San Gimignano, Volterra, and Certaldo: Tuscany's Medieval and Secret Heart

Medieval towers, ancient apothecaries, the Fortress of Volterra, and street theater in Certaldo: discover what to see, buy, and taste in Tuscany's most charming villages.

Tucked between the Val d’Elsa and the hills of Volterra lies a corner of Tuscany that instantly transports you back in time. Here, soaring towers rise above rolling green hills, ancient Etruscan walls embrace hilltop villages, and narrow stone alleys keep traditional craftsmanship very much alive, passed down through generations.

It makes for a fantastic day trip! From our homes, you can easily reach this region in just over an hour's drive along some of the most scenic roads in Tuscany.

San Gimignano: The Medieval Manhattan (and its Alchemical Secrets)

World-famous for its medieval towers (originally 72, 14 of which remain perfectly intact today) San Gimignano is a UNESCO World Heritage site offering a true plunge into the 13th century.

What to See

• Piazza della Cisterna & Piazza del Duomo: The beating heart of the village, surrounded by noble palaces and dominated by Torre Grossa (the highest tower in town, which you can climb for a 360° view of the Val d'Elsa).
• Duomo Frescoes: The Collegiata church holds 14th-century fresco cycles of extraordinary beauty, including masterpieces by Bartolo di Fredi and Benozzo Gozzoli.
• Rocca di Montestaffoli: The ruins of this ancient fortress offer the absolute best panoramic viewpoint to photograph the town's skyline at sunset.
• The Apothecary of Santa Fina Hospital (The Insider Gem): Far from the crowds beneath the towers, this lesser-known spot preserves the medieval pharmacy of the ancient hospital. You can admire hundreds of 16th-century majolica jars, albarelli, and vessels filled with spices, ointments, and medicinal herbs used by monks to treat pilgrims traveling along the Via Francigena.

What to Buy

• San Gimignano Saffron PDO: A highly prized spice cultivated here since the Middle Ages, perfect for flavoring pasta dishes or cheeses.
• Hand-Painted Ceramics: Local artisan shops in the historic center offer beautiful Tuscan pottery.

Food, Wine & Aperitivos:

• The Wine: Vernaccia di San Gimignano DOCG, one of Italy's oldest and most famous white wines, crisp, mineral, and perfect for warm summer days.
• Local Sweets: Traditional Ricciarelli almond cookies and classic Cantucci meant to be dipped in Vin Santo.
• Gelato & Aperitivos: In Piazza della Cisterna, a stop at the world-renowned Gelateria Dondoli is a must (try the Crema di Santa Fina flavor with saffron and pine nuts). For an aperitivo overlooking the vineyards, stop by the Vernaccia di San Gimignano Wine Experience at the Rocca di Montestaffoli.
• Where to Eat: Osteria del Carcere, an unconventional, simple yet meticulously cared-for spot—not a classic restaurant, but a place serving food and drinks crafted with love to make guests feel welcomed as friends rather than customers. If you are looking for refined, modern Tuscan cuisine, try Ristorante Dorandò.

Volterra: Etruscan Soul and the Fortress of Rebirth

Perched on a ridge dominating wild clay cliffs (le Balze), Volterra boasts thousands of years of history where Etruscan charm blends seamlessly with Roman and medieval heritage.

What to See

• Piazza & Palazzo dei Priori: The oldest civic square in Tuscany, dominated by the palace that inspired the Palazzo della Signoria in Florence.
• Roman Theater & Etruscan Acropolis: One of Italy's best-preserved Roman archaeological complexes, located just outside the city walls.
• Guarnacci Etruscan Museum: Home to "L'Ombra della Sera" (Shadow of the Evening), a famous bronze statuette dating back more than 2,300 years.
• The Medici Fortress & Compagnia della Fortezza (The Insider Gem): A massive structure overlooking the city, the fortress currently houses the Volterra State Prison. This medium-security facility is famous throughout Italy for its extraordinary social and vocational rehabilitation programs. Chief among them is the Compagnia della Fortezza, an internationally acclaimed theater project founded by Armando Punzo. Once a year (typically in late July or early August), the prison exceptionally opens its doors to the general public for breathtaking performances inside the complex.

What to Buy

• Volterra Alabaster: The true symbol of local craftsmanship. In the workshops of the historic center, you can watch master artisans carve this translucent alabaster stone into unique sculptures, lamps, and home decor.

Food, Wine & Aperitivos

• Local Dishes: Zuppa Volterrana (hearty bread, black cabbage, and bean soup), game dishes (slow-cooked wild boar and hare stew), and Pecorino delle Balze Volterrane PDO cheese.
• The Wine: Local Rosso di Montecatini Val di Cecina or Tuscan IGT red wines.

• Aperitivo Spots: Enjoy a glass of red at sunset at Lupo Nero or at the outdoor tables in Piazza dei Priori.
• Where to Eat: Ristorante La Delizia for fantastic wild boar pappardelle, or Osteria dei Poeti, a characteristic medieval tavern with vaulted stone ceilings.
• Quick Bites & Picnics: If the weather is nice, take a break inside Parco Archeologico Enrico Fiumi, located right in front of the Medici Fortress: you'll find a kiosk-bar immersed in greenery, perfect for relaxing among the ruins. A short walk away in the historic center sits La Sosta del Priore (in Vicolo delle Prigioni), an excellent shop for warm panini, traditional products, and vegetarian or vegan options. Alternatively, Al Vicolino is another historic sandwich spot downtown, ideal for a quick bite featuring local specialties like lampredotto.

Certaldo Alto: Boccaccio, Street Theater, and Forest Mysteries

Perched on a hilltop above Certaldo, this red-brick walled village is a perfectly preserved hidden gem, best known as the birthplace of Renaissance poet Giovanni Boccaccio.

What to See

• Getting There: Riding the scenic funicular railway from lower Certaldo up into the heart of the medieval village makes for a scenic and charming arrival.
• Palazzo Pretorio: Featuring a facade adorned with glazed terracotta coats of arms from former Vicars, with ancient medieval prison cells open to visitors inside.
• Boccaccio’s House & Museum: The tower-house where the poet lived and died, now converted into a museum, research center, and library.
• Mercantia – International Street Theater Festival (The Unmissable Event): Every July, Certaldo Alto transforms for four days into the magical stage of Mercantia, Italy's premier street theater festival, featuring fire-eaters, acrobats, musicians, and artisans from around the globe.
• Canonica Park & The "Pyramid" (The Insider Gem): A few minutes from the village lies a lush green area hiding an artificial, pyramid-shaped hill shrouded in mystery and linked by local legends to Etruscan or medieval origins, ideal for a relaxing nature walk.

What to Buy

• Certaldo Onion Jam: The famous red onion known for its sweet flavor (even mentioned in Boccaccio's Decameron) is made into delicious jams, perfectly paired with aged pecorino cheese.

Food, Wine & Aperitivos:

• Local Dishes: Zuppa di Cipolle alla Certaldese (sweet onion soup), Francesina (beef stewed with onions), and grilled Tuscan meats.
• Local Sweets: Traditional fig and walnut desserts served with a glass of Vin Santo.
• Aperitivo Spots: Aia del Pittore, featuring a lovely patio where you can sip a Negroni or a glass of Chianti while admiring the Val d'Elsa view.
• Where to Eat: L'Aretino or Osteria del Vicario, where you can dine in a panoramic garden overlooking the surrounding hills.

Ready to go? Find your ideal base

After a day spent exploring the towers of San Gimignano, the alabaster secrets of Volterra, and the red-brick alleys of Certaldo, unwinding in the peace and quiet of one of our homes is the perfect way to cap off the day. Choose your ideal base for your Tuscan vacation:

Lucca and Surroundings

Versilia and Seaside

Pisa and Surroundings

Pistoia and Surroundings