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You should look into Long Island Sound. There are many free anchorages on both the CT coast and on the Long Island side. Then if you want to go a bit further there is Narragansett Bay, Buzzards Bay and Nantucket Sound, all of which have many many free anchorages as well as marinas. However, the marinas may be a bit more expensive; but, we never stay in a marina. Then if you really feel comfortable with your boat you can go through the cape Cod Canal and make your way to Maine which is really fantastic sailing. The only problem with Maine is the Fog; but, a good chart plotter can alleviate most of the difficulty of navigating in the fog.
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