Every year Tuscany is visited by crowds of travelers. Hundreds of millions of tourists have tromped through, but is Tuscany hopelessly over-touristed? Well, while no stone has been left unturned in Tuscany, it’s still possible to get off the beaten path.
In an area so overwhelmingly dense with attractions, finding Tuscan tranquility often boils down to timing. Though it’s well-worn advice, it bears repeating: avoid Tuscany in June, July and August. It’s hot, crowded and pricey – prices rise the day after Easter through the end of September. Unless you’re aiming to attend one of the worthwhile summer festivals, plan for late March through early May or late September through early November, when even hotels in Florence are reasonably priced.
Having said that, let’s talk some less-trodden Tuscan geography, ranging from low(er) profile cities and towns to straight up middle of nowhereness.
Arezzo
Arezzo is a real city, with the expected local bustle, but not on most Tuscany tour itineraries. It’s an easy day-trip from Florence, but with accommodations and eating value being superior, why not shift your bags for a couples nights? Furthermore, the city serves as an ideal staging area for a day-trip to Sansepolcro. The lopsided, architectural jumble of Piazza Grande is riveting, as is the renowned fresco cycle by Piero della Francesca in Chiesa di San Francesco, and the Romanesque epitome awaits at Pieve di Santa Maria.
Cortona
It may be a stretch to describe tour-bus-bait Cortona as “off-the-beaten-path”, it being a standout hilltop town in a region known for hilltop towns, but thin public transport connections keep it less hectic than its all-star neighbors, particularly at night. Cortona’s beautifully messy layout is indicative of someone dumping a bucket of ‘Etruscan town’ down a hillside. Though there are a few fine museums, the steep, captivating streets, some twisting off at impossible angles, are the real attraction. These idyllic lanes have been frequently deemed film-worthy, most popularly in Under the Tuscan Sun.
Montalcino
Anyone casually versed in Tuscan wine will know of retiring Montalcino. While it satisfies the hilltop town quota for sadistically steep ’streets’, the real attraction is the internationally coveted wine Brunello di Montalcino, known for its borderline outlandish exclusivity and price as much as for its extraordinary quality. Rosso di Montalcino, a slightly more modest red, is just as tempting. Both can be sampled here for a fraction of the price you’d find in your home country. Montalcino’s imposing 14th-century Fortezza, in addition to dominating the south end of town, has an enoteca where you can enjoy a tasting after touring its fortified walls.
Sansepolcro
An atypically flat, but captivating Tuscan walled town dating from AD 1000, Sansepolcro is best known as the probable birthplace of legendary painter Piero della Francesca. The historic center is tightly packed with stone structures abutting somewhat less historic structures, but it’s all a pleasant jumble. Step into any church with open doors, as they’re all lovely, but make a point of visiting the recently renovated cathedral, containing the Volto Santo (Holy Visage), a striking wooden crucifix with a wide-eyed Christ dating to AD 950, and San Antonio church, which has a magnificent two-sided processional banner painted by Luca Signorelli.
Montemerano
The walled, medieval, southern town of Montemerano only warrants an hour or so, but oh what an hour. Pick up a bottle of the excellent local Morellino di Scansano, drop into Chiesa di San Giorgio, decorated with 15th-century frescoes of the Sienese school, and finally stroll up to the unspeakably harmonious, oh-so-photogenic Piazza del Castello.
Tomb of the Infernal Chariot
In 2003, archaeologists excavating an intact 4th-century-BC tomb in the necropolis of Pianacce discovered the Tomb of the Infernal Chariot. Among the unique frescoes on the walls surrounding the alabaster sarcophagus – their colors still as bright as the day they were applied – is a demonic figure with wild flowing hair driving a chariot pulled by a pair of lions and two griffins. The tomb entrance has a panoramic view over the Val di Chiana. Reserve tours through the Archaeological Civic Museum in nearby Sarteano.
San Galgano Abbey
One of the country’s finest Gothic buildings in its day and now an atmospheric ruin. The mammoth, roofless, stone and brick shell stands in an empty field, which is often enshrouded in a spooky fog on spring mornings. On the hill overlooking the abbey is the tiny Monte Siepi Chapel, which houses a real-life “sword in the stone”.
Ghiaccio Forte abitato Etrusco
You’ll need a car and, ideally, GPS to find this nugget, located at the end of a couple, poorly-signed dirt roads south of Scansano. The ruins of this Etruscan fort are admittedly meager, and information boards severely weathered, but the top-of-the-world panoramic views are unbeatable. There are serviceable tables for lazy picnics.