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Princess Cruises from San Juan

Start your journey from San Juan with 51 unique Princess cruise itineraries to choose from. November is the most popular month to begin your cruise from San Juan and Princess have 78 trips departing this season.
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28 Days
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51 Cruises (78 Cruise Departures)
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 23 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+4 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,332
OCEANVIEW
$2,607
BALCONY
$3,223
SUITE
$4,164
From (per person) 2,332
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+4 more), Dominica, Barbados, Guadeloupe, Grenada
Exclusive Deal
INSIDE
$2,198
OCEANVIEW
$2,443
BALCONY
$3,148
SUITE
$3,881
From (per person) 2,198
View Trip
19 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

19 Days (18 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Grand Princess
Departure: 29 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+9 more), Grenada, Barbados, Saint Kitts and Nevis, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA
Exclusive Deal
INSIDE
$2,528
OCEANVIEW
$2,760
BALCONY
$3,716
SUITE
$4,607
From (per person) 2,528
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (2)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Jan 2027 to Feb 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Saint Kitts and Nevis, Dominica, Grenada
Exclusive Deal
INSIDE
$1,729
OCEANVIEW
$1,967
BALCONY
$2,838
SUITE
$3,987
From (per person) 1,729
View Trip
8 Day Southern Caribbean with Barbados Holiday with Princess
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 27 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,439
OCEANVIEW
$1,647
BALCONY
$2,251
SUITE
$3,062
From (per person) 1,439
View Trip
12 Day Southern Caribbean Islander with Princess
Cruise
 (5)

12 Days (11 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Grand Princess
Departure: 05 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Aruba (+5 more), Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA
Exclusive Deal
INSIDE
$1,546
OCEANVIEW
$1,642
BALCONY
$2,209
SUITE
$2,675
From (per person) 1,546
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 25 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Guadeloupe, Barbados
Exclusive Deal
INSIDE
$901
OCEANVIEW
$1,011
BALCONY
$1,495
SUITE
$1,990
From (per person) 901
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 07 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+5 more), Saint Vincent, Barbados, Sint Maarten, Antigua and Barbuda, Dominica
Exclusive Deal
INSIDE
$2,164
OCEANVIEW
$2,415
BALCONY
$3,189
SUITE
$3,619
From (per person) 2,164
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
$901
OCEANVIEW
$1,011
BALCONY
$1,475
SUITE
$1,763
From (per person) 901
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$960
OCEANVIEW
$1,075
BALCONY
$1,554
SUITE
$1,980
From (per person) 960
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 15 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$1,913
OCEANVIEW
$2,154
BALCONY
$3,032
SUITE
$3,765
From (per person) 1,913
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (2)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 07 February 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+4 more), Dominica, Barbados, Saint Kitts and Nevis, Grenada
Exclusive Deal
INSIDE
$1,739
OCEANVIEW
$1,977
BALCONY
$3,036
SUITE
$4,353
From (per person) 1,739
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 March 2026
Countries Visited: Puerto Rico, Sint Maarten, Guadeloupe, Dominica (+5 more), Grenada, Barbados, Virgin Islands, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$1,868
OCEANVIEW
$2,099
BALCONY
$3,094
SUITE
$3,888
From (per person) 1,868
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (2)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 10 January 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+5 more), Saint Lucia, Barbados, Grenada, Dominica, Saint Kitts and Nevis
Exclusive Deal
INSIDE
$1,739
OCEANVIEW
$1,977
BALCONY
$2,858
SUITE
$3,997
From (per person) 1,739
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 March 2026
Countries Visited: Puerto Rico, Sint Maarten, Guadeloupe, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$971
OCEANVIEW
$1,073
BALCONY
$1,516
SUITE
$1,961
From (per person) 971
View Trip
8 Day Southern Caribbean Islander with Princess
Cruise
 (2)

8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 March 2027
Countries Visited: Puerto Rico, Curacao, Aruba, Bonaire (+1 more), USA
Exclusive Deal
INSIDE
$1,092
OCEANVIEW
$1,241
BALCONY
$2,092
SUITE
$2,547
From (per person) 1,092
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 22 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Deal
INSIDE
$1,943
OCEANVIEW
$2,190
BALCONY
$3,042
SUITE
$3,775
From (per person) 1,943
View Trip
15 Day Southern Caribbean Adventurer with Princess
Cruise
 (2)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 31 January 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Saint Martin, Antigua and Barbuda
Exclusive Deal
INSIDE
$1,709
OCEANVIEW
$1,947
BALCONY
$2,907
SUITE
$4,145
From (per person) 1,709
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 18 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+3 more), Dominica, Barbados, Guadeloupe
Exclusive Deal
INSIDE
$1,760
OCEANVIEW
$1,977
BALCONY
$2,987
SUITE
$3,918
From (per person) 1,760
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 30 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Dominica, Barbados, Saint Kitts and Nevis, Saint Lucia, Saint Vincent
Exclusive Deal
INSIDE
$2,164
OCEANVIEW
$2,415
BALCONY
$3,194
SUITE
$3,718
From (per person) 2,164
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ships: Crown Princess, Grand Princess
Departures: Oct 2025 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$884
OCEANVIEW
$1,003
BALCONY
$1,438
SUITE
$1,837
From (per person) 884
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 22 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Martinique, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Deal
INSIDE
$1,883
OCEANVIEW
$2,114
BALCONY
$3,031
SUITE
$3,903
From (per person) 1,883
View Trip
28 Day Panama Canal and Caribbean Adventurer with Princess
Cruise
 (5)

28 Days (27 Nights) San Juan to Los Angeles
Cruise Line: Princess
Ship: Grand Princess
Departure: 05 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Aruba (+8 more), Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA, Panama, Costa Rica, Mexico
Exclusive Deal
INSIDE
$4,166
OCEANVIEW
$4,569
BALCONY
$6,116
SUITE
$8,126
From (per person) 4,166
View Trip
8 Day Southern Caribbean with Barbados with Princess
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 17 January 2027
Countries Visited: Puerto Rico, Barbados, Grenada, Dominica (+2 more), Saint Kitts and Nevis, Virgin Islands
Exclusive Deal
INSIDE
$884
OCEANVIEW
$1,003
BALCONY
$1,438
SUITE
$2,013
From (per person) 884
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 02 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Martinique, Grenada
Exclusive Deal
INSIDE
$1,947
OCEANVIEW
$2,156
BALCONY
$2,819
SUITE
$3,482
From (per person) 1,947
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Dec 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,036
OCEANVIEW
$1,163
BALCONY
$1,550
SUITE
$1,986
From (per person) 1,036
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 26 October 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$1,928
OCEANVIEW
$2,139
BALCONY
$3,173
SUITE
$3,541
From (per person) 1,928
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 28 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$2,734
OCEANVIEW
$2,997
BALCONY
$3,710
SUITE
$4,561
From (per person) 2,734
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
$1,110
OCEANVIEW
$1,253
BALCONY
$1,763
SUITE
$1,981
From (per person) 1,110
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (5)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 09 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+4 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,021
OCEANVIEW
$2,270
BALCONY
$2,842
SUITE
$3,654
From (per person) 2,021
View Trip
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