Need road trip advice: NYC to Quebec and back
 

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. Have also posted this in the US forum.

Im going to think about some suggestions but I will warn you on one little thing. Quebecers love to party on Saturday nights and more than once we have been stuck not able to get a hotel on this night so you may want to book even up till a few days before for this night.

sounds like a cool trip.

one thing to note is that there is an F1 race in Montreal over the June 10 - 12th weekend. as a result, the city is super pricey with hotels and restaurants jacking their prices, and reservations are hard to come by... unless you and your kids are racing enthusiasts (it's an amazing weekend to be in Montreal if you are) i'd avoid the city during that time.

Wow, thanks so much for the info about Saturday nights in Quebec and the race in Montreal! Looks like our Canadian leg of the trip definitely should not be left up to our last minute whims!

Don't let the Sat. night comment seize your cells. If one hotel is booked, you can drive a little way to the next one. I travelled on business for 20 yrs in Quebec by car and never had a problem.
My only warning is to keep some money handy to pay speeding tickets in NH or Vermont. It is so easy to get a ticket there. I recently discovered I have an outstanding speeding ticket in NH which I cannot ever recall receiving and I have not been there for 35 years. But I did get at least one which I did pay.