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Puerto Rico Cruises Starting In December 2026 and 2027

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73 Cruises (209 Cruise Departures)
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
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,473
From
US$674
Save 571
Per Person
View Trip
14 Day Transatlantic Cruise: Malaga, San Juan & Miami with Azamara Cruises
Cruise
 (5)

14 Days (13 Nights) Malaga to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 04 December 2026
Visit: Spain, Morocco, Puerto Rico, USA
Azamara Circle Member - Quarterly Saving
Azamara Always Included
Inside
-
Oceanview
-
Balcony
$2,759
Suite
$5,219
From
US$2,759
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 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
$849
Oceanview
$949
Balcony
$1,129
Suite
$1,349
From
US$849
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
$1,099
Oceanview
$1,289
Balcony
$1,509
Suite
$2,309
From
US$1,099
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
$589
Oceanview
-
Balcony
$719
Suite
$984
From
US$589
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
$1,649
Oceanview
-
Balcony
$1,699
Suite
$2,749
From
US$1,649
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
$1,179
Oceanview
$1,369
Balcony
$1,599
Suite
$2,409
From
US$1,179
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
$579
Oceanview
$755
Balcony
$723
Suite
$1,049
From
US$579
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
Departure: 11 December 2027
Visit: Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Lucia, Aruba
Inside
$833
Oceanview
$973
Balcony
$1,323
Suite
$3,850
From
US$833
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
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,800
Suite
$7,300
From
US$4,800
Save 3,000
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: Dec 2027 to Dec 2027
Visit: Puerto Rico, Saint Kitts and Nevis, Saint Martin, Curacao, Aruba
Inside
$1,139
Oceanview
$1,329
Balcony
$1,559
Suite
$2,369
From
US$1,139
Per Person
View Trip
8 Day A Journey of Tropical Spirits & the Colourful Beauty of the Antilles with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,815
From
US$4,815
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
$1,079
Oceanview
$1,149
Balcony
$2,022
Suite
$2,417
From
US$1,079
Save 558
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 27 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,740
Oceanview
$2,101
Balcony
$2,121
Suite
$10,010
From
US$1,740
Save 1,000
Per Person
View Trip
8 Day Eastern Caribbean Holiday with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 20 December 2026
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,322
Oceanview
$1,481
Balcony
$1,464
Suite
$3,337
From
US$1,322
Save 694
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: 20 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy
Preferred Fare + Bonus Savings
Exclusive Savings
Inside
-
Oceanview
$5,186
Balcony
-
Suite
$6,824
From
US$5,186
Save 1,609
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
$3,000
Balcony
$3,700
Suite
$6,100
From
US$3,000
Save 2,000
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
$4,900
From
US$4,900
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
$7,435
From
US$7,435
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
$558
Oceanview
$738
Balcony
$898
Suite
$2,898
From
US$558
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
$699
Oceanview
$899
Balcony
$949
Suite
$1,299
From
US$699
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
Exclusive Savings
Inside
$1,079
Oceanview
$1,289
Balcony
$2,324
Suite
$2,376
From
US$1,079
Save 686
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
$741
Oceanview
$956
Balcony
$1,257
Suite
$3,982
From
US$741
Save 562
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: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,900
Balcony
$4,500
Suite
$8,800
From
US$3,900
Save 1,500
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
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,700
Suite
$9,600
From
US$4,800
Save 2,500
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 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 Plus Fare
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,400
Balcony
$4,900
Suite
$9,500
From
US$4,400
Save 1,500
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
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: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$567
Oceanview
$763
Balcony
$897
Suite
$1,444
From
US$567
Per Person
View Trip
Results: 31-60 of 73

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