Cuttyhunk Harbor

Cuttyhunk is the outermost island in the Elizabeth Island chain, sitting right at the mouth of Buzzards Bay — about six miles from New Bedford and seven from Martha's Vineyard. You anchor off here and take in a place that somehow stays genuinely unhurried despite being a well-known stop on this stretch of coast. It's a small, walkable island with a real end-of-the-road feel, and the surrounding waters offer solid protection from Buzzards Bay's notorious chop.