It’s one thousand miles from Boston to Hilton Head Island, SC. Two days of driving each way and about 8 hours of driving each day. It’s well worth the drive for the right weather and the right people! Fredericksburg is well situated at the halfway point and will break up the trip nicely. There is a Krispy Kreme in Fredericksburg and I suggest you go there when the donuts are fresh - you won’t regret it (unless you finish off a half dozen)!