Join Date: Mar 2006
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Newport 28 would be a nice choice; or a Newport 27. The 28 is a C&C design. IIRC there is an Islander 28 also that would be similar to the Newport 28 or equivalent Ericson.
Prices on used boats are down/dropping right now so you might even find a 30' boat in your price range that might need some minor fixing. As far as "comfortable on the bay" goes; most sub-36' boats are going to be wet on days when the wind and chop is up. I think if you are looking for "comfort" while sailing a sub-30' boat on the bay the best thing to do is to find a marina that is not directly in the wind of The Slot when you head out. Marinas like Brickyard Cove, Marin, Alameda, TI, Richmond (Marina Bay), or South of the Bay Bridge would be good places to get a slip. If it's too heavy on the central bay there are always places to sail and stay out of the direct wind coming in through The Gate. I'm at Marina Bay and it's great because if we don't want to sail on the central bay we can sail up into San Pablo Bay or over to Marin via Raccoon Strait without sailing in the 35kt winds.