The best road trip in Tuscany from my Lonely Planet research trip

Today’s Tuscany Month excitement highlights my favorite scenic/interesting drive in the region. Probably my favorite new feature in the 2010 Lonely Planet Tuscany & Umbria are all the numerous driving tours we added. In some cases we just took a logical grouping of villages that were already listed in the book and just tied them all together as a driving tour. I’ve documented the best driving tour in Tuscany driving tour (more best road trip in Tuscany, since at the end of the day you end up too prohibitively far away from where you started to circle around and head back) cuts across the Le Crete region, south of Siena. Below is a Leifed up version of what appears in the guidebook.


The best road trip in Tuscany: Abbazia di San Galgano to Pretoio

Distance: ~92km  Duration: 6-8 hours
San Galgano abbey, part of the best road trip in TuscanyAfter a week in Siena, as amazing as it is, the claustrophobia of it all begs for a scenic, low-impact road trip like this. Even fighting the dense traffic to get out of town, it still only takes about 20-25 minutes to travel the 20km southwest of Siena on the SS73 to the 13th-century San Galgano abbey, in its day one of the country’s finest Gothic buildings. Now it’s an impressive, haunting ruin (especially if you arrive in early morning fog) that still speaks strongly of its past.

The monks of this former Cistercian abbey were among Tuscany’s most powerful, forming the judiciary and acting as accountants for the comuni (municipalities) of Volterra and Siena. Sir John Hawkwood, the prolific English mercenary, sacked the abbey on at least two occasions in the 14th century. By the 16th century the monks’ wealth and importance had declined and the church had deteriorated to the point of ruin. In 1786 the bell tower simply collapsed, as did the ceiling vaults a few years later. Today the great, roofless, stone and brick monolith stands silent in the fields. There’s a small tourist office with limited hours next door in a stretch of cloister housing.

On a hill overlooking the abbey is the tiny, round Romanesque Cappella di Monte Siepi. (You can either walk or drive up here) Inside the chapel are badly preserved frescoes by Ambrogio Lorenzetti depicting the life of San Galgano, native to the area, who managed the neat trick of being both a soldier and saint. San Galgano is said to have had a vision of St Michael on this site and, as one does after such an event, lived his last years here as a hermit. More intriguing is a real-life ‘sword in the stone’, sitting under glass in the floor of the chapel. Legend has it that San Galgano himself plunged it there, as the mother of all exclamation points, during his renunciation of worldly life.

The best road trip in Tuscany continues with the tricky drive to Buonconvento, even with a GPS helping you out. Wiggle east past Monticiano, through San Lorenzo, Fontazzi and Murlo, then curl down the Strada Provinciale di Murlo 34 which eventually runs into Buonconvento, sitting there like a large roadside rest stop on a rare, perfectly flat stretch of plain. The low-slung fortified walls of this farming center hide a quiet little medieval town. The rather brief amount of time it takes to wander the historic center can be supplemented by its two museums: the Museo della Mezzadria Senese, with its life-size figures, antique farm tools, and multimedia presentation of what life was like living off the land until quite recently, and the Museo d’Arte Sacra, containing religious art collected in the town and from neighbouring churches and hamlets.

Ten very pretty kilometers northeast is the 14th-century Abbazia di Monte Oliveto Maggiore, still serving as a retreat for around 40 monks. The congregation was founded in 1313 by John Tolomei, though construction didn’t begin on the monastery until 1393. The grounds are very atmospheric, but most people come here for the outstanding fresco series in the Great Cloister, painted by Luca Signorelli and Il Sodoma, illustrating events in the life of the ascetic St Benedict, founder of the Benedictine order. The fresco series wraps around the four-sided Great Cloister, illuminated naturally by an inner courtyard.

I never get tired of the hilarious dichotomy between these two artists. Signorelli, reputed to be a widely respected, kind man, had previously done minor work on the Sistine Chapel and would later produce his masterpiece Resurrection of the Flesh in the Chapel of San Brizio, in Orvieto’s Duomo. He started work in the monastery in 1497, producing nine frescoes. In stark contrast, Il Sodoma, born Giovanni Antonio Bazzi, was purported to have been something of a character, even by artist standards. He dressed flamboyantly, kept a “Noah’s Ark” of unusual pets, sung original ditties of dubious taste and, according to Giorgio Vasari in the book The Lives of the Artists, earned the moniker “Sodoma” “because he always surrounded himself with boys and beardless youths whom he loved beyond measure.” He added 17 frescoes, completing the series around 1505.

The best road trip in Tuscany continues with the drive from Monte Oliveto Maggiore to Asciano, which is, for pure scenery, about as good as Tuscany gets. It’s also quite a thrill for drivers, being a 1 1/2 lane wide, winding, heel-toe challenge. Tiny Asciano won’t keep you long. It has a trio of small museums dedicated to Sienese art and Etruscan finds in the area. You may be ready to eat by this stage, which is perfect as there are several no-nonsense restaurants in town, including my favorite, La Brace at Via Mameli 9/11, featuring warm proprietors and tattered, hand-written paper menus.

Make sure your clutch-foot is well rested before setting off on the twisting 20km road up to Montisi, little more than a one-street, medieval blip capping a steep hill. Its allure speaks to a certain disposition, particularly the expat artist community hunkered down here. A little asking around can win you entrance to a few of the town’s small churches, stuffed with aging paintings, town effects dating back to the 15th-century and a tiny crypt. The copious activities in this retiring town and the surrounding area is kind of remarkable, including contemporary art exhibitions, cheese tastings, horseback riding tours and eight-day ballooning tours. Taverna Montisi, on the edge of town, is the primary eatery; with a seasonal menu fueled by organic farmers in the immediate area. The owner doubles as the town-fixer-cum-tourism-coordinator, arranging everything from tours to emergency dentist visits.

Finally, nearby wedding cake-shaped Pretoio, is a wanderable, quiet place and home to the Museo della Terracotta, run by a local, prolific terracotta artist. If you can drive no further, Palazzo Brandano is a swish and stylish place to spend the night. Otherwise, slightly more budget-friendly places in are in nearby Pienza or Montepulciano.