To get to Puglia, we took a train from Rome to Bari, and in Bari we picked up our perfect road trip companion: a convertible Fiat Cinquecento. Securing a convertible did require an extra step (taking a train from the Bari train station to the car rental location at the Bari airport) but it was easy enough and absolutely worth it!
Our first destination in Puglia was Masseria Le Carrube, located about 10 km inland from the coast, 10 km away from Ostuni, and an hour drive from Bari. Masserias are fortified farmhouses typically built around the 16th century in olive groves of the Puglia region. Many of them have been converted to hotels, and they pack all the comforts of modern life inside their centuries old stone walls.