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John, a group of gentlemen did that a few years ago ... they were all over 80 and called it the "Over 80 Cross Florida" hike. Kenneth Smith, who's a member on this site, organized the trip. If you get in touch with him he can give you logistical details. They went from Flagler Beach to the end of the Withlacoochee Bay Trail south of Inglis, on the Gulf.
Yes, you need a tent unless you're hammock camping or tarping.
You might get used equipment by checking WhiteBlaze.com or ask around here.
© 2010 Created by Sandra Friend.