Boondocking (anchoring out) is much much easier on a boat than in an RV. We called the Chesapeake Bay home for a few years and loved all the gunkholes. In an RV, on the east coast, good boondocking locations (with views) are few and far between. Head west, and the boondocking is almost limitless.
The amount of space in an RV when compared to a similar sized boat is amazing. We felt we were in a luxury mansion in comparison. And the fact that you could take a walk any time you wanted... Everything is much easier in an RV except traffic and crowds.
We started out in a travel trailer but, after 6 months, switched to a class A. A class A with a toad is like a boat and dinghy. A truck and trailer just didn't work for us.
But, we figure another 2-3 years of full time RVing and we will go back to a boat. We really miss it.
Best of luck in with your future plans!