Running from Piazza Dante to Piazza Trieste e Trento, this thoroughfare traces a straight line through the heart of Naples’ downtown. One of the city’s most historic streets, Via Toledo is also home to highlights like the Church of Santa Maria delle Grazie, the Teatro Augusteo, and the soaring 19th-century Galleria Umberto I shopping arcade. No walking, Segway, or bike tour of the center is complete without a turn down this main artery, along with stops at nearby sights like Teatro di San Carlo (the oldest opera house in Italy), Piazza Plebiscito, and the Royal Palace. You can also visit Via Toledo as part of a food tour that combines sightseeing with tastings of pizza and other local street food. The Pompeii archaeological park is located just outside Naples, so Roman history buffs can opt for a tour that includes a visit to these famous ruins along with Naples’ historic center.