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Puerto Rico Cruises Starting In December 2026 and 2027

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74 Cruises (222 Departures)
74 Cruises (222 Departures)
Departures
Duration
7 Days
22 Days
Countries Visited
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$800pp
$28,480pp
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8 Day Grand Turk & St. Maarten Holiday with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departures: Dec 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Saint Martin
Exclusive Savings
Inside
$1,546
Oceanview
$1,547
Balcony
$2,016
Suite
$6,181
From (Per Person)
A$1,546
Save 1,913
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: Nov 2027 to Apr 2028
Visits: Puerto Rico, Aruba, Curacao, Antigua and Barbuda, Saint Martin
Inside
$1,129
Oceanview
$1,337
Balcony
$1,853
Suite
$5,695
From (Per Person)
A$1,129
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
Visits: Portugal, Gibraltar, Saint Martin, Puerto Rico, USA
Exclusive Savings
Balcony
$6,968
Suite
$13,426
From (Per Person)
A$6,968
Save 4,882
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico & Celebration Key with Princess
Cruise
 (3)

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Sky Princess
Departure: 13 December 2026
Visits: USA, Bahamas, Turks and Caicos Islands, Dominican Republic, Puerto Rico
Exclusive Savings
Inside
$1,034
Oceanview
-
Balcony
$1,377
Suite
$2,229
From (Per Person)
A$1,034
Per Person
View Trip
8 Day Eastern Caribbean with Celebration Key Holiday with Princess
Cruise
 (7)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 20 December 2026
Visits: USA, Puerto Rico, Turks and Caicos Islands, Bahamas
Sanctuary Collection
Exclusive Savings
Inside
$1,232
Oceanview
$1,440
Balcony
$1,717
Suite
$3,271
From (Per Person)
A$1,232
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
Visits: USA, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Inside
$1,409
Oceanview
$1,763
Balcony
$2,119
Suite
$5,799
From (Per Person)
A$1,409
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
Ship: Azamara Quest
Departure: 04 December 2026
Visits: Spain, Morocco, Puerto Rico, USA
Azamara Always Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,612
Suite
$7,140
From (Per Person)
A$3,612
Save 57
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
Visits: USA, Saint Martin, Virgin Islands, Puerto Rico, Dominican Republic
Just Cruise Fare
Exclusive Savings
Inside
$2,551
Oceanview
$2,775
Balcony
$4,040
Suite
$4,219
From (Per Person)
A$2,551
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
Visits: USA, Saint Martin, Virgin Islands, Puerto Rico, Bahamas
Inside
$1,726
Oceanview
$1,451
Balcony
$1,718
Suite
$5,445
From (Per Person)
A$1,451
Per Person
View Trip
8 Day Southern Caribbean & Aruban Nights with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 11 December 2027
Visits: Puerto Rico, Saint Martin, Antigua and Barbuda, Saint Lucia, Aruba
Inside
$1,234
Oceanview
$1,440
Balcony
$1,931
Suite
$5,696
From (Per Person)
A$1,234
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
Visits: USA, Bahamas, Puerto Rico, Dominican Republic
Sanctuary Collection
Exclusive Savings
Inside
$954
Oceanview
$1,093
Balcony
$1,291
Suite
$1,945
From (Per Person)
A$954
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
Visits: USA, Dominican Republic, Puerto Rico, Bahamas, Mexico
Exclusive Savings
Inside
$2,910
Oceanview
$3,454
Balcony
$3,811
Suite
$6,097
From (Per Person)
A$2,910
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
Ships: Emerald Kaia
Departures: Dec 2027 to Nov 2028
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy
Exclusive Savings
Oceanview
$7,318
Suite
$9,265
From (Per Person)
A$7,318
Save 3,128
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
Visits: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$6,884
From (Per Person)
A$6,884
Save 141
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, Rotterdam
Departures: Nov 2026 to Mar 2028
Visits: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Fare Saver
Exclusive Savings
Inside
$923
Oceanview
$1,081
Balcony
$1,536
Suite
$2,536
From (Per Person)
A$923
Save 18
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
Visits: Puerto Rico, Virgin Islands, Montserrat, Saint Lucia, Martinique
Exclusive Savings
Oceanview
$4,047
Balcony
$5,282
Suite
$10,192
From (Per Person)
A$4,047
Save 1,853
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
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Kitts and Nevis
Exclusive Savings
Oceanview
$5,762
Balcony
$6,448
Suite
$16,072
From (Per Person)
A$5,762
Save 2,638
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 2027
Visits: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Fare Saver
Exclusive Savings
Inside
$923
Oceanview
$1,002
Balcony
$1,467
Suite
$2,764
From (Per Person)
A$923
Save 15
Per Person
View Trip
8 Day Eastern Caribbean Holiday: San Juan & St. Thomas with Holland America
Cruise

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ship: Zuiderdam
Departure: 30 December 2027
Visits: USA, Bahamas, Virgin Islands, Puerto Rico, Turks and Caicos Islands
Fare Saver
Exclusive Savings
Inside
$2,492
Oceanview
$2,799
Balcony
$3,413
Suite
$5,412
From (Per Person)
A$2,492
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
Visits: USA, Dominican Republic, Puerto Rico, Bahamas
Exclusive Savings
Inside
$2,495
Oceanview
$2,495
Balcony
$2,708
Suite
$9,952
From (Per Person)
A$2,941
Save 839
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
Visits: USA, Puerto Rico, Sint Maarten, Virgin Islands, Dominican Republic
Exclusive Savings
Inside
$1,583
Oceanview
$1,508
Balcony
$2,193
Suite
$5,233
From (Per Person)
A$1,762
Save 585
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
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
Exclusive Savings
Oceanview
$5,008
Balcony
$5,900
Suite
$14,798
From (Per Person)
A$5,008
Save 2,292
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
Visits: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Sanctuary Collection
Exclusive Savings
Inside
$1,143
Oceanview
$1,311
Balcony
$1,529
Suite
$2,083
From (Per Person)
A$1,143
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
Visits: Puerto Rico, Virgin Islands, Dominican Republic, Bahamas, USA
Exclusive Savings
Suite
$7,742
From (Per Person)
A$7,742
Save 158
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
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
$1,616
Oceanview
$1,665
Balcony
$1,661
Suite
$4,442
From (Per Person)
A$1,889
Save 611
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
Visits: USA, Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Dominican Republic
Exclusive Savings
Inside
$1,026
Oceanview
$1,294
Balcony
$1,521
Suite
$4,571
From (Per Person)
A$1,026
Per Person
View Trip
15 Day The Magnificent Atlantic with Regent Seven Seas
Cruise

15 Days (14 Nights) Barcelona to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 06 December 2027
Visits: Spain, Puerto Rico, USA
Exclusive Savings
Balcony
-
Suite
$7,338
From (Per Person)
A$7,338
Save 11,602
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 2027
Visits: Puerto Rico, Virgin Islands, Bonaire, Curacao, Aruba
Exclusive Savings
Inside
$1,801
Oceanview
$1,983
Balcony
$3,291
Suite
$4,045
From (Per Person)
A$2,120
Save 670
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
Visits: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$11,201
From (Per Person)
A$11,201
Save 229
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
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Barthelemy
Exclusive Savings
Suite
$7,610
From (Per Person)
A$7,610
Save 155
Per Person
View Trip
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