A properly fitted out 28' boat should be fine for coastal and island hopping, and may be a better choice than a larger boat. If you're interested in learning more about cruising in small boat, I'd go see Sailfar
. Boats that size have circumnavigated, and have been used by many for long-term cruising.
Larger boats cost more to own, moor, dock, haul, paint, and maintain. They're also often harder to handle, and often have deeper drafts, which can limit the waters that you will be able to visit.
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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.