Please help- Florida- Long Island with a toddler! Looking to make different stops

Hello traveling experts!

My family and I are looking for a little adventure this summer, and are traveling up to visit family in NY. We have done the boring 95 route before with the Fayetteville overnight, simply just to get there as fast as we could. We would like to plan this trip so that we will have three days of driving (frequent stops for the little one) and staying over two nights at different places each way. We are actually leaving from Fernandina Beach Florida, which is right on the Georgia border. We really like seeing historic buildings and small towns.
If anyone has ideas on interesting stops to make/stay along the way that they could recommend, I would really appreciate it!

Thanks!
Jennifer

Welcome aboard the RoadTrip America Forums!

One good alternative to I-95 that doesn't add that many miles but will give you an entirely different perspective in the drive would be to leave I-95 in central South Carolina and take I-26 to Columbia and then I-77 up to Wytheville, VA. From there -81 and I-78 would complete the journey to New York City and Long Island while avoiding Richmond, Washington, Baltimore, Philadelphia and the New Jersey Turnpike. At a shade under 1100 miles you could still make the drive in two days with an overnight around Roanoke. Or, if you'd rather have a relaxing three day drive, you could spend some time in historic and quaint cities such as Savannah GA and Lexington VA, visit Presidents' homes such as Monticello and Ash Lawn-Highland, spend some time amidst the scenery of the Shenandoah Valley, see old frontier forts like Fort Frederick in Big Pool MD, etc. In that case, two roughly equally spaced overnight stops would be in Rock Hill SC and Winchester VA.

AZBuck

Thanks so much for your input!! I am going to research Rock Hill and Winchester to see where we could stay for over nights- Here is our goal-
We plan on leaving Ferandina Beach early morning, driving 3 hours, stopping for lunch, then driving another 2 hours to our overnight destination. We were hoping that we could space it so that when we stopped somewhere for lunch, there were other things in that area in which we could sight-see, like a historic house, unique museume, etc. before we got back on the road.

It looks like I have a little research ahead of me, but it is getting me more excited about making this long drive!

Thanks again!
Jennifer

Fernandina Beach to Savannah is about 2.5 hours, that may be a good lunch and sightseeing stop. However, that's so close to home, you could do that as a day trip just about anytime. If you can drive about 4.5 hours before lunch, you could make Charleston.