Why it's so great: Where Nantucket and Martha's VIneyard are monied and tourist-clogged, Block Island -- a 30-minute, high-speed ferry ride from Newport -- has more of an easygoing, soft-sell vibe that is far less intimidating. Iconic clapboard homes and restored grand hotels mix it up with honky-tonk watering holes and a boating -- not yachting -- crowd. Also: there's terrific surfing. Who knew?
Must-do: Rent a bike to tour the island, nearly two-thirds of which is protected land. A hike along the Ireland-esque Mohegan Bluffs. Cocktails and cornhole at the Oar (go for either the $2 'Gansetts or the house special, the frozen mudslide).
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Meaghan Agnew has lived on three islands so far and isn't done yet. Meantime, follow her landlocked exploits at @meaghandeth.