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Block Island
New Harbor (Great Salt Pond) is an easy sail and landfall from the jumping off points in Connecticut or from Greenport, Sag Harbor, or Montauk on the Long Island side.
Crowded and expensive during the summer, but just the opposite after Labor Day. Avoid Block Island Race Week, when you can walk across the Pond on the boats.
Most of the restaurants are in Old Town. The walk is just the right distance to build up an appetite on the way over and to walk off dessert on the way back. During the day, rent a bike and circumnavigate the island. If it's hot, bring a water bottle and wear your bathing suit. Cool off in Sachem Pond on the northern end or on the beaches adjacent to Old Town, one of which is a nude beach (you'll have to determine which one this is by inspection).
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