By Md. law 8' 6'' is the max. for width.I know someone who pulls a 27' Grady with a 9' 6'' beam with no hassles. Anything over 10' and you really need a permit.That's alot of boat to trailer although someone had a 30' Grady at Point Look Out this year.Call Md. DOT for all the rules. Skip
I dont think length is a concern, like skip said 8'6" is the legal width. You can tow a 40' boat 8'6"wide and be legal, but finding one that width will be a tough. I know someone else that tows 9'6"wide no hassles yet
Seems like you your looking at a Wellcraft 290 Coastal. That's a nice boat.
As for trailer an over width boat, I do, but I son't think I would do a 10'5" boat. Then again, if I had one, I'd probably do it, but I'd look at boats under 10ft.
I've seen people trailing with over 10' and I spoke with one guy. He said it was just like towing a 8'6" boat. Maybe he hasn't been through any tolls... Who knows, but not only was he over width, but he was over height too. He said that at times, he tapes a piece of cardboard on top so if he this a wire, it doesn't take off his radar.
Me, I tow 9'8" width boat and width wise, it's like trailering any other trailer I've towed. It doesn't seem to be a problem, but I haven't had to go through any tolls. As for height, I'm right there at the legal limit of 13'8"s and that makes me nervous. Every time I see traffic light or a wire, I feel like I'm going to catch it. Thank God most everything is over 14 ft off the ground.