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I was researching pocket cruisers here a while back. I think the Compac Legacy would be a sweet option for you, and you could certainly raise the mast after ducking the bridge... full length keel, and board to lower after the fact and a cozy cabin. Stable little craft, but pricey... The Sanibel 18 would be hard to beat as well. A little more sleeping room below on the Sanibel, and slightly more beachable than the compac. There are some great mast raising tools that come with the mcgregors, but I had bad experience with the 26s model, and its ability to "point." I think I would go for the Sanibel in that situation...
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