Why Siena is a Top Choice for Tours
Siena isn’t just a postcard-perfect Tuscan town; it’s a place where walking through its narrow streets feels like stepping back into medieval Italy. Its well-preserved architecture, lively contrade traditions, and iconic Piazza del Campo make guided tours not only practical but enriching. We especially love the Siena: Horseback Riding Tour in the Tuscany Countryside for its unique blend of outdoor adventure and scenic beauty, and the Discover the Medieval Charm of Siena on a Private Walking Tour for a personalized dive into its history.
Siena’s compact old town is perfect for exploring on foot, whether you’re interested in its ancient churches, lively markets, or Palio horse race. With this variety of tours, you can choose everything from private walks and food tastings to full-day wine adventures.
Quick Overview
Siena offers a range of tours to suit different tastes and schedules. You might enjoy a half-day private walking tour (link) if you want an intimate look at its history, or a full-day wine tour (link) if wine and scenery are your priorities. For those craving local flavors, the Siena’s Ultimate Food Tour (link) offers a tasty way to experience Tuscan cuisine. Fancy an outdoor ride? The Horseback Riding is perfect for scenic hill-country explorers, while the Vespa & Chianti Tour combines speed, style, and wine.
1. From Florence: San Gimignano, Siena, and Chianti Wine Tour
This 9-hour guided small-group tour is a fantastic way to see Tuscany’s highlights in one day. Starting at Florence’s Piazza del Duomo, you’ll venture into the countryside to visit San Gimignano, famed for its medieval towers and Vernaccia wine, and then head to Siena, the city of the Palio. The tour includes a visit to a Chianti estate, where you’ll taste five exclusive wines, followed by a Tuscan lunch featuring cheeses, meats, and truffle lasagna.
What makes this trip stand out is the blend of historic towns, scenic drives, and wine tasting—all with a friendly guide and small-group intimacy. Reviewers love the well-organized itinerary and excellent guides like Marco and Lyla, who share stories and wine tips. A typical day includes stops at Fortezza Medicea, San Gimignano’s towers, and a Chianti estate, with plenty of free time for exploring.
Bottom line: This tour offers a perfect mix of culture, scenery, and wine, making it ideal for travelers wanting a comprehensive day in Tuscany.
2. Discover the Medieval Charm of Siena on a Private Walking Tour
For those who prefer a personalized experience, this 2 to 3-hour private walking tour is a stellar choice. Led by a local guide, you’ll stroll Siena’s picturesque streets, visiting landmarks like Piazza del Campo, the Basilica of San Domenico, and the Sanctuary of St. Catherine. You can also opt to add a visit to Siena’s magnificent Duomo, which houses incredible Renaissance art.
This tour is perfect if you want a flexible schedule and tailored commentary. Reviewers appreciate guides like Sabrina and Barbara for their knowledge and friendliness. The tour’s highlights include stories about the Palio horse race and Siena’s contrade districts, bringing the city’s living traditions to life.
Bottom line: An excellent option for first-time visitors wanting a deep, personalized introduction to Siena’s history and culture.
3. Siena: Horseback Riding Tour in the Tuscany Countryside
If you’re craving an outdoor adventure, this 1.5-hour horseback ride takes you through vineyards, olive groves, and cypress-lined roads just outside Siena. Suitable for all levels, the tour includes learning about local flora and fauna from your guide, plus options to enjoy a picnic by the river or a wine tasting at a nearby winery.
Guests rave about how well-trained the horses are and the stunning landscapes. The guide’s friendly and attentive nature ensures even nervous beginners feel safe, while experienced riders enjoy the scenic gallops. The tour’s highlights include a relaxed ride through beautiful Tuscan scenery and insights into local agriculture.
Bottom line: Perfect for outdoor lovers and first-time riders who want to experience Tuscany from horseback.
4. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
This 8-hour full-day tour from Siena is the ultimate way to indulge in Tuscan wines and local cuisine. Starting with a visit to two Brunello wineries, you’ll taste regional wines and learn about their production. Afterward, explore Montepulciano, a Renaissance town with spectacular views of the Val d’Orcia, and enjoy a tasty lunch paired with local wines.
What sets this tour apart is the depth of wine tastings and the chance to meet the winemakers. Reviewers like Talia and Michaela praise the knowledgeable guides, delicious food, and scenic drives. Hotels and accommodations are included in the pickup, making the day seamless.
Bottom line: Ideal for wine lovers who want an immersive experience with regional food and without the hassle of planning.
5. Private Tour: Siena Walking Tour
If you prefer the exclusivity of a private guide, this 2-hour private walking tour is a great choice. Led by a licensed local guide, you’ll explore Siena’s key sights, such as Piazza del Campo, Duomo, and Basilica of San Domenico. The guide customizes the itinerary to suit your interests, allowing for a more relaxed pace and personalized insights.
Reviews highlight guides like Chiara and Silvia for their enthusiasm and knowledge. The tour includes skip-the-line tickets for the Duomo, saving you time. It’s especially good for travelers short on time but wanting a rundown of Siena’s art and architecture.
Bottom line: A flexible, intimate option for those who want a tailored Siena experience with expert guiding.
6. Siena’s Ultimate Food Tour: Full Tuscan Meal with a Local
For foodies, this 3-hour walking tour combines culinary delights with cultural insights. Led by a local food expert, you’ll visit historic eateries, cafes, and local restaurants to sample Sienese specialties like regional cheeses, cured meats, and Lasagne al Tartufo. Along the way, you learn about Siena’s food traditions and culture.
Reviews like Sandra and Alexandra mention the delicious food, knowledgeable guides, and walking around the heart of Siena. The tour is perfect if you want to taste authentic cuisine while discovering the city’s hidden culinary spots.
Bottom line: Best suited for travelers wanting a delicious and cultural introduction to Siena’s gastronomic scene.
7. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
This 11-hour guided day trip from Florence makes exploring three iconic towns easy. Start in San Gimignano’s medieval streets, then head to Monteriggioni, a tiny fortress town, and finish with a winery visit in Chianti. The tour features free time at each stop and a lunch with wine tasting.
Guests appreciate the comprehensive itinerary and the informative commentary from the tour leader. It’s well-suited for travelers wanting to see multiple towns in one day without the stress of planning logistics. The lunch and wine tasting add a great flavor of local culture.
Bottom line: Excellent for those looking to maximize sights and tastes in a full-day experience.
8. Chianti: Wine and Olive Oil Tasting with Cellar Tour
A short but sweet 1-hour tour into the heart of Chianti. Visiting an authentic farmhouse, you’ll taste local wines and olive oils and explore the 18th-century wine cellar. It’s a practical choice for sampling Tuscan flavors without a big time commitment, and the rustic setting adds charm.
Guests mention the friendly staff and delicious tastings. This tour is especially good for those who want a quick, authentic experience of Chianti’s culinary traditions. It’s also budget-friendly at just $35 per person, offering great value.
Bottom line: Perfect for a brief, authentic taste of Chianti’s wines and oils.
9. Siena Guided Tour with Cathedral and Optional Crypt & Museum
This 2 to 3-hour guided tour offers a rich introduction to Siena’s highlights, including Piazza del Campo, the Duomo, and San Domenico. It includes skip-the-line tickets and the option to visit crypts and museums. The guide shares insights into Siena’s religious and artistic history.
Reviewers like Ludovica rave about her knowledge and friendliness, and many value the skip-the-line access which saves precious time. The tour is a good pick for travelers wanting an in-depth overview with flexible options.
Bottom line: An excellent choice for those interested in art, architecture, and religious sites.
10. Private Guided Tour of Siena with a Licensed Local Tour Guide
This 2-hour private tour offers a customized exploration of Siena’s top sights, including Piazza del Campo, the Duomo, and St. Catherine’s Church. Your guide tailors the route to your interests, providing personalized commentary and skip-the-line tickets.
Guests note the friendly, knowledgeable guides like Chiara and Silvia, who make the experience feel like exploring with a friend. The private setup is ideal if you want flexibility and a more intimate encounter with Siena.
Bottom line: Best for travelers who want a bespoke tour with personal attention.
11. From Siena/Badesse: Vespa & Chianti Tour in the Tuscan Hills
For a stylish adventure, this 4-hour Vespa tour takes you through Chianti’s rolling hills. Starting from Siena or Badesse, you’ll ride vintage Vespa scooters past vineyards and olive groves, with stops for wine tastings and photo opportunities.
Riders rave about how easy and fun the Vespas are, even for beginners. The guide’s friendly demeanor and the stunning scenery make it a memorable experience—especially for those who want to combine sightseeing and adventure.
Bottom line: Perfect if you want to explore Tuscany in style and speed on two wheels.
12. Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private
This 2.5-hour tour combines culture and cuisine as you walk Siena’s medieval streets, sampling local delicacies like panini and almond cookies. Led by a friendly guide, you’ll visit sites like Piazza del Campo and the Basilica of San Domenico, with food tastings in between.
Reviewers appreciate the small-group intimacy and the insightful commentary. It’s a great way for food lovers to experience Siena’s culinary traditions alongside its historic sights.
Bottom line: Well-suited for those seeking a flavorful taste of Siena’s food and history in a short, friendly tour.
13. Chianti Wines and San Gimignano Tour from Florence (1 Winery)
This 5-hour tour from Florence visits San Gimignano’s towers, Monteriggioni, and includes a wine tasting at a Chianti winery. It’s ideal for those who want to combine sightseeing with wine tasting in a condensed day. You’ll have free time in San Gimignano to explore, shop, or just enjoy the scenery.
Guests love the quality of wines and the expert commentary from the guide. It’s a convenient way to see multiple towns without planning logistics.
Bottom line: A practical, wine-focused day trip for those staying in Florence but eager to explore Siena and surroundings.
14. Siena walking tour with lunch & Chianti wine
This 2.5-hour tour combines Siena’s landmarks, local food, and Chianti wine in a relaxed setting. Starting with a walk through Siena’s medieval streets, you’ll sample regional foods and enjoy a lunch paired with Chianti wines. Led by a friendly guide, you’ll also discover hidden alleys and spectacular views.
Reviews mention the excellent food and knowledgeable guides like Angie and Sandra. The tour is perfect if you want a balanced mix of sightseeing, eating, and drinking.
Bottom line: An enjoyable way to experience Siena’s culinary delights and historic sights in one outing.
How to Choose Your Siena Tour
When selecting a tour, consider your interest level and pace. If you want a deep dive into Siena’s art and architecture, the Private Guided Tour offers tailored insights. For wine lovers, the Full-Day Montepulciano Wineries or Chianti wine and olive oil tasting provide immersive tastings.
Budget-conscious travelers might prefer shorter excursions like the Chianti: Wine and Olive Oil Tasting or the Vespa & Chianti Tour. If you’re pressed for time, a Siena Guided Tour with Cathedral can give you a quick yet rundown.
Booking early is wise, especially in peak season, to secure your preferred time and tour.
To sum it up, Siena offers a variety of tours tailored to different interests—whether you want a private stroll, a hearty food experience, or a scenic ride through Chianti. For first-timers, a private walking tour combined with a full-day wine adventure makes for a memorable visit. For those seeking a more active experience, horseback riding or Vespa tours deliver unique perspectives of the rolling Tuscan landscape.
Whatever your choice, Siena’s charm lies in its medieval streets, lively contrade, and delicious food, so don’t wait—book early and enjoy a truly authentic Tuscan experience.