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Moving west from Stonington for a day would put you in the vicinity of Milford CT which has a nice town dock and other marinas and great/safe walking access to shops and restaurants a short distance from the waterfront. Moving west, I would avoid the Housatonic River marinas due to strong...

You should be able to find a good weather window with 2-3 days of southerly's this time of the year. Try using the this app: https://www.windy.com I am a weather guy and that app works very well for route planning and being able to "see" the actual and forecast conditions. While I am not a...