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NYC to FLA Road Trip..stopovers (I-81) in Virginia and Sea Islands?

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Two of us will be embarking on a road trip in mid December. The final destination is in the Delray Beach area of SE Florida. We plan on spending 3-4 nights on the road. One of those nights, probably the second, will be at the home of friends in Winston Salem. After that, I am considering two nights on the Georgia Coast before making the final drive to our destination.

It's been decades since I've attempted this drive and I have a few questions.

1. We are fairly flexible about dates and can set off anytime from about the 10th to the 16th of the month. Does it make sense to leave NYC on a Saturday, to avoid traffic? If we do this, and spend a night in Virginia en route, are there hotbeds of college football that will mean fully booked hotels?

2. I would like recommendations on where to stop the first night. I would love a hotel with an indoor swimming pool. Hopefully something more interesting than the typical highway hotel/motels that I remember from the last time I took this drive. The corridor from Harrisonburg, Lexington, Staunton looks like a likely first stop, right? (We are willing to drive 30 minutes or so off the main road) What about Charlottesville? I don't mind booking in advance, but would like to be able to cancel up to a day or two in advance in case of heavy snow.

3. Anything else I need to consider when deciding which day of the week to leave NYC?

3. From Winston, we will drive toward the Coast and eventually meet up with I-95. I'm considering the Jekyll, St. Simons area but I've not researched this yet. (Savannah also a possibility). Any ideas on this would be most welcome!

4. Also, we are always looking for tempting places to eat.

The focus here would be on local specialties, not fancy restaurants, so any good regional BBQ, Low Country cooking, local shrimp, oysters, etc (I already have the North Carolina BBQ Society Trail map: http://www.ncbbqsociety.com/bbqmap/trail_map.html )

Please share any tips so I can make this drive more of an adventure than a boring chore!
Anything to need to pack/have handy in the car for the drive?

Also, do I have to unpack the car each time we stop at a hotel? What about theft from the parking lots?

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