Otranto

On the heel of Italy’s boot on an eponymous strait connecting the Adriatic and the Ionian, Otranto is one of in-vogue Puglia’s most picturesque towns. Keeping glorious watch over the water is the glorious Castello Aragonese, its moat and stunning perimeter walls a reminder of a tumultuous, gory history thanks to Otranto’s strategic position at the heart of the Mediterranean. The Cathedral di Santa Maria Annunziata, with its relics of martyrs, mosaic floors and rose windows, begs a visit before walking the wide promenades to excellent seafront restaurants and the beautiful sandy beach with shallow turquoise waters.