You guys are incredibly lucky to have so many waterways, islands and town anchorages along the east coast. I've always been jealous. 10 minutes after we leave the slip we're in open ocean with not many places to go. Here in Southern California we only have the Channel islands, beautiful but there are only 6 of them and for the most part, full of fun seekers from the mainland.
Forget about Catalina, it's like going to Los Angeles (to me).