Ten cities in 37 days, that was the plan. My husband, Don, retired from the newspaper business, and we lost no time pursuing a move to Italy, our favorite European destination. We headed for the region of Puglia (or Apulia) in the southeast, and Sicily—the only places with enough sun and sea for our tastes—to find the perfect place to live.

On the way from the whitewashed hill town of Ostuni to the chic, seaside city of Trani, we stopped for lunch in Monopoli, on the Adriatic coast. Suddenly there were 11 cities on our list. Despite the luminous Baroque architecture of Lecce, the sumptuous Venetian influence in Siracusa, the beachy, laid-back beauty of Trapani, we couldn’t get that simple lunch in Monopoli out of our minds. We parked in the large main square and watched men play cards under the oaks. Then we strolled through the evocative medieval old town to the working port, where we, two career journalists and ardent travelers, took our first-ever selfie.