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I've pulled boats over every bridge, tunnel and road in and around Boston, even stopping in Chinatown to get a bite, double parked and didn't even get a second look from the meter enforcers, they walked on by this past Friday evening. Tow all you want over the Zakim Bridge. I went over it Friday night and through the tunnel, into the financial district and in Chinatown to get food and I do it going home as well all year round.
I remarked to my Dad that it must a strange site to see a boat in downtown when just then a well-heeled woman said to her 3-piece husband, as they were walking by, "Now there is something you don't see everyday."
If you guys are going over the Tobin Bridge, go over it, there isn't even a toll going that way and who is going to stop you anyhow? There are no signs anywhere prohibiting trailered boats on the road and I've never heard of any grumblings of trailered boats being prohibited anywhere. Tractor trailers go whereever they please so long as they fit.
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