Re: 10 days south of Cuttyhunk
I grew up boating in western LI Sound out to Fishers Island and the rare trip to Block and now prefer RI.
You may want to visit Gardiners Bay and Shelter Island. I only went last year for the first time. So so.
Montauk is fun. That's worth a shot. You'll need a slip, unless you can get way in back.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.