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Puerto Rico Cruises Starting In January 2027 and 2028

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50 Cruises (220 Cruise Departures)
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
$2,447
From
US$1,169
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
$2,447
From
US$1,169
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
Departure: 15 January 2028
Visit: Puerto Rico, Virgin Islands, Dominica, Antigua and Barbuda, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$756
Oceanview
$826
Balcony
$1,455
Suite
$1,606
From
US$1,128
Save 50
Per Person
View Trip
9 Day St. Maarten, Antigua & San Juan with Celebrity Cruises
Cruise
 (2)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Eclipse
Departure: 31 January 2026
Visit: USA, Sint Maarten, Antigua and Barbuda, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
-
Oceanview
$1,332
Balcony
$2,128
Suite
-
From
US$1,583
Save 578
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
$750
Oceanview
$1,149
Balcony
$949
Suite
$1,450
From
US$750
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
$799
Oceanview
-
Balcony
$899
Suite
$1,599
From
US$799
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
Departure: 30 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Bonus Onboard Credit
Exclusive Savings
Inside
$736
Oceanview
$797
Balcony
$1,447
Suite
$1,566
From
US$1,100
Save 50
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$900
Oceanview
$1,100
Balcony
$1,350
Suite
$1,550
From
US$900
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departure: 09 January 2028
Visit: Puerto Rico, Saint Martin, Curacao, Saint Lucia, Saint Kitts and Nevis
Inside
$1,169
Oceanview
$1,369
Balcony
$1,619
Suite
$2,447
From
US$1,169
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,130
Suite
$4,760
From
US$4,130
Per Person
View Trip
9 Day St. Maarten, San Juan & St. Thomas with Celebrity Cruises
Cruise

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
$3,640
From
US$1,449
Save 515
Per Person
View Trip
7 Day Southern Caribbean Cruise 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
Inside
$834
Oceanview
$1,014
Balcony
$1,194
Suite
$3,540
From
US$834
Per Person
View Trip
12 Day Eastern Caribbean From New York To New York with Norwegian Cruise Line
Cruise

12 Days (11 Nights) New York to New York
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Bliss
Departure: 15 January 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis, Virgin Islands
Inside
$1,289
Oceanview
$1,689
Balcony
$1,937
Suite
$2,228
From
US$1,289
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departures: Jan 2027 to Jan 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$749
Oceanview
$849
Balcony
$750
Suite
$1,200
From
US$749
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Jan 2026 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$719
Oceanview
$749
Balcony
$909
Suite
$3,615
From
US$719
Save 410
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
$1,114
Oceanview
$1,214
Balcony
$1,514
Suite
$3,258
From
US$1,114
Per Person
View Trip
8 Day Eastern Caribbean: San Juan & St. Thomas with Holland America
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Eurodam, Nieuw Statendam
Departures: Nov 2026 to Mar 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Fare Saver
Inside
$644
Oceanview
$744
Balcony
$994
Suite
$1,644
From
US$644
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: Jan 2026 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Dominica, Barbados
Exclusive Savings
Inside
$612
Oceanview
$717
Balcony
$970
Suite
$1,226
From
US$642
Save 519
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
Departures: Feb 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,209
Oceanview
$1,379
Balcony
$1,609
Suite
$2,264
From
US$1,209
Per Person
View Trip
Results: 31-50 of 50

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