Looking for a nice town to break up long drive and spend the night.
No doubt about it, it's a long drive. We crossed the peninsula at the beginning of the journey as I think the driving is easier on the eastern Adriatic coast, though a touch longer. We stopped at Vasto and enjoyed it. It's a small city with good views and a classic Italian feel and it made a good break. We found a good restaurant (Il Re Pescatore) to enjoy the local specialty Brodetto alla Vastese, which is worthy of a much better translation than fish soup.
We enjoyed a few nights in the small town of Sant'Agata de' Goti 5 hours south of Florence. It's a lot of fun to walk around in this town and if you look at some photos of it, you'll see how it's perched on some steep cliffs and is very picturesque. We stayed at Agriturismo Mustilli (yes, an in-town agriturismo and we got a tour of their in-town wine cellars) and parked our car in their courtyard: https://www.airbnb.com/rooms/632104?guests=1&adults=1&s=67&unique_share_id=cbc8e3ce-3212-4190-b597-5a8a5ddf14e7