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Puerto Rico Cruises Starting In December 2026 and 2027

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73 Cruises (213 Cruise Departures)
8 Day 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
Departures: Dec 2027 to Dec 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Martin, Curacao, Aruba
Exclusive Savings
Inside
$1,119
Oceanview
$1,319
Balcony
$1,569
Suite
$2,399
From
US$1,119
Save 55
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 28 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Kitts and Nevis
All-Inclusive Fare
Inside
-
Oceanview
$5,600
Balcony
$6,100
Suite
$10,700
From
US$5,600
Per Person
View Trip
10 Day A Journey of Palm - Shaded Elegance & Caribbean Cultural Fusion with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 04 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Barthelemy
Inside
-
Oceanview
-
Balcony
-
Suite
$4,685
From
US$4,685
Per Person
View Trip
8 Day A Journey Through Art Deco Wonders & Caribbean Adventures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 23 December 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,745
From
US$4,745
Per Person
View Trip
10 Day Caribbean Cruise From Jacksonville to Jacksonville with Norwegian Cruise Line
Cruise

10 Days (9 Nights) Jacksonville to Jacksonville
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 09 December 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Dominican Republic
Inside
$1,069
Oceanview
$1,269
Balcony
$1,839
Suite
$2,131
From
US$1,069
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 20 December 2026
Visit: Puerto Rico, Virgin Islands, Montserrat, Saint Lucia, Martinique
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,200
Balcony
$4,900
Suite
$8,600
From
US$4,200
Save 1,500
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key 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
Inside
$789
Oceanview
$949
Balcony
$1,024
Suite
$1,399
From
US$789
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 07 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Select Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,398
From
US$5,398
Save 1,057
Per Person
View Trip
14 Day Caribbean And Antilles with MSC Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departure: 18 December 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Inside
$2,013
Oceanview
$2,332
Balcony
$2,571
Suite
$4,124
From
US$2,013
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 27 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Preferred Plus Fare + Air Credit
Select Fare
Exclusive Savings
Inside
-
Oceanview
$6,327
Balcony
-
Suite
$7,916
From
US$6,327
Save 818
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Saint Vincent
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,200
Balcony
$4,900
Suite
$9,200
From
US$4,200
Save 2,500
Per Person
View Trip
14 Day Caribbean And Antilles with MSC Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departure: 11 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas, Mexico
Inside
$1,663
Oceanview
$2,022
Balcony
$2,202
Suite
$3,668
From
US$1,663
Per Person
View Trip
8 Day Eastern Caribbean: San Juan & St. Thomas with Holland America
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Holland America
Ship: Zuiderdam
Departures: Dec 2026 to Dec 2026
Visit: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Fare Saver
Inside
$699
Oceanview
$749
Balcony
$999
Suite
$1,699
From
US$699
Per Person
View Trip
Results: 61-73 of 73

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