Southwest of Siena, there's a Tuscany less traveled.

By Elizabeth Heath
July 03, 2021
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Massa Marittima, Tuscany, medieval town in Italy, the Cathedral
Credit: Getty Images

San Gimignano, Siena, the Val d'Orcia, and the Chianti hills are all well-trodden areas of Tuscany — and rightly so. They form the iconic scenery of one of Italy's most famous and romanticized regions, with medieval cities, rolling fields, ancient hill towns, and acres of vineyards. For wine, food, history, and stunning views, why go anywhere else?

Well, for one reason, a lot of people have the same idea. And with Italy reopening to travelers from the U.S., U.K., and elsewhere, those idyllic Tuscan cities, towns, and country roads are about to get crowded again.

But southwest of Siena, a series of twisting provincial roads reveal old stone villages of just a few hundred people. Tour buses don't pass through here, but travelers savvy enough to visit will find a bucolic area where things move at a slower pace and local charms don't advertise themselves quite so readily. And those who prefer to spend their vacation immersed in nature rather than being jostled in a busy piazza need not look further. Tucked between the marshy Maremma plain, the mineral-rich hills of the Colline Metallifere, and the woodsy Val di Merse, the quiet towns and verdant landscapes of this "in-between" part of Tuscany will leave travelers feeling like they've stumbled upon the region's best-kept secret.

You'll need a car — or maybe a motorcycle — to explore this rural area. Base here, and you can enjoy a quiet stay, but you'll still be surprisingly close to a lot of Tuscany's heavy-hitters: Siena, the sea, and the wine-rich hills and hill towns of the Val d'Orcia are no more than an hour away. But don't forget to explore right where you are, too. Here are some of the top experiences you shouldn't miss on your meander.

Distant landscape view of san galgano abbey in the summer fields between two cypresses. Chiusdino, Tuscany, Italy.
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Abbey of San Galgano

You might think you've time-warped to rural Scotland when you lay eyes on this ruined Cistercian abbey whose poignant skeletal remains stand in a field between the towns of Chiusdino and Monticiano. Built in the 1200s, the Abbazia di San Galgano enjoyed a brief heyday of only a century or so when it was aligned with the powerful Republic of Siena. But that alliance didn't keep it from being razed by Papal mercenaries, and by 1400, the monastery was all but abandoned. Today, a small museum and restored monastery buildings stand adjacent to the abbey ruins, which can be visited without a reservation. For a full-service luxury resort, check out nearby Borgo Santo Pietro, where you can enjoy several days of pampered, rural R&R without ever leaving the property.

Tourist in hot springs Bagni di Petriolo - Monticiano in Italy.
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Bagni di Petriolo

In several areas of Tuscany, the earth percolates with hot mineral water, which bubbles up in a number of delightful, free bagni (baths). At Bagni di Petriolo, sulfuric thermal water springs forth and forms a series of calcified "bathtubs" suitable for soaking your cares away. The water exits the ground at a toasty 110 degrees Fahrenheit, but gradually cools as it cascades into natural basins before flowing into the Farma River, which serves as a heated swimming pool. Getting to the baths involves a quick walk through the woods and some scrambling over rocks. If you'd like a spa experience that's a little less rustic, the Mercure Petriolo Siena Terme Spa Hotel is just down the road and has its own thermal pools, whirlpools, and saunas.

Street in Monticiano, Tuscany
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Monticiano and the Val di Merse

Hikers and nature lovers will want to branch out from the pretty medieval town of Monticiano on one of several paths that weave along the Merse River, which itself curls through miles of forest. Rocky patches on the riverbed form rushing waterfalls and cool, clear pools perfect for taking a dip. Unusual for much of Tuscany, this area is almost completely forested, meaning you're never far from shade. One path follows an ancient trail of the transhumance — the biannual transfer of sheep and other herd animals between high and low ground. Accommodations and dining options in Monticiano are on the simple side, but suitable for hikers or bikers who need a soft bed, hot shower, and decent meal.

Massa Marittima

Closer to the Tyrrhenian coast, Massa Marittima is an ancient hill town that has survived the Black Plague, sieges, malaria, and Nazi invaders. Thanks to its developed tourism infrastructure, it's a fine base for exploring much of central Tuscany, as well as the beaches fanning out from nearby Follonica. The town itself is still hemmed in by its ancient walls punctuated with watchtowers, and its cathedral (or duomo) dates back to the 1200s and contains several important frescoes and carvings.

Be sure to go next door for a glimpse of the Fonte dell'Abbondanza. Inside an antique water basin, the medieval fresco depicts women collecting fallen leaves under the "Tree of Fecundity." The archaeological museum illuminates the area's Etruscan past — the pre-Roman tribe lived here as far back as the 6th century B.C.E. You'll get a fine, hearty meal at La Tana dei Brilli, and four-star La Fenice Park Hotel offers large rooms right on the edge of the old town.