Begin by taking in the cultural highlights in Arezzo, home to important medieval and Renaissance palaces and churches. Take a guided walking tour of the historic center to discover masterpieces such as Vasari’s elegant Loggia lining the Piazza Grande and Piero della Francesca’s magnificent 16th-century frescoes in the cathedral and Church of San Francesco.

Set in the heart of Tuscany, Arezzo is a prime spot to sample the region’s iconic food and wine; a hands-on cooking class in town or the surrounding countryside is a fun way to learn how to prepare classic Tuscan dishes. Oenophiles can instead head to the vineyard-covered hills for a winery tour and tasting.

Enjoy the charm of Arezzo as the sun sets by heading to the Medici fortress above town for views over the valley, or relaxing at a sidewalk restaurant or café in the Piazza Grande. Photography enthusiasts can capture this and other striking Tuscan scenes during a nighttime photography walking tour in the historic center.

Cortona may be half the size of Arezzo, but it rivals its neighbor in scenic charm. Explore the medieval town center made famous in Under the Tuscan Sun —the bestseller later made into a film—by joining a themed walking tour through its pocket-size squares and tiny churches, including San Damiano, frescoed by Fra’ Angelico.

With its popularity as a tourist destination, it’s no surprise that Cortona is thick with excellent eateries. You can linger over lunch or, better, learn to make the area’s delicious dishes at home by joining a cooking class in town. If you’d rather spend a few hours at the beach, the placid waters of Lake Trasimeno are just minutes away.

Your Tuscan immersion is drawing to a close, so be sure to toast your final evening by watching the sun set over the valley and Lake Trasimeno. One of the most panoramic spots in town is outside the pretty cathedral, with a sweeping view over the hills of Tuscany and neighboring Umbria.