There is a good launching ramp on Shelter Island. The parking lot is big and well lit. All the local marine stores are nearby and some great eating establishments are there too. Humphrey's has outdoor concerts which can be viewed from a dinghy for free. Usually 50 dinks are "holding hands" during the events. Marina Cortez on Harbor Island will let you keep your trailer in their lot while you are paying for a slip. Some great restaurants are on Harbor Island too. The trip up to Mission Bay is easy and a night or two anchored in Mariner's Cove (basin?) is fun. The roller coaster is right there and a walk on the ocean side fun. If you spend a night in Glorietta Bay, you can go ashore and visit the Hotel Del Coronado. This is the place where "Some Like it Hot" was filmed. Always bring warm clothes because the evening temps cool off, even in July. As for sailing, I ghosted along in the bay under a full moon, and have been reefed beating back up the bay to get back the marina. It can be exciting. Have fun; Sandy