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One month road trip from Niagara to Nova Scotia--itin help please!!

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We are doing my favorite type of vacation--a long road trip. Right now the plan is to fly from California to Buffalo using United miles, pick up a car and head east across Canada to Nova Scotia, then return west to Buffalo through Maine, Vermont and New York. Nothing is booked yet, depending upon United saver fares, but ideally we will go this year around Sept. 10 and return around Oct. 15. We like to spend a mix between city life and quaint hamlets, outdoors and museums, light hiking, good food and roadside joints--we're into getting to see as much local life as we can. I realize we may not hit the perfect leaf peeping season in New England but I am more concerned about finding rooms in Vermont than anything else at this point. I don't much care for B&Bs so that may help us out. Before I can look for rooms I have to lay down an itinerary so please offer me any tips on my basic route. I will ask plenty of questions later on side trips, must sees and and don't miss attractions. Your help is always appreciated. My general route, 1st attempt:

# DAYS ROUTE
3 Buffalo - Niagara - Toronto
4 Toronto - Montreal
4 Montreal - Quebec City
5 Quebec City - PEI
5 PEI - Nova Scotia
6 Maine
6 Vermont
3 New York (Cooperstown, Ithica, return to Buffalo)

Two problems I need extra help with:
1-We want to go to 1000 Islands, how much time to allow? and how should itinerary change to accommodate that
2-We are at 36 days and want to shave that down to 35.

Thanks.

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