One of the World Monuments Fund’s 100 Most Endangered Sites, Civita was founded Estruscans 2500 years ago. The town was mostly abandoned in the 17th century due to an earthquake that accelerated erosion of the volcanic plateau. Only a handful of permanent residents remain in “La città che muore” (The Dying City), but plenty of tourists cross the long bridge on foot to spend a few hours there.

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, frescoed chapels, and a papal villa.

Montefiascone has perched on the edge of a defunct volcanic crater overlooking Lake Bolsena since the Etruscans. Its ancient, off-the-beaten-path vibe is part of its charm along with its striking seventeenth century Duomo. Nearby, you can see the carved capitals and frescoes of 12th-Century church of San Flaviano.

The striking town of Todi was first an Etruscan and then a Roman settlement boasting what some call 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.

Like Orvieto, Pitigliano grows on an outcrop of 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. Impressive aqueducts add to the drama of the town’s scattered Renaissance monuments, remnants of Etruscan walls, and ruined synagogue.

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. But watch out for TwiHards—parts of the Twilight movies were shot in Montepulciano (doubling for Volterra). If it’s not too late in the day, visit lovely Pienza to the west, where Zeffirelli’s Romeo & Juliet was filmed.

An immense crater lake frequented by swimmers, boaters, and windsurfers, 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.

Originally founded by the Estruscans and nowadays home to author Frances Mayes (Under the Tuscan Sun) and Italian superstar Jovanotti, Cortona is one of the oldest hill towns in Tuscany and the site of PageCraft’s first three retreats. The town is a maze of old streets and medieval buildings with breathtaking views. 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 top of the town.

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 gets crowded on the weekends.

The capital of the Italian Renaissance, Florence is one of world’s can’t-miss destinations. A proper visit takes two days, but if you plan ahead you can hit the key sights in one. Go online to reserve advance tickets to L’Accademia (for Michelangelo’s David) and the Uffizi (prioritize Giotto, Botticelli, and da Vinci). Then see the Duomo and the churches of Santa Croce (tombs of Michelangelo, Macchiavelli and Galileo) and Santa Novella. Finally, walk across the Ponte Vecchio to the Boboli garden for a view of the city. Florence is a very easy train ride from Orvieto.