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Need road trip advice: NYC to Quebec and back

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We're a family of 4 (2 parents and 2 young adult kids) planning a 3 week road trip from NYC to Quebec and back, departing early June. We live in northern CA and the kids have never been back east. We'll be flying into and out of NYC. Looking for suggestions and feasibility of our plans.

We'd like to spend 4 (maybe only 3?) nights in NYC, then head out to the Hamptons/Montauk. From there, we'd like to take the ferry to the mainland, head north into Maine and then turn northwest to Quebec. We'll return via Montreal, upstate NY and/or Vermont roads. The kids really want to get a taste of small towns in New England, so we'd rather stay off the major interstates if other routes are viable options.

Our preference would be to take the ferry from Montauk to Martha's Vineyard and then to the mainland, but none of the 2011 schedules are posted online yet, so I don't know if that's feasible. Looks like if so, it would be passenger ferry only. Orient Point to New London, CT is our backup, which could accommodate a vehicle.

We've decided not to spend any time significant time in Boston, and would be okay with completely bypassing it altogether. (Nothing against Boston, but we felt like something had to give somewhere and Boston was it.)

To the extent possible, we'd like to be spontaneous and not book hotel rooms in advance, allowing ourselves to play it by ear and stop for the day/night when and where we feel like it. We're tech-savvy and will have internet access, so we can research our options on the road.

Some specific questions: At what point should we rent a car? Definitely not in NYC, but where's the best place to pick one up for the drive out to the Hamptons?I know we can take the train, but we'd prefer to drive and have a car while there.

Other than NYC, where is it critical to book lodging ahead of time?

Is three weeks enough time? We love to road trip and do well for extended periods in the car, but we also want to be able to stop and enjoy attractions along the way, and spend at least a couple nights each in Quebec and Montreal.

Anything else we should know? Advice and suggestions much appreciated. Am also posting this in the Canada forum.

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