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Puerto Rico Cruises Starting In December 2026 and 2027

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73 Cruises (213 Cruise Departures)
9 Day Eastern Caribbean & Bimini Holiday with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 19 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Bahamas
Limited Time Offer
Inside
$1,432
Oceanview
$1,571
Balcony
$1,672
Suite
$4,472
From
US$1,432
Per Person
View Trip
8 Day St. Thomas, San Juan & Bahamas with Celebrity Cruises
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departure: 13 December 2026
Visit: USA, Dominican Republic, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$883
Oceanview
$1,074
Balcony
$1,205
Suite
$3,227
From
US$1,040
Save 414
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
Departure: 13 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Antigua and Barbuda, Saint Martin
Inside
$1,099
Oceanview
$1,349
Balcony
$1,699
Suite
$2,042
From
US$1,099
Per Person
View Trip
10 Day Eastern Caribbean & Bimini Holiday with Virgin Voyages
Cruise
 (1)

10 Days (9 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Brilliant Lady
Departure: 14 December 2026
Visit: USA, Saint Martin, Virgin Islands, Puerto Rico, Bahamas
Limited Time Offer
Inside
$981
Oceanview
$1,251
Balcony
$1,431
Suite
$4,491
From
US$981
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: Vision of the Seas
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Bonaire, Curacao, Aruba
Bonus Onboard Credit
Exclusive Savings
Inside
$723
Oceanview
$773
Balcony
$1,243
Suite
$1,458
From
US$723
Save 632
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 27 December 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,553
Oceanview
$1,843
Balcony
$2,714
Suite
$2,586
From
US$1,553
Save 806
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: 05 December 2026
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Dominican Republic
Inside
$638
Oceanview
$818
Balcony
$978
Suite
$2,819
From
US$638
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departures: Dec 2026 to Apr 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$973
Oceanview
$1,183
Balcony
$1,393
Suite
$3,703
From
US$973
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
$599
Oceanview
$699
Balcony
$999
Suite
$1,499
From
US$599
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visit: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Limited Time Offer
Inside
$763
Oceanview
$903
Balcony
$1,253
Suite
$3,850
From
US$763
Per Person
View Trip
9 Day Eastern Caribbean with Tortola Holiday with Princess
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departure: 19 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Princess Standard
Inside
$1,289
Oceanview
-
Balcony
$1,474
Suite
$2,269
From
US$1,289
Per Person
View Trip
9 Day A Journey Of Sparkling Skies & Bright Beginnings with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 27 December 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,460
From
US$6,460
Per Person
View Trip
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: Nov 2027 to Dec 2027
Visit: Puerto Rico, Aruba, Barbados, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,419
Oceanview
$1,619
Balcony
$1,817
Suite
$2,690
From
US$1,419
Save 52
Per Person
View Trip
12 Day Caribbean Cruise From Philadelphia To Philadelphia with Norwegian Cruise Line
Cruise
 (1)

12 Days (11 Nights) Philadelphia to Philadelphia
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Pearl
Departure: 23 December 2026
Visit: USA, Saint Martin, Virgin Islands, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,919
Oceanview
$1,967
Balcony
$2,549
Suite
$3,199
From
US$1,919
Save 50
Per Person
View Trip
8 Day Eastern Caribbean Cruise: Barbados, Saint Kittsand Nevis & Puerto Rico with Azamara Cruises
Cruise
 (8)

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 07 December 2027
Visit: Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, USA
Azamara Always Included
Exclusive Savings
Inside
$4,729
Oceanview
$5,447
Balcony
$6,494
Suite
-
From
US$4,729
Save 130
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Martin, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$1,052
Oceanview
$1,122
Balcony
$1,902
Suite
$2,187
From
US$1,052
Save 546
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
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,473
From
US$689
Save 568
Per Person
View Trip
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
Departure: 05 December 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Lucia, Barbados, Aruba
Inside
$1,119
Oceanview
$1,319
Balcony
$1,569
Suite
$2,399
From
US$1,119
Per Person
View Trip
8 Day Southern Caribbean Holiday with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 26 December 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$1,529
Oceanview
$1,545
Balcony
$2,668
Suite
$2,941
From
US$1,529
Save 796
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
Departures: Dec 2027 to Feb 2028
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Bonus Onboard Credit
Exclusive Savings
Inside
$732
Oceanview
$792
Balcony
$1,332
Suite
$1,537
From
US$732
Save 435
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departure: 26 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Turks and Caicos Islands
Princess Standard
Inside
$1,749
Oceanview
-
Balcony
$1,724
Suite
$2,699
From
US$1,724
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico Holiday with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 27 December 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$1,421
Oceanview
-
Balcony
$1,586
Suite
$1,981
From
US$1,421
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 05 December 2026
Visit: USA, Virgin Islands, Puerto Rico, Dominican Republic, Bahamas
Limited Time Offer
Inside
$952
Oceanview
$1,192
Balcony
$1,432
Suite
$3,432
From
US$952
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (2)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 13 December 2026
Visit: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Princess Standard
Inside
$649
Oceanview
-
Balcony
$829
Suite
$999
From
US$649
Per Person
View Trip
9 Day Eastern Caribbean & Bimini Beach Club with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departures: Dec 2027 to Mar 2028
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Limited Time Offer
Inside
$952
Oceanview
$1,192
Balcony
$1,432
Suite
$3,920
From
US$952
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 Prima
Departure: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Inside
$1,209
Oceanview
$1,409
Balcony
$1,659
Suite
$2,487
From
US$1,209
Per Person
View Trip
16 Day Lisbon to Miami, Fl with Silversea
Cruise
 (1)

16 Days (15 Nights) Lisbon to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 03 December 2027
Visit: Portugal, Gibraltar, Saint Martin, Puerto Rico, USA
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,000
Suite
$9,100
From
US$5,000
Save 1,500
Per Person
View Trip
9 Day Eastern Caribbean From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Getaway
Departure: 14 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Bahamas
Inside
$889
Oceanview
$1,079
Balcony
$1,159
Suite
$1,489
From
US$889
Per Person
View Trip
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
$5,355
From
US$5,355
Per Person
View Trip
10 Day Eastern Caribbean Cruise with Royal Caribbean
Cruise

10 Days (9 Nights) Tampa to Tampa
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 07 December 2026
Visit: USA, Puerto Rico, Sint Maarten, Virgin Islands, Dominican Republic
Exclusive Savings
Inside
$853
Oceanview
$1,021
Balcony
$1,478
Suite
$3,804
From
US$853
Save 558
Per Person
View Trip
Results: 31-60 of 73

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