A quick drive from the villa (only 10 - 15 minutes) brings you to charming Orvieto, where you will fall in love with the notion of medieval hill town. Its ornate Gothic cathedral is considered Italy’s best. Twice a week, a renowned outdoor market offers the freshest produce culled from the surrounding countryside. You’ll discover picturesque piazzas and lovely shops, wine bars and restaurants, including one of our favorites in all of Italy. Explore Etruscan tombs and underground caves. Views range from glances down tiny, ancient lanes to vistas over the ramparts to the valley below.

Welcome to your new home town!

St. Francis was born in this hill town in 1181, and the Monastery and Basilica of St. Francis remain a standing tribute to the native son who would become one of Italy’s patron saints. Inside, frescoes by Giotto and Cimabue portray his life.

This hidden gem of a medieval hill town, less than 30 minutes from the villa, is far off the tourist track. The only way in is by a long footbridge, through a stone passageway carved by the Etruscans. The town has been slowly wearing away (it’s lost 20 percent of its terrain since 1705, thanks to rainfall and earthquakes), and even buildings have tumbled down the cliffside. Even so, new restaurants and B&Bs have recently opened to cater to curious—and intrepid—visitors.

It’s one of our favorite places to recommend to guests to visit; you won’t be disappointed!

Spend a leisurely afternoon at Europe’s largest volcanic lake, just a 30 minutes’ drive from the villa. You can relax on one of its uncrowded black-sand beaches, gear up for some water sports (including boating, swimming, and fishing), or wander through several enchanting villages dotting its shoreline. Whatever you do, be sure to taste its regional fish dishes, served up in trattatorias along the shoreline with sublime lake views.

The Eternal City, just an hour from the villa, needs no introduction. Whether you come to explore its Roman history, its papal history, or simply to enjoy sipping a cappuccino on a fountain-graced piazza, you won’t be disappointed. Top sights include the Pantheon, the Roman Forum, the Colosseum, Trevi Fountain, the Spanish Steps, the Vatican (home to the Sistine Chapel) and so much more.

Italy's most perfect medieval town remains delightfully ensconced in the past, with such beautiful buildings as the Gothic Duomo, the cathedral museum filled with gilded treasures, and the art-filled Palazzo Pubblico. This is a town made for wandering, its maze of pedestrian lanes edged with ancient buildings occupied by boutiques, pizzerias, cafés, and gelaterias. Twice a year the town bursts to life with the renowned Palio bareback horse race around the Campo (central square), complete with flag waving, drumming, and parades in a tradition that goes back more than 700 years.

The heart of the Renaissance—and home to the best Renaissance art in Europe—awaits less than two hours from the villa. Everywhere you look in this walkable city you’ll discover fresco-adorned churches, historic villas, statue-dotted piazzas, monuments, and gardens. You'll see some of the world’s most famous paintings (including Botticelli’s Birth of Venice) at the Uffizi, pay homage to Michelangelo’s David, and climb the Duomo’s famous dome. Or simply wander the cobbled streets—the same once walked by Dante, Michelangelo, Machiavelli and Galileo—eating the world’s best gelato.

One of Tuscany’s prettiest hill towns, Montepulciano, about an hour’s drive from the villa, sits atop its tufa ridge with breathtaking views of the surrounding vine-striped countryside. Its historic center is one of the Italy’s most intact; you’d never guess that little renovation has taken place since 1580. Several restaurants serve up hearty southern Tuscan fare. And don’t forget to taste the wine—Montepulciano is one of Tuscany’s boldest wines.

One of Tuscany’s oldest hill towns, Cortona may be most famous for being Francis Mayes’ Italian home, as recounted in her heart-warming story, Under the Tuscan Sun (later made into a movie). Its twisting medieval lanes, artistic heritage (Renaissance artists Luca Signorelli and Fra Angelico hailed from here), plethora of wine bars and far-reaching views of the quintessential Val di Chiana all along its walls make it a popular destination from our villa. It’s about an hour drive away, near the Tuscan-Umbrian border.

Native son Pope Pius II, with the help of superstar architect Bernardo Rossellino, transformed his birthplace into the epitome of a harmonious Renaissance town. The beautiful central square is graced by the cathedral, towering above the other buildings as a symbol of faith; and five palaces. The tiny town—essentially one long street—offers charming regional shops, interesting museums, and Instagram-worthy views of the surrounding Val d’Orcia.