A walk through town usually includes a stop at Molesini, Piazza della Repubblica 3, a local institution that will pour you a glass of wine and also offers a big selection of cheese, olive oil, and other local products. The shop has a good selection of wines from Cortona vineyards, where Syrah grapes are producing increasingly sophisticated yields. A standout is Usciòlo, from Cantina Doveri, just outside of town. Caffe Tuscher, Via Nazionale 43 (www.caffetuschercortona.com; tel. 0575/62053), is the most elegant spot in town for a cocktail, served in a welcoming two-story space, along with snacks and lights meals throughout the day. Enoteca Enotria, Via Nazionale 81, sells wine by the glass and sandwiches, making the rustic room a popular hangout well into the late evening.
Even if you are not staying in Cortona, try and snag at least one meal at the charming Relais Il Falconiere. Dolce Vita, Via Nazionale 71 (tel. 0575-630-102; www.gelateriadolcevita.it), wins the gelato stakes with its exotic (papaya) and quirky (Lion bar, Coca-Cola) flavors, but Gelateria Snoopy opposite MAEC at Piazza Signorelli 29 is a decent standby.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.