Hello guys, Im really new to this, can you please help me on this.

Im planning to do a roadtrip Miami to Northampton Massachusetts, from Dec. 27th to January 5th. I beleive its possible, but I dont have experience doing this.

Can some one help me, and give any advice where to stop, we are 15 people , Kids and adults, we wanto to skip Florida and focus more in the norht side of the country.

Please help me