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Discover Siena’s highlights and flavors in a 2.5-hour small-group or private walking tour featuring iconic sights and delicious local food tastings for $88.73

The Siena Sightseeing Walking Tour with Food Tastings offers an engaging way to experience the heart of this medieval Tuscan hilltown. Priced at $88.73 per person, this 2.5-hour tour is perfect for those eager to combine sightseeing with tasting Siena’s local flavors. It caters to small groups or private bookings, providing an intimate experience with a knowledgeable guide.
This tour covers key highlights such as Piazza del Campo, the Cathedral, and the Basilica Cateriniana di S. Domenico, all while offering delicious food stops along the way. It’s especially suited for visitors who want a relaxed pace, focus on culture, and enjoy sampling regional specialties. A notable strength is the inclusion of food tastings, which deepen the connection to Siena’s culinary traditions, though the tour involves a fair amount of walking through uneven medieval streets.

This tour’s main appeal is the combination of cultural landmarks and local food tastings within a manageable timeframe. The small group or private format ensures personalized attention, with a maximum of 12 participants. Tours are booked on average 59 days in advance, indicating high popularity and confidence in the experience.
You’ll meet your guide in the historic heart of Siena, ready to lead you through its most treasured sites. The price of $88.73 is competitive, especially considering the food tastings and guided commentary included. The tour takes place rain or shine, making it a reliable activity despite weather conditions.
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Your journey begins at the Basilica Cateriniana di S. Domenico, an important religious site that houses the relics of Saint Catherine of Siena. This stop is free of charge and lasts about 30 minutes, offering an opportunity to learn about the city’s spiritual history and the significance of Saint Catherine for Siena.
This basilica also plays a vital role in Siena’s Palio tradition, connecting faith, culture, and local identity. Visitors can appreciate the architecture and the history behind this influential church without feeling hurried, thanks to the relaxed pace of the tour.

Next, the tour guides you through Piazza Salimbeni, a historic area featuring the Contrade, Siena’s districts and teams of the Palio. Each Contrada has its own symbol, flag, and motto, and the guide shares stories about their rivalries and traditions.
A highlight here is the visit to one of the Contrada neighborhoods, providing a firsthand look at these lively, deeply rooted community identities. The free 30-minute stop offers insights into how the Palio’s district-based competition shapes Siena’s social fabric, making it a meaningful cultural experience.

The tour’s most recognizable stop is the Piazza del Campo, a shell-shaped square famous worldwide. The Palazzo Pubblico and the high tower dominate this square, revealing Siena’s medieval grandeur. This is also the location of the twice-yearly Palio horse race, drawing crowds from around the globe.
Here, the tour features a food tasting of local sweets such as ricciarelli biscuits, served at a traditional shop. This pause not only satisfies the palate but also offers a chance to learn about Siena’s culinary heritage. The 45-minute segment is leisurely enough to soak in the atmosphere and take photos of one of Italy’s most picturesque squares.

A short walk takes visitors to the Siena Cathedral, an exquisite Gothic structure celebrated for its architectural beauty and artistic treasures. The guide highlights the cathedral’s elegance and historical importance, including its role as a pilgrims’ hospital in medieval times.
Spending around 30 minutes here, visitors can admire the famous façade, interior artworks, and pilgrims’ hospital structure, gaining appreciation for Siena’s medieval wealth and cultural prominence.
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The final stop is Via di Città, a medieval street where the tour wraps up. This relaxed stroll allows for last-minute photos and reflections on the sights seen. The tour ends here after approximately 15 minutes, giving guests the chance to continue exploring Siena independently or head to nearby sites.

The tour starts at the Basilica Cateriniana di S. Domenico, located at Piazza S. Domenico. The end point is Piazza del Campo, a central and easily accessible location. The tour is suitable for most travelers, including families with children under 12, who receive children’s menus.
The walking route involves streets with uneven surfaces, typical of medieval towns, so comfortable shoes are recommended. The tour operates rain or shine, making it a reliable activity regardless of weather. Service animals are allowed, and public transportation options nearby facilitate access.

The $88.73 price includes guiding services, food tastings, and entry to key sites, making it a good value for those interested in both culture and cuisine. It is recommended to book about 2 months in advance, reflecting its popularity. The tour is designed for small groups of up to 12, ensuring a more personalized experience.
Guests can cancel for free up to 24 hours before the experience, providing flexibility in planning. The small group size encourages interaction and tailored commentary, especially beneficial for first-time visitors or those wanting in-depth insights.
Reviews highlight the expertise and personable nature of guides like Elena, Claudia, Ania, and Anna. They are praised for their knowledge, friendliness, and ability to tailor the experience—making the tour feel more like a friendly exploration rather than a formal lecture.
Guests appreciate the balance of sightseeing and food tastings, with many noting that the food stops—including panini stuffed with Tuscan delicacies and almond cookies—are memorable highlights.
This tour suits those eager to combine cultural sights with culinary experiences in Siena. It’s ideal for visitors who enjoy small, intimate groups or private tours for a more customized outing. The moderate pace and manageable duration make it perfect for families, seniors, or anyone wanting an overview without feeling rushed.
The inclusion of local food tastings adds a flavorful layer to the sightseeing, appealing to food lovers and curious travelers alike. However, guests should be prepared for moderate walking on uneven streets and a tour in any weather.
This 2.5-hour tour offers a well-rounded glimpse of Siena’s most iconic sites combined with delicious local foods. The small group or private format, expert guides, and authentic tastings create an engaging and authentic experience.
While not a deep dive into Siena’s entire history, it provides enough depth to appreciate the city’s art, architecture, and culture, all in a relaxed setting. It’s especially suitable for first-time visitors who want a taste of both Siena’s sights and flavors without the stress of large tours or extensive walking.
“We lucked out and had an amazing tour with Elena. She was absolutely phenomenal and so knowledgeable and personable. My husband and I really enjoy…”
How long does the tour last?
The tour lasts approximately 2 hours and 30 minutes.
What is included in the tour price?
The guided walk, food tastings, and entry to key sites are included.
Can I cancel the tour?
Yes, free cancellation is available up to 24 hours before the experience.
Is the tour suitable for children?
Yes, children under 12 are welcome and will receive children’s menus.
Where does the tour start and end?
It starts at Basilica Cateriniana di S. Domenico and ends at Piazza del Campo.
Is this tour accessible?
The route involves walking on uneven medieval streets, so comfortable shoes are recommended.
What if it rains?
The tour operates rain or shine.
How many people can join?
A maximum of 12 travelers ensures an intimate experience.
Do guides have special expertise?
Guides are praised for their knowledge, personable approach, and ability to share stories about Siena’s culture and traditions.
Is there a food component?
Yes, multiple food tastings like panini with Tuscan delicacies and almond cookies are included at various stops.