Congratulations on nearing the end of your Great Loop experience!
The two previous responses are spot on. Below is my recent towing experience:
Last month, I towed, our new to us, a Ranger 29 S from Pensacola, Fl to the Minneapolis area, a 1,250 mile trip. I used JJ Keller to secure the permits I needed for the 7 states that I traveled through. I highly recommend them. The agents I spoke with were extremely helpful and patient. Because of heavy rain and flooding in the Midwest, they kept me informed if there were any needed route changes as I made the 2 ½ day trip north.
Prior to owning the Ranger, I had owned 4 different sailboats including a J/92 (30’ loa, 10’ beam) that we towed into the Chicago area 6 times for the Chicago to Mackinac sailboat race. I had the boat splashed by Crowley’s, once on the Chicago River when they were in the loop and twice on the Calumet River when they moved their yard to the southside of Chicago. We launched 3 times at Larsen Marine in Waukegan, Il. I highly recommend Larsen’s. They are 50 miles north of downtown Chicago. You will be able to avoid the nasty traffic in Chicago and would have access to I-94 which might be your primary route back to Washington.
I towed the Ranger with a Ram 2500 diesel on a new Float On trailer. The boat and trailer tracked beautifully—no swaying whatsoever. I had brought with me a load leveler hitch, but because of the trailer design I was unable to use it, but I did not need it. Traveling to Florida, I averaged 18-21 mpg. On the return trip with the boat in tow, I averaged about 10 mpg with a low of 9.1 mpg while going through the rolling hills of Arkansas and Missouri. Be sure to check your lug nuts for proper torquing (that’s another story). You will need 2 Oversize Load signs, front of truck and on the stern of the boat along with 6 flags—2 for the front corners of the truck, 2 midship on the boat, and 2 at the corners of the stern of the boat. If you don’t already have them, you can get them at Amazon. I used 2-2” ratchet straps to secure the boat to the trailer. I made sure where the aft straps came in contact with the boat that I had padding to prevent any chafing. The mast was lowered and secured to the cabin top. The VHF antenna was lowered and zip tied to the cabin top hand hold railing. I taped the two wire stays that support the mast to railing. We secured everything in the cabin. The only item that came loose was one of the forward cabin radio speakers.
Safe travels.