Start with the AGLCA (America's Great Loop Cruising Association) Website. Lots of information and, if you decide to join, the membership will be invaluable as you decide your level of interest. You will learn that the exact route will determine your draft and air draft restrictions of future loop boat.
Curtis Stokes is a broker on the East coast who is an AGLCA sponsor, attends the various rendezvous and works a lot with folks who buy a boat specifically for the loop then sell it as soon as they finish the trip.
I find "loopers" tend towards 2 general categories: Those who start from Fl in the Spring and race around the loop in approx 1 year, They move in a large wave - meeting up loosely with fellow loopers at each night's destination for docktails. Their schedule and timing is determined by the May - October season of the NY, Canadian & Chicago canals.
The second group take several years, often stopping to explore each region more extensively, lots of side trips, may get off the boat for weeks or months at a time for family of other reasons then resume the trip. No fixed schedule.
It's a great opportunity - hope you enjoy it!
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Jeremy
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