A question with a an infinite number of answers! Our trip aboard Classy Lady (Alaskan 46 14)began when we left the Detroit Yacht Club (Sept 2004). Went down the Detroit River, across Lake Erie, thru the Erie Canal, Down the Hudson to NYC. Then down the coast, down the Chesapeake, ICW to Charleston. Wintered there, then spring '05, started the CCW route Took till fall the year of Katrina ('05) to reach Tuscaloosa Al, wintered, found much damage along the coast at next intended destinations (Pensacola, Biloxi) so decided to move ashore.
Classy Lady is now le Voyageur home port Auckland NZ.
The trip can be what ever you wish. To enjoy, go slow, permit lots of side trips, explore extensively. The rivers are remarkable in themselves, and operating with the tow barges, communicating with the captains, planning passages next to these incredible vessels and their cargos is an experience to be savored! I still remember one towboat (Sugarland) and her captain with fond memories of discussions of maneuvering plans (one whistle or two) as we approached in the Mississippi southbound. Sugarland was up bound on the west side, and another towboat with several oil barges was also up bound to the East (right) of Sugarland. My call to Sugarland resulted in him saying (regarding passage "one whistle or two" "come on right thru the middle, and we'll call it a three whistle pass" Now the Mississippi was more than a mile wide at tis spot, so lots of room and it made a memory that I'll never forget!
So take all the time you can and enjoy
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