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Old 02-26-2011
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you might consider something like an O'Day Daysailer or the slightly smaller Javelin. They're not new, but they're decent boats and small enough that you can trailer them behind the vehicles you've listed, step the rig by yourself and large enough to handle you, your wife and two kids. The Javelin might be a bit tight depending on how big you, your wife and two kids are as it is only a 14' boat.

Another, probably better option, would be to get something like a Compac 17 Sun Cat. While only a few feet longer than your sunfish, it is a much bigger boat, since it is much beamier. The catboat rig means it has but a single sail to raise. The mast is designed to be easily raised by a single person. Might be a bit heavier than you want though.
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Telstar 28
New England

You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.

—Cpt. Mal Reynolds, Serenity (edited)

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