San Gimignano is a small town packed with big experiences. Known for its medieval towers and stunning views, it also offers plenty of opportunities to get under the skin of Tuscany’s food and wine culture. Whether you’re a wine lover, a foodie, or just looking to explore this hilltop jewel with an expert guide, San Gimignano’s tours deliver. We especially like the olive oil mill visit for its hands-on approach (more) and the Brunello wine tour for a deeper dive into Italy’s most celebrated reds (more). Each offers a different taste of Tuscany’s culinary charm, perfect for different kinds of travelers.
While some tours focus on the town’s historic core, others take you into the countryside to sample wines and local products. Whether you’re after a quick city walk or a full-day wine expedition, San Gimignano has options that fit nearly every schedule and interest.
Quick Overview
Our list includes olive oil tasting, mini wine tours, full-day Brunello excursions, Chianti wine adventures, and a private city tour. Each offers a unique way to experience San Gimignano’s flavors, scenery, and history. Check out the options below to see what suits your itinerary and taste.
1. Frantoio di San Gimignano: tour of the oil mill and tasting
At number one, we highlight the Frantoio di San Gimignano for its engaging, hands-on approach to olive oil. For only $24 per person, this 1.5-hour tour offers an immersive experience into the process of making high-quality Tuscan olive oil. The visit features an interactive journey through a state-of-the-art oil mill, with multimedia panels, virtual reality stations, and multitouch lecterns that make the science and art behind olive oil production easy to understand.
What makes this tour stand out is the final tasting, which includes a selection of the estate’s best oils and other gastronomic specialties based on olive oil. It’s perfect for foodies or anyone curious about how Tuscan olive oil is crafted. The guide is knowledgeable, and the tour’s interactive elements make it more engaging than a simple walk-through. It’s a good value for such a comprehensive experience, especially if you enjoy tasting and learning about local ingredients.
Bottom Line: If you want an engaging, educational introduction to one of Italy’s most treasured products, this tour hits the mark — especially for those who love hands-on experiences and tasting.
2. San Gimignano: Mini Wine Tour with Tuscan aperitif
At number two, the Mini Wine Tour with Tuscan aperitif combines visits to a vineyard and wine cellar with a tasting of five wines, including Vernaccia di San Gimignano. For around 1.5 hours, you’ll explore Guardastelle — a well-regarded estate — with stops at a vineyard and wine cellar, where your guide explains the wine production cycle in simple terms.
The highlight is the tasting of regional wines paired with local products like Tuscan charcuterie and cheese. The tour also includes an aperitif session with regional foods, making it ideal for those who want a taste of the region’s wine and culinary culture in a relaxed setting. Guests appreciate the informative guided tour and the opportunity to sample a variety of wines, including a Chianti Riserva and a Supertuscan.
This experience is especially suited for travelers short on time but eager to sample multiple wines and regional specialties. The only potential downside is that availability varies, so check ahead.
Bottom Line: A compact, enjoyable way to taste Tuscany’s best wines and learn about local viticulture, ideal for wine newcomers or casual enthusiasts.
3. From San Gimignano: Brunello Wine Tour
At number three, the Brunello Wine Tour offers a full 6.5-hour immersion into one of Italy’s most celebrated wines, Brunello di Montalcino. This tour is perfect for serious wine lovers looking for a deep dive into Tuscany’s premier reds. The day includes visits to two renowned wine estates where you’ll tour the vineyards and wine cellars, followed by tastings of multiple Brunello vintages.
Plus, you’ll explore the hilltop town of Montalcino, including its ancient fortress and charming streets, giving you a taste of history and scenery alongside the wine. The tour includes tasting local products such as pecorino cheese and cured meats, enhancing the experience. While reviews note some variability, the majority find it offers excellent value considering the length and depth of the experience.
This tour is best suited for those with a full day to spare and a keen interest in premium wines. Keep in mind, the travel time means it’s more of a dedicated day trip than a quick outing.
Bottom Line: An excellent choice for wine aficionados who want to explore Brunello in its native landscape and enjoy a comprehensive taste of Tuscany’s top-tier wines.
4. From San Gimignano: Chianti Wine tour with 2 wineries
Number four on our list is the Chianti Wine Tour with 2 wineries, a 5.5-hour guided experience ideal for discovering the iconic Chianti landscape. Led by a local guide, you’ll visit two different wineries, each with its own approach and style, and taste nine different wines, including the famous Chianti Classico and extra virgin olive oil.
The tour emphasizes professional wine tasting lessons, helping you understand the nuances of Tuscany’s most prominent wine region. Alongside wine, you’ll sample balsamic vinegar, Tuscan products, and olive oil, making it a full sensory experience. Reviews mention the friendly guide and the rich variety of local products, adding to the tour’s value.
This experience is best suited for those with a moderate budget who want to sample many wines in one afternoon. The tour’s pace is relaxed enough to enjoy the scenery and learn about Tuscany’s wine-making traditions. Some might find the number of wines overwhelming, so pace yourself accordingly.
Bottom Line: A well-rounded, flavorful introduction to Chianti’s wines and scenery, great for wine enthusiasts wanting variety and local insights.
5. San Gimignano Private Guided City Tour
Finally, at number five, the San Gimignano Private Guided City Tour offers a concise, personalized introduction to the town’s medieval architecture. Lasting 2 hours, it’s suitable for travelers who want a quick, focused visit rather than a full-day excursion. The tour includes climbing Torre Grossa for panoramic views, exploring the Piazza del Duomo, and discovering the Piazza della Cisterna with its picturesque charm.
While reviews are mixed—some note the 1.6/5 rating—this tour remains popular among visitors seeking a guided overview of the town’s main sights. It’s ideal for first-time visitors or those short on time. The guide will point out the famous towers and share stories about the town’s history, but it may not delve deeply into local food or wine.
This tour is best for those who want a quick, guided orientation or are traveling with limited time. It’s less suited for visitors looking for an in-depth experience or a focus on food and wine.
Bottom Line: Perfect for a snapshot of San Gimignano’s highlights when time is tight, but consider the mixed reviews and plan accordingly.
How to Choose the Right Tour
When deciding between these options, consider your interests, budget, and schedule. For a hands-on experience with local ingredients, the Olive Oil Mill Tour offers a compelling, interactive experience. If wine is your passion, the Brunello tour or Chianti tour will satisfy your curiosity and palate.
For those wanting a quick overview of San Gimignano’s medieval architecture, the private city tour provides a guided snapshot, while the mini wine tour balances tastings with a relaxed pace. Budget-conscious travelers can focus on the olive oil tasting or opt for the short city tour, depending on their priorities.
Booking early is advisable, especially for popular wine tours, which can fill quickly during peak seasons. Check availability and times in advance to match your itinerary.
Final Thoughts
San Gimignano’s tour options offer a range of ways to savor Tuscany’s flavors and history. For foodies, the olive oil and local product tastings provide a taste of authentic ingredients. For wine lovers, the Brunello and Chianti tours offer a deeper dive into Tuscany’s most famous wines. And for a quick glimpse of the town’s medieval towers, the private city tour delivers.
If you’re planning your trip, consider your interests and time constraints. A full-day Brunello tour is perfect if you’re passionate about reds, while a shorter city walk suits travelers with limited time. Whichever you choose, booking early ensures you’ll secure your preferred experience. Tuscany’s treasures are waiting—don’t miss out.