15 Best Siena Tours

Siena, located in the Tuscany region of central Italy, just a short drive south of Florence, is a medieval city known for its impressive architecture and rich historical sights as well as twice a year held near the central square famous for horse racing.

The city has been likened to a large open-air gallery with a priceless collection of art. For those interested in exploring its history and culture, there are plenty of tour options, ranging from a few hours to full-day activities.

Here are 15 of the best tours in Sienna, exploring everything from food and natural attractions to archaeology and medieval history.

1. Siena 2-Hour Walking Tour with Cathedral Skip-the-Line Ticket

Campo Square, Siena

Piazza del Campo in Siena is the central square where many of the most iconic sights are located.

On this two-hour walking tour, guests and their guide will visit a UNESCO World Heritage Site, explore other important historic buildings such as the Palazzo Tolomé and the Basilica of San Domenico, and enjoy skip-the-line access to the Basilica tickets.

Dating back more than 1,000 years, the city’s many attractions, with impressive architecture, fascinating history and interesting cultural aspects, may be missed by self-guided tourists.

The tour lasts about two hours and requires a lot of walking, so please dress appropriately and wear appropriate shoes.

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2. Educational wine tours and tastings

Wine Tour and Tasting, Siena

Italy is one of the most important wine cultures in the world, and no matter which part of the country you choose to visit, you won’t be far from a vineyard or winery.

While many wine-focused tours focus solely on tasting, this one delves into the history of wine, its cultural significance, and how grapes grow in temperate climates and become such delicious and beloved intoxicants.

Guests will explore organic wineries on the outskirts of Siena with their guide and host, after which they will enjoy wine tastings and a light Tuscan-style lunch in a beautiful rural setting.

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3. 4-Hour Tuscan Cooking Class in Siena

Tuscan cooking class

Many tourists to Italy spend as much time dining as seeing and experiencing the country’s impressive sights.

While there’s nothing wrong with that, for true foodies and amateur chefs, taking a cooking class with a local is definitely a value-added option for those who prefer a hands-on tour.

This four-hour morning cooking class combines culinary and cultural aspects. Before putting their new knowledge into practice, guests will learn about basic Tuscan cooking techniques and how to choose the right ingredients.

Guests are free to enjoy the fruits of their labor and spend the rest of the afternoon and evening free for other adventures.

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4. Half-Day Guided Walking Tour from Siena to Monteriggioni

Monteriggioni, Italy

For those who have just spent countless hours on an international flight or a crowded transfer bus, a trip to the great outdoors is a great way to reactivate dormant muscles and see things from a local’s perspective.

This half-day tour starts from Siena and includes the services of a local guide who will lead healthy and enthusiastic tour participants to an impressive array of sites, including scenic vineyards, extensive olive groves and the city walls medieval fortress.

In Monteriggioni, guests will explore historic places, taste local organic wines, and have time to relax or explore on their own.

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5. Small Group Electric Bike Tour and Winery Lunch

Electric Bike Tour with Winery Lunch

Electric bike tours are perfect for those who like to experience the great outdoors without breaking a sweat and getting unnecessarily tired.

Along with their experienced cyclists and local guides, guests on this small-group tour will explore the scenic Chianti Roads, learn about the history and culture of the area, and interact with the hordes of tourists who tend to congregate around more of the city’s attractions Keep enough distance.

The tour includes stops at a local convent and family-owned winery, where they will enjoy wine tasting and a full lunch, before returning to Siena in a comfortable air-conditioned van.

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6. Guided walking tour with optional cathedral visit

Siena Cathedral

With its narrow streets, impressive architecture and historic charm, Siena is a walkable city popular with active holidaymakers who prefer shoe leather and sports over air conditioning and tourist buses.

Despite being a relatively short two-hour period, the tour covers a lot, including stops at many of the city’s attractions, such as Piazza del Campo, the Public Palace, and the Contrada Museum.

The museum is a treasure trove of information about the city’s history, traditions and unique communities, as well as art, archaeology and artifacts.

If time permits, guests can also choose to visit the Libreria Piccolomini.

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7. Vintage Fiat 500 Tour and Chianti Roads from Siena

500 Retro Tour

While they’re a far cry from the Ferraris and Lamborghinis that appeal to many car enthusiasts, the Fiat 500 is a quintessentially Italian car and a popular means of transport for locals and tourist suppliers alike.

Starting at 9:30am, this 8-hour drive-thru tour is limited in size and offers guests breathtaking views of the city and countryside they may not otherwise be able to see, while experiencing the personal service of a driver and guide.

The tour includes a light, traditional lunch at a Chianti winery and stops at many scenic sights, historical sites, and medieval villages that time seems to have forgotten.

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8. Horseback riding from Siena

Horseback riding from Siena

From fiats and e-bikes to horseback riding and hiking, there really isn’t a bad way to experience the splendor of Siena and the surrounding area.

While horses can be intimidating to the uninitiated, this horseback trek from Siena provides guests with all the training and safety equipment they need, each equipped with a patient steed with plenty to transport newbies tourist experience.

The speed of the tour may vary depending on the age and skill of the participants, and along the way everyone will enjoy idyllic natural areas, ancient vineyards and stunning views of the countryside.

The tour lasts approximately 90 minutes and includes round-trip transportation to and from Siena.

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9. Pienza and Montepulciano Small Group Tour from Siena

Montepulciano, Italy

Today, travel that packs great value into affordable small-group packages is gaining traction with savvy international travelers.

If that sounds like you, then this 8-hour multi-stop tour from Siena would be a great option.

While learning about the history and culture of the area from a driver-guide, guests will put the city in the rearview mirror as they explore the villages of Pienza and Montepulciano.

Attractions include palatial palaces, local family-run dairy and award-winning wineries.

Along the way guests will also enjoy a traditional lunch as well as a variety of food and wine.

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10. Medieval Legends Exploration Games and Tours

Fonte Gaia, Siena

Self-guided exploration games are becoming a popular tourist activity for those who value mental engagement, physical activity, and seeing things at their own pace.

Using the mobile app as a guide, guests will begin a fun and educational tour of Siena using riddles and clues to guide them from one attraction to the next.

This is a great activity for small groups and families traveling with young children. Excursion stops include the majestic Gaia Fountain, Piazza del Duomo and Palazzo Tolomei.

Tours usually last less than two hours, and participants often discover things they want to explore on their own later.

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11. 5-Hour Chianti and San Gimignano Tour from Siena

San Gimignano, Italy

During the hot summer months, an air-conditioned coach is a great way to quickly see many sights without having to spend unpleasant hours in the sun.

On this five-hour tour from Siena, guests will enjoy the services of a local guide and commentary as they leave the city to explore Chianti and San Gimignano.

The region is characterised by rolling hills, quaint little villages and an abundance of wineries producing world-famous red wines.

Guests will learn about viticulture and winemaking, and sample a variety of wines with local delicacies such as cheeses, cured meats and bruschetta.

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12. Life at St Catherine’s Tour

Basilica of San Domenico, Siena

More than 500 years ago, Siena was the birthplace of St. Catherine. 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 shrine. It consists of three different speeches from different eras detailing her life journey.

Participants will also visit the Basilica of San Domenico and the Baptistery. Depending on the time available, they may choose to enter other attractions for a modest additional fee if they want to spare no expense.

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13. Vespa Tour in Chianti and Tuscan Hills


The mountains of Tuscany offer visitors some of the most stunning landscapes and attractions in the country. For those who don’t mind spending most of their time on two wheels, the Vespa is a go-to tourist vehicle.

From Siena, guests will take a bus to Chianti, where they will meet the guide and get their Vespas.

They’re fun, safe and easy to drive, and everyone gets an in-depth guide before hitting the open road.

The tour lasts about 7 ½ hours and includes wine tasting and a traditional Tuscan lunch, and those who are uncomfortable with driving can sign up for a ride behind the guide.

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14. Siena Street Food Tour with a Local Guide

Narrow street, Siena, Italy

While this may sound like a cliché now, there’s no better way to experience cultural immersion than avoiding the tourist crowds and dining with the locals.

Food-loving guests will do so on this 2 ½ hour tour. They’ll see some of Siena’s most famous sights and learn a lot about the culture along the way.

Tours cover multiple neighborhoods within the city. Although they are all relatively close to each other, they have their own unique traditions and cuisines.

Guests will visit four different restaurants, rub shoulders with working men and women, and sample everything from soups and homemade pasta to cured meats and traditional Tuscan ice cream.

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15. Historic Siena Guided Walking Tour

Campo Square, Siena

Siena is a treasure trove of artistic, historical, religious and cultural attractions. Most of them are so close to each other that many of them can be seen in just a few hours.

This means that no time is wasted traveling between sites. During this tour, guests will spend most of their time learning from local guides.

Tourist highlights include Piazza del Campo, Palazzo Communale and the impressive Basilica of San Domenico in the city centre.

Depending on the time and the interests of the guests, it is also possible to visit the cathedral.

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