Dave - I assume the CT River is navigable for a sailboat with a 54' clearance and 5'8" draft? Jim - I just dropped an e-mail to Dutch Wharf to get some pricing.
Anyone have any other suggestions?
Oh yea, The one fixed bridge is over route 95 with a 86' clearance. Two other Bridges exist a opening railroad in Saybrook and a swing bridge in Haddam. The river is one of the last rivers in America that is navigable and is not developed. The fall foliage is should you time it right is absolutely grand. as far as depth, no issue, they run coal barges up to Hartford a couple of times a week. During the winter the coast guard uses an ice breaker to keep the river clear for the barges. I've done it a few times in my last sailboat with a 5' draft and never had a concern.
I also think that Portland is inside your 3 hour travel window. I live in Bristol CT and can get to Albany in 2 hours heading west. Portland is 30 minutes east of me.
2007 Hunter 49