He went South, through Chicago and into the Mississippi before taking the Tenn-Tom to the Gulf. He crossed the Intercoastal and stayed in Miami at a High School friend of ours and replaced some of the faulty electronics before heading to the Islands- that alone was 37 hours because it's not a go-fast boat and when I say that, I mean it gets best fuel economy at about 8 knots. OTOH, the boat doesn't give a rat's but if the water is smooth, or not.
Some other friends have a Carver Santego 38 and I could easily live on it. The fly bridge seats 14 and it has pads for the Sun Deck. The cockpit has seating for 4 plus deck chairs and the interior is very spacious. Even has a blender built into the counter. I made replacements for the white steps on the ladders from some Redwood I have, to match the extended ones his cousin made for the dog and anyone who has problems climbing in, that attach to the two lowest ones. They can be moved to Starboard, if the boat is docked on that side.
YouTube has a lot of videos that were posted by people who now live on boats, describing the lifestyle, with pluses and minuses. I worked for a boat dealer and he lives on his boat during the season- he pays $2700/season for his slip and it comes with shore power, it's relatively secure, the marina has laundry, showers, restrooms, food, a room for group activities and it's right there, at Lake Park, Bradford Beach, the Art Museum and downtown MKE are is less than 1/2 mile away and if he wants to head upriver for dinner, he can do that. He has a little electric bicycle that he tools around on and there's ample parking for his car, truck or motorcycle. That comes to about $450.month, with electricity.