Drenched in Middle Age charm dating back to somewhere between 900-400 BCE, historic buildings everywhere you look, and a traditional horse race unlike anywhere in the world – Siena is a city that dazzles visitors and offers an immersive look into Tuscan history.

A walk through the city’s historic center declared a UNESCO World Heritage Site is a complete step back to the time of Etruscan origins, mixed with Roman heritage from the Palazzo Pubblico to the Piazza Salimbeni.

But what’s unique about Siena goes way deeper than the beautiful Medieval structures. Below Siena, lies a secret aqueduct dating back to the middle ages, spanning 27 kilometers of tunnels!

With various museums sprinkled throughout its 17 historic districts, museum hopping is something that will satisfy every intellect’s appetite for learning. Situated in the middle of the Tuscan region, sampling some of the best wine and locally crafted pecorino cheese is a must!

Let’s get ready to jump in to see what a trip to Siena has in store for you in our list of the best things to do in Siena. Andiamo!

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Siena tours

1 – Gaze at the beauty of the Duomo di Siena

Duomo di Siena

Absorb one of the most beautiful examples of Italian Gothic architecture at the Duomo di Siena, built in 1196.

Dedicated to the Assumption of Mary, take in the beauty of the frescoes by Pinturicchio, the black and white striped marble all around, and the stunning blue and gold detailed dome.

Afterward, step inside the Museo dell’Opera del Duomo. Wander through the 3 floors of the museum, traveling back in time to the 11th century, as you gaze at the over 700 different works of art and fascinating sculpture galleries.

Next, hit the Biblioteca Piccolomini to see ancient manuscripts, and even the Three Graces sculpture. The Baptistery of Siena is a must-visit to see the baptismal font on the baptismal basin.

Siena Cathedral tickets and tours

2 – Walk on the fortress walls of the Fortezza Medicea

Fortezza Medicea, Siena

Visit the ancient Fortezza Medicea (Medicea Fort), and step back to 1561 when the fort was built with the order of Duke Cosimo after the Battle of Marciano against Florence, and against the Spanish army.

The structure of this impressive fort has the Medici Coat of Arms and outstanding lion statues, to signal the power and strength of Siena against any invaders. Walk on the wide walls, take in the amazing views, and take a walk through the incredible gardens and even a stadium.

Today, the fortress can be visited near the north side of the historic center of Siena and is also known for hosting outdoor exhibitions, and a weekly market nearby on Wednesdays.

3 – Take a memorable walking tour of the Piazza del Campo

Piazza del Campo, Siena

Explore the gorgeous historic center of Siena, and see firsthand some of the historical landmarks and sights as you learn from your guide all the historical and interesting facts.

Walk past what used to be considered the tallest tower in medieval Italy, the Torre del Mangia, sitting in the middle of Piazza del Campo. Check out the Palazzo Pubblico nearby known to be the governing seat of the council of Siena in the late 13th century.

On the way, you’ll also see the Museo Civico, the museum housing some of the most prestigious works of art created by the Senese School.

A walking tour of Siena is one of the best ways to get acquainted with the city!

walking tours in Siena

4 – See an expansive collection of Renaissance art at the Pinacoteca Nazionale di Siena

Pinacoteca Nazionale di Siena

Considered one of the most important Italian art museums, the Pinacoteca Nazionale di Siena (Siena National Gallery), is a stunning art museum encompassing pieces of art specifically from the late medieval age and the Renaissance.

See pieces from some of Italy’s most famous painters like Duccio di Buoninsegna, Piero and Ambrogio Lorenzetti, and many more. Originally opening in 1932, the museum came about as an idea from two Italian scholars who wanted to collect all of the Sienese paintings of the time in one place.

Walk through an immersive time capsule, as you analyze some of Siena’s greatest art pieces, throughout the 3 floors. Afterward, sneak to the rooftop for impressive views of Siena!

5 – Take a peek inside the Church of San Domenico

Church of San Domenico, Siena

Another important church to stop by in Siena is the Church of San Domenico, a gothic church dating back to 1226.

Due to a few natural disasters, the church now boasts a facade with a few baroque details, which is something you’ll notice quite immediately, as well as the renovated stained glass windows that retell the Stories of Saint Catherine.

Inside, you can see beautiful pieces of art like a 14th-century fresco of Saint Catherine, and even take a look at a 14th-century crypt. Stop by the Chapel of the Vaults, also known as the Chapel of Miracles, where you’ll see a figure of Saint Catherine.

The Church of San Domenico is free to enter.

6 – Visit one of Europe’s oldest hospitals, the Santa Maria della Scala

Santa Maria della Scala, Siena

Though the Santa Maria della Scala (Saint Mary of the Stair) used to be a hospital that cared for children, and the poor, today, is one of Siena’s cultural centers not to skip out.

You could plan to spend a few hours at this museum campus, with its over 10,000 square meters, the “hospital” houses a variety of different museums inside to pop into.

Walk through the halls, and find yourself standing in front of impressive frescoes, and sculptures, including the Old Sacristy (Sacred Nail Chapel) in the first section, the precious items on display made of silver and gold inside the second section, and various tunnels literally transporting you back in time.

Santa Maria della Scala tickets

7 – Check out the impressive Medieval Walls of Siena

Medieval Walls of Siena

Check out the 7-km long fortified Medieval Walls of Siena, a UNESCO World Heritage, divided by various portals, each added at different points of Siena’s history as an influential city in art.

Porta Pispini also known as the Gate of the Water-Spout, was one of the first portals to be built in the now Medieval Walls of Siena.

Dating back to 1325, both Porta San Marco and Porta Tufi were built and designed with 3 beautiful, rounded arches, and a central marble arch. Inside, you’ll be able to see an icon of Madonna and a few other engravings.

Porta Camollia also boasts 3 beautiful marble arches, with engravings such as the Medici heraldic shield, while the Porta Romana welcomes visitors walking through 2 separate arches.

Porta Ovile’s impressive appearance is made completely out of brick, and on one side has a fresco of Madonna and Child.

8 – Contemplate the art inside the Santuario Casa di Santa Caterina

Santuario Casa di Santa Caterina, Siena

Visit the Santuario Casa di Santa Caterina, a sanctuary dedicated to the patron saint of Siena.

Inside, you’ll see impressive art pieces dedicated to Saint Catherine, including the frescoed oratory, large walls, and ceiling. From the artwork to the gold details and interior architecture, it’s truly a sight to see!

Spend some time analyzing some of the thought-provoking paintings inside like the image of St. Catherine liberating a girl from the possession of the devil, or the image of St. Catherine receiving Holy Communion.

Go through the different areas of the sanctuary, from the Church of the Crucifix to the oratory, the cubicle, and many more spaces.

Entry inside the sanctuary is free.

9 – Enjoy a wine tour or a vespa ride in Chianti

Chianti tours from Siena

Plan for an exciting day trip to the beautiful region between Florence and Siena, called Chianti.

From exquisite wine tours to fun Vespa rides, and a history lesson on one of the most picturesque sights in Tuscany, there are plenty of ways to get to know this region not too far from Siena.

Take a bike tour and explore on wheels, with lunch included, the quaint olive groves, sleepy Italian villages, and even a few castles.

Lastly, don’t forget to check out the Chianti Sculpture Park. A fascinating and modern art display that was created by artists from all over the world, and mixes with nature’s beauty. The best time to visit is between November-March.

Chianti tours from Siena

10 – Get spooked at the Museum of Torture Siena

Museum of Torture, Siena — Credit to Museo delle Torture

See the cruel reality of how crimes were paid back in the Italian medieval age at the Museum of Torture Siena.

Go through the different exhibits, each sharing ways in which the humans underwent torture to pay for crimes they committed, with actual artifacts and devices used to torture.

From the famed “Heretic’s Fork” to the “Guillotine” and the “Spiked Punishment Collar” – you’ll be horrifically amazed at the extent to which these tools were designed to punish.

Learn about the history of human torture, and about how some of the worst ways that people underwent torturous pain through the various exhibits, including some of the specific temporary exhibits.

Museum tickets start at 10 euros.

11 – Learn about medicinal herbs at the Orto Botanico dell’Università di Siena

Orto Botanico dell'Università di Siena

The Orto Botanico dell’Università di Siena (botanical garden) dates back to 1588 and was built as a garden for the University of Siena to grow medicinal plants and herbs to study.

Today, you can escape the bustle of the city for a breath of fresh air at the botanical garden, where you can also take a look at other local plants, co-existing with exotic plants. See the greenhouse plants, smell the vibrant fruit from the fruit and olive trees, and even a few carnivorous and succulent plants.

Located beside the university, the 2.5 hectares of garden and park are one of the best ways to unwind from a busy day touring through Siena.

12 – Wave hello from the air on a hot air balloon

hot air balloon rides in Siena

Fly over the beauty of the Tuscan region for a true pinch-me moment, whether you’re solo traveling or you’re trying to surprise your partner.

Reach up to 3,000 feet high, and feel the stillness of earth as you glide through the air on the hot air balloon, taking a moment for yourself in the beauty of a classic Italian landscape.

Opt for a tour package that picks you up at your hotel, and drives you directly to the sight of your hot air balloon departure. You’ll receive a brief safety training and then you’ll be off to the sky!

When you land, you’ll celebrate your successful journey with prosecco and a certificate!

hot air balloon rides in Siena

13 – Hop through the various churches and basilicas in Siena

other churches and basilicas in Siena

See the architectural mix of Romanesque mixed with Gothic at the Basilica of Saint Francis. After suffering various fires, today, the interior is not as ornate as it once was. However, the stained glass windows are a sight to see, and a few frescoes that did survive.

Hop over to the Chiesa di Santa Maria in Provenzano, dedicated to the mystery of the Blessed Virgin Mary, and her appearance to Saint Elizabeth. Try to visit on July 2nd, when the image of the Madonna di Provenzano is honored with a special celebration.

Sitting a little outside Siena is the Basilica dell’Osservanza, known as a hermitage originally, and then turned into a church in 1420. Step inside and up to the altar to view terra-cotta sculptures, and an original hand-painted crucifix.

Church of Santa Maria dei Servi beautifully stands with stunning views of the Duomo and Palazzo Pubblico of Siena, while the church itself holds treasures to see inside like the Coronation of the Virgin altarpiece and a few original frescoes.

14 – Soak in the Tuscan landscapes in Montepulciano

Montepulciano tours from Siena

Explore the charming tows of Montepulciano, one of Tuscany’s most beautiful little towns, overflowing with trattorias, beautiful views of the hilly Tuscan landscape, and so much more.

With frequent day trips leaving Siena daily, you can choose between a small-group tour for an intimate encounter with the town or a specialized full-day wine tasting with lunch experience.

Art buffs will love the art and wine tours led to Montepulciano, and stopping for lunch at a traditional and local restaurant.

If you want to stretch your day activities, make sure to opt for a day trip that includes a stop in the beautiful town of Pienza, the capital of pecorino cheese, and stunning views of Val d’Orcia.

Montepulciano tours from Siena

15 – Learn about local natural sciences at the Musei dell’Accademia dei Fisiocritici

Musei dell’Accademia dei Fisiocritici, Siena

Situated inside an old monastery, visit the Musei dell”Accademia dei Fisiocritici (Natural History Museum) which holds over 2 centuries’ worth of items inside detailing the natural history, from taxidermied animals, minerals, animal skeletons, and other fascinating finds.

Curated to look almost identical to how it looked like back in the 19th century, spend a few hours wandering through the different sections of the museum, on the 2 floors of the building. The most famous piece inside? The 15-meter-long whale skeleton!

When you’re done learning about all that’s inside, take a breather in the beautiful central courtyard, predating the museum.

Guided tours are available upon request at the time of your visit to the museum.

16 – Giddy up on a horse riding adventure

horse riding near Siena

Whether you’re a pro at riding horses, or you’ve never gotten on one, this is your chance to hop on a horse for an adventure of a lifetime in the Tuscan region.

You’ll be passing by some of the iconic and most photographed Tuscan rolling hills dotted with farms and historic homes, and towering Italian cypress trees.

Visitors rave about this experience being one of the best things to do in Siena, so give it a go!

If you’re worried about getting on a horse for the first time, you’ll be receiving safety instructions and helpful tips for a successful journey. Ride along in a line as your guide shows you fascinating landmarks in the region.

horse riding near Siena

17 – Stare at the beautiful neo-gothic architecture of the Palazzo Salimbeni

Palazzo Salimbeni, Siena

Located in the equally beautiful Piazza Salimbeni, the Palazzo Salimbeni is a building that used to belong to an affluent family in Siena, and today is a building that houses government offices, as well as offices for the oldest bank in the world, Banca Monte dei Paschi di Siena.

In front of the Palazzo, you’ll be greeted by a statue of Sallustio Bandini, a local religious figure. Step inside and take a look at some of the beautiful works of art, created by local artists Pietro Lorenzetti, Jacopo della Quercia, and a few others artists.

Depending on when you visit, you may even access other items like archives and seals of the bank.

18 – See Siena like a local on a vespa tour

vespa tours in Siena

What’s a trip to Italy without a ride on a classic Vespa? Don’t stay with the curiosity, and book your slot to ride with a professional Vespa driver, to whisk you away on your Italian joy ride.

Choose from a Vespa tour that includes a winery and lunch stop option, a sole ride through the traditional Tuscan region, or for those feeling a little extra brave, drive your own Vespa as you follow your guide.

No matter which option you go with, a true Italian adventure awaits you! Some tours offer hotel pick-up, while all tours include a helmet and a safety briefing. The tours last around 5-7 hours, so don’t make extra plans!

vespa tours in Siena

19 – See the oldest fountain in Siena, Fontebranda

Fontebranda, Siena

Other than being known as the oldest fountain in Siena, Fontebranda is also the site close to the birthplace of Saint Catherine. For these reasons, this fountain is an important sight for the locals.

Dating back to A.D. 1081, the fountain served great importance as a source of water for Sienese locals. Each of its 3 spacious vats was historically used for different purposes, from drinking to even doing laundry.

Today, you can visit the fountain to take in its gothic arches, four lion-shaped fountain spouts, geometric shapes, other animal carvings, and the emblem of the city of Siena in the middle.

The Fontebranda is a 5-minute walk from the historic city center.

20 – Get panoramic views over Medieval piazzas at the Facciatone of Siena

Facciatone of Siena

Visit the marvelous Facciatone of Siena, situated within the Cathedral of Siena museum complex to get privileged views of the city below as well as the Tuscan countryside.

Initially built in 1339 as an expansion of the Siena Cathedral, the work was never completed due to outside circumstances, including the plague of 1348. Today, visitors are able to see some of the remnants of the incomplete construction work, specifically when visiting the right nave.

When visiting, make sure to get your ticket to allow you entrance to the top of the tower, as well as the other incredible sites within the Cathedral of Siena.

Tickets for the Facciatone of Siena are priced between 8-15 euros.

21 – Plan an exciting day trip to San Gimignano

San Gimignano, Tuscany

Only a 40-minute drive from Siena lies San Gimignano, “the Town of Fine Towers” due to its impressively well-preserved medieval architecture around the town.

Enjoy a day trip from Siena to San Gimignano, with a stop in Chianti for regional wine and traditional lunch. If you want to see more charming Tuscan towns in one day, opt for the tour that stops in other towns including Montalcino, known for Montalcino red wine, a stop in Monteriggioni, another Tuscan town stuck in time and thriving in medieval architecture.

Volterra is another common stop on the day trips to San Gimignano, a wonderful town known for its large Etruscan walls, Medieval art, and 6th-century BC circular tombs.

San Gimignano tours from Siena

22 – Put on your thinking cap for some scavenger games

scavenger games in Siena

Make the city your live playground, as you play an exciting scavenger game in Siena!

Think fast as you take on different prompts and riddles, and visit different corners of the city. See secret gems that even locals miss, as you follow the prompts on the game, pointing you to your next clue.

Go at your own pace, or see if you can beat a personal record of finding all the clues dotted throughout the city in this fun game.

Another way to see the city? An outdoor escape game! Get your thinking caps on and enjoy a themed game with riddles and clues that will test your teamwork!

scavenger games in Siena

23 – Take a thrilling ATV tour through the Tuscany countryside

ATV tours near Siena

Here’s one of the most thrilling things to do in Siena – a quad tour through the Tuscany countryside! Book yourself for this next tour, taking you to the picturesque rolling hills and cypress trees landscape for the afternoon.

On a 2-hour journey, you’ll be able to drive through some of the small Tuscan villages including Chianti and Val d’Orcia, as well as some UNESCO World Heritage sites that you’ll probably recognize from TV and movies.

You don’t have to be a pro at riding ATVs, as all skill levels are welcome to join in on the fun! Everyone will receive a safety briefing, as well as be able to do a few practice rounds before taking off.

Pro tip: pack athletic clothes!

ATV tours from Siena

24 – Get into the mind of an artist at Salvador Dalí Siena

Only a 2-minute walk from the Siena Cathedral is one of the most interesting art museums in the city. Salvador Dalí Siena is a fascinating art museum that unavoidably includes some of Dalí’s intrigue with science, which is evident in many of his art pieces.

Walk through the various galleries and exhibits inside to really get inside the mind of Dalí, and see how science inspired many of his paintings, from the concept of time to themes relating to the subconscious, math, and more.

Be sure to also check out some of the other pieces inside from the time, such as sculptures, furniture, and glass figures.

Tickets for the museum start at 8.50 euros.

25 – Get a good seat at the Palio di Siena

Palio di Siena

Witness the local tradition of the Palio di Siena (Siena’s Palio Horse Race) taking place in the heart of Piazza del Campo, in honor of the apparition of the Virgin Mary.

The celebration takes place each year on July 2nd and August 16th, in which the city closes down to witness a horse race unlike anywhere else. Nearby neighborhoods in Siena come together to compete in this centuries-old race.

Days before the event, the city shuts down some of its streets for parades to take place, each representing a neighborhood competing in the race.

Stay for the race, and see which team ends up winning the “Palio” with the image of the Virgin Mary!

26 – Go centuries back inside the Synagogue of Siena

Synagogue of Siena

Dating back to the 14th century, visit the Synagogue of Siena for an encounter with the Jewish influence that existed in Siena way back then.

At only a quick 1-minute walk from the Palazzo Pubblico, walk through the different rooms inside the Synagogue from the prayer hall, taking in its richly decorated interior, to the women’s gallery. The women’s gallery is divided into 2 floors, and you can learn about the early figures, and see items like ancient Torah scrolls, texts, and ritual dress.

Check out the Jewish Museum to learn more about the impact that the Jewish community had on the economy and culture of Siena. The museum opens between November 1st – March 31st.

Synagogue of Siena tickets

27 – Putter around on a vintage car tour

Fiat 500 tours in Tuscany

Small, colorful, and charmingly designed, Fiats are a true Italian staple… so why not hop into a classic one when it’s time to see the sights! Hop into your lovely little chariot and enjoy a nice drive through the countryside, stopping for wine tastings and meandering through traditional little towns all along the route.

Drive with a professional local, guiding you with directions and tips, so no need to worry about getting lost along the scenic way. Since the Fiats are very small, you’ll be able to fit into even the narrowest streets! Fiat rentals range between 6 and 7.5 hours long.

You’ll feel like you’re starring in a classic vacation movie!

500 vintage tour in Siena

28 – Pack for a day of fun on the Elsa Trail and Diborrato Waterfall

Elsa Trail and Diborrato Waterfall, Siena

At only 25 minutes from Siena, the Elsa Trail and Diborrato Waterfall are the perfect day trip to enjoy on a hot summer day in Siena.

Enjoy the 2.5-kilometer trail, which starts at Spugna Bridge, near the village of Colle di Val d’Elsa. The trail wonderfully curves along a turquoise-blue river and crosses over wooden bridges, large stone river crossings with ropes, and many trees.

You’ll know you’re reaching the end of the trail when the beauty and sound of the 15-meter-high Diborrato Waterfall start to come into vision. You’re allowed to jump in and swim in the river and feel the waterfall’s magic up close, so make sure to pack your bathing suit!

29 – Eat to your heart’s content on a food tour

food tours in Siena

Come hungry when you come to Siena, and get ready to devour a little bit of the city’s most recognized dishes like Penne alla fiesolana, Malfatti (dumplings), and Berriquocoli (cookies) on a food tour!

As you hop from markets to hole-in-the-wall restaurants, you’ll gain a deeper appreciation for the local dishes, wines, and desserts that have fed generations of locals over the years. Learn about the interesting story behind some of the dishes you’ll be trying and sample local pecorino cheese with the perfect wine.

In between eating, you’ll also learn more insight into the city and its beautiful culture, from its famous sites to its famous restaurants and food shops to stop by!

food tours in Siena

30 – Satisfy your appetite at the best restaurants

Ristorante Pier Pettinaio, Siena — credit to Ristorante Pier Pettinaio

Speaking of wonderful local foods to try in Siena, why not try them at the best restaurants?

For a classic Siena restaurant serving both coziness and delicious food, visit Le Logge, located not too far from Piazza del Campo, for a bite of the specialty – Spaghettoni with Rigatino.

Osteria La Mossa is where you can enjoy a variety of meat and seafood dishes, prepared in the most traditional ways. While you’re there, try the delicious pumpkin ravioli!

If the weather permits, do yourself a favor and have a lovely organic lunch at the outdoor garden of All’Orto de’Pecci, located behind the Torre del Mangia.

Guido is both a local and tourist favorite, offering mostly classic and wonderful dishes using simple and local ingredients. Try the famous Florentine steak with the bruschetta.

Lastly, for a Medieval-inspired dinner, visit Gallo Nero, where the atmosphere lends itself to a romantic dinner.

31 – Walk through the medieval walls of Monteriggioni

Monteriggioni tours from Siena

A city drenched in medieval charm, Monteriggioni is a town/commune that dates back to the 13th century and is mostly known for its beautiful and strong medieval fortifications and watchtowers.

Although you could get away with seeing the beautiful town in a short amount of time, you’ll want to spend some time truly absorbing the architecture and historic nature.

Don’t know how to get to Moneriggioni? A fun and unique way to see this medieval town is to visit it on a hiking trip from Siena!

Take a hiking tour from Siena, which make a stop in Monteriggioni for a wine visit, where you can taste and learn about the regional wines.

Monteriggioni tours from Siena

32 – Practice your recipe skills at a cooking class

cooking classes in Siena

Sure, eating at a local market, or one of the best restaurants in Siena are incredible ways to enjoy the local foods of Siena, but what about learning and making some of these dishes yourself?

Enjoy a beautiful dining experience where you become the chef! Cook alongside a professional cook in a restaurant kitchen or a local foodie in their home, and learn about the authentic art of Italian cooking.

Shop for ingredients with your guide, try new ingredients, learn the specific secrets of Tuscan cooking, and of course, drink the perfect wine pairing to your dish!

Whether you’re an expert cook at home, or not, this is bound to be a delicious experience!

cooking classes in Siena

33 – Visit Fonte Gaia and discover the heart of the city at the ancient aqueducts

Fonte Gaia, Siena

Walk through some of the tunnels that used to collect rainwater during ancient times, located underneath the city of Siena.

The important ancient network of aqueducts, called the Bottini, measures around 25 kilometers in length.

Divided into two branches, each tunnel was responsible for providing water to different parts of the city, from springs to fountains. The longest branch, Fonte Gaia, was constructed in 1343.

Today, along with dozens of interesting and spooky folklore stories, the ancient aqueducts have become a fun attraction to visit. Make sure to book your guided tour and gain access to a few Bottinis, including Fonte Gaia.

Pro tip: Pack warmer clothes and non-slip shoes to walk the slippery tunnels.

34 – Enjoy dinner in the vineyards of Tuscany

dinners in Siena

Savor an excellent and traditional 4-course meal under the Tuscan star-studded night when you book a dinner in the vineyard experience.

Enjoy a comfortable journey from Siena to the quaint hill village of Chianti, and set foot in a Tuscan vineyard, complete with string lights, delicious wine, and an unforgettable meal. As part of your wonderful dinner, you’ll also visit the vineyard’s chapel, and learn a bit about the people behind the vineyard.

Mingle with friends, new and old, and listen to soft Italian music in the background, while indulging in this complete scene taken straight out of a movie.

Dinner experiences start at $87 USD and last between 4-5 hours.

dinners in Siena

35 – Look around at the local markets

local markets in Siena

Enjoy the leisure art of strolling through a local market!

If you’re a market lover, you won’t want to miss out on visiting the city’s most famous outdoor market, La Lizza Market, anywhere between 8:30 AM – 1:30 PM on Wednesdays. Here, locals and tourists come together, trying to find the best bargains when it comes to clothing, accessories, home goods, fruits, and vegetables.

Take in the beauty of the medieval architecture and Medici fortress at the Mercato delle Merci. Also taking place on Wednesdays from 8:00 AM – 1:30 PM. Explore some of the items sold at the market, from jackets, dresses, and pants, to delicious local cheeses and fruits.

36 – Dress up for a night at the performing arts theater

See a show at the spectacular Teatro dei Rinnovati in Siena, located near Piazza del Campo. Appearing in its historical beauty, the interior architecture and design of the theater dates back to 1560, when it was frequented by the Grand Duke Cosimo I dei Medici.

At the Teatro dei Rinnovati, you can expect to see comedy, theater, musical, and classical concerts taking place.

Teatro Dei Rozzi is another famous theater that takes visitors back to 1531. Inside, be amazed at the beautiful white and blue colors, enchanting chandelier, and beautiful balcony seats surrounding the stage.

At this theater, expect to see drama theater, musicals, and classical Italian opera concerts.

37 – Visit Montalcino for some wine tasting

Montalcino, Siena

Enjoy a beautiful day trip to Montalcino for the incredible scene of Tuscany as well as stunning sips of the local wine.

Go along with a guide, as you stop by a family-owned winery for lunch in the vineyard and a tour around the fields. Afterward, sip a great variety of wines as you’re surrounded by the beauty of rolling hills and cypress trees.

The perfect pairing to wine is cheese, so book the best cheese tasting in Siena! Enjoy taste-testing the best of Italian cheeses, while surrounded by Tuscan beauty all around.

Montalcino tours from Siena

38 – Reach the finish line to Siena Circuit

Combining both a circuit and a restaurant in one place, fans of NASCAR and even those who aren’t will feel intrigued to see just what this place is all about.

Visit the Siena Circuit known to be one of the best places in Siena to race with your friends for a friendly little competition, only 7 minutes away from Siena city center.

Measuring 1,037 meters and plans for even more extension, the Siena Circuit is a great place to check out whether you do some go-karting yourself or go to watch! As you play or watch, admire the views of the Tuscan hills, interrupted only by the cheering of the locals!

39 – Sign up for a wine class at the Tuscan Wine School

wine class in Siena

Tuscany is known for its renowned talent and taste when it comes to wine production, so why not choose to learn a thing or two about this historic beverage in Siena?

Consider booking a wine class in Siena, and get the details and know-how on all things wine! Learn about how to distinguish the notes in each wine you’ll sample, and experience an authentic wine cellar and vineyard to learn about the production side of Tuscan wines.

While in class, you’ll get to sample the best wines along with the perfect snack pairings, and if you want to get the full experience, opt for a cooking class with your wine pairing!

wine classes in Siena

40 – Get dressed up for an Italian Opera experience

opera in Siena

Dip your feet into the world of Italian opera, and consider booking an Italian opera experience that will enchant your ears and heart with some of the most beautiful music and Italian culture, any day of the week!

Soak in the beautiful opera theater for starters, and then relish the beautiful music performed by the talented opera singers, performing renditions of popular songs including La Bohéme, Madame Butterfly, and more!

If you’re looking for an evening cultural experience to enjoy, whether you’re traveling with a significant other, or on your own, this is the perfect activity!

The opera experience in Siena starts at $27 USD and lasts 1 hour and 20 minutes.

41 – Consume local goods in a traditional house dinner

dine at a locals home in Siena — credit to Eatwith

Feel like a local for a moment as you take the opportunity of a lifetime to dine inside a traditional home in the middle of the Tuscan hills, with a local and a group of other like-minded individuals.

With a regularly rotating menu, enjoy dishes like Florentine chicken liver, homemade tagliatelle pasta, and of course, a sweet tiramisu, and a delicious helping of locally produced wine. If you have dietary restrictions, the menu can be adaptable.

Relish a moment of connection, and good conversation with strangers who will turn into good friends, including the host! With only a maximum limit of 8 people, this 3-hour-long experience will be one to remember!

42 – Get social exploring nightlife in Siena

Check out the live performers taking the stage at unTubo on Tuesdays! Sample a lovely selection of wine, as the sophisticated sound of live jazz takes over the ambiance.

Feeling hungry and thirsty? Visit Enoteca I Terzi, a lovely bar with a modern, medieval touch.

Bottega Roots Siena is a chic bar with a variety of craft beer, signature cocktails, and a wildly fun atmosphere of live music and delicious bites.

For a taste of Edinburgh in Siena, hit up The Sindie, a favorite drinking spot for locals where the night goes from drinking casually to hitting the dance floor into the wee hours of the next day.

How to get to Siena?

The closest airport to Siena is Florence Airport, Peretola, which is about 1 hour north of Siena.

Because of the distance between Siena and the airport, the best and most comfortable way to get to your hotel is by looking to pre-book one of the best airport transfers in Siena. It’s the seamless, and stress-free way to arrive at the door of your hotel!

Where to stay in Siena?

Enjoy a traditional Tuscan stay at the IL Chiostro Del Carmine, drenched in medieval charm, and equally beautiful rooms. Guests really love the close proximity to Piazza del Campo, as well as the free breakfast available every morning.

Hotel Duomo is another lovely stay, situated within a 12th-century mansion, in the historic center of Siena. Although the hotel itself dates back that far, the modern amenities like fast wifi, flat screen TV, and more make a stay at the Hotel Duomo very comfortable. Enjoy the free breakfast served every morning inside the romantic dining room, as you plan your itinerary for the day.

Hotel Executive is a 10-minute walk from the main train station in Siena, as well as the historic downtown, close to the main sights. Raved by past guests for its lovely in-house Tuscan restaurants, and complimentary breakfast, the dining options are the cherry on top of this hotel!

best hotels in Siena

Visiting Siena on a budget?

Check out the Siena Pass, allowing you access to some of Siena’s main attractions, from the Duomo Museum, the Siena Cathedral Complex, and more, in a simple and cost-effective way.

Want to see the city’s must-see sights without breaking the bank? Look through the best free walking tour in Siena! Enjoy a stroll in the city, with a tour guide, learning about the city’s history, on foot.

Where to go next?

Looking for the best things to do in Tuscany? Start with checking out all the wonderful things to do in Florence, starting at the Boboli Gardens, and for the ultimate example of Renaissance art, check out the Palazzo Vecchio’s magnificent art.

Soak up the small, medieval vibes and more as you explore the most amazing things to do in Lucca! Start at the historic Lucca Cathedral, located in the equally beautiful Piazza San Martino.

Check out the beautiful figures at the Cathedral of Santa Maria Assunta and more breathtaking things to do in Pisa! Of course, don’t leave Pisa without your iconic shot with the leaning tower!

Do some people-watching in the lively Piazza Maggiore and more as you uncover the amazing things to do in Bologna, or better yet, get a bird’s eye view of it all when you climb up the Bologna Towers!

Drink up the Italian sun in full force as you embark on discovering the beautiful things to do in Cinque Terre. Visit the beautiful Santuario di Nostra Signora di Montenero on top of the cliffs for incredible views.

These are just a few of the magnificent places to visit in Italy, that are close to Siena, but make sure to explore more, and see just where else you can get up to in this beautiful country!

Final thoughts

From virtually untouched medieval structures to exquisite wine samplings, Siena awaits every traveler ready for a traditional Tuscan experience, and then some.

We hope that our list of the best things to do in Siena has inspired you to dream up your next trip to this city stuck in the middle ages. Let us know which is first on your list!

Happy travels!

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42 Fun & Unusual Things to Do in Siena, Italy