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Puerto Rico Cruises Starting In December 2026 and 2027

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73 Cruises (209 Cruise Departures)
8 Day A Journey of Salsa Beats, Spectacular Fireworks & Dominican Charm with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 30 December 2027
Visit: Puerto Rico, Virgin Islands, Dominican Republic, Bahamas, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$5,505
From
US$5,505
Per Person
View Trip
8 Day Eastern Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Explorer of the Seas
Departure: 28 December 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Haiti
Exclusive Savings
Inside
$855
Oceanview
$1,261
Balcony
$1,414
Suite
$2,298
From
US$855
Save 626
Per Person
View Trip
8 Day Perfect Day Cococay & Caribbean Holid with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Independence of the Seas
Departures: Nov 2026 to Apr 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$532
Oceanview
$674
Balcony
$845
Suite
$1,508
From
US$532
Save 526
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
$649
Oceanview
$699
Balcony
$949
Suite
$1,499
From
US$649
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 Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,501
Balcony
-
Suite
$7,139
From
US$5,501
Save 1,644
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
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,552
From
US$4,552
Save 1,903
Per Person
View Trip
9 Day Eastern Caribbean Holiday with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departure: 18 December 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,676
Oceanview
$1,906
Balcony
$1,966
Suite
$3,921
From
US$1,676
Save 795
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Symphony of the Seas
Departures: Nov 2027 to Dec 2027
Visit: USA, Saint Kitts and Nevis, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,084
Oceanview
$1,233
Balcony
$1,273
Suite
$2,509
From
US$1,084
Save 735
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
$5,050
From
US$5,050
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
$2,392
Balcony
$2,638
Suite
$4,239
From
US$2,013
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
$2,258
Suite
$3,769
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
$949
Suite
$1,599
From
US$699
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
$999
Oceanview
$1,179
Balcony
$1,599
Suite
$1,969
From
US$999
Per Person
View Trip
Results: 61-73 of 73

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