[efhughes3]

I've had a number of boats from 14' to 37', and have crewed extensively on a Swan 57. It would be hard to go wrong with a Catalina 30 or similar to knock around on with some comfort. While people have sailed boats less than 20' around the world, that isn't the boat I'd do it in.

Go with something affordable and try it for a while, you may decide you don't want to venture outside the bay. On the other hand, if you go into it head over heels, you'll have plenty of time to decide what boats you like and don't like, and what is important to you on a boat. Then make the big decision.

Yes, they are holes in the water in which to pour money. Boats are referenced in the saying "if it flies, floats or F@#ks, it's cheaper to rent."