The Far Harbor 40 would fit...it was designed to fit into a standard shipping container.
On the rail question, I am no expert, but there is a reason that the containers and all cars are the same height. Sailboats of any size would not fit in a container, and for that reason they would not fit in the tunnel.
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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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Still—DON'T READ THAT POST AGAIN.