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Originally Posted by BigCity76
Yeah I still have fond memories of a family summer vacation to Castine, ME in the early 80's when I was a young lad, mostly the sailing excursion from that trip. I'll never forget we went out on this fairly large captained sailboat for about half a day (just my immediate family) in Penobscot Bay I believe. We stopped at several different little islands along the way. We were far from a sailing family growing up in NNJ and my parents both being from NYC. That being said, the captain was awesome, the sailing was amazing and beautiful views everywhere. We picnic'd on one of the islands and it's been a cherished family memory ever since.
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Personally, sailing Merchants Row off Stonington ME with all the little granite islands is one of the most beautiful places on the planet. “Cruise to Maine” was something I grew up with. Through the Cape Cod Canal and an overnight sail to Tenants Harbor. I’ve done that passage a bunch of times. I have a Cruising Guide to Maine that’s all annotated with details about various places I’ve been.