If you are serious about spending weekends on board with 4 people, then I agree with Hailkai about the 27. IMHO, 27 is too small (or will be soon). However, I don't think you need to go all the way to 30. It sounds a little silly, but when I was looking to move up from my Catalina 22, I found that 27' was too small, but 28 was not. I was looking for a 28-32 boat. I would have loved to get a Catalina 30, but they (and most 30' boats) are significantly more money than 28' boats like O'day 28, Newport 28, S2 8.6, etc. This way, if, in a few years, you want to move up, it will be to a 34-38 boat anyway.
Whatever size you end up with, for weekend use make sure you have standing head room, a real marine head, decent galley (sinks that work, some sort of stove, ice box you can reach), and berths you fit in.
Regarding sailing ability, you don't need a full keel, heavy cruiser. You want something that will sail well in light air. Face it, if the weather forecast for the weekend is gale force winds, you won't be going to the cape anyway. However, if the wind is 5-10 it would be nice to sail there instead of motoring the entire way.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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