HitTheRoad

Last year I did two trips with Hit the Road — one from Calgary to Richmond Hill via Canada and the other from Ottawa to Victoria (mostly via the US) driving over 8100 km in total.
Hit the Road is a vehicle deliver service. I can’t speak for the aspect of getting a vehicle delivered, because I’ve only used Hit the Road as a driver. As a driver you go to their website and find a route that interests you. The routes will vary from where the start to where they go to, and when they occur. You get your paperwork in order (valid driver’s licence, driver’s abstract, etc are just some of the things you’ll need for a trip) and apply for a route. You’ll be given a contract to sign before you can drive a vehicle. Driver’s are required to pay a deposit, but this is an insurance for both you and the vehicle owner. As long as you deliver the vehicle to the destination on time and in good condition then you’re deposit will be returned to you (although the returning portion takes time). Driver’s will also be given some reimbursement for gas costs — it likely won’t cover everything, but it helps.
I chose to drive with Hit the Road because I had to go to Toronto, and because I love road trips and wanted to see more of Canada (and later the US). My first trip to (Calgary to Toronto) went off without any issues. It is a long drive particularly by yourself. You can have another driver with you, but you would need to discuss this with Hit the Road first. Hit the Road gives drivers plenty of time to get from point A to point B. They don’t want their drivers on the road in the evening or for driving long periods of time, so the longest days I had on the road were about 8 hours. Driver’s are also warned not to speed, obey traffic laws, etc. Basically Hit the Road wants you to deliver the vehicle in good condition, but they want to make sure your doing this safely and lawfully.
On my 2^nd trip from Ottawa to Victoria I hit a couple of small snags, but it wasn’t anything that would deter me from using Hit the Road again in the future. Going from Ottawa to Victoria I had asked if it would be okay to drive through the US (via Sault Ste. Marie) because it would save me time. I experienced a bit of a delay at the US border crossing and was pulled into secondary screening at customs. Normally, as I was later told by Hit the Road’s owner, dropping off a vehicle from Canada to the US involves specific paperwork and forms, but because I wasn’t dropping off a vehicle in the US, just delivering it to Canada going through the US, the Customs officers were a bit hesitant to let me through; it was a bit stressful. I think border officials were also a bit confused at whether or not I was working for Hit the Road. Again this isn’t a job, and really with other costs of travel (lodging, food, etc) you definitely won’t be earning any kind of livable way of doing this. Hit the Road is a way to travel cheaply, and see different parts of Canada (and the US depending on your route), but it isn’t a way to make money.
The second small snag happened in rural Michigan when a vehicle in front of me spit a rock up, and cracked part of the windshield. It was noticeable, but I still felt it was safe enough for me to continue driving (didn’t affect my visibility). I made sure to pull over (when it was safe) and take a photo of the window. I also phoned the owner of Hit the Road to let him know what had happened. He made sure to find out if I was okay first and foremost, and contacted the vehicle owner to find out what should happen. The vehicle owner was very understanding, and didn’t charge or ask me to pay out of pocket for the window repair. I can’t guarantee everyone’s experience will be like this if damage happens to the vehicle they are driving, but this is how it was for me. This is also why you pay a deposit, in case something happens then you are covered or can at least get in for a repair.
Hit the Road won’t be for everyone. You need to have a good driving record, be reliable, and flexible. Both of my trips took about a week each, but I was able to see parts of my country and the US that I had never seen before. It is important to remember that Hit the Road doesn’t offer return trips, so you’ll need to find a way to get home or to wherever you’re going to next yourself. I took the second trip (Ottawa to Victoria) trip because I hadn’t booked a way to get home, and while Victoria isn’t anywhere near where I live (Edmonton, Alberta) I was going in the right direction, and I still wasn’t ready to stop traveling. If you only have a week or two of vacation time Hit the Road might not be for you, but if you have some flexibility with your job (or if you’re retired) then Hit the Road is a great way to see North America.

I have been engaged with
on three occasions, once down to Florida from Toronto, once cross-​continent to California, and once from Florida back up to Toronto. They were all more-​or-​less well organized by the operator of the business and all three went off without any delay. The clients themselves were quite content to have their cars delivered safely, clean and on time and on two occasions I even got tipped.
On all three trips I had a few days lee-​way to check out national/​state parks enroute or linger in a fun city. I would send periodic updates to let both the operator and client know of my progress.
The only slight drag is having to wait the 30 days for the returned deposit. The first time around, I tried to challenge the policy by emailing repeatedly — my many emails were (now understandably) ignored, but at the 30 day mark, I was payed as promised and so it happened the other two trips. Rest assured, the deposit does get returned, but it requires some patience.
An excellent way to travel on a tight budget and see the land.