A word to the wise: Plan your meals on Cuttyhunk Island  carefully. Wait just a little too long, and you’ll find yourself fresh out of options, as the few eateries available here close quite early. The most reliable is Soprano’s Pizza (Broadway, 508/992-7530, 11:30 a.m.–7 p.m. Mon.–Sat.; closed Sun., $10–19), which is essentially a pizzeria run out of a local’s garage.
At the Fish Market (Town Dock), you place your orders for fresh seafood—shucked oysters or cooked lobster—early in the day and pick them up at 6 p.m. sharp.
Catch dessert a few doors (literally) down at The Ice Cream Stall.