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Join Date: Aug 2010
Location: Madison, WI
Posts: 11,212
Bikes: 1961 Ideor, 1966 Perfekt 3 Speed AB Hub, 1994 Bridgestone MB-6, 2006 Airnimal Joey, 2009 Thorn Sherpa, 2013 Thorn Nomad MkII, 2015 VO Pass Hunter, 2017 Lynskey Backroad, 2017 Raleigh Gran Prix, 1980s Bianchi Mixte on a trainer. Others are now gone.
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If you have never done a bike tour before, if you decide part way through that maybe it is not what you enjoy, having a closer route to home might be a good idea. Like, maybe head towards Key West and if you don't get there within two weeks, (1) turn around early and head for home or (2) keep going that way but have a plan for how to get home. With this option, if you decide after a week and a half that you want to go home, it is easier to throw in the towel.
My first bike tour was 4 days. The 2nd, 3rd and 4th each were a week long. By then I had the confidence that I knew what I was doing, how to plan itineraries, etc. Now I do multi-week tours.
I did a lot of bike tours before I tried a solo trip. When you are traveling with someone, if you are injured or sick or have a mechanical or a crash, someone can help. If I was trying a solo trip as my first one, I would stay closer to home.
Do what you want and I hope you have a great time, I am just throwing out a few considerations in case you need a contingency plan.