If flying up to Michigan three days before the New York Marathon was crazy. I was about to take risky to the next level. The issue was finding a truck and trailer to bring the car to Florida from Michigan. I don’t have a pickup. My friends say I need one, but, I always seem to figure out a way to get whatever I need towed. This time, however, was different. It was much riskier.

First, I had to find a truck to rent with a hitch. I wasn’t convinced this was even possible. When I flew into Detroit a couple weeks earlier for the prepurchase inspection, though, I noticed that some of the pickups at the rental facility had hitches. Assuming I could rent a truck with a hitch, however, it wasn’t clear UHaul would even rent me the trailer. UHaul won’t rent a trailer to you if their system indicates it isn’t large enough to handle their heavy trailers. And I didn’t know which trucks their system had coded as car trailer eligible.

Regardless of the uncertainty, I wanted to get the car home. Over the course of the marathon weekend, I had struck a deal with the seller, and then wired him the funds to purchase the car. Thanksgiving was coming, and we had family coming into town. But, I knew that, with the end of the semester quickly approaching, I needed to act fast to get the car home. If I didn’t go the week before Thanksgiving, it could be weeks before I had another chance. I wasn’t accustomed to having a car that cost me so much, parked so far away. It made me antsy. I needed to go. Now.

So I devised a plan: I would fly into Detroit, rent a pickup truck, then rent a UHaul trailer, pick up the car, and trailer it home. But, there was another problem. In addition to not being sure I could rent a pickup with a hitch, and being uncertain UHaul would then rent me the trailer I needed, I had to do the whole trip in less than 36 hours. I had made a commitment on the Saturday before Thanksgiving, to pick up a rug for my wife. I had to be back Saturday.

So off to Michigan I flew. Again.

To hedge my bets, I reserved two pickup trucks, each from different companies. I also reserved two UHaul trailers, each from different UHaul locations. A quick trip to a dealer in my hometown a couple days before my flight revealed that the Enterprise Rental Car truck was likely to be the larger of the two trucks I reserved. I figured that would be the one I tried first. That was until I got a curtesy call from Enterprise the night before my flight. They were calling to confirm my reservation. However, while on the phone, they asked if I was planning to tow anything with the truck. They then explained that their trucks were not equipped with hitches. Enterprise was out!

That left me a single truck reservation. But the flight was already booked. And I had a round trip ticket. Worse case was that I would fly back home the same night, without the car, and look for another plan. As I left the house for my flight the next morning, my wife asked, “What is the c’hance you can get the car?” I replied with a confident, “95%.” I was lying. My chances were much, much slimmer.

As I touched down in Detroit, I thought, “here goes nothing.” I crossed my fingers as I walked up the counter at the car rental company adjacent to the airport. “Go out and pick out which truck you want,” the lady at the counter said. “No problem,” I thought. 5 minutes in the lot, and I had chosen the largest pickup there. A Dodge Ram 1500. With a 5.7 liter Hemi. And it had a hitch receiver. Off to the local auto parts store to get a hitch, I went.

$30 and I was out the door with a ball on the truck. Next stop was UHaul. I had two UHauls reserved in the Detroit area. Just in case one of them gave me a hard time about the truck, I could try the other one. But, it proved to be unnecessary. Picking up the trailer went off without a hitch. No pun intended. Off to the shop where the car had been stored since the PPI.

I got the 356 loaded and was headed south in less than an hour. So far, so good. Honestly, I was astounded it was going so well. Now I just had to make the 1,134 mile trip home.

Read the next part of the story HERE.