Road trip to Florida from Montreal
 

Hi!

We are planning on going on a 2-3 week road trip at the end of June/beginning July this summer.
We are 4 adults.
We will leave from Montreal, going to Florida (possible Miami, if not Orlando).

We were wondering what are some places we should stop by.
We thought NYC, Boston, NJ, Washington, apparently Savanah and Charleston are great places...
Any ideas/recommendations?

Thank you!

With three weeks, your trip is doable but I would leave out Boston since it is off your route.

Montreal to NY 1 day
NYC 3 days
Washington 3 days (most of the attractions are free!)
Washington to Charleston 1 day
Charleston 2 days (you will want more but you can't do it all)
Savannah 2 days (1 full day with one day for the drive from Charleston on US 17 via Beaufort)
Savannah to Miami 1 day
Miami 2 or 3 days
Miami to Naples via US 41 (stopping at Turner River for alligators, Everglades City) 1 day
Naples 1 day
Naples to Montreal 3 days almost all driving.

You could break up the trip by stopping in Washington or Charleston on the northbound leg.

You could drive to Lorton, Virginia (just south of Washington) and put your car on the auto-train for the rest of the trip down to Florida, then stop at Savannah and Charleston on the way north.

You could fly to Miami and make the trip one way northbound in a rental car. Yes, you will pay a dropoff fee, but it will be cheaper and easier than X extra days on the road. Leave the car in Burlington, Vt, so you don't have international drop off fees. You could do this in reverse, dropping the car off in Florida, but there is generally a surplus of rentals in Florida, and it is likely to cost you more.

Strongly consider doing this trip as early as possible. It will be tropically warm and humid from Washington south, possibly in NY.

How far do you normally like to drive in one day.

Savannah to Miami is a distance of 500 miles. Whether or not there is a drop fee for a rental car in Florida depends on the company you use sometimes.

Frankly this is not doable in 2 weeks. Yes - you can drive down and back - but you will have practically no time for seeing anyplace (unless you follow the traditional college kids plan of driving straight there - use all 4 drivers in shifts of 5 or 6 hours at the time with the others sleeping in the car - so it takes you only about 36 hours there - with minimal stops for fuel and quick food). You could then see the sights (quickly) in the 12 days on the way back,

If you want to travel normally and stop on both ways going to and from I would leave at least 3 weeks - with 3 days each (minimum) in Miami, DC, NYC and Boston (plus Orlando if you want to do the theme parks) and a full day each (which means 2 nights) in Charleston, Savannah, Colonial Williamsburg, Philadelphia, etc.