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Our Definitive Guide Of Things To Do In Siena, Italy

Published April 6th, 2018
Travel Guides

About Siena, Italy

Sienese countryside is one of the most beautiful countrysides in the world…

Man has worked this earth to advantage and has spread its dwellings over it, but from the most pricey villa to the humblest cottage they all have similar grace and harmony with their ocher walls and curved tiles.

Both God and man have shown their genius in Siena

Maurice Druon, The Lilly and The Lion

Equity Residences picture of the Siena old town

French writer Maurice Druon was writing about the XIV Century Siena, and not much has changed since that time about the old city in Tuscany. The buildings Druon describes in his books still stand in Siena. The Tolomei Palace and the Siena Cathedral have been around for centuries serving as cultural institutions, sights for tourists, and places of worship for the faithful and for pilgrims who come to Siena to this day.

Siena’s fame and power grew in the Middle Ages when it became home to the Lombards, the famous Italian bankers who lent money (and learned secrets) to the most prominent noble houses of Europe. Siena‘s role in the world’s banking industry is notable because it is home to the world’s oldest bank – Banca Monte dei Pashci di Siena, which was established in 1472, and subsequently became the city’s largest employer and an issuer of bad loans as of late.

UNESCO describes Siena as “an outstanding medieval city that has preserved its character and quality to a remarkable degree.” The historic center of the city, where the Equity Residences penthouse is located, has preserved its medieval walls construction of which dates as far back as the 15 century.

Today, Siena is a busy tourist center in the Tuscan region. Visitors come to the city to see the famous artistic monuments like Siena Cathedral, which contains works of Donatello and Lorenzo Ghiberti.

Various churches around the city, like the church of San Francisco, still preserve frescoes of a prolific XIV century Italian painter Ambrogio Lorenzetti. We recommend walking to the church, which is only a few blocks from our penthouse, to see the famous artists’ frescoes for yourself.

Siena offers an array of things to do all year around. Summer is famous for the Palio festival; Fall is known for grape and olive harvests; Winter can be enjoyed with the Christmas mass. Going to Siena in Spring means experiencing the full-fledged Tuscan spring with its sweet-smelling air and warm sun that forces out chilly winds. If you are lucky to be in the city for Easter, enjoy the bright energy of the visitors and locals who attend the Mass and then crowd into gelaterias and pizzerias to celebrate the festivities.

Siena is a perfect launching pad for exploring the Tuscan region with all the cooking, wine and nature walks it can offer.

Siena is home to one of the oldest universities in Italy, founded in 1240. The city is alive with students who have the privilege of studying in 800-year-old halls and absorbing the knowledge.

You cannot imagine Siena without its contradas. The civic life of the city revolves around the contradas, who still hold the friendly rivalry. Palio is a manifestation of the contradas’ ability to present themselves in the most splendid light. Locals live year-around awaiting for the festivities to start.

The history of the contradas dates back to the middle ages. Once upon a time, they were units recruited to defend the city and to maintain order. 17 out of 54 original contradas survive to this day. Local citizens identify with contradas near and dear to them. Contrada flags mark the buildings and building walls still hold iron rings where riders can tie their horses.

Fun fact: our penthouse building is located in the Contrada del Lecorno territory. Look for the contrada flag on the buildings in the area.

Siena offers a multitude of things to do and places to visit.

Below are our best picks.

Museums to visit in Siena

Siena’s old town is like an open-air museum where every building has a story to tell. Churches contain frescoes by Lorenzetti and works by Donatello. Contradas have their own museums as well.

Our local Concierge can recommend city tours and arrange museum tickets.

We recommend visiting these museums because they are the most important to understanding the history of Siena and observing the city from the dizzying heights.

Siena Cathedral

Piazza del Duomo, 8, 53100 Siena SI, Italy

This is a living museum where every floor marble is a masterpiece. Make sure to get an OPA pass, which will allow you to visit the entire museum complex, starting with the crypt that features frescoes from the XIII century to the Panorama, that offers a breathtaking view of the city below.

You can see the cathedral by attending a mass with the Sienese.

Santa Maria Della Scala

Piazza del Duomo, 1, 53100 Siena SI, Italy

Located directly across a square from Siena Cathedral, this museum offers a permanent collection of Italian art and many exhibitions of important Italian artists.

Museo Civico

Piazza dell Campo, 1, 53100 Siena SI, Italy

This museum is located right in the Siena’s main square, Make sure to climb Torre del Mangia to admire magnificent views of the city and to looks at frescoes on the Sienese government by Ambrogio Lorenzetti.

Cultural events and festivities

Siena holds events year – round. Our local Concierge can recommend events and arrange tickets.

The most well-known event is Palio. It is like the New Year ball drop in Times Square – the main event lasts for about a minute, but you need to buy tickets to get the best seats. Tourists can also mingle with the locals for free in Piazza del Campo. Either way, you will be a witness to a centuries-old tradition that the entire city looks forward to all year.

Where to eat in Siena

You cannot walk two blocks in Siena without finding a restaurant, a pizza shop, or a gelateria. The city bursts with places that serve Tuscan cuisine and local wine.

We created a list of our favorite establishments and ranked them based on price, ambiance, and quality of food.

Antica Osteria da Divo, Via Franciosa 25-29

We found the service, the presentation, and the menu spectacular at this cozy yet high-end spot. The wine list alone is worth coming over for. It features everything from the simplest Tuscan wines to the more expensive reserve bottles. The dining room is divided into two levels. Depending on your preference, you can sit in the cellar or upstairs. We preferred to have a table under the vaulted ceilings of the cellar in the company of a few other diners.

Try local delicacies like pasta with wild boar and risotto served out of a giant wheel of local pecorino cheese.

Risotto served in cheese at Osteria da Divo

 Ristorante Il Biondo, Via Del Rustichetto, 10

The food at this restaurant is excellent. Pay attention to the fresh seafood and homemade pasta dishes.

The atmosphere is a simple and toned down, but the food is what makes this restaurant truly stand out.

Emanuele, the manager, can bring his team to our penthouse for a private dinner demonstration. To arrange this service, please contact the Equity Residences concierge at least three days in advance.

 Taverna Del Capitano, Via del Capitano, 6/8

If you want to come in for a satisfying, inexpensive, and traditional Tuscan meal served in a rustic atmosphere, look no further than this restaurant tucked away on a quiet street.

We found the service to be fast and reliable, food portions generous and delicious.

We sat next to locals who came here to enjoy a meal after a day’s work over wine and enjoy a quiet room full of Palio memorabilia.

 Osteria Il Grattacielo, Via dei Pontani, 8

The best things about this little eatery are the simplicity of the menu and a sense of community you feel when dining seated at a long table alongside noisy locals.

The entire dining room is no bigger than a living room in our penthouse and looks like it can barely fit little more than 15 guests. All appetizers are displayed in a glass-covered counter and served immediately. The kitchen has a menu that changes daily and is written by hand on a simple yellow paper.

On the day we came, the kitchen had two choices of pasta and ribollita soup. The wine is a house wine that comes in 0.5 liters and 1-liter carafes.

You should come here if you want to experience the taste of homemade Tuscan food and feel like a Sienese stopping for dinner on a way home from work.

 For dessert, definitely stop by Gelateria Kopakabana, Via dei Rossi 52/54

We hear from the locals it’s the best gelato in town.

Where to go shopping in Siena

Arrive in Siena with a suitcase half-empty. You will want to bring back the local products: wine, truffles, cheese, and locally – made leather goods you can find in Tuscany.

Via Banci di Sopra is the main street in Siena long which most shops are located. Some recommendations are below. When you buy items that cost over 154 Euro, you will get a 10% VAT refund.

 Cortecci, Via Banchi di Sopra, 27, Il Campo, 30-31

Latest collections by Gucci, Brunello Cucinelli, Moncler, Fendi and more are on display at this store. Service is also excellent. They have great selections for men and women.

  Max Mara, Via Banchi Di Sopra, 81

This boutique has a wide selection of all Max Mara brands and products. Factoring in the VAT “discount”, prices are very attractive.

 Falconeri, Via Banchi di Sotto, 2

For a great selection of Italian cashmere, visit this boutique.

 Boggi Milano, Via di Citta, 9

This brand offers a great selection of sleek apparel for men. You can find everything from shoes to suits at this Italian brand outpost.

Where to buy local groceries in Siena

You can find a variety of shops that sell produce and specialty treats throughout the city. Below are the names and the addresses of American-style grocery stores.

Coop Supermarket, St. Del Paradiso, 13-31

Simply Store Siena, Piazza Maestri del Lavoro, 30

Locals like to shop in specialty stores that feature local wines, in-season produce, and local meats. You will find shops on every street corner in Siena. There are pastry shops, organic produce stores, and more located throughout the old walled city and a few steps to the Equity Residences penthouse.

Where to go for meat.

Locals go to a specialty store called Maclleria. The best one is La Bottega Di Solimano located on Via delle Terme, 19

Where to stock up on groceries for your next dinner.

Consorzio Agrario Siena. Via Piangiani, 9

This specialty grocery store has been a farmer’s co-op since 1901. It features everything from bread made with ancient Italian flour to local wine to freshly made pasta it is a favorite of everyone from tourists to bankers who work in nearby offices. Lunchtime is a crowded affair, but we highly recommend it for the variety of local products, wine, as well as an ambiance.

Equity Residences investor recommendations

Experience Tuscany by escaping the city walls for a day and enjoying a wine tour. The most renown wine regions in the world are located in Tuscany. You can sip wine in Chianti, enjoy famous Brunello grown and bottled in Montalcino, and taste white Vernaccia wine made with grapes unique to San Gimignano.

One of our investors recommends spending a day at a Tuscan villa tasting wine with a private guide Dario Castagno.

Equity Residences guests can ask our concierge to arrange private and group wine tours. The opportunities to explore Tuscany are endless!

How to travel to Siena from Rome

You can fly direct to Rome from the major US airports. When you land in Rome, you can rent a car and drive to Siena, take a train, or take a bus. All these options take about 2.5-3 hours.

Although public transportation is excellent in Italy, we recommend renting a car at the airport. That way, you don’t have to rely on public transportation schedules and can comfortably travel around the Tuscan countryside when you arrive.

Travel by train: You can leave from Termini train station in Rome and take a direct train to Siena Train station. If you are taking a train from the Fiumicino airport, you will have to make one or two connections to get to Siena train station.

Travel by bus: A bus from Rome to Siena is cited as a good option by travelers. Our residence is located in the historic city center where cars are prohibited. When a bus drops you off at Piazza Gramsci, you will have to walk to the residence for about 10 minutes.

Travel by car (recommended): Cars cannot drive or park in the old walled city of Siena without a special permit. When you arrive from Rome, you can park a car in one of the parking garages outside of the walled city and take a cab to the apartment, or walk. Our Concierge can arrange your transportation from a parking garage via a private driver if you prefer.

Parking costs vary between 25 to 30 Euros a day, depending on a garage location and a size of your car.

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