A gem of a seaport on Penobscot Bay, Camden (pop. around 5,200) is popular not just because of its picturesqueness, its shops, galleries, and B&Bs, but also its fleet of its windjammer sailing ships - several of which you can book for cruises through the Maine Windjammer Association. It's one of the places that made me fall in love with Maine when I was a kid. Just be prepared for crowds if you go in summer/early fall!
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