While the Tuscan city of Siena can get overshadowed by Florence, her big sister to the north, the city is well worth a day trip to stroll the pedestrian-only medieval lanes radiating out from the Piazza del Campo in the city center. This central square is unique in the country for its shell-like shape and design, with the brickwork depicting nine radiating fans, symbolizing the Council of Nine who oversaw its design in 1349. It’s also the site of Siena’s famous Palio, a horse race around the edge of the square that happens twice each summer. At the origin point from which the nine fans radiate sits the Palazzo Pubblico, with its nearly 300-foot-tall tower, the Torre del Mangia. Climb the tower’s 400 steps to experience an exceptional panoramic view of the square with the historic city stretching out around it. After you have built up your appetite, John will send you to his favorite restaurant in town, whose name he only shares with friends and clients.