Located in central Italy’s Tuscany region, just a short drive south of Florence, Siena is a medieval city that’s known for its impressive architecture and abundant historical attractions, as well as the horse race that’s run near the central piazza twice annually.
The city has been likened to a large open-air gallery that’s home to an array of priceless art collections. For those interested in exploring its history and culture, there are ample tour options ranging from just a few hours to all-day affairs.
Below are 15 of the best tours of Sienna that explore everything from cuisine and natural attractions to archaeology and medieval history.
1. Siena 2-Hour Walking Tour with Skip-the-Line Duomo Tickets
Siena’s Piazza del Campo is the central square around which many of its most iconic attractions are located.
On this two-hour walking tour, guests and their guide will visit the UNESCO World Heritage Site, explore other key historical structures like Palazzo Tolomei and Basilica San Domenico, and enjoy skip-the-line tickets to the duomo.
Many of the city’s attractions date back more than 1,000 years and feature impressive architecture, fascinating histories, and interesting cultural aspects that those on self-guided tours may miss.
Tours last about two hours and require significant amounts of walking, so dress accordingly and wear appropriate footwear.
2. Educational Wine Tour and Tasting
Italy is one of the world’s premier wine cultures, and no matter what part of the country you choose to visit, you’ll never be very far from a vineyard or winery.
Whereas many wine-centered tours focus solely on tasting, this one delves into wine’s history, cultural significance, and how grapes are grown in the temperate climate and turned into such tasty and much-loved intoxicants.
Along with their guide and host, guests will explore an organic winery just outside Siena, after which they’ll enjoy a wine tasting as well as a light Tuscan-style lunch in an amazingly beautiful country setting.
3. Siena 4-Hour Tuscan Cooking Class
Many visitors to Italy spend as much time eating as they do seeing and experiencing the country’s impressive attractions.
Though there’s nothing wrong with that, for true foodies and amateur chefs, cooking classes with locals are definitely value-added options for those who prefer tours with hands-on activities.
This four-hour, mid-morning cooking class has both culinary and cultural aspects. Guests will learn about basic Tuscan cooking techniques and how to select suitable ingredients before putting their new knowledge into practice.
Guests will get to consume the fruits of their labor and have the rest of the afternoon and evening free for other adventures.
4. Half-day Guided Hike from Siena to Monteriggioni
For those who’ve just spent countless hours on international flights or overcrowded transfer buses, outdoor activity tours are great ways to reactivate dormant muscles and see things from a local’s perspective.
This half-day tour begins in Siena and includes the services of a local guide, who will lead fit and eager tour participants to an impressive array of attractions, including scenic vineyards, sprawling olive groves, and a medieval fortress in a walled city.
In Monteriggioni, guests will explore historic attractions and participate in a tasting of local, organic wines, as well as have time to relax or explore on their own as well.
5. Small Group E-Bike Tour with Winery Lunch
E-bike tours are perfect options for those who like to experience the great outdoors without working up a sweat and wearing themselves out needlessly.
Along with their experienced biker and local guide, guests of this small-group tour will explore scenic Chianti roads, learn about the area’s history and culture, and put sufficient distance between themselves and the hordes of tourists that tend to congregate around more urban attractions.
Tours include a stop at a local monastery and a family-owned winery, where they’ll enjoy a wine tasting and full lunch before returning to Siena in the comfort of an air-conditioned van.
6. Guided Walking Tour with Optional Cathedral Visit
Featuring narrow streets, impressive architecture, and gobs of historic allure, Siena is a pedestrian-friendly city that’s popular with active vacationers who prefer shoe leather and exercise to air conditioning and tour buses.
Despite its relatively short duration of just two hours, the tour covers lots of ground and includes stops at many of the city’s attractions, like Piazza del Campo, Palazzo Publico, and the Museum of the Contrada.
The museum is a treasure trove of information pertaining to the city’s history, traditions, and distinct neighborhoods, as well as art, archaeology, and artifacts.
Guests may also choose to visit Libreria Piccolomini if time permits.
7. Vintage Fiat 500 Tour and Chianti Roads from Siena
Though they’re a far cry from the Ferraris and Lamborghinis that capture so many car enthusiasts’ minds, Fiat 500s are quintessentially Italian automobiles that are popular means of transportation for locals and tour providers.
Starting at 9:30 AM, this eight-hour driving tour is limited in size and offers guests incredible views of the city and countryside that they may not see otherwise, all while experiencing personalized service from their driver and guide.
Tours include a light, traditional lunch at a Chianti winery and stops at a number of scenic vista points, historical attractions, and medieval villages that seem to have been forgotten by time.
8. Horseback Riding from Siena
From Fiats and e-bikes to horses and hikes, there really are no bad ways to experience the splendor of Siena and the surrounding area.
Though horses can be intimidating for the uninitiated, this horseback trek from Siena offers guests all the training and safety equipment they’ll need, and everyone is paired with a patient steed with tons of experience transporting rookie tourists.
Tour pace can vary depending on the ages and skills of participants, and along the way, everyone will enjoy idyllic natural areas, old vineyards, and amazing views of the countryside.
Tours last about 90 minutes and include round-trip transportation to and from Siena.
9. Pienza and Montepulciano Small Group Tour from Siena
Tours that pack big value into reasonably priced, small group packages are becoming all the rage with savvy international travelers these days.
If that sounds like you, then this eight-hour, multi-stop tour from Siena would be a good fit.
While learning about the region’s history and culture from their driver-guide, guests will put the city in the rearview mirror while exploring the villages of Pienza and Montepulciano.
Attractions include an opulent palace, a local family-owned dairy, and an award-winning winery.
Guests will enjoy a traditional lunch and a number of food and wine samplings along the way too.
10. Medieval Legends Exploration Game and Tour
Self-guided exploration games are becoming popular tour activities for those who value mental engagement, physical activity, and seeing things at their own pace.
Using a phone app as their guide, guests will embark on a fun and educational tour of Siena using riddles and clues to lead them from one attraction to the next.
It’s a great activity for small groups and families traveling with little ones. Tour stops include the majestic fountain of Gaia, Piazza del Duomo, and Palazzo Tolomei.
Tour games generally last less than two hours, and participants often discover things they’d like to explore on their own later.
11. 5-Hour Chianti and San Gimignano Tour from Siena
When the weather is hot during the summer months, air-conditioned coach tours are great ways to see lots of attractions quickly without spending unpleasant time out in the sun.
On this five-hour tour from Siena, guests will enjoy the services of a local guide and narrator as they leave the city and head out to explore Chianti and San Gimignano.
The area is characterized by rolling hills, quaint hamlets, and abundant wineries that produce red wine known around the world.
Guests will learn about grape growing and winemaking and sample a variety of wines with local fare, like cheese, cured meats, and bruschetta.
12. The Life of St. Catherine Tour
Siena was the birthplace of St. Catherine more than 500 years ago. The mid-15th century sanctuary built after her canonization is one of the city’s most iconic attractions.
On this three-hour guided tour, guests will learn about her life and explore the sacred sanctuary. It is comprised of three distinct oratories from different eras that describe her life’s journey in great detail.
Participants will also visit the Basilica of San Domenico and the Baptistery. Depending on available time, they may choose to enter additional attractions at only moderate extra cost if they’d like to leave no stone unturned.
13. Vespa Tour of Chianti and Tuscan Hills
Tuscany’s hill country offers visitors some of the country’s most amazing scenery and attractions. For those who don’t mind spending most of their day on two wheels, Vespas are a premier means of tour transportation.
From Siena, guests will make their way to Chianti by bus, where they’ll meet their guide and get their Vespas.
They’re fun, safe, and easy to drive, and everyone gets an in-depth orientation before heading out onto the open road.
Tours last about 7 ½ hours, include a wine tasting and traditional Tuscan lunch, and those who don’t feel comfortable driving can sign up to ride behind a guide.
14. Siena Street Food Tour with Local Guide
Though by now it may sound like a well-worn cliché, there aren’t many better ways to experience cultural immersion than by avoiding the tourist crowds and dining with locals.
On this 2 ½-hour tour, food-loving guests will do just that. They’ll see some of Siena’s most prominent attractions and learn a lot about the culture along the way as well.
Tours cover multiple neighborhoods within the city. Though they’re all relatively close to one another, they’ve got their own unique traditions and cuisines.
Guests will hit four different eateries, rub elbows with working men and women, and sample everything from soup and homemade pasta to cured meat and traditional Tuscan ice cream.
15. Historic Siena Guided Walking Tour
Siena is a treasure trove of artistic, historic, religious, and cultural attractions. Most of them are located so close to one another that it’s possible to see many of them in just a few hours.
That means no time wasted traveling between sites. On this tour, guests will spend the majority of their time on their feet learning from their local guide.
Tour highlights include the centrally located Piazza del Campo, Palazzo Communale, and the impressive Basilica of San Domenico.
Depending on time and the interests of guests, it may be possible to visit the Cathedral as well.