I've been following this from the beginning and am really enjoying your account. I haven't seen the logistics of the trip and now see you have a professional hauler towing the boat. Can you share some details of you're approaching this epic trip?
Sure. Typically, I put the boat on Tony's trailer and then I fly to the destination. I will have already selected a marina with a good boat ramp and a hotel either on site or within walking distance. I try to arrive a day before the boat to make sure the ramp is as good as I thought. It also gives me a chance to talk with locals about my planned route. Local knowledge has been very valuable at times.
(I was introduced to Tony by my Grady dealer. They use him when they need one boat brought from the factory or sometimes to deliver a customer's boat. But I know there are at least several others like him in West Palm alone.)
These requirements for a marina, ramp and hotel and a fairly nearby airport sometimes require studying google maps and making some phone calls. And sometimes it means I don't begin my trip exactly where I want to. But the advent of Uber and Lyft has opened up many more options.
I will have already selected the same combination of facilities for a take-out point at the end of the trip. Sometimes I'll have multiple options, depending on how far I get. But to be fair to Tony, I need to give him a reasonably firm date and location for pull-out. Tony will do the best he can to arrange a haul each way of a trip.
If I can, I'll have reserved a Southwest flight home. I almost never make the date/time I planned and Southwest doesn't charge change fees. If I can't get Southwest, then I just won't have an airline ticket home. I'll wait until the day before and start making calls. Somebody is always willing to fill an empty seat at the last minute at a good price.
One time I couldn't get home before the boat. So my wife and her friends met Tony at the boat ramp near the marina where we keep our boat and had a girls day on the boat.
The first time I did this I had no intention of doing the Loop. I just wanted to take a boat trip down the Atlantic ICW. So I rode with Tony up to Wrightsville Beach, NC from West Palm Beach, FL in one long day. I had no idea how long it would take me to get home. But I knew I had to be back at work in 10 days. So I rushed. The next year I started out at Atlantic ICW mile marker 0 in Norfolk and took a more relaxed approach.
I'm not a hardy soul. I was prepared to overnight in my 258 Journey as needed, but I prefer a hotel. So I had mapped out every marina with a motel along the ICW. And I had the phone numbers printed on laminated sheets near the helm. So when i got far enough along in a day that I thought about stopping, I started calling. I should point out that until I did Lake Erie, I've always done my trips in the off-season. I call my destination area and ask several marinas and hotels when their slowest season is. That way, rarely have I not gotten a room or a slip.
I moved up to the 282 with the idea of spending more nights aboard. The Lake Erie trip showed me that, with such a compressed boating season, I can't count on a slip and a room in the Great Lakes as I have been doing. And I'm sure not making reservations weeks in advance. Kinda spoils what I'm doing. Hence the more livable cabin of the 282. And the great air conditioning experiment of this last trip - from which i still have yet to warm up!
With some, but not nearly all exception of Lake Erie so far, and the one night that you have to overnight in the Mississippi River, I think I have shown that the majority of the Loop can be done by a small boat without a cabin. Someday, when I get around to it, I'm going to neaten up my ten years worth of Excel spread sheets with all the marina and hotel options on them and do a self publish and put them out there somehow.