Siena is a city that packs a punch for travelers eager to explore Italy beyond the usual tourist spots. Its compact, walkable center bursts with medieval architecture, vibrant traditions like the Palio, and some of Italy’s finest wines and cuisine. We love how small-group tours like the Brunello di Montalcino wine-tasting trip let you get intimate with local winemakers, while iconic sights like the Siena Cathedral come alive through skip-the-line access. Whether you prefer tasting wines, exploring historic streets, or learning to cook, Siena offers a variety of experiences that reveal its authentic charm and character.
In this list, you’ll find wine tastings, guided city walks, cultural visits, and hands-on cooking classes. Each experience provides a different window into Siena’s rich culture, delicious food, and stunning landscapes. Let’s dig into the details of each tour and see which one might be best for your trip.
1. Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
At number 1, this small-group wine trip offers a full day exploring three wineries and tasting the legendary Brunello di Montalcino. The tour kicks off with visits to two family-run wineries where you can walk through vineyards, tour cellars, and sample both Rosso and Brunello wines. Midday, you’ll enjoy a Tuscan meal paired with more wine, making the experience as much about food as it is about wine. Before heading back, visit the Abbey of Sant’Antimo, renowned for its peaceful atmosphere and ancient Benedictine roots.
What makes this tour stand out is the intimate size—guaranteeing personal attention—and the chance to taste wines directly from local producers. Guests consistently praise the knowledgeable guides, with one reviewer noting that “Mattias was an exceptional teacher, full of stories, history, and conversation.” The tour costs around $213.29 per person for about nine hours of insider access to some of Italy’s finest vineyards. It’s ideal for wine lovers who want depth, quality, and a relaxed pace. Bottom line: a rich experience for those serious about Tuscan wines, with plenty of local flavor.
2. Siena: Siena Cathedral and Piccolomini Library Entry Ticket
Number 2 on our list is a budget-friendly skip-the-line ticket that opens the doors to Siena’s grand cathedral and the breathtaking Piccolomini Library. For just $9, you’ll avoid long lines and get inside to marvel at the cathedral’s ornate interior, including stunning mosaics and sculptures by Donatello, Michelangelo, and Nicola Pisano. The highlight is Pinturicchio’s frescoes in the Piccolomini Library, which tell stories in vivid color, making it one of Siena’s most treasured artworks.
Guests say that skipping the lines makes all the difference, especially during high season when crowds can be overwhelming. One reviewer remarked, “The cathedral is beautiful and the frescoes are worth the visit.” This ticket is valid for a full day, so you can explore at your own pace. It’s perfect for travelers looking for a quick, high-impact visit that enriches your understanding of Siena’s religious art and architecture without breaking the bank.
3. Skip the Line: Siena Duomo and City Walking Tour
Number 3 offers an interactive two-hour walking tour that covers Siena’s most famous sights—plus skip-the-line entry to the Duomo. This tour is led by an expert guide who brings Siena’s stories to life, from Piazza del Campo to the Basilica of San Domenico. You’ll walk through the city’s narrow alleys, learn about the Palio horse race, and get a rundown in a compact timeframe.
Guests consistently praise the guide’s knowledge and storytelling, with one calling Elio a “remarkable guide.” The highlight is the Duomo’s stunning Gothic architecture and the chance to see masterpieces by Bernini and Michelangelo. The tour costs just $46.34, making it a good value for a quick immersion in Siena’s history and culture. It’s suited for first-time visitors eager to see the city’s top highlights efficiently.
4. Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Number 4 provides a flexible, multi-day access-all-areas pass for Siena’s Cathedral complex. For $21, you can explore the Crypt, Baptistery, Piccolomini Library, and Museum at your own pace, with an audio guide available in your smartphone. This pass is ideal if you want to take your time and see everything, including the Facciatone viewpoint with panoramic views of Siena.
Many reviews highlight how handy it is to skip lines and customize your visit. One reviewer shared, “Lines were enormous, so I highly recommend buying this pass ahead of time.” It’s perfect for travelers who prefer self-guided exploration and want to absorb Siena’s treasures without rushing. It’s a flexible, hands-on option that deepens your understanding of Siena’s artistic and religious heritage.
5. Siena: Walking Tour and Skip-the-Line Duomo Tickets
At number 5, this guided walking tour combines highlights of Siena’s UNESCO-listed old town with fast-track access to the Duomo. Led by a knowledgeable local guide, you’ll visit Piazza del Campo, Palazzo Pubblico, and San Domenico, finishing with skip-the-line entry into the cathedral itself. Inside, you’ll see incredible artworks by Renaissance masters.
Guests love the combination of sightseeing and art, with one saying, “Our guide Ambra was fabulous, very interesting and with a great sense of humor.” The tour is about two hours and costs $45.55, offering good value if you want a concise, well-guided introduction to Siena’s history and art.
6. Florence: Siena, San Gimignano and Chianti Small Group Tour
Number 6 is a full-day small-group tour that ventures beyond Siena to explore the picturesque towns of San Gimignano, Pienza, and Chianti. Starting from Florence, the tour includes guided walks, visits to historic sites, and plenty of tasting opportunities, including a traditional Tuscan lunch with local wines. The small group size (up to 25 people) ensures a personal experience.
Guests praise the guide’s knowledge and the well-organized itinerary, noting that “the countryside views are beautiful,” and the towns provide plenty of photo opportunities. For about nine hours, you get a balanced experience of culture, food, and scenery. It’s perfect for those wanting a comprehensive day trip with a taste of Tuscany’s best.
7. Siena: A Wine Tour and Tasting Experience
Number 7 offers an intimate, three-hour wine tasting in a historical cellar. Led by a sommelier, you’ll visit a local winery, learn about organic winemaking, and taste at least four wines paired with a light Tuscan lunch. The small-group setting ensures personalized insights into Tuscany’s wine industry.
Reviews highlight the warmth of the guide and the delicious, generous tastings. One reviewer said, “The wines were incredible and the lunch was delicious.” This tour is ideal for those wanting a relaxed, educational wine experience with a focus on organic, local wines. It provides good value given the quality and depth of tasting.
8. Tuscan Cooking Class in Central Siena
Number 8 is a hands-on Tuscan cooking class, lasting about four hours. Led by a professional chef, you’ll learn to make classic dishes like handmade pasta and hearty meat sauces, then enjoy your creation with wine. The class is in a professional kitchen and limited to 15 people for an intimate feel.
Guests rave about the fun atmosphere and the chance to learn authentic recipes. One said, “Food was amazing and the chef very friendly.” It’s perfect for foodies who want to get their hands dirty and take home a real taste of Tuscany.
9. Wine Class – Tuscan Classics
At number 9, this informal wine class offers a quick, two-hour overview of Tuscany’s most important wines. You’ll learn how to recognize local grape varieties, taste four or five wines, and hear about the region’s winemaking history—all in a relaxed setting.
Guests appreciate the knowledgeable instructor and generous tastings, with one noting, “I learned a lot about the region and the wines.” Ideal for beginners or those short on time, it provides a solid foundation for understanding Tuscan wine.
10. Small-Group Montepulciano and Pienza Day Trip from Siena
Number 10 is a full-day trip to two beautiful hill towns: Montepulciano and Pienza. The tour includes scenic drives through the Val d’Orcia, a UNESCO site, and visits to a Pecorino cheese farm. You’ll also tour a winery in Montepulciano and enjoy a traditional lunch.
Guests rave about the guide’s knowledge and the chance to see Tuscany’s iconic landscapes. One reviewer wrote, “We saw so many sites that we wouldn’t have found on our own.” It’s suited for travelers wanting a mix of culture, scenery, and food in one day.
11. Discover the Medieval Charm of Siena on a Private Walking Tour
Number 11 offers a tailored, private walking experience for 2 to 3 hours. Your guide shows you Siena’s most important landmarks, including the Piazza del Campo and Basilica San Domenico, and shares stories about the city’s districts and traditions.
Reviewers praise the personalized attention and the depth of historical detail. One said, “Sabrina shared lots of interesting history and catered the tour to our needs.” It’s ideal for those seeking a flexible, private introduction to Siena’s artistic and cultural highlights.
12. Total Immersion Wine Tour in Chianti
Number 12 features a small, family-run organic winery where you learn about organic wine making and taste Chianti Classico wines. The tour emphasizes hands-on experience, including smelling, tasting, and understanding the production process.
Guests appreciate the intimate setting and the chance to learn directly from the winemakers. One reviewer shared, “The knowledge of the guide and the depth he went into was impressive.” It’s perfect for wine enthusiasts interested in organic practices and authentic Chianti wines.
13. From Siena: Chianti and Castles Tour with Wine Tastings
Number 13 offers a half-day exploration of Chianti’s scenic vineyards, medieval castles, and small villages. Traveling by minivan, you visit two wineries and the charming town of Castellina in Chianti. The tour includes wine tastings and scenic views of rolling hills.
Guests mention that “the landscape is beautiful” and the stops are well-paced. It’s suited for travelers who want a shorter, scenic, and wine-focused experience in Tuscany.
14. Siena: Educational Wine Tour & Tasting
Number 14 is a three-hour educational wine tour held at an organic winery. You learn about the winemaking process, visit vineyards, and taste four organic wines paired with a light lunch. The guide shares insights into the seasonal work involved.
Guests find it informative and relaxed, perfect for those who want a deeper understanding of organic Tuscany wines. One reviewer appreciated the “gorgeous Tuscan hills and the wine tasting combined with a nice lunch.”
15. A Brunello Cooking Class with Vineyards View Winery
Number 15 offers a unique experience: a half-day cooking class on a panoramic terrace, paired with a tour of a 13th-century castle and vineyard in Montalcino. You learn to cook Tuscan classics like tagliatelle and braised beef, then enjoy your meal with local wines.
Guests describe the experience as “spectacular” and a highlight of their trip. The lesson combines culinary skills, wine tasting, and history—ideal for food and wine lovers wanting an indulgent, immersive day. It’s particularly suited for those wanting a full sensory experience of Tuscany’s culinary riches.
How to Choose the Right Tour in Siena
When selecting your Siena experience, consider your interests and pace. If you’re passionate about wine, the Brunello trip offers depth, while the wine classes are great for beginners. For history and architecture lovers, the guided city walks or private tours provide personalized insights.
Budget-conscious travelers will find value in entry tickets and short tours, while those seeking hands-on experiences should consider cooking classes. For a scenic day, the full-day small-group trips showcase Tuscany’s countryside and hill towns.
Timing is key: summer offers lively festivals, while winter provides quieter visits. Book early, especially for popular guided tours, to ensure your spot.
Siena’s diverse tours mean there’s something for every traveler. Whether you want to sip Brunello at a family winery, walk through medieval streets with a knowledgeable guide, or learn to cook like a Tuscan chef, this city delivers authentic, memorable experiences. For a truly enriching trip, pick a tour that matches your interests, and don’t hesitate to reserve in advance—these experiences fill up fast. Happy exploring!
