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Puerto Rico Cruises Starting In December 2026 and 2027

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15 Days
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59 Cruises (191 Cruise Departures)
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
Bonus Onboard Credit
Inside
$2,009
Oceanview
$2,339
Balcony
$2,611
Suite
$4,153
From
US$2,009
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
$1,199
Oceanview
-
Balcony
$1,619
Suite
$2,049
From
US$1,199
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,020
Suite
$5,840
From
US$5,020
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: Mar 2026 to Apr 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$833
Oceanview
$973
Balcony
$1,113
Suite
$3,493
From
US$833
Per Person
View Trip
8 Day Valiant Caribbean Holidays with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 December 2026
Visit: Puerto Rico, Saint Kitts and Nevis, Martinique, Aruba, Curacao
Inside
$1,183
Oceanview
$1,393
Balcony
$1,603
Suite
$4,620
From
US$1,183
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
$1,199
Oceanview
$1,298
Balcony
$2,629
Suite
$2,501
From
US$1,767
Save 50
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico 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
$604
Oceanview
$725
Balcony
$622
Suite
$884
From
US$604
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,685
Suite
$5,285
From
US$4,685
Per Person
View Trip
9 Day San Juan to Miami with Silversea
Cruise
 (1)

9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 29 December 2026
Visit: Puerto Rico, Virgin Islands, Dominica, Antigua and Barbuda, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,080
Suite
$8,160
From
US$6,080
Save 1,520
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 Fare
Exclusive Savings
Inside
-
Oceanview
$3,680
Balcony
$4,240
Suite
$8,560
From
US$3,680
Save 920
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
$1,101
Oceanview
-
Balcony
$1,451
Suite
$1,831
From
US$1,101
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
$750
Oceanview
$1,149
Balcony
$949
Suite
$1,450
From
US$750
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
$1,149
Oceanview
-
Balcony
$1,299
Suite
$2,299
From
US$1,149
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico 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
$900
Oceanview
$1,100
Balcony
$1,350
Suite
$1,550
From
US$900
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
Inside
$872
Oceanview
$1,112
Balcony
$1,352
Suite
$3,560
From
US$872
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
Bonus Onboard Credit
Inside
$688
Oceanview
$838
Balcony
$948
Suite
$2,790
From
US$688
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
Inside
$1,809
Oceanview
$2,178
Balcony
$2,750
Suite
$4,040
From
US$1,809
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,690
Suite
$6,620
From
US$5,690
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
Bonus Onboard Credit
Inside
$1,629
Oceanview
$1,999
Balcony
$2,213
Suite
$3,668
From
US$1,629
Per Person
View Trip
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
Inside
$1,272
Oceanview
$1,512
Balcony
$1,752
Suite
$4,520
From
US$1,272
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
Inside
$1,252
Oceanview
$1,341
Balcony
$1,611
Suite
$5,130
From
US$1,252
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
$644
Oceanview
$744
Balcony
$994
Suite
$1,644
From
US$644
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,072
Oceanview
$1,084
Balcony
$1,662
Suite
$3,641
From
US$1,072
Save 552
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
$917
Oceanview
$1,009
Balcony
$1,209
Suite
$3,746
From
US$1,075
Save 393
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
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,303
Balcony
-
Suite
$7,073
From
US$5,303
Save 7,687
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
Bonus Onboard Credit
Exclusive Savings
Inside
$1,484
Oceanview
$1,591
Balcony
$2,063
Suite
$3,094
From
US$1,484
Save 727
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
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$3,563
Balcony
-
Suite
$4,921
From
US$3,563
Save 5,827
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,745
Suite
$5,545
From
US$4,745
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 Fare
Exclusive Savings
Inside
-
Oceanview
$3,920
Balcony
$4,620
Suite
$9,660
From
US$3,920
Save 1,680
Per Person
View Trip
Results: 31-59 of 59

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