Cortona
15 miles (24 km) from Villa Michelangelo

Originally founded by the Estruscans and nowadays frequented by fans of local resident Frances Mayes' Under the Tuscan Sun, Cortona is one of the oldest and most scenic hill towns in Tuscany. The town is a maze of old streets and medieval buildings with breathtaking views over southeastern Tuscany and Lake Trasimeno. Due to its steep location, virtually all modern development has been limited to the lower suburb of Camucia, where the train station is also located.

Via Nazionale is the main thoroughfare and the only level street, leading from the southeastern gate to Piazza della Repubblica and Piazza Signorelli, dominated by the Palazzo Comunale and its bell tower. We recommend taking the steep walk up to Santa Margherita sanctuary, at the very top of the town. Other sights include the the Etruscan museum in the Palazzo Casali behind the Palazzo Comunale; the Museo Diocesano, with works by Signorelli and Angelico; and Santa Maria del Calcinaio (also called Madonna del Calcinaio), a Renaissance church just outside town on the road to Camucia.

Lake Trasimeno
13 miles (20 km) from Villa Michelangelo

An immense crater lake, Lago Trasimeno has three inhabited islands and an average depth of just five meters. Isola Maggiore can be reached by ferries from Passignano sul Trasimeno and Tuoro sul Trasimeno on the north shore. Trasimeno's third main town is Castiglione del Lago, a fortified promontory jutting into the lake on the western shore. In 217 BC, Hannibal won a great victory over the Romans on the shores of the lake. Nowadays there are fewer elephants, and more swimmers, boaters, and windsurfers.

Umbertide
11 miles (18 km) from Villa Michelangelo

Umbertide isn't a tourist destination — just a regular town with a small walled medieval center, and the privately owned castle of Civitella Ranieri just to the northeast. Umbertide can still be a charming place to visit, and it's where the nearest supermarkets and Internet cafes can be found. The hospital staff at the ER is remarkably attentive should you show up with a possible ankle sprain.

Perugia
31 miles (49 km) from Villa Michelangelo

The capital of the Umbria region, Perugia is a center for international students, and its medieval streets, museums, and monuments are well worth a visit. One of central Italy's largest hill towns, Perugia's origins date back to the Umbrians and the Etruscans. In the Middle Ages, Perugia was a major power center ruled by guilds and condottieri, until it finally came under Papal control in 1538. Visit the central square, Piazza IV November, with Pisano's Fontana Maggiore and the Palazzo dei Priori (pictured in the slideshow at the top of this page). Also stop in the church of San Pietro at the south end of town. To get to Perugia, go to Umbertide and pick up the toll-free highway going south.

Assisi
41 miles (65 km) from Villa Michelangelo

One of Italy's top tourist attractions and a pilgrimage destination, Assisi is known all over the world as the birthplace of Saint Francis. See Giotto's frescoes and St. Francis's tomb in the 13th-Century Basilica of Saint Francis (pictured to the left and in the slideshow at the top of this page), then walk the length of town along pink-stoned streets to the Duomo and the church of Santa Chiara, burial place of St. Francis's most renowned follower, St. Clare. The fastest route to Assisi is to pick up the toll-free highway from Umbertide to Perugia. Assisi is fifteen minutes beyond Perugia.

Montepulciano
33 miles (52 km) from Villa Michelangelo

At 605 meters above sea level, Montepulciano is one of Tuscany's highest and most picturesque hill towns. Enter from the northern gate and follow the main street as it spirals up to the central square, Piazza Grande. There you will find the Renaissance-era Duomo and several palaces. But watch out for Twi-Hards—part of Twilight: New Moon was shot in Montepulciano (doubling for Volterra). As you leave the area, stop by the Tempio di San Biagio, a High Renaissance church, just off the road to the southwest of town. If it's not too late in the day, continue along the same road to tiny, lovely Pienza, where Zeffirelli's Romeo & Juliet was filmed. Don't forget to try the local reds!

Arezzo
33 miles (53 km) from Villa Michelangelo

The wealthy provincial seat of eastern Tuscany, Arezzo is not as famous as other Tuscan turist destinations, but it should be. Among Italians, it is well known for its antiques market and jewelry industry, the Piazza Grande, and Piero della Francesca's famous frescoes in the church of San Francesco.

Gubbio
29 miles (46 km) from Villa Michelangelo

Located deep in the forested Appenines on the slopes of Mt. Ingino, this terraced medieval town in the north-east corner of Umbria is remarkably picturesque and well-preserved. Like Cortona, Gubbio became an independent city-state in the 11th Century, then it was ruled from Urbino by the Dukes of Montefeltro, then eventually was absorbed by the Papal States. Gubbio doesn't take long to visit. The main attraction is the Palazzo dei Consoli (pictured) on the Piazza della Signoria, with expansive views to the west. Also visit the Ducal Palace and the Duomo just above, and walk along the Via dei Consoli. From Villa Michelangelo, go to Umbertide. From there, Gubbio is well signposted.

Siena
52 miles (83 km) from Villa Michelangelo

Once a rival to Florence, Siena is smaller today than it was at the height of its power in 1348, when its population was halved by the Black Death. Siena nevertheless remains world famous for its spectacular medieval streets, its gorgeous cathedral, and its vast Piazza del Campo (pictured), where the Palio, Tuscany's most celebrated festival, occurs twice a year. Siena is easy to reach by car—simply pick up the toll-free highway from Tuoro or south of Cortona going west, and keep going past the intersection with the Florence-Rome autostrada.

Florence (Firenze)
84 miles (135 km) from Villa Michelangelo

What do we need to say about Florence? The capital of the Italian Renaissance, Florence is one of world's can't-miss destinations. A proper visit takes two days, but you can manage to hit the main sights in one. Go online to see if you can reserve tickets in advance to L'Accademia (home of Michelangelo's David) and the Uffizi (where you should prioritize Giotto, Botticelli, and da Vinci). Then see the Duomo (pictured), the church of Santa Croce (where Michelangelo, Machiavelli and Galileo are buried), and maybe the church of Santa Novella. Finally, walk across the Ponte Vecchio to the Boboli garden for a view of the city.

Lake Bolsena
14 miles (23 km) from Orvieto

Poke around one of the lake towns, laze on the shore, or hike through the woods! A mild micro-climate makes for picturesque cultivated hillsides all around Lago di Bolsena. Medieval nooks and crannies beckon in the town of Bolsena on the northern shore. Capodimonte reaches into the lake from a wooded peninsula on the southern shore where there are great swim spots. Catch a boat out to the Isola Bisentina, which features Etruscan tombs, five frescoed chapels, and a villa that was a popular papal summer retreat.

Montefiascone
19 miles (30 km) from Orvieto

Montefiasco has perched on the edge of a defunct volcanic crater since the time of the Etruscans. Its ancient, off-the-beaten-path vibe is part of its charm along with its striking seventeenth century Duomo. Nearby, the carved capitals and frescoes of 12th-Century San Flaviano captivate the religious and tourists alike. It also features the tomb of Bishop Giovanni Fugger who reportedly died from drinking too much of Caesar’s favorite: local treasure Est!Est!Est! wine. Montefiascone is very close to Lake Bolsena.

Todi
24 miles (39 km) from Orvieto

The striking town of Todi was first an Etruscan and then a Roman settlement boasting what is now often called the "most perfect medieval piazza in Italy." Many impressive art-filled churches covering all the major periods in Italy’s rich art history will keep you busy but you may be too distracted by the charming alleys, cute shops and heart-stopping views to get to all of them. A lovely town to lose yourself in for a day.

Pitigliano
32 miles (52 km) from Orvieto

Like Orvieto, Pitigliano seems to grow out of an immense outcrop of tufa—soft, volcanic limestone. A medieval gem, this town was once a flourishing center of Jewish life. A maze of alleys and shops sits atop ancient caves that have been used for millennia to house locally produced wine and olive oils. The town’s quarters are linked by impressive aqueducts which add to the drama of its scattered Renaissance monuments, remnants of Etruscan walls, and ruined synagogue.

Sovana
35 miles (55 km) from Orvieto

As the medieval capital of this southern Tuscan region, Sovana enjoyed great prosperity. A swift decline left the town remarkably well-preserved and off the tourist track, making it a great choice for a unique day trip. Nearby, you'll find exquisite Etruscan tombs featuring façades carved from the rock. The 12th-Century church of Santa Maria features 15th-Century Siena School frescoes as well as art from earlier churches on the site, including a 9th-Century canopy.

Saturnia
49 miles (78 km) from Orvieto

Saturnia is famous for its natural thermal pools or terme. Take your pick of a day of pampered relaxation at the modern spa or soak for free in the hot sulphur water at the Cascate del Gorello (Gorello Falls), also known as Cascate del Molino (the falls at the mill), which form natural hot tubs.

Montepulciano
43 miles (68 km) from Orvieto

At 605 meters above sea level, Montepulciano is one of Tuscany's highest and most picturesque hill towns. Enter from the northern gate and follow the main street as it spirals up to the central square, Piazza Grande. There you will find the Renaissance-era Duomo and several palaces. But watch out for Twi-Hards—parts of the Twilight movies were shot in Montepulciano (doubling for Volterra). As you leave the area, stop by the Tempio di San Biagio, a High Renaissance church, just off the road to the southwest of town. If it's not too late in the day, continue along the same road to tiny, lovely Pienza, where Zeffirelli's Romeo & Juliet was filmed. Don't forget to try the local reds!

More information:  write.michelangelo@yahoo.com