Siena’s charm extends far beyond its striking medieval architecture. It’s a city alive with tours and experiences that reveal its rich traditions, mouthwatering cuisine, and breathtaking landscapes. Whether you’re into tasting world-class Chianti wines, walking along paved alleys lined with history, or soaring above Tuscany in a hot air balloon, Siena offers something for every kind of traveler. We especially love the From Florence: San Gimignano, Siena, and Chianti Wine Tour, because it combines a scenic drive with visits to iconic towns and exclusive wine tastings, making it a top choice for a full day of indulgence. For those seeking a more intimate exploration, the Discover the Medieval Charm of Siena on a Private Walking Tour offers a deep dive into the city’s hidden stories, perfect for discovering Siena at your own pace.
If you’re craving a culinary adventure, the A Brunello Cooking Class with Vineyards View Winery provides hands-on lessons paired with spectacular vineyard vistas—and a delicious, homemade Tuscan meal. Or, for a truly unforgettable experience, consider the Siena: Balloon Flight Over Tuscany—an exhilarating way to see the rolling hills from above, ending with a toast of prosecco. Whatever your interests, Siena’s vibrant mix of food, wine, history, and landscapes will leave you wanting more.
Quick Overview
In this guide, we’ve gathered 14 of the best tours and experiences in Siena, focusing on everything from wine tastings and cooking classes to guided city walks and adventure activities. Whether you want a full-day tour exploring Chianti and San Gimignano, a private walking tour tailored to your interests, or an adrenaline-filled balloon ride, each offers a unique way to savor Siena’s atmosphere. For a detailed look at each, keep reading.
1. From Florence: San Gimignano, Siena, and Chianti Wine Tour
At number 1, this 9-hour small-group guided tour takes you through Tuscany’s most picturesque towns. Starting from Florence, you’ll visit San Gimignano, famous for its medieval towers and Vernaccia wine, and explore Siena, known worldwide for its Palio horse race. The tour includes a visit to a Chianti estate with five exclusive wine tastings and a traditional Tuscan lunch featuring cheeses, meats, and truffle lasagne. The mix of scenery, history, wine, and food makes this a well-rounded experience. Customers consistently praise the guides’ friendliness and the smooth organization. One reviewer notes, “The views were breathtaking, and the wine was incredible.” This tour is ideal for those wanting a comprehensive day of sightseeing and tasting in Tuscany, with plenty of time to enjoy each stop.
Bottom line: A great choice for first-timers or anyone wanting a complete Tuscan experience in one day, especially if you’re traveling from Florence.
2. Discover the Medieval Charm of Siena on a Private Walking Tour
This 2 to 3-hour private tour offers a personalized look at Siena’s medieval streets and landmarks. Led by a local guide, you’ll walk through historic lanes, see the Piazza del Campo, visit the Basilica of San Domenico, and explore the Sanctuary of St. Catherine. You can also opt to add a visit to Siena’s magnificent Duomo, filled with Renaissance art. The guide shares insights into Siena’s traditions, like the Palio, and the significance of each site. Reviewers mention guides like Barbara, who are “professional, intelligent, and very pleasant,” making the tour both educational and fun. It’s perfect for travelers who want a flexible, in-depth overview of Siena without rushing.
Bottom line: Best suited for those who want a personalized, in-depth introduction to Siena’s history and culture in a short time.
3. A Brunello Cooking Class with Vineyards View Winery
For around $278, this 4-hour hands-on cooking class in Montalcino combines culinary skills with a stunning vineyard setting. You’ll learn to make local dishes such as pici pasta and braised beef, then enjoy your creations with carefully paired wines, including the renowned Brunello di Montalcino. The experience also includes a tour of a 13th-century castle and wine cellar, adding a historic touch to your meal. Guests highlight the chef’s warmth and humor, calling it “the highlight of our trip,” with many saying the recipes are simple and delicious enough to recreate at home. This class is perfect for food lovers who want an immersive, authentic Tuscan cooking experience.
Bottom line: An excellent choice for culinary enthusiasts eager to learn authentic recipes in a scenic vineyard setting.
4. Siena: Horseback Riding Tour in the Tuscany Countryside
This 1.5-hour horseback ride offers a laid-back way to explore Tuscany’s scenic countryside. Riders of all levels can enjoy trotting past vineyards, rivers, olive groves, and cypress-lined roads while learning about local flora and fauna from your guide. Many reviews mention the friendly horses and the stunning landscapes, with some riders noting it’s perfect for beginners. The tour can include a picnic or wine tasting at a local winery, making it a flexible experience. The guide’s patience and knowledge stand out, with one reviewer calling the guide “very friendly,” and the scenery “unbelievable.” It’s ideal for those who want a relaxing, outdoor adventure with authentic countryside views.
Bottom line: Perfect for outdoor lovers or anyone wanting a gentle, scenic ride through Tuscany’s hills.
5. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
At number 5, this full-day tour pairs visits to two Montepulciano wineries with a lunch in the town. You’ll taste Brunello and other regional wines at a boutique estate, explore Montepulciano’s Renaissance streets, and enjoy a local cheese tasting. The highlight is the lunch at a charming winery, where you’ll indulge in three-course Tuscan fare paired with wines. Reviewers call it a “great experience,” praising thedriver’s professionalism and the quality of the wines and food. This tour suits travelers who want a deep dive into Tuscan wine culture without renting a car, combining tastings, sightseeing, and a scenic town stroll.
Bottom line: Best for wine lovers seeking an immersive, stress-free day with excellent food and wine in Montepulciano.
6. “CLASSIC” Wine Tasting and Typical Tuscan Products
For just about $33, this hour-long tasting experience on a terrace offers six local wines, along with charcuterie and cheeses. The host guides you through each sip while sharing stories about the Chianti region. Guests love the breathtaking views and the chance to sample authentic Tuscan flavors in a relaxed setting. One reviewer notes, “The wine was incredible, and the host was charming,” making it ideal for those seeking a short, quality wine experience with beautiful scenery. It’s a great pre- or post-visit activity when you want to avoid heavy commitments but still enjoy tuscany’s best.
Bottom line: Perfect for a quick, authentic taste of Chianti wine paired with local products.
7. Small-Group Chianti and San Gimignano Sunset Trip from Siena
This 8- to 9-hour small-group tour takes you through Chianti’s rolling hills and San Gimignano’s towers. Starting in Siena, you visit a Chianti winery for a tasting, then explore Monteriggioni, a medieval fortress town. In the late afternoon, you arrive in San Gimignano to catch the sunset over its famous towers. The tour includes a Tuscan dinner at a farmhouse, with wine to match. Customers love the personalized small-group setting and the stunning views at sunset. It’s perfect for those wanting a relaxed, scenic day with plenty of wine and authentic small towns.
Bottom line: Ideal for travelers seeking an intimate, scenic experience with great food and wine.
8. Private Tour: Siena Walking Tour
This 2-hour private tour provides a tailored look at Siena’s most important sights, like the Piazza del Campo and the Duomo. Led by a guide who customizes the experience, you’ll walk through the medieval streets, hear stories about Siena’s patron saint, and see hidden corners not accessible on larger tours. Reviewers highlight guides like Silvia, who are “very knowledgeable” and make the city come alive. The tour is perfect for those wanting a personalized, flexible experience that focuses on Siena’s highlights and secrets.
Bottom line: Best for travelers wanting a customized, intimate introduction to Siena’s top sights.
9. Siena’s Ultimate Food Tour: Full Tuscan Meal with a Local
This 3-hour culinary walk takes you through Siena’s best restaurants and cafes, sampling regional dishes and wines. Led by a local food expert, you’ll explore hidden eateries and learn about Siena’s food traditions. Many reviewers praise the variety of tastings and the knowledgeable guide who shares stories behind each dish. If you want a foodie-focused tour that combines sightseeing with delicious bites, this is a great pick. It’s especially suited for those wanting a relaxed, tasty introduction to Siena’s culinary scene.
Bottom line: Excellent for food lovers who want to experience Siena’s local cuisine and culture in a small-group setting.
10. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
This 11-hour tour from Florence covers three iconic towns with free time in San Gimignano and Monteriggioni. It includes a lunch and wine tasting at a Chianti winery, along with informative commentary during the drive. Reviewers mention how smoothly everything runs and enjoy the balance of guided visits and free exploration. It’s suited for travelers who want a comprehensive day trip with transportation provided, making it perfect for those with limited time but a desire to see a lot.
Bottom line: Great for those wanting a full-day, guided overview of Tuscany’s highlights.
11. Chianti: Wine and Olive Oil Tasting with Cellar Tour
This short one-hour tour immerses you in Chianti’s flavors, with tastings of local wine and olive oil. You’ll visit an authentic farmhouse cellar, dating back to the 18th century, and learn about traditional production methods. It’s a relaxing, educational experience that’s perfect as a quick stop or to complement a day of sightseeing. Reviewers appreciate the informative guide and the rustic atmosphere. If you’re pressed for time but want an authentic taste of Tuscany, this offers quality over quantity.
Bottom line: Ideal for a quick, authentic taste of Chianti’s wines and oils with a historic twist.
12. Siena: Balloon Flight Over Tuscany with a Glass of Wine
Number 12 offers a 3-hour hot air balloon experience over Siena’s beautiful landscape. You’ll reach heights up to 3,000 feet, marveling at the patchwork of vineyards and hills, then toast with prosecco. Reviewers rave about the stunning views and the smooth flight, with some saying it’s “worth every penny.” This is perfect for travelers looking for a once-in-a-lifetime adventure that combines scenery, thrill, and a celebratory toast. The flight is weather-dependent, so planning ahead is key.
Bottom line: Suitable for those craving a spectacular aerial view and a memorable experience in Tuscany.
13. Siena: Guided visit of the city in German
This 2-hour small-group tour in German offers a focused exploration of Siena’s 13th-century architecture and local stories. Led by a passionate guide, you’ll see the Piazza del Campo, Palazzo Pubblico, and other highlights, along with hidden corners. Reviewers comment on the guide’s extensive knowledge and engaging storytelling, making Siena’s medieval atmosphere come to life. It’s perfect for German-speaking travelers or those wanting a condensed, informative visit.
Bottom line: Great for travelers seeking a culturally tailored and insightful tour of Siena.
14. Siena: Guided Tour with Cathedral and Optional Crypt & Museum
This 2 to 3-hour tour combines a walk through Siena’s historic center with skip-the-line tickets to the cathedral. You’ll explore the cathedral’s stunning interiors, crypt, and museum, with commentary that highlights art, architecture, and local stories. Reviewers note guides are knowledgeable and the skip-the-line access saves time. It’s suitable for travelers who want a rundown with the option to go deeper into the cathedral’s treasures.
Bottom line: Perfect for those wanting a timed, efficient tour that emphasizes Siena’s artistic highlights.
How to Choose the Right Siena Tour
When selecting the perfect experience, consider your budget, time available, and what excites you most about Siena. For full immersion in Tuscan wine and scenery, the From Florence: San Gimignano, Siena, and Chianti Wine Tour offers an excellent day-long adventure. If you prefer a personalized city exploration, the Private Siena Walking Tour provides tailored insights. For a culinary highlight, the Brunello Cooking Class combines cooking skills with the scenic vineyards of Montalcino.
Budget travelers might enjoy the Classic Wine Tasting or the Chianti Olive Oil & Wine Tour. For those craving a thrill, the Balloon Flight offers an unforgettable view. Booking early is advisable, especially during peak season, to secure your preferred date and time.
Final Thoughts
From cultural tours and gastronomic adventures to scenic flights and active pursuits, Siena offers a diverse array of experiences to suit every traveler. If you’re short on time, the guided city walks provide a rich taste of Siena’s medieval treasures; for a full-day escape, the Chianti wine tour is hard to beat. For those seeking something special, the hot air balloon ride takes your trip to new heights—literally. Whatever your style, booking early ensures you won’t miss out on these remarkable Siena experiences.