We sometimes tow our boat behind our TT. Here in Ontario it is legal if you fit the requirements. Please read carefully all the information given by the Ontario Ministry of Transportation.
We went directly to the ministry and the Ontario Provincial Police to get our info.
Out TT, boat and Avalanche is 73' in length. 2' under limit. Our weight combo fits also. The TV has black plates.
Hubby said he does not feel the boat behind us at all. We had an officer follow us one time and he pulled in behind us. We thought he was stopping us but he also was stopping for coffee, LOL. He said there was no sway or movement of the boat at all.
If you do it be realistic on where and when you pull. Don't go down a highway such as the 401 during busy hours, try to take the less travelled route. It makes no difference in pulling but it sure makes it more comfortable for other drivers out there.