Siena Italy: A Medieval Wonderment

December 4, 2023

Written by Joelle & Ryan from Wanderers Compass

“Italy is a dream that keeps returning for the rest of your life.”
anna Akhmatova

Exploring the eminent medieval Tuscan City of Siena

Having visited a large part of Italy, there are those few places that stand out above all the others. Siena, Italy, a Tuscany gem, is one of the places that stays with you long after you have moved on to your next destination. Joelle first visited it during her solo trip to Italy. It left a mark she returned twice in the next two years. First, with a group of friends, and the following year, she returned with Ryan.

While preparing for a social media post, the pictures brought back so many great memories. That led to the question, why not do a post so our readers learn about this amazing Tuscan Hill wonder? However, we warn you that once you learn about Siena, Italy, and see the photos, you may find yourself pulled into its magic. The next thing you know, you are planning a visit.

What is Siena, Italy?

Siena is a renowned medieval city with a UNESCO-listed historic center. Surrounded by a well-preserved 1,000-year-old wall is a city that transports you back to the Gothic period of the Middle Ages. Towerhouses, palaces, churches, and other religious structures remain intact inside the walls. Also of note are the city’s fountains, which continue to be fed by the vast original tunnels.

Tucked away in the Tuscan hills, Siena is packed with culture and is an ideal destination for lovers of Italian cuisine, stunning architecture, and world-famous medieval masterpieces. Siena is where pedestrians rule, and strolling is the best way to experience its magic. Siena is an easy day trip by train or car, just 43 miles south of Florence. The journey along the route is through lovely Tuscany with vineyards as far as the eye can see.

A key city during the Renaissance

Five hundred years ago, Siena and Italy were the heart of Renaissance humanism. The city has held on to that and has preserved its Gothic appearance, established during the 12th and 15th centuries. The whole city of Siena was designed as a work of art that blends into the surrounding landscape.

The history of Siena began as a Roman military colony at the time of Emperor Augustus. It was not until the 10th century that Siena gained great political and economic importance. It was at the center of the leading trade routes, and during the turbulent years of the wars with Florence, the city flourished. Great artists such as Duccio di Boninsegna, Simone Martini, and the Lorenzetti brothers had the opportunity to showcase their art in the city. In 1240, the University of Siena, one of the oldest continuously running universities in the world, was opened.

The city is historically linked to commercial and banking activities, having been a major banking center until the 13th and 14th centuries. Siena is also home to the oldest bank in the world, which has been operating continuously since 1492.

A UNESCO World Heritage Site

The heart of Siena is the Piazza del Campo, the main town square, with its jaw-dropping number of monuments and sights is a UNESCO World Heritage site. UNESCO speaks best of the city’s offerings. “A masterpiece of dedication and inventiveness in which buildings were designed to fit into the overall design of the urban structure.” It was placed on the World Heritage List in 1995 for skillfully preserving essential features of its medieval structure: an old town center bordered by the ancient ramparts built between the 14th and 16th centuries and a central square,

The journey to discover the city starts from the rivetting Piazza del Campo. This is also home to the Palio, perhaps the most infamous horserace in the world, run twice a year in July and August. The medieval tradition involves bareback riders racing within the Piazza del Campo. It draws visitors worldwide.

Once you explore the Piazza, climb the Torre del Mangia with its 400 steps to have a unique vantage point over the square and the rooftops of Siena. Follow that with a visit to the Palazzo Pubblico, which houses the Civic Museum with masterpieces such as Simone Martini’s Maestà and Ambrogio Lorenzetti’s frescos. There are several museums to choose from in Siena.

The Siena Duomo, the spiritual heart of the city

The next most logical destination is Siena’s Duomo, an Italian Romanesque Gothic cathedral. The Duomo houses Nicola and Giovanni Pisano, Donatello, Michelangelo, and Bernini sculptures. Almost no words can describe how breathtaking the Cathedral is once you cross the threshold, it is a masterpiece. Take your time to admire every nook and cranny of the Duomo, including a visit to the crypt and the nearby Baptistery of San Giovanni. The Baptistery is one of the finest examples of 15th-century Sienese painting, with its original vaulted naves fully frescoed. Hopefully, you will be able to view the captivating floor of the Cathedral, which is only uncovered a few times a year, usually between June and July and August and October.

Explore beyond the main sites

Once you have seen the Piazza and Cathedral, it is time to wander and discover all this city offers. Aimlessly going down random alleys, you realize this is a living city with laundry hanging out to dry and locals coming home from their daily shopping. Though packed with tourists often, when off those main areas, we see the city’s heart, its people. When we went off the beaten path, Siena captured our hearts and never let go.

Take the time to shop for local pottery, relax with a cappuccino, or have some delicious Italian cuisine. But make sure to take the time to sit back and observe the residents and recognize they are the core of why this city’s history survives to this day.

Where is Siena, Italy?

Siena can be reached by bus, train, and car. The “Centro storico,” Siena”s center, is predominantly pedestrian only. The easiest way to travel there is by foot from a parking lot, train station, or bus.

For all three of our visits, we drove to Siena. We found the drive easy and scenic. We found that the roads to Siena, particularly the main roads, were well-marked and frequent. Of course, always defer to Google Maps in case of road closures. Driving also allowed us to visit many other spectacular Tuscany sites. If you are driving, do not waste your time looking for free parking, there really isn’t any.

If driving alone isn’t your thing, you have many options. There are endless group tours that will take you to Siena; we suggest booking through Viator. There are also lots of excellent public transportation options. The train will likely be the fastest, and the station is in the valley below the town. Luckily, they have escalators installed to get you up to the town. Buses might be slower, but they drop you off at the top of the hill with a short walk to the main square.

Florence is the airport in Italy closest to Siena, followed by Perugia, Pisa, Bologna, and Rome, in that order. Pisa airport is the most popular for flights to Siena within Europe, while Florence and Rome are the most likely arrival airports for North American visitors.

Siena, Italy Map

Are you considering a trip to Italy? Check out our country travel guide on beautiful Italy

Top things to do in Siena, Italy

1. Piazza del Campo, also called Il Campo, is the main square of Siena. Medieval buildings, shops, and outdoor cafes surround this wide-open space. The square’s focal point is Palazzo Pubblico and its iconic tower (Torre del Mangia). Il Campo is where the Palio horse races are held twice a year. Imagine a horse race being held here, and what a sight that would be.

2. Palazzo Pubblico, also called the town hall, is the seat of Siena’s government. This medieval building was constructed in 1297 and sits on Piazza del Campo. Made of stone and brick, Palazzo Pubblico is one of Italy’s most recognizable buildings.

3. Torre del Mangia (the Tower of Mangia) is the tall, skinny tower rising from Palazzo Pubblico. Construction began in 1338, and it took ten years to complete this over 260 feet tall building. From the top of Torre del Mangia, you get breathtaking views of Siena. It is though quite a bit of work to get here. It is over 400 steps to the top, and there is no elevator.

4. The Siena Cathedral, Duomo di Siena, is one of Italy’s most beautiful cathedrals. It was constructed with white and black marble in a striped appearance. It is intriguing and stunning. If you are impressed with the outside, the inside will blow your way. The striped walls, colorful ceilings, and ornately tiled floor make this one of the most unique cathedrals you will see in Italy. There is a dress code to enter the church, so cover those bare shoulders and no short skirts. It is ideal to get tickets in advance to avoid longs and ensure you get to see the inside of the Cathedral.

What not to miss in the Cathedral

Piccolomini Library. The entrance is inside the Cathedral, on the left-hand side of the nave. This colorful room is covered with vibrant frescoes that tell the life story of Pope Pius II. This room also protects the books that the pope collected on his travels.
The Crypt is an area of the complex that was recently excavated. The frescoes in the crypt were painted in the 12th century and portray stories from the Old and New Testaments.
The Baptistery was added to the Siena Cathedral in the early 14th century. The interior of the Baptistery is covered with beautiful frescoes. Donatello, Giovanni di Turino, Lorenzo Ghiberti, and Jacopo della Quercia all contributed to the creation of the Baptismal font.

And there is even more

The Cathedral Museum, also called the Museo dell’Opera, contains many of the original works of art made for the Siena Cathedral. This list includes the stained-glass Rose Window by Duccio di Buoninsegna, Pisano and Donatello sculptures, Duccio di Buoninsegna’s altarpiece, and the Treasury.
The “New Cathedral” is the portion of the Cathedral that was constructed in the 1300s but never finished. The arrival of the Black Death halted construction. What is left behind are the walls and a portion of the nave of the New Cathedral. Referred to as the Panorama or Facciatone, you will find two levels of terraces where you can view the Siena Cathedral and the town of Siena. It is one the best experiences you can have when visiting Siena so don’t miss it.
The Gate of Heaven is a guided tour of the roof and terraces of the Siena Cathedral. It’s one of the best things to do at the Siena Cathedral since you can tour “hidden” areas and get unique views of the nave. Get your tickets in advance.

Beyond the Cathedral

5. Santa Maria della Scala was one of Europe’s first hospitals. Siena is located along the Via Francigena, a pilgrimage path to Rome. This hospital was founded along this route in 898. Over the centuries, the hospital was enlarged several times until it became the enormous complex we see today. This complex contains chapels, frescoes depicting the Life of the Virgin, famous altarpieces, and an archaeological site. Santa Maria della Scala is now a museum where you can visit much of this complex.

6. Fonte Gaia is a fountain located on Piazza del Campo. It was completed in 1342, and the water that supplied the fountain was piped in from almost 16 miles away. In 1419, Jacopo della Quercia sculpted the marble panels that decorate the fountain. Many of the original sculptures were moved to Santa Maria della Scala in 1858 and replaced by copies sculpted by Tito Sarrocchi.

City gates

7. The Siena city gates are similar to those of many Tuscan towns; the city of Siena is surrounded by medieval walls, still mainly intact. Some of these gates are still used as entrances to the city. Most likely, as you enter the historic city center of Siena, whether from the train station or bus station, you will pass through one of these gates. Check out the Porta Camollia, Porta Pispini, and Porta Romano.

8. One of the best things to do in Siena is to explore the maze of streets. Start from Piazza del Campo and wander away. Have a map or your GPS available; it is easy to get lost. The historic heart of Siena is pedestrian-only, except for delivery vehicles. We adored casually strolling the city streets of Siena. You’ll pass by smaller squares, small churches, cafes, shops, and restaurants. There is some good shopping in Siena!

Don’t miss the Basilica

9. The Basilica of San Domenico, also known as Basilica Cateriniana, dates back to the mid-13th century but has been enlarged several times. Inside are several relics of St. Catherine of Siena. St. Catherine was canonized as a saint in 1461 by Pope Pius II and was declared a patron saint of Italy in 1939 by Pope Pius XII.

10. The Palio is a horse race held every year on July 2 and August 16. Ten horses and riders compete, each representing their contrada or neighborhood. Each Contrada has its own colors and mascots, which you can see hanging on flags as you walk through the historic city center. The race is held in Piazza del Campo and lasts only 90 seconds, as the horse and riders make three laps around the square. People gather on grandstands and in the center of Il Campo. It is thrilling to witness if you don’t mind the crowds.

Useful tips for your visit

Buy your entry tickets before your arrival. Even in the shoulder seasons, the lines are long. If there are sites you do not want to miss, get those tickets!
Bring water even in the cooler months to avoid dehydration. This walk has many steps; if sunny, you will be exposed to the full sun for the whole visit.
Wear comfortable and sturdy shoes. Surfaces are always uneven, and stairs are everywhere. You are walking on stone; you may regret that choice if you wear poor footwear.
Go early in the morning to avoid the heat and the packed crowds.
Plan the visit for at least half a day, if not overnight.
Go in the off-season if you can. We went in September, which was our favorite time to visit; the weather was perfect.
Wear sunscreen, a hat, and sunglasses on clear, sunny days, even in the Spring and Fall.

When to visit Siena, Italy

This is a destination you can visit year-round; dress accordingly. We are shoulder season travelers; when tourists pack it in, we avoid it. Many can only travel in the summer based on kids’ school schedules or work obligations, but be prepared for dense crowds. That said, Siena is still worth a visit, even during the busy tourist season.

Siena’s summers are short, hot, and mostly clear skies. The winters can be long, cold, and often cloudy. Over the year, the temperature typically varies from 32°F to 88°F and is rarely below 21°F or above 95°F. Spring and fall, in our view, are the best times to visit. The pictures in this post show the visits in April and September. It was perfection.

Where to Stay in Siena, Italy

Siena has extensive options if you wish to stay there, from luxury to rooms for rent. In our three visits, we never stayed in Siena. We stayed a week in Florence twice and Montisi once. Florence is one of our favorite cities, so it was a great place to launch from. At the same, it would be fun to see what Siena is like in the evening when all the day tourists are gone. On our next visit, we will do just that.

Keep in mind Siena is on a hill. If you want to experience the old city, you need to find accommodations inside the city walls. Since it is a pedestrian-only zone, check with your accessibility accommodations. If you have significant luggage or have mobility issues, that can become an issue. Also, many of these older buildings do not have elevators.

It is important to price out accommodations on various sites. Expedia is a US-based company, whereas Booking.com is Europe-based. Not all properties appear on both, so it is ideal to check both out. Our personal first choice is Booking.com. If the establishment has a website, check the price there as well. Click the link below to check out hotels and vacation homes in the area. It may be just the motivation you need to start planning that next grand adventure.

BOOK NOW

Final Thoughts

Siena, Italy, is a step back in time that draws you in and never lets go. After three visits to this historic city, we would return tomorrow in a heartbeat. The stunning beauty draws you in, and somehow, despite the tourist draw, this is still a vital community deserving of our respect when visiting.

Italy is an incredible country, and places like Siena make it one of our favorite countries in the world. Make sure to look beyond the obvious beauty of this enchanting city and open your heart to the stories the city has to tell. It will enhance your experience in ways you could never imagine and stay with you long after you leave.

Check out the official website for Siena, Italy, for more information.

A Photo Journey to Siena, Italy

Want to learn about Wanderers Compass?

Click Here

Our Top Recommended Travel Products and Services

Travel Insurance

Squaremouth.com
Our favorite travel insurance site!

We could not be stronger advocates of being well-insured—not just for the little stuff but for the big things like medical emergencies. We never leave home without it. Our go-to place is Squaremouth.com. It does a fantastic job with its user-friendly interface and uses top-rated and reputable insurance carriers. They also mediate on your behalf if you have problems.

To empower you as a consumer, we suggest you read our blog post on the importance of travel insurance and how to get the best coverage from top-rated companies for an affordable price.

buy now

MedjetAssist
Medical transport back home from anywhere in the world

They are the premier global air medical transport. One caveat to travel insurance is that medical evacuation usually gets you to the closest facility to care for you. Medjet gets you back to the U.S. to the hospital of your choice once you are stable enough to fly. A Medjet membership is only for medical transport. Medjet Horizon offers expanded coverage. They have individual trip policies starting at $99 and annual policies for around $300. Most of their policies limit the age to 74.

To learn more about how Medical Evacuation membership with Medjet Assist works, check out our blog post for a more detailed review.

Buy now

Accommodations and Airfare

Expedia and VRBO
Hotels, home rentals, BNBs, flights, and other transportation & tours

Expedia is a US-based company whose mission is to power global travel for everyone and everywhere. Wanderers Compass focuses on independent travel, and using sites like Expedia makes that possible. Every aspect of travel you need, from airfare, accommodations, rental car, and cruises to activities to do at your destination, can be booked on Expedia.

Book now

Booking.com
Hotels, Home rentals, BNBs, Flights, and other Transportation & Tours

Booking.com connects millions of travelers to memorable experiences, various transportation options, and incredible places to stay – from homes to hotels and much more. It is one of the world’s largest travel marketplaces for established brands and entrepreneurs of all sizes. It is our preferred booking site.

Book now

Transportation

Daytrip
Personalized city-to-city private car transfer service

Daytrip is an affordable private car service for city-to-city transfers around the world. We love their service, and it costs much less than renting a car. You can enjoy comfortable, stress-free travel with the added bonus of scenic sightseeing stops along your journey. For example, we used them between Budapest and Vienna, making some fantastic stops along the way. Their professional drivers and customizable routes ensure a smooth ride while allowing you to explore hidden gems and local attractions.

To learn more about how Daytrip, check out our blog post for a more detailed review.

Book now

Travel Experiences

Viator
The leading marketplace for travel experiences

Viator believes that making memories is what travel is all about. And with 300,000+ experiences to explore—everything from simple tours to extreme adventures (and all the niche, interesting stuff in between)—making memories that will last a lifetime has never been easier. We use them often during our travels and love their liberal cancellation policy.

Explore now

Communication products for seamless connectivity overseas

GigSky International eSIM Data Plans
Local Prices. No Roaming. Fastest Networks.

GigSky eSIM keeps travelers seamlessly connected worldwide without the hassle of swapping physical SIM cards or facing unexpected roaming charges. With affordable data plans and instant activation, you can enjoy reliable internet access in over 190 countries, making travel more convenient than ever. They have a great offer, a 100 MB data plan for free, and no credit card is required. They are that confident you will love their product!

Enjoy 10% off all GigSky Plans (except cruise and inflight) with our discount code WCOMPASS10

To learn more about how GigSky, check out our blog post for a more detailed review.

SHOP NOW

Shopping

Wanderers Compass Amazon Storefront
An excellent source for all travel essentials and guides

Amazon is one of the most comprehensive online shopping sources in the world. Teams worldwide provide lower prices, better selection, and rapid delivery on behalf of customers. They offer a vast inventory, and their 1.7 million small and medium businesses worldwide selling on Amazon.com offer extensive options to customers.

Shop now

This article contains affiliate links. If you use these links to buy something, we may earn a small commission at no additional cost to you. Thank you!