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SAIL LOCO
 
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Default Best used boat deal under $40,000

If he wants a boat to really sail, here's one that could also be cruised

http://www.boats.com/listing/boat_de...tityid=9562961


You'd spend your nights bumping your head on the pipes that hold up the
deck. Good looking boat though.
S/V Express 30 "Ringmaster"
Trains are a winter sport