061
Balcony
$1,190
Suite
$1,942
From (Per Person)
A$1,014
Per Person
View Trip
8 Day Southern Caribbean From San Juan To San Juan with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Jan 2028
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,121
Oceanview
$2,434
Balcony
$2,777
Suite
$4,087
From (Per Person)
A$2,121
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Operator: Princess
Ship: Regal Princess
Departures: Jan 2028
Visits: USA, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$744
Oceanview
-
Balcony
$1,110
Suite
$1,803
From (Per Person)
A$744
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 29 January 2028
Visits: USA, Bahamas, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,953
Oceanview
$2,166
Balcony
$2,112
Suite
$6,395
From (Per Person)
A$1,953
Save 784
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Symphony of the Seas
Departure: 15 January 2028
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,992
Oceanview
$2,217
Balcony
$2,326
Suite
$6,556
From (Per Person)
A$1,992
Save 803
Per Person
View Trip
7 Day Caribbean & Perfect Day with Royal Caribbean
Cruise

7 Days (6 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Royal Caribbean
Ship: Legend Of The Seas
Departure: 03 January 2027
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$2,058
Oceanview
$2,220
Balcony
$2,303
Suite
$6,324
From (Per Person)
A$2,058
Save 844
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Operator: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Sep 2027
Visits: USA, Saint Martin, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,505
Oceanview
$1,826
Balcony
$1,832
Suite
$5,470
From (Per Person)
A$1,505
Save 1,064
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 03 January 2028
Visits: Puerto Rico, Bonaire, Curacao, Aruba
Exclusive Savings
Inside
$1,288
Oceanview
$1,362
Balcony
$2,318
Suite
$3,867
From (Per Person)
A$1,288
Save 521
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
Operator: Explora Journeys
Ship: Explora I
Departure: 11 January 2027
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Suite
$8,266
From (Per Person)
A$8,266
Save 169
Per Person
View Trip
15 Day Festive Crossing with Oceania Cruises
Cruise

15 Days (14 Nights) Lisbon to Miami
Operator: 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
8 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Operator: Royal Caribbean
Ship: Independence of the Seas
Departure: 24 January 2027
Visits: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,350
Oceanview
$1,694
Balcony
$2,305
Suite
$11,250
From (Per Person)
A$1,350
Save 470
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (3)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Operator: Princess
Ship: Sky Princess
Departure: 23 January 2028
Visits: USA, Bahamas, Puerto Rico, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
$1,012
Oceanview
$1,278
Balcony
$1,333
Suite
$1,745
From (Per Person)
A$1,012
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departure: 30 January 2027
Visits: USA, Dominican Republic, Puerto Rico, Saint Martin, Bahamas
Inside
$1,357
Oceanview
$1,471
Balcony
$1,699
Suite
$5,119
From (Per Person)
A$1,357
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Aruba, Saint Lucia, Antigua and Barbuda, Saint Martin
Inside
$1,088
Oceanview
$1,685
Balcony
$1,886
Suite
$5,280
From (Per Person)
A$1,088
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Operator: Virgin Voyages
Ship: Resilient Lady
Departures: Dec 2027 to Mar 2028
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,355
Oceanview
$1,926
Balcony
$2,154
Suite
$5,407
From (Per Person)
A$1,355
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visits: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$1,287
Oceanview
$1,387
Balcony
$1,487
Suite
$4,977
From (Per Person)
A$1,287
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
Operator: Holland America
Ship: Nieuw Amsterdam
Departures: Jan 2027 to Mar 2027
Visits: USA, Antigua and Barbuda, Virgin Islands, Puerto Rico, Bahamas
Fare Saver
Exclusive Savings
Inside
$1,537
Oceanview
$1,844
Balcony
$2,309
Suite
$4,913
From (Per Person)
A$1,537
Per Person
View Trip
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