outfits provide the truck and the labor to fasten it securely to the truck. You have to pay a boatyard to get the boat ready for shipment and get it on the truck via travelift or crane. And then you pay a yard at destination
to take it off and recommission it.
If it was me, I wouldn't want to pass up the chance of taking a trip like that. Even if the cost was double, you'll be getting experience making a trip with a professional. If you were planning to do it by yourself (and there are many who post in here proposing to do just that, with no experience), I would be responding with dire warnings (as would others). People have no idea what's involved and don't know what needs to be done to prepare a boat for a 500 mile trip.
But since you want to hire a captain, that solves two problems. The captain will be there for you if things get interesting, and a captain won't do the trip if the boat isn't ready. Unless trucking the boat is significantly cheaper and the money
is an issue for you, I'd say go for the cruise
. When will you have a chance like that again? You'll learn what a real trip is like. Then you'll have a good understanding of what you need to learn from sailing instruction. I think it'll make you a better student.
Just weigh the options and decide what makes most sense for you.
Edit: "fasten securely to the trailer"? As opposed to fastening insecurely? What I was thinking when I typed that was, most boat transport companies do the blocking, etc so the boat can be carried. But that's something you should clarify when talking to them. Make sure you know what's included. The rate they quote could possibly depend on you having a cradle
for the boat. Most, however, include the blocking in their price
. As a matter of fact, many have special trailers just for sailboats, with adjustable supports to make the job easier.