14 Day/14 Night Cruises out of San Juan, Puerto Rico

Are you looking for 14 day cruises that leave from San Juan, PR? As of today - May 10, 2026 - there are 10 such cruise options. These cruise options are offered by two cruise lines - Princess (total of 9 sailings, all of them on Crown Princess) and Seabourn (just 1 sailing on Seabourn Ovation).

In the following table you can see all 14 day cruises that depart from San Juan sorted by departure date.
Seabourn Ovation December 5, 2026
Dec. 5, 2026
From
$7,299
per person
$/Day:
$522
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
Barbados
Ship:
Seabourn Ovation
Select
Seabourn Ovation December 5, 2026
Crown Princess December 27, 2026
Dec. 27, 2026
From
$3,426
per person
$/Day:
$245
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess December 27, 2026
Crown Princess January 3, 2027
Jan. 3, 2027
From
$2,756
per person
$/Day:
$197
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess January 3, 2027
Crown Princess January 10, 2027
Jan. 10, 2027
From
$2,476
per person
$/Day:
$177
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess January 10, 2027
Crown Princess January 17, 2027
Jan. 17, 2027
From
$2,426
per person
$/Day:
$174
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess January 17, 2027
Crown Princess January 24, 2027
Jan. 24, 2027
From
$2,362
per person
$/Day:
$169
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess January 24, 2027
Crown Princess January 31, 2027
Jan. 31, 2027
From
$2,452
per person
$/Day:
$176
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess January 31, 2027
Crown Princess February 7, 2027
Feb. 7, 2027
From
$2,466
per person
$/Day:
$177
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess February 7, 2027
Crown Princess February 21, 2027
Feb. 21, 2027
From
$2,966
per person
$/Day:
$212
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess February 21, 2027
Crown Princess March 7, 2027
Mar. 7, 2027
From
$2,406
per person
$/Day:
$172
Duration:
14 Nights
Region:
Caribbean
Depart:
San Juan
Arrive:
San Juan
Ship:
Crown Princess
Select
Crown Princess March 7, 2027