Cruising Cuttyhunk


By Rich

Cuttyhunk was the first destination of our 2015 circumnavigation of Nantucket Sound and was certainly a front-runner for one of the best of our cruise. Moorings here are first come, first serve, so we gave up some really scenic, light-air upwind sailing to be sure we got one on July 3rd.


It was a good call: we arrived in time for a late lunch and got one of the last two or three remaining in the inner harbor. The anchorage is crazy protected (read: the anti-Jamestown!) with very densely spaced moorings, so (i) be sure you’re comfortable maneuvering your boat into a very tight “parking space” (literally) and (ii) be ready to raft up. You may be asked to.

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With those caveats stated, the mooring field and Cuttyhunk is a very unique treat. We thought it was super cool to be in a yacht “parking lot” and thoroughly enjoyed taking dinghy rides to check out other boats. I found a very cherry example of a 1970s Pearson 36, which was the first cruising boat my family owned when I was a small child.

There are no onshore shower facilities at Cuttyhunk, but there is awesome fresh-off-the-boat seafood market that allowed us to luxuriate in a cockpit dinner of grilled corn on the cob, scallops and fresh lobster.

Before dinner time, though, be sure to take a dinghy ride to see the beach views.


And whatever you do, don’t forget to hike to the top of the island to see some totally insane views and super-quaint New England architecture.



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