Hoisting the dinghy aboard using a handy-billy makes pretty short work of it. However, for shorter coastal passages, towing the dinghy behind the big boat is a pretty good option.
I have a porta-bote, as well as a hypalon inflatable, and would point out that assembling the portabote on a monohull will be a bit challenging. I don't have that issue, since my boat is 18' wide.
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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.