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Puerto Rico Cruises Starting In January 2027, 2028 and 2029

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57 Cruises (194 Cruise Departures)
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
Princess Premier
Inside
$529
Oceanview
$704
Balcony
$691
Suite
$1,069
From
US$529
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
Cruise Line: Princess
Ship: Sun Princess
Departures: Dec 2026 to Jan 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$524
Oceanview
$644
Balcony
$794
Suite
$1,189
From
US$524
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
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Pearl
Departures: Nov 2026 to Feb 2028
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic
Inside
$939
Oceanview
$1,119
Balcony
$1,599
Suite
$1,789
From
US$939
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (1)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Regal Princess, Sun Princess
Departures: Apr 2027 to Jan 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$724
Oceanview
$904
Balcony
$1,074
Suite
$1,419
From
US$724
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
Cruise Line: Princess
Ship: Sun Princess
Departure: 03 January 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic
Princess Standard
Sanctuary Collection
Inside
$574
Oceanview
$674
Balcony
$884
Suite
$1,059
From
US$574
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
Exclusive Savings
Inside
$653
Oceanview
$683
Balcony
$1,293
Suite
$1,421
From
US$653
Save 378
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
$2,519
From
US$1,169
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
$1,339
Oceanview
$1,559
Balcony
$1,749
Suite
$2,089
From
US$1,339
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
$481
Oceanview
$501
Balcony
$527
Suite
$1,963
From
US$571
Save 231
Per Person
View Trip
11 Day Caribbean Cruise From Jacksonville To Jacksonville with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Jacksonville to Jacksonville
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 18 January 2028
Visit: USA, Bahamas, Dominican Republic, Virgin Islands, Puerto Rico
Inside
$1,049
Oceanview
$1,169
Balcony
$1,699
Suite
$1,959
From
US$1,049
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,920
From
US$5,920
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
Departure: 15 January 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,159
Oceanview
$1,319
Balcony
$1,359
Suite
$2,694
From
US$1,159
Save 589
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 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
Sanctuary Collection
Inside
$764
Oceanview
$904
Balcony
$974
Suite
$1,349
From
US$764
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
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,765
From
US$4,765
Save 1,940
Per Person
View Trip
7 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

7 Days (6 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 03 January 2028
Visit: Puerto Rico, Bonaire, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$709
Oceanview
$759
Balcony
$1,409
Suite
$1,604
From
US$709
Save 422
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
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Independence of the Seas
Departures: Nov 2027 to Jan 2028
Visit: USA, Dominican Republic, Puerto Rico, Aruba, Curacao
Bonus Onboard Credit
Exclusive Savings
Inside
$966
Oceanview
$1,086
Balcony
$1,384
Suite
$2,234
From
US$966
Save 508
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,460
From
US$6,460
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Nov 2026 to Sep 2027
Visit: USA, Saint Martin, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$759
Oceanview
$1,094
Balcony
$1,106
Suite
$2,205
From
US$759
Save 798
Per Person
View Trip
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
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$3,638
Balcony
-
Suite
$4,808
From
US$3,638
Save 1,457
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
Departure: 29 January 2028
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,132
Oceanview
$1,283
Balcony
$1,322
Suite
$2,616
From
US$1,132
Save 576
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
Departure: 24 January 2027
Visit: USA, Bahamas, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$670
Oceanview
$829
Balcony
$1,182
Suite
$4,183
From
US$670
Save 356
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: Jun 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$567
Oceanview
$763
Balcony
$897
Suite
$1,314
From
US$567
Per Person
View Trip
10 Day Seagrass & Sky with Regent Seven Seas
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 29 January 2029
Visit: USA, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,399
Suite
$9,749
From
US$9,399
Save 9,399
Per Person
View Trip
9 Day Caribbean And Antilles with MSC Cruises
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC Meraviglia
Departure: 30 January 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin, Virgin Islands
Inside
$578
Oceanview
$758
Balcony
$908
Suite
$2,848
From
US$578
Per Person
View Trip
11 Day Caribbean Cruise From Jacksonville to Jacksonville with Norwegian Cruise Line
Cruise

11 Days (10 Nights) Jacksonville to Jacksonville
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Dawn
Departure: 28 January 2028
Visit: USA, Bahamas, Dominican Republic, Virgin Islands, Puerto Rico
Inside
$1,079
Oceanview
$1,199
Balcony
$1,729
Suite
$1,989
From
US$1,079
Per Person
View Trip
Results: 31-57 of 57

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