The question begets questions
Well, there's a lot of boats in the 27'-35' family and as there are many and varied types, there's also many and varied prices depending on condition and that sort of thing, so, since you didn't specify a price range, it's a little difficult to answer your question specifically.You have day and bay cruisers, you have true bluewater craft and there's all sorts of stuff out there surprisingly still floating after passages. Personally, right now, I'm sailing a 1978 Hunter 30 that is in near-bristol condition with new engine and sails. I'm an experienced bluewater sailor, but the H30 isn't a bluewater boat, so I don't take her out across the Briny Deep; she stays in the bays and close to shore during fair weather coastal cruises. That fits my mission and my budget...for now. Any of her sisters are worth a look and can be had for under $20,000 in reasonable shape.Her slightly larger sister, the H34, is a good boat as well with similar sailing in mind. Catalinas are sound boats, too, and both, I think could handle fair weather passages through the Bahama chain and into the Virgins on down to the West Indies and Grenadines. Sometimes a boat's abilities are enhanced by the skill of the skipper. That's a call you have to make.All of these boats can be had in reasonable condition for under $40 in earlier models, i.e., late '70s/early '80s. You seem to be fairly reaonable in your expectations and I would say that puts you a little further ahead than perhaps some others.You might also look at Islanders, C