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Hi vmi2008,
You will enjoy San Diego. It's great to be able to sail year-round. We were members of Harbor Sailboats and met some great people, but it is geared more to people without boats who want to use their boats. I would also ask about groups at Downwind Marine and some of the employees at the big West Marine store are active cruisers in the area and probably have suggestions. Seabreeze Books is a great place to find all the local guides and charts, as well as infomation.
With 3-5 days you can do a lot of trips, to Mexico, exploring Catalina and you may want to sail north to some marina near the Channel Islands, leave your boat until the next weekend, then sail to the islands, returning to San Diego when you have the available days.
Another fun daysail it out and around the Coronado Islands (but they are part of Mexico so you need to check in with customs.
Enjoy San Diego. It's our Home Port and someday we will return.
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