San Gimignano, Siena and Chianti Small Group Wine Tour

Traveling through Tuscany with a full-day tour from Florence offers a chance to see some of Italy’s most iconic towns, taste excellent wines, and experience authentic countryside charm. This particular tour covers San Gimignano, Siena, and the Chianti wine region, blending guided exploration with free time for personal discovery. With a focus on small groups, knowledgeable guides, and a mix of sightseeing, wine tasting, and delicious Tuscan food, it promises a well-rounded day.

What we love about this experience is the way it balances guided insights with the freedom to wander. The inclusion of lunch at a local winery, paired with a selection of five wines and artisanal oils, makes it more than just a scenic trip. However, be aware that some travelers have found the timing in each town a little rushed, especially in San Gimignano, and the optional Siena cathedral entry is not included.

This tour suits those who enjoy both cultural exploration and wine tasting, particularly travelers with a sense of curiosity about Italy’s countryside and medieval towns. If you want a day that combines history, scenery, and good value, this tour might just be the perfect fit.

Key Points

Comfortable transport and small groups ensure a more personal experience.
Guided city walks in Siena and San Gimignano are informative and engaging.
Wine tasting at a local winery includes five wines and artisanal products, providing excellent value.
Free time in Siena and San Gimignano allows for independent exploration.
Lunch is a full Tuscan feast, with traditional dishes and local wines.
Timing can be tight—expect to move quickly through each stop, especially San Gimignano.
Entrance to Siena’s cathedral and some attractions are NOT included, so plan accordingly.
Most reviews highlight knowledgeable guides and breathtaking views as main highlights.
Price at around $168 per person offers good value considering the included experiences.
Weather preparedness is advised, as the tour runs in all conditions.

Starting the Day: Meeting Point and Transport

The tour kicks off at 8:30 am from Piazza del Duomo in Florence, with most travelers booking about 47 days in advance, indicating high demand for this Tuscan adventure. The bus ride is comfortable, with a maximum of 30 travelers, ensuring a friendly atmosphere without the chaos of large groups. Multiple reviews praise the smooth transportation, with some mentioning the bus being efficient and cozy—a significant plus for a day full of sightseeing.

Exploring Siena: Medieval Charm and Landmarks

The first major stop is Siena, a city famed for its medieval architecture and the legendary Palio horse race. The official guides lead a walk through the city’s historic center, which is a UNESCO World Heritage site. Travelers will enjoy viewing the Piazza del Campo, a shell-shaped square that hosts the Palio twice a year. It’s a lively hub where locals gather, and travelers can soak in the atmosphere.

One of the favorite stops within Siena is the Duomo di Siena — a Gothic-Romanesque masterpiece featuring intricate marble facades, stunning sculptures, and artworks by masters like Donatello and Pinturicchio. While not included in the ticket price, many guests find visiting the cathedral worthwhile if they have the time and interest in art and architecture.

Reviews mention the informative guides, like Erica, who shared stories about Siena’s noble families, its palaces, and the traditions that still thrive today. Some travelers found the time in Siena enough to get a good feel but wished they had more time to explore deeper.

The Iconic San Gimignano: Tower Houses and Free Exploration

Next, the tour takes you to San Gimignano, often called the “Manhattan of the Middle Ages” due to its skyline of medieval towers. This UNESCO World Heritage site offers postcard-perfect views, cobbled streets, and a lively town square. Tourists have plenty of free time—about two hours—to wander, shop, and sample the town’s famous Gelato Dondoli, considered one of the best in the world.

Multiple reviews emphasize the spectacular scenery and the chance to explore at your own pace. The Collegiata di Santa Maria Assunta, the main church, is a highlight for those interested in medieval art and architecture, though entry is optional.

Visitors often climb Palazzo Pubblico e Torre Grossa for stunning panoramic views over the Tuscan countryside. If you’re feeling adventurous, the climb is a must-do, offering a chance to see the town’s famous towers up close and appreciate the medieval architecture that made San Gimignano so unique.

Chianti and the Winery: Tasting and Tuscan Flavors

A highlight of the day is the stop at Agricola Poggio Ai Laghi, a family-run winery set amidst rolling hills. Here, you can enjoy a private tour of the winery facility, followed by a tasting of five regional wines, paired with artisanal olive oils including extra virgin, truffle, and spicy pepper varieties. Many reviewers praise the quality of the wine and the knowledgeable staff who gladly share insights about wine production.

The included lunch is a true Tuscan experience: starting with cheese, cured meats, bruschetta, and salads, then moving on to Lasagne al Tartufo and hearty Tuscan ribollita. The dessert, Cantucci with Vin Santo, rounds out the meal. Some guests felt the €20 charge for a bowl of pasta was overpriced, but overall, the meal is seen as a genuine taste of Tuscan cuisine.

The Return and Overall Timing

The entire day lasts about 9 hours—a long but rewarding experience. The schedule is well-planned but somewhat tight, especially in San Gimignano, where two hours can feel rushed for those wanting to explore every alley or shop for souvenirs.

Multiple reviews note the efficient transportation and friendly guides, like Marta and Marco, who are praised for their knowledge and ability to keep the group engaged. However, some travelers warn to be punctual, as missing the bus can mean missing part of the tour.

Authentic towns and scenic views: The towns visited are true gems, with San Gimignano’s towers and Siena’s medieval streets providing perfect backdrops for photos and memories. The free time allows for personal exploration, which many travelers enjoy as a chance to discover hidden corners or indulge in local treats.

Quality wine and food experience: The wine tasting at Poggio Ai Laghi is a standout, offering five wines paired with artisanal oils and a Tuscan feast. For many, this elevates the tour from a sightseeing trip to a culinary adventure.

Expert guides: Reviewers consistently praise the guides’ knowledge, friendly demeanor, and ability to share local insights, making each stop more meaningful.

Value for money: At around $168.36 per person, it’s a fair price considering the transport, guided city walks, winery visit, and lunch. Some travelers felt the experience justified the cost, especially given the small group size and personalized feel.

While the tour offers many positives, there are some considerations. Timing can be tight, especially in San Gimignano, which might leave some wishing for more time to explore. Entrance fees to Siena’s cathedral and some other sites are not included, so if you’re keen on visiting, budget accordingly.

Travelers have varying opinions on the lunch experience—some find it excellent, others think the €20 charge for extra pasta is too high. Weather can influence the experience, so dress appropriately, especially since a good part of the day involves walking and outdoor sightseeing.

Lastly, be punctual—the bus departs promptly, and missing it can result in missing out on part of the tour, as several reviews attest.

This experience appeals to history and architecture buffs, wine lovers, and those seeking authentic Tuscan scenery. If you enjoy guided city walks combined with free time to explore at your own pace, you’ll love this tour. It’s also ideal for small groups seeking a more intimate experience, and for travelers who value good value given the inclusion of transportation, wine tasting, and a hearty lunch.

However, if you prefer more time in each town or want an in-depth guided tour of Siena’s cathedral, you might want to consider customizing your day or choosing a different option.

Is hotel pickup included? No, the tour starts at Piazza del Duomo in Florence, so you’ll need to make your way there.

How long is the total tour? The entire experience lasts about 9 hours, from 8:30 am to around 5:30 pm.

Does the tour include guided visits inside Siena and San Gimignano? Not exactly; the guides lead walks with explanations, but entry to attractions like Siena’s cathedral is optional and not included.

What should I wear? Comfortable shoes are recommended, as a moderate amount of walking is involved, and the weather can vary.

Are the wine tastings suitable for non-drinkers? The tour includes five wines, but non-drinkers can opt to skip the tastings and enjoy the scenery and food.

Can I visit the Siena Cathedral? Entrance is NOT included, so you can choose to visit at your own expense, depending on opening times.

Is there free time at San Gimignano? Yes, about two hours for wandering, shopping, and tasting the town’s famous gelato.

What languages are the guides available in? The tour is guaranteed in English unless the Portuguese or Chinese options meet the minimum of four participants.

How much does the lunch cost? The lunch is included in the tour price, but the €20 charge for extra pasta at the winery is an optional addition.

What if it rains? The tour operates in all weather conditions, so dress appropriately and be prepared for outdoor sightseeing.

This tour offers an excellent way to get a taste of Tuscany’s rich cultural tapestry, stunning landscapes, and delicious wines—all in one well-organized day. It’s suited for those who want a balanced mix of guided insights and personal exploration, all at a reasonable price. Whether you’re a first-time visitor or returning to Italy’s heartland, this experience provides a memorable glimpse into Tuscany’s soul.