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The Scenic Route through Tuscany

If you had to pick one underlying theme to describe Tuscany, it would have to be... beauty. The stunning beauty can be found in its scenic roads, elegantly purified architecture from the renaissance age, the beauty of the masterpieces found in the museums and halls (which in and of itself are impressive structures), and the natural beauty that is all encompassing in the slow countryside. Located in the western region of Italy, Tuscany holds an astounding seven UNESCO World Heritage sites to its name. Once you’ve witnessed the landscape, the Tuscan rolling hills, meandering mountain foot paths, neatly unified vineyards, and charming hill, it will be difficult to forget. This route embarks from the Cradle of the Renaissance, Florence, arriving at the humanist utopia, Siena, along with the hidden treasures of Val D'Orcia. Step back in time and enjoy the Scenic Route through Tuscany.

Route info

  • Route name: The Scenic Route through Tuscany
  • Suggested days: 2 weeks
  • Best time to go: Early spring, or late summer, closer to the beginning of autumn
  • Best by car

Typical road in Tuscany


The Cradle of the Renaissance, Florence, is surely one of the most popular destinations in Tuscany. Tourists flock to catch a glimpse of the age old city full of Florentine glories. The timelessness of the city can be felt through the century old streets, the well-crafted buildings and squares, and the geniuses that have propelled their legacy until today. You’ll get to experience the grandeur of all the landmarks that have defined the city, but also the inviting gems that have continued to persevere. The 15th-century old architecture remains in impeccable detail and still upholds its intricate designs, even though some of the buildings now houses modern, high-end fashion retailers. Stroll through the stone-lined streets adjacent to the main roads, and you'll still find tiny grocery stores selling the finest produce of the region or an Osteria that have not forgotten their traditions.

Things to do in Florence

Even if it's your first, second or third time in Florence, you'll always be amazed by the city's ability to surprise you in the subtle ways. Some of the greatest minds once walked the very same streets and contributed in the field of art, history, architecture and design, science, philosophy, literature. Paved the way for a new era that would shake the modern world as we know it. As powerful Florentine families, such as the Medici, have built up their wealth to support a sophisticated art scene in Florence, giving way to masterpieces such as the Mona Lisa and Michelangelo's David, which remains even when the families and artist have long gone.

  • Orientate yourself at the Piazza del Duomo, where you can choose to either climb the Campanile di Giotto or the Cupola del Brunelleschi. Both vantage points will give you a panoramic view of the entire city
  • The Town Hall, known as the Palazzo Vecchio, is a fantastic and affordable way to view many of the masterpieces of Florence. Admire the perfect marble statues and the replica of David. Walk around the main hall and courtyard to view the textbook example of Roman achitecture
  • If this is your first run of the city, don't forget to visit the world famous Uffizi Gallery, Basilica di Santa Croce, and Ponte Vecchio.
  • However, if you've already perused these popular attractions, consider heading to Museo di Palazzo Davanzati Museo Novecento (modern art museum), view the manicured gardens of Boboli and Orto Botanico, and Museo Opificio Delle Pietre Dure, Museo di Palazzo Davanzati.
  • For some traditional Tuscan cuisine, experience some local dishes at Osteria dell’Enoteca, where they'll prepare you their fresh pasta or signature steak. Located on Via Romana, 70, just beyond the city walls. If you're curious about to try a Roman style pizza, you'll be dazzled by this rectangularly shaped masterpiece. Baked to perfection with a light and crispy dough, topped off with fresh ingredients, only at BiancaZeroZero. (Note: Most restaurants are closed on Mondays)
  • Venture to the Mercato Central to try some Tuscan street in the neighborhood of San Lorenzo. Choose your pick from an array of pastries from La Pasticceria, Bollito Sandwiches (boiled brisket) from Da Nerbone, or some freshly made pizza at Primo Piano.


If you're traveling by car, which we highly recommend, then the route to Siena is a 70KM drive. It will roughly take an 1 hour and 20 minutes, so follow the Raccordo Autostradale Firenze to Sienna. Another option is a direct train to Siena, which will cost you € 8.60.

Siena Town Hall


The proud city of Siena was once a great republic before succumbing to the Florentines. Siena's medieval infrastructure, communal piazza, historical and artistic legacy sets the city apart from the rest of Tuscany. Today, its people uphold strong traditions and fierce allegiance to their contrada (neighborhood), which is evident in the II Palio competitive horse race. The laid back Piazza Del Campo becomes a stage for the highest form of rivalry. Perched on top of three hills, the city's UNESCO Heritage Site recognition gives it a sense of preservation, keeping to strong traditions, defying time by its distinct Medieval brick colored buildings, and prioritizing pedestrian areas within the center.

What to do in Siena

  • Set foot in the Piazza Del Capo where the heart of the city lies. Watch the locals relax on the fanned out square and bathe in the sun. While most Piazzas are located next to churches and cathedrals, Siena's main square has the city hall towering over its presence, as a symbol of independence to the old republic. Walk up the 300 steps of the tallest secular tower in Italy to the very top and you'll be rewarded by a gorgeous view of the entire city, stretching beyond the Tuscan landscapes.
  • The Sienese society was well ahead of its time when it came to social structures and governance. The progressive republic envisioned a utopia that was based on good governance and humanism. Visit the City Hall and Santa Maria della Scala (once a hospital) to discover the deep-seeded traditions which are found on the frescos sharing tales of altruism and daily life back in the 1400s.
  • Visit the Siena Duomo, a cathedral decorated with marbled stripe, art pieces outlining the story of Christianity in Gothic style, and replicas of distinct pope heads. After admiring the panel paintings of Christ by Duccio di Buoninsegna in the cathedral museum, you can walk up the steps to a surprising view of the Duomo.
  • Get a taste of the local delicacies called Panforte, a traditional Italian dessert with a chewy consistency containing nuts and fruits, similar to a spicy fruit cake. If that's not to your taste, then try a vintage chianti, handmade pasta, and prosciutto.
  • Lastly, spend hours getting lost in the city's narrow backstreets and brick-hued alleyways.


Just an hour away from Siena is Montalcino. Take the SS223/SS73 and find yourself wrapped in the beauty of the Tuscany.

Scenic Tuscany Road


Out in Tuscany's rolling hills is where you can finally enjoy the slow life. Montalcino is a sleepy, hilltop town with a powerhouse reputation for their world famous wine, Brunello di Montalcino. Located in the heart of wine region, Val d'Orcia, Montalcino's past is painted by the rivalry between Florence and Siena that spewed into the surrounding region. Its medieval walls stretch on all sides of the city and tell a tale of a period of war and destruction, but also rebuilding of some of the age old structures, such as the main castle. The town has remained unchanged since the 16th century, preserving its rich history and traditions, however, there's no denying that when you're in Montalcino, you'll want to taste the wine of the town.

Winetasting in Montalcino

If you are in Montalcino, you must experience the wine making process. The 24,000 hectares of fertile land and sun-soaked soil creates the ideal condition for growing the perfect grapes, but only 4000 hectares of this land is used for grape cultivation! The birth of Brunello Di Montalcino started with a man called Clemente Santi in the 1800s. He wanted to create wine that differed from the predominately white wine production called Moscadello di Montalcino. Through his hard earned efforts, he was later recognized by the Agrarian Exhibition of Montepulciano and became one of Italy's treasures across the globe.

The secret to this wine is using 100% Sangiovese grapes. The process to ferment the liquid in an oak barrel can take up to 2-5 years. The bottling process can take up to 20 years before the wine could be opened and thoroughly enjoyed.

With over 200 wine producers, you have a great selection of wineries to choose from. We highly recommend visiting the Museo della Comunità di Montalcino e del Brunello, to hear the stories behind the wine itself.

  • Santi: a big player in the Brunello Wine Production
  • Altesino: charming local winery that give an extra special touch to their story of winemaking
  • Tenuta Fanti: a historic vineyard producing wine for hundreds of years.

Montalcino-Bagno Vignoni

Get back on the road and take the SR2 towards Bagno Vignoni. You'll be greeted by the classic rolling hills of Tuscany.

Bagno Vignoni Hot Springs in Town City


When you're driving through the Val D'Orcia, you'll want to make a stop in the hilltop town of Bagno Vignoni, the original Tuscan tourist destination. What makes this town distinct is the thermal springs that have attracted visitors for its healing properties. Yes, this was your traditional spa and baths that date back to the Etruscan era and utilized by the Romans. In the heart of the town, you'll find a large hot water pool fed by the Monte Amiata, which is more of a nonfunctional center piece than a bathing tank. This particular stop used to be a waypoint stop for travelers making the pilgrim route to Rome (Via Francigena).

What to do in Bagno Vignoni

  • To experience a thermal hot spring for free, go to Parco dei Mulini which are ruins of medieval mills where you can find flowing streams of thermal water. Locals and visitors come here for to bathe in the natural properties of the water, which was said to heal some of the ailments experienced by Lorenzo il Magnifico, Pope Pio II Piccolomini and Catherine of Siena.
  • If you would like a more secluded and well-kept option for bathing, head to Hotel Posta Marcucci for an experience in the Piscina Val di Sole, is a tranquil and pristine, overlooking Castiglione d'Orcia. Entrance fee is 25 Euros for an all day pass during the summer.
  • If you're looking for a walk before or after your plunge, take the Castello di Ripa d'Orcia trail that connects Bagno Vignoni with Vignoni Alto
  • Reward yourself with some antipasti dishes at Bottega di Cacio, where you can sample delicate cold cuts of ham and locally made Pecorino cheese.

Bagno Vignoni-Pienza

From Bagno Vignoni, take the Strada Provinciale 53/SP53 and then onto the SP18 straight to Pienza

Catching the view from Pienza


Pienza is the urban hub of the Renaissance, beautiful in terms of its architectural and geometric style, and amplified by its stunning surrounding. It was the birthplace of Pope Pius II, also known as Aeneas Silvius Piccolomini, who instructed the city to be built into a Renaissance utopia. Today it is a well preserved Tuscany dream, with a sense of timelessness distilled within humanism.

Things to do in Pienza

  • Start off your day at Piazza Pio II, the center square where you can witness the detailing of the Renaissance design. Under the request of Pope Puis, three main buildings were completed to uphold the Renaissance facade, which turned Pienza into not only an escape for the Pope from Rome, but into an urban sanctuary. The Piccolomini Palace, Town Hall and the Pienza Cathedral all exemplified the geometric designs on an impressive scale.
  • A stroll around in town and will show you just how picture perfect everything is placed. The surrounding Val d'Orcia is defined by the cypress trees lining the zigzagging roads, overcoming the distinctive rolling hills, and the horizon that stretches as far as the eye can see No wonder it is recognized as a UNESCO World Heritage site.
  • Pienza is renowned for its cheese- pecorino. The cheese is made out of sheep's milk, which gives it an extra luxurious and rich taste, which can be made with homemade pasta, sheep fondue, or on a bruschetta board.

Montepulciano walled city

Discovering more of Tuscany

From Pienza, you'll be able to explore other smaller, hilltop towns in Tuscany with ease and accessibility. Here are some more picturesque towns to add to your list:


Not far from Pienza is the charming town of Monticchiello. It's defining characteristic is the Porta Sant'Agata gothic gate, defensive stoned wall, towers, castle, and cobblestoned streets. An annual event that makes this town shine is the Teatro Povero (peasant theatre) that takes place at The Piazza del Teatro, where residents produce and write their play based on the village.

Getting to Monticchiello

Make your way towards Via di S. Bartolomeo which turns into Viale Marino Cappelli.


Montepulciano is a rare beauty in the heart of Val d'Orcia. The town is a panoramic paradise perched on top of a hill, which gives it a vantage point of the entire Tuscany countryside. Today, it houses beautiful Renaissance palaces, ancient churches, harmonious squares, and nearby vineyards. One of the main events in Montepulciano is the barrel-racing Bravio delle Botti in August, where two people hand push a wine barrel through the streets of Montepulciano

Getting to Motepulciano

Drive along the Via S. Gregorio/SP146 and look out for signs pointing to "Firenze-Roma/Montepulciano/Chianciano T."

Tuscany road trip

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Florence by nightfall

Siena Cathedral