Sugar is the best Gelatteria in Castellana, located in the historic center at the end of the pedestrian street. Do it like the locals and do a Passeggiata after dinner. That is basically a late evening stroll around the town when you eat ice cream and chit chat with your friends.
Il Piatto Fumante
One of our favorites! Il Piatto Fumante is located just outside Castellana on the road to Monopoli. They have a nice outdoor area with a small playground that will keep the kids entertained during the long Italian dinners.