hu Montescudaio village is in a truly strategic spot: close to the sea, but also on the way to some of Tuscany’s most fascinating destinations – Volterra, San Gimignano and Bolgheri.
Take your time to explore each of them! Bolgheri is just 20 minutes away and perfect for a short visit, while Volterra and San Gimignano are ideal for a full-day trip: leave in the morning and come back in the evening, with a head full of beauty.
Volterra: a city with thousands of years of history
To reach Volterra, you’ll drive along a winding road that snakes up the hill where the town sits gracefully perched.
From afar, you can already spot the imposing and noble bulk of the Medici Fortress towering over the city – today, it houses a prison.
But the whole of Volterra tells the story of its thousand-year-old past, with visible traces from the Etruscan era through to the Middle Ages and the Renaissance, passing through evocative Roman remains.
What to see and do in Volterra
An early morning walk through the medieval heart of Volterra is the best way to discover hidden corners and scenic viewpoints, all before the streets fill with other visitors. Head straight to the centre: Piazza dei Priori, surrounded by historic buildings like the proud Palazzo dei Priori.
You could easily spend the whole day admiring this square alone – but Volterra has so much more to offer, so let’s keep going.
If you're into Etruscan history, one place you simply can't miss is the Guarnacci Etruscan Museum, home to one of the most important Etruscan collections in all of Italy.
Prefer Renaissance art? Then make a stop at the Art Gallery (Pinacoteca), where you'll find a masterpiece that makes the trip worthwhile: The Deposition from the Cross by Rosso Fiorentino, recently restored.
And before leaving Volterra, don’t miss a peek at the Roman Theatre – one of the largest and best-preserved in the country – which you can admire from the walls along Via Lungo le Mura del Mandorlo.
As you wander through the centre, keep an eye out for the city’s artisan shops. Volterra is famous for its alabaster – step inside alab’Arte or Rossi and admire these timeless works of art.
And finally, treat yourself to a meal in one of the many traditional trattorias in the old town.
Our tip? Try La Carabaccia, especially if you love fresh pasta and rich Tuscan sauces.
San Gimignano: the perfect Tuscan postcard
A UNESCO World Heritage Site, the historic centre of San Gimignano is dominated by its famous tall towers rising above vineyards, olive groves and golden wheat fields – a picture-perfect scene that helped make Tuscany world-famous.
Crossed by the ancient Via Francigena, the town flourished thanks to its strategic position, which boosted trade – especially in a rare and precious product: saffron, still known today as San Gimignano’s “gold”, along with its renowned white wine, Vernaccia di San Gimignano.
San Gimignano
What to see and do in San Gimignano
Originally there were as many as 72, but today only 14 towers remain – and yet they still tell the story of the medieval noble families who built them as a symbol of power: the taller the tower, the wealthier the family.
Climb the Torre Grossa – the tallest one, reaching 54 metres – for stunning views over the city and the countryside beyond.
To get an idea of what San Gimignano looked like before 58 towers collapsed, head to San Gimignano 1300, a miniature reconstruction of the town.
At the foot of the towers, you’ll find a maze of charming alleys and lively squares, all leading to the triangular Piazza della Cisterna and, just around the corner, the Duomo of San Gimignano. The outside is quite plain, but step inside and you’ll find it covered in beautiful frescoes.
Don’t miss the Palazzo Comunale and its Art Gallery either. And if you love contemporary art, plan a visit to Galleria Continua, a gallery that features work by major international artists.
After your art fix, it’s time to treat yourself: either with a glass of Vernaccia di San Gimignano at the Montestaffoli Fortress, where the Vernaccia Wine Experience awaits, or with a world-famous gelato from Gelateria Dondoli, right on Piazza della Cisterna.
Bolgheri: more than just wine
Famous all over the world for its fine wines, Bolgheri is first and foremost a charming little village – and its entrance is nothing short of spectacular: a 5 km-long avenue lined with cypress trees, a national monument that deserves to be taken slowly. This very road inspired the famous lines of poet Giosuè Carducci:
"The cypresses that in Bolgheri tall and true / from San Guido in double rows go through..."
Once you reach Bolgheri’s gate, topped by the medieval castle’s tall tower, you’ll find that visiting the village doesn’t take long. Everything here feels perfectly in place – though you may have to weave through the crowd, past dozens of boutiques and souvenir shops (best to avoid weekends and peak summer if you can).
If you haven’t booked a winery tour, don’t worry: you can still enjoy a glass of wine in one of the many wine bars in town. One we recommend? Enoteca Tognoni, known for its wide selection – including the iconic Sassicaia and Ornellaia.
