Your total trip with all stops is around 800 miles / 1290 km, taking roughly 12 hours for the whole trip. If you want to see every small town along the way, you can get a full list of cities between Winston-Salem, NC and Boca Raton, FL.
Start from Winston-Salem, North Carolina.
Columbia, South Carolina is stopping point #1 after driving about 170 miles (280 km) or 2.5 hours.
Jacksonville, Florida is stopping point #2 after driving about 290 miles (470 km) or 4 hours. Your total trip so far is about 470 miles or 750 km over roughly 7 hours of driving.
Orlando, Florida is stopping point #3 after driving about 140 miles (230 km) or 2 hours. Your total trip so far is about 610 miles or 980 km over roughly 9 hours of driving.
Finally, Boca Raton, Florida is your destination after driving about 190 miles (310 km) or 3 hours. Your total trip with all stops is around 800 miles or 1290 km, taking roughly 12 hours for the whole trip.
Travelmath helps you figure out where to stop when planning a long road trip from one location to another. The best stopping point for an overnight hotel stay or a break from driving often depends on how far or how long you want to drive before pausing to rest. You can find the closest city to your stopping point to look for hotels, or explore other cities and towns along the route. Use this as a road trip planner when you're driving cross-country or mapping a route with multiple stops.