Towns, Archaeological Sites, and Hidden Gems around Grosseto
In the south of Tuscany, the province of Grosseto (and the southern section of the province of Siena) holds some of the region’s less-traveled treasures—places where history and beauty intertwine. Whether you’re a history buff, an art lover, or just someone who enjoys a good glass of wine with a view, this corner of Italy has something special to offer.
Grosseto: An underrated town in Southern Tuscany
Tucked away in the heart of the Maremma, Grosseto often gets overshadowed by its more famous Tuscan siblings. And the approach is not promising, with some modern houses masking the delights of the medieval town centre, but it's a town rich in medieval charm and surrounded by breathtaking landscapes.
The Walls of Grosseto: A Walk Through Time
Grosseto’s well-preserved Medici walls enclose the historic center in a protective embrace. Built in the 16th century, the walls now serve as a pedestrian-friendly promenade—perfect for a leisurely evening stroll. From here, you can take in views of the town’s red-bricked rooftops and get a sense of its quiet but dignified past.
The city is unusual in Tuscany because, unlike most towns and villages that were built on easily-protected hilltops, Grosseto is in the middle of a plain. In the eighth century it was little more than a village but was growing as inhabitants of the nearby city of Roselle moved to it. By the middle of the twelfth century it had grown to a size that motivated Pope Innocent II to move the Bishopric from the empty city of Roselle down to Grosseto.
In the heart of Grosseto’s centro storico, the Cathedral of San Lorenzo was built in the thirteenth-century but has a facade that was re-designed in the 19th century. The pink-and-white marble facade is striking, but step inside, and you’ll find delicate frescoes and an atmosphere of hushed reverence. Even if you’re not religious, it’s hard not to appreciate the craftsmanship and history embedded in every stone.
Roselle: Echoes of the Etruscans
Just outside Grosseto lies the ancient Etruscan city of Roselle, a beautiful archaeological site that dates back to the 7th century BC. Once a port, it is now quite a few miles inland as the large plain has silted up, removing the reasons behind its founding. The city of Grosseto took over Roselle's role, leaving the ancient city empty on its hill. Today it is an extensive dig, with traces of the Etruscan origins and of the Roman city that followed it. The cyclopic stone walls are worth seeing, as is the amphitheatre and the forum. Wander through the outline of the ancient city and imagine the bustling life of its long-gone inhabitants, and soak in the panoramic views over the Maremma countryside.
Hidden Gems and Day Trips: Beyond the Tourist Trail
Pitigliano: Tuscany’s “Little Jerusalem”**
Built dramatically atop a tufa rock outcrop, Pitigliano looks like something straight out of a fantasy novel. Its Jewish heritage runs deep—traces of the once-thriving Jewish community can still be found in the historic synagogue and underground caves. Explore it by wandering throught the labyrinthine alleys, and stop awhile for a glass of Bianco di Pitigliano wine, and let the town's age-old magic seep into you.
Saturnia’s Thermal Springs: Nature’s Spa
Tuscany has a variety of natural thermal baths, and Saturnia’s natural hot springs are arguably the most impressive. Cascading down white limestone terraces, these steaming pools are free to the public and believed to have healing properties. Whether you believe in their mystical powers or not, there’s no denying the sheer pleasure of soaking in warm, mineral-rich waters as the countryside stretches around you.
San Galgano: The Real Sword in the Stone
The British have the legend of King Arthur, while Tuscany has its own version in San Galgano. In a small chapel by a ruined abbey outside Siena lies a “sword in the stone.” The story goes that a nobleman-turned-hermit, Galgano Guidotti, thrust his sword into the rock as a sign of his renunciation of war. The sword still stands there today, encased in glass. Whether you see it as a relic of faith or a medieval curiosity, it’s an undeniably fascinating place to visit. The roofless abbey next door is turned into a magical venue for classical concerts during the summer.
Castiglion della Pescaia: Seaside Charm and Medieval History
On the coast, Castiglion della Pescaia is a picturesque seaside town whose medieval fortress overlooks golden beaches, and beautiful sunsets. The old town is fun to explore, with some great restaurants and vibrant night life during the summer. Whether you’re after a morning espresso with a sea breeze or an afternoon dip in the crystal-clear waters, Castiglion della Pescaia is worth a visit.
Monte Amiata: Tuscany’s dormant volcano
Mont'Amiata is an ancient volcano and the highest peak in southern Tuscany. In summer, the beech and chestnut forests provide cool, shady trails for hiking. Come winter, it transforms into a ski resort—a rare sight in this part of Italy. The mountain is also steeped in legend, with tales of hermits, saints, and hidden monasteries adding to its mystique.
It's worth driving (or cycling or hiking) to the summit, there's an enourmous steel cross, as well as lovely little restaurant. On the surrounding slopes there are places to go climbing and bouldering, as well as a beautiful and rare ninth-century lombard crypt under a church in Abbadia San Salvatore.
Wild Swimming in the Farma.
For those who love a bit of adventure, the Farma River is one of Tuscany’s best-kept secrets. Flowing through a lush, untouched valley between Siena and Grosseto, it’s perfect for wild swimming. Natural rock pools, cascading waterfalls, and crystal-clear waters make it an idyllic spot to cool off on a hot day. The best location is known as "Canaloni del Farma" and you can find directions here: Best Wild Swimming in Tuscany
Massa Marittima: A Medieval Gem with a Twist
Massa Marittima is one of those places that feels like a hidden treasure. Its beautifully preserved medieval center boasts one of Tuscany’s most stunning cathedrals—Duomo di San Cerbone—perched dramatically on a sloping piazza. But what really makes this town stand out is its quirky side: the famous ‘Fountain of Abundance’ fresco, which depicts a rather unexpected fertility scene, is both bizarre and fascinating. If you visit in May, you might catch the Balestro del Girifalco, a traditional crossbow tournament that brings the town’s medieval heritage to life.
Siena: Medieval Majesty and Timeless Traditions
No matter how many times you visit, Siena always manages to surprise you. The city’s medieval soul is alive and well, woven into its winding alleys and piazzas. If you’re lucky enough to visit during the Palio, Siena’s famous horse race, you’ll witness a spectacle of passion and tradition unlike any other.
Piazza del Campo: The Beating Heart of Siena
Few squares in Italy can rival the sheer drama of Piazza del Campo. This shell-shaped piazza is the city’s social hub, home to the iconic Torre del Mangia and the site of the biannual Palio horse race. Grab a seat at one of the cafés, order an espresso (or something stronger), and let the world go by—it’s the perfect way to soak in Siena’s energy.
The Duomo of Siena: A Masterpiece in Marble
Even in a country overflowing with stunning cathedrals, Siena’s Duomo manages to stand out. The intricate black-and-white striped facade is mesmerizing, but the real magic happens inside. From the breathtaking marble floor mosaics to the Piccolomini Library’s frescoes by Pinturicchio, every inch of this cathedral tells a story. If you have time, climb to the Panorama del Facciatone for a sweeping view over the terracotta rooftops.
Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
24th Feb 2025 24th Feb 2025