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Itinerary in Tuscany: traveling between Volterra, San Gimignano and Siena

Are you planning a trip to Tuscany? Nothing more romantic and relaxing! Today we take you to discover Volterra, San Gimignano and Siena, in an area of rolling hills, rows of cypresses, vineyards and olive groves.

  • Volterra
  • San Gimignano
  • Siena
  • Where to sleep
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Travel with us to a beautiful area of Italy where we’ll provide helpful tips on what to see, do and eat, plus suggestions on where to stay in agriturismo.

Itinerary in Tuscany: Volterra

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A small Tuscan wonder that truly merits a visit, Volterra is located a short distance from important cities such as Pisa, Florence and Siena. Perched on a hill just an hour from the sea, it’s surrounded by the countryside of Val di Cecina, a spectacular expanse of unspoilt nature.

Start your itinerary at Palazzo dei Priori. Built in 1239, it is entirely made of stone and boasts a facade adorned with coats of arms and battlements. Continue to the cathedral with its Romanesque exterior and lustrous ceiling, and then the octagonal-shaped Baptistery made of white and green striped marble. Piazza dei Priori, the main square of Volterra, is considered one of the most beautiful medieval squares in Italy.

It won't be long before you realize that the atmosphere in Volterra is truly magical. For this very reason the city center was chosen as the setting for the famous Twilight film saga. Lose yourself in its alleys and historic shops, and pause to admire the alabaster statues and objects, a time-honored tradition and pride of the local craftsman.

For art lovers, a worthwhile stop is the Art Gallery housed in the Palazzo Minucci Solaini where you can view an impressive exhibition of both paintings and sculptures.

Just a few minutes walk from the center you will find the Roman Theatre, testimony to the town’s ancient Roman past. Dominating the highest point of Mount Volterra, the imposing Medici Fortress overlooks all of Volterra.

Have you worked up an appetite? Have a seat at one of the many trattorias and enjoy the best of Volterra's cuisine. The local dishes, inspired by the surrounding woodlands and countryside, feature game, a wide variety of mushrooms and excellent truffles. There is no shortage of fresh homemade pasta, aged cheeses, cold cuts, roasts and homemade desserts. All to be washed down with a delightful Tuscan wine!

Our agriturismi in Tuscany

Itinerary in Tuscany: San Gimignano

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Did you know that San Gimignano is a UNESCO World Heritage Site? Or that it’s known as the City of One Hundred Towers?

What makes this Tuscan village special is its 13th century charm, amazingly preserved over hundreds of years since the town’s moment of maximum splendor. Unfortunately, of the 72 towers built during the Middle Ages only 13 remain, but this doesn’t deter from the alluring view. For its architectural beauty, local wines and gorgeous landscape, San Gimignano remains one of Tuscany’s most visited villages by tourists from around the world.

After leaving your car in Piazzale dei Martiri di Montemaggio, enter Porta San Giovanni and get ready to explore the village at a slow pace: Piazza delle Erbe, the cathedral, Piazza della Cisterna, the fortress of Montestaffoli, and the church of Sant'Agostino.

Worthy of mentioning is the Piazza della Cisterna, whose name comes from the octagonal well located in the square’s center. Considered the most beautiful piazza in San Gimignano, it’s surrounded by local workshops and historical buildings with a breathtaking tower view. Long the commercial heart of the village, Piazza della Cisterna has been home to the town’s bustling markets and fairs since ancient times. 

Not to be missed during your visit to San Gimignano is the Vernaccia Museum where you can taste and learn about local Vernaccia wine. 

Itinerary in Tuscany: Siena

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After visiting Volterra and San Gimignano, how about a stop in Siena, a city rich in history, art and culture?

If you’re visiting for the first time, we advise going straight into the heart of the city to the beautiful Piazza del Campo, the symbol of Siena. Between Piazza del Campo, home of the famous Palio horse race, and the cathedral, are the city’s main attractions: Palazzo Pubblico, Fonte Gaia, the Duomo and Baptistery, Santa Maria della Scala and Torre del Mangia...

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We recommend climbing the 88 meters of steps to the top of Torre del Mangia: from above the panoramic view of Siena is stunning!

Also worth a visit is the Civic Museum of Siena where you can find one of the most famous allegorical paintings in the world: The Allegory of Good and Bad Government by Ambrogio Lorenzetti. The Duomo, with its black and white facade, is a special gem: inside you will find floors full of esoteric symbols and religious stories, numerous treasures by Donatello, Pisano, Michelangelo and Pinturicchio, and the famous Piccolomini library.

You can't leave Siena without trying the local cuisine. The traditional dishes are incredibly tasty and include wild boar, crostini, meats, pecorino cheese, Tuscan bread soup, and biscuits like cantucci and ricciarelli.

Where to sleep

The ideal home base for visiting this area of Tuscany is Diacceronia farmhouse and glamping lodge that offers hospitality in a b&b format. If you want to sleep immersed in the green Tuscan countryside and spend your days discovering Volterra, San Gimignano, Siena, Lucca and Florence, this is the place for you.

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The farmhouse has been completely renovated and offers comfortable accommodations to all of its guests, as well as splendid views of the surrounding hills. For more adventurous families who love camping but prefer not to give up material comforts, there is also glamping. All guests can enjoy the swimming pool and restaurant featuring homemade cuisine and traditional local ingredients.

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Pool season is almost upon us! What’s your favorite Diacceroni location pool? #Pelagaccio #Diacceroni #Tuscany #Pool #Italy #TuscanyVacation

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Diacceroni offers many activities onsite: you can take riding lessons, cooking classes, organize an oil tasting or a guided tour of the cellars, or go on a bike ride. The farm also has activities for the little ones including creative workshops and group games.

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☀️ Good morning from Diacceroni! Do you like your breakfast sweet🍰 or salty🥐? #livingdiacceroni #diacceroni #tuscanyfood #glampingitaly

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Read more about the farm on our website and book Agriturismo Diacceroni for a truly authentic Tuscan vacation!

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