I've sailed from San Juan on the Destiny three times. Last year we did the same itinerary that the Victory is now doing and LOVED it. I want to do that cruise again. Loved not having any sea days and a new port each morning. When I sail from San Juan, I prefer to stay at the Sheraton Old San Juan. It's right across the street from the pier and we walked over to the ship. (but we don't take a lot of luggage lol). I've always enjoyed San Juan. Lots to do and places to eat and shop. There are free shuttles around Old San Juan.