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Puerto Rico Cruises Starting In February 2026, 2027 and 2028

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15 Days
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57 Cruises (246 Cruise Departures)
8 Day Lesser Antilles: Valentine's Day with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 13 February 2027
Visit: Puerto Rico, Aruba, Curacao, Martinique, Saint Kitts and Nevis
Inside
$1,043
Oceanview
$1,253
Balcony
$1,463
Suite
$4,130
From
US$1,043
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Princess
Ship: Regal Princess
Departure: 20 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$850
Oceanview
-
Balcony
$1,069
Suite
$1,750
From
US$850
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: 21 February 2027
Visit: USA, Bahamas, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$653
Oceanview
$873
Balcony
$833
Suite
$1,193
From
US$653
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 28 February 2026
Visit: USA, Virgin Islands, Sint Maarten, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,257
Oceanview
$1,897
Balcony
$1,598
Suite
$3,855
From
US$1,257
Save 622
Per Person
View Trip
12 Day Caribbean East/West Adventurer with Princess
Cruise
 (6)

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Sun Princess
Departure: 22 February 2026
Visit: USA, Bahamas, Puerto Rico, Virgin Islands, Mexico
Princess Standard
Princess Premier
Inside
-
Oceanview
-
Balcony
$2,265
Suite
$3,568
From
US$2,265
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
10 Day Paradise Beaches from the U.S. Virgin Islands to The Bahamas with Emerald Cruises
New ReleaseCruise

10 Days (9 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 10 February 2028
Visit: Puerto Rico, Virgin Islands, Turks and Caicos Islands, Bahamas, USA
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,574
Balcony
-
Suite
$8,854
From
US$6,574
Save 8,916
Per Person
View Trip
8 Day Eastern Caribbean with Holland America
Cruise
 (2)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Holland America
Ships: Eurodam, Nieuw Statendam
Departures: Feb 2026 to Mar 2026
Visit: USA, Turks and Caicos Islands, Puerto Rico, Virgin Islands, Bahamas
Advantage Fare
Have It All Fare Option
Inside
$834
Oceanview
$934
Balcony
$1,184
Suite
$1,484
From
US$834
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
8 Day Southern Caribbean Cruise San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 14 February 2027
Visit: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Inside
$1,239
Oceanview
$1,419
Balcony
$1,659
Suite
$2,332
From
US$1,239
Per Person
View Trip
10 Day A Journey Through Caribbean Delights & Wildlife Wonders with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 19 February 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Anguilla
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,960
Suite
$6,560
From
US$5,960
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: 07 February 2027
Visit: USA, Turks and Caicos Islands, Puerto Rico, Dominican Republic, Bahamas
Princess Standard
Inside
$674
Oceanview
$844
Balcony
$854
Suite
$1,154
From
US$674
Per Person
View Trip
8 Day Eastern Caribbean Cruise From Orlando To Orlando with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Joy
Departures: Feb 2026 to Mar 2026
Visit: USA, Dominican Republic, Virgin Islands, Puerto Rico, Bahamas
Inside
$779
Oceanview
$899
Balcony
$999
Suite
$1,199
From
US$779
Per Person
View Trip
8 Day A Journey of Intimate Island Bliss & Caribbean Breeze with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,180
Suite
$4,820
From
US$4,180
Per Person
View Trip
8 Day Caribbean Yachting Discovery with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Kaia
Departures: Feb 2026 to Mar 2028
Visit: Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Virgin Islands, Puerto Rico
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$4,787
Balcony
-
Suite
$4,816
From
US$4,816
Save 7,412
Per Person
View Trip
9 Day Eastern Caribbean Cruise with Virgin Voyages
Cruise
 (1)

9 Days (8 Nights) Miami to Miami
Cruise Line: Virgin Voyages
Ship: Brilliant Lady
Departure: 12 February 2026
Visit: USA, Dominican Republic, Puerto Rico, Saint Martin, Virgin Islands
Inside
$872
Oceanview
$952
Balcony
$1,032
Suite
$4,960
From
US$872
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Nov 2027 to Mar 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,209
Oceanview
$1,409
Balcony
$1,659
Suite
$2,487
From
US$1,209
Per Person
View Trip
9 Day Antigua, St. Maarten, & San Juan with Celebrity Cruises
Cruise
 (2)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Eclipse
Departure: 28 February 2026
Visit: USA, Antigua and Barbuda, Saint Martin, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,248
Oceanview
$1,438
Balcony
$2,200
Suite
-
From
US$1,483
Save 544
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
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 14 February 2026
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,793
From
US$8,850
Save 222
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: Jewel of the Seas
Departures: Jan 2026 to Apr 2026
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Dominica, Barbados
Exclusive Savings
Inside
$612
Oceanview
$717
Balcony
$970
Suite
$1,226
From
US$642
Save 519
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Inside
$1,259
Oceanview
$1,459
Balcony
$1,709
Suite
$2,536
From
US$1,259
Per Person
View Trip
8 Day Southern Caribbean Cruise From San Juan To San Juan with Norwegian Cruise Line
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Feb 2027 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Inside
$1,209
Oceanview
$1,379
Balcony
$1,609
Suite
$2,264
From
US$1,209
Per Person
View Trip
12 Day Southern 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 Breakaway
Departure: 03 February 2026
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Martin
Inside
-
Oceanview
$1,269
Balcony
$1,519
Suite
$1,749
From
US$1,269
Per Person
View Trip
8 Day A Journey From Glorious Shorelines To Nature's Allure with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,720
Suite
$5,440
From
US$4,720
Per Person
View Trip
11 Day Caribbean Splendor with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 02 February 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,977
Suite
$7,014
From
US$4,977
Save 5,221
Per Person
View Trip
15 Day Discover Island Rhythms & Coastal Dreams with Emerald Cruises
Cruise

15 Days (14 Nights) San Juan to Miami
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 05 February 2028
Visit: Puerto Rico, Virgin Islands, Turks and Caicos Islands, Bahamas, USA
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$12,492
Balcony
-
Suite
$16,033
From
US$12,492
Save 13,188
Per Person
View Trip
Results: 31-57 of 57

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