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I came down the Tenn-Tom last year from Kentucky Lake in a 24' sailboat. I found the trip interesting, and sometimes beautiful. The only part of the waterway that was a "ditch" was a stretch south of Lake Pickwick. The rest was river and lakes behind the 11 or so locks. I found several great anchorages, but sometimes had to anchor along the river channel. Another thing to concider, is your draft. I ran aground twice near the edge of the channel, and I only draw 3 1/2'. I often saw depths of 6' or less near the sides of the channel, when moving over for the 3 or 4 barges a day I passed.
You can probably pick up a cruising guide for the Tenn-Tom at Dog River on Mobile Bay. The Grand mariner Marina had them and maps when I stopped there. The maps for the Tenn-Tom are in two parts. One for the upper section, one for the lower. I didn't realize this when I bought my charts. I ended up navigating with an Alabama road map on the southern half.
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