Private guided tour: Siena San Gimignano and Chianti

Discover the Charm of Siena, San Gimignano, and Chianti for $414.86

This private guided tour from Florence offers an intimate way to explore three iconic Tuscan locations in around 10 hours. For $414.86 per person, you’ll visit Siena’s lively main square, stroll through San Gimignano’s medieval towers, and enjoy a Chianti wine tasting at a local winery. The tour is designed for small groups of 15 or fewer people, ensuring a personalized experience with flexible timing and direct interaction with your guide.

This tour combines cultural highlights with culinary delights and scenic drives. It departs from Piazza Adua in Florence at 8:30 am and includes hotel drop-off at select hotels, making it convenient to end the day comfortably. While the tour is praised for its knowledgeable guides and beautiful views, some reviews suggest that the experience varies depending on individual expectations, especially regarding guided sightseeing versus free time.

Key Points

• Private tour with small group size for a more personalized experience
• Includes wine tasting of Chianti Classico and Supertuscan wines at a local winery
• Covers Siena, San Gimignano, Castellina in Chianti, and other Tuscan gems
• Hotel drop-off available at selected locations for added convenience
• Transport is by air-conditioned minivan with WiFi onboard
• The tour does not include lunch, so plan accordingly

Starting Point and Transport Logistics in Florence

The tour begins at Piazza Adua in Florence at 8:30 am. The group travels in a private air-conditioned minivan, which ensures comfort during the approximately 10-hour day. The vehicle is equipped with WiFi, allowing for quick sharing of photos and instant updates during the journey. The small group size helps maintain an intimate atmosphere, with group discounts possibly available for larger bookings.

The tour ends back at the initial meeting point, or at select hotels if this option is chosen. The drop-off service is a highlight for those who prefer to relax after a full day of sightseeing and tasting.

Exploring Piazza del Campo in Siena

The first stop in Siena is Piazza del Campo, a renowned civic square famous for hosting the Palio horse race. Here, visitors admire the Tower of the Mangia, which ranks as the third tallest tower in Italy, along with the Public Palace and the Fountain Gaia. The square’s lively atmosphere offers an authentic taste of Siena’s vibrant public life.

Guests typically spend about 1 hour 45 minutes exploring this area. The tour includes free time to relax at a local café, soak up the medieval ambiance, and take photos of the stunning architecture. This stop provides a perfect introduction to Siena’s historic charm and cultural significance.

San Gimignano’s Tower-Studded Skyline and Vernaccia Wine

Next, the tour moves to San Gimignano, often called the “Medieval Manhattan” for its tower-filled skyline. The Piazza Della Cisterna is the main square, where guests admire towers such as Tower Grossa, Rognosa, and Ardinghelli. This small town is celebrated for its medieval architecture and climatic views.

At this stop, visitors spend roughly 1 hour 45 minutes exploring Piazza Duomo and the surrounding streets. The guide shares insights into Vernaccia wine, a local specialty, and visitors are treated to world-famous gelato. This part of the tour combines cultural exploration with culinary pleasures.

Tasting Tuscan Wines at Casa Emma

The highlight for many is the wine tasting session at Casa Emma, where the focus is on Chianti Classico. The guide leads the group through tasting rosé, Chianti Classico, and Chianti Classico Reserve, as well as Supertuscan wines. Accompanying the wines, visitors sample olive oil and balsamic vinegar, gaining insight into Sangiovese grape cultivation.

This tasting lasts about 1 hour and is included in the tour price. It provides an authentic opportunity to appreciate Tuscany’s wine-making tradition and learn about the region’s viticulture directly from experts.

Castellina in Chianti and the Via delle Volte

The journey continues to Castellina in Chianti, one of the most picturesque towns in the Chianti wine region. Visitors explore Via delle Volte, a historic street lined with medieval architecture and hidden passages. The town’s scenic views and historic charm make it a standout stop.

The exploration here lasts about 45 minutes, during which guests can enjoy the peaceful Chianti countryside and spectacular landscapes. The visit provides a relaxed atmosphere for walking and photography, with some free time to soak in the rural beauty.

Chianti Wine Tasting and Olive Oil Sampling at Casa Emma

Casa Emma is the focal point of the wine and olive oil tasting. The guide introduces guests to sangiovese grapes and discusses the wine production process. Tasting Chianti Classico, Reserve, and Supertuscan wines offers a deep dive into the region’s viticultural excellence.

Plus, guests sample olive oil and balsamic vinegar, elevating the experience into a true culinary showcase. The tasting lasts about 1 hour and is included in the tour cost, making it an ideal opportunity for wine enthusiasts and food lovers alike.

Scenic Drives Through the Tuscan Countryside

Throughout the day, the scenic drives between stops showcase Tuscan landscapes—rolling vineyards, lush hills, and charming villages. The private transportation ensures comfort and flexibility, allowing the guide to adapt timing based on the group’s interests.

The route emphasizes views of the Chianti region, giving travelers a chance to enjoy photo opportunities and relax amid nature. The slow-paced drives are complemented by informative commentary from the guide.

The Tour’s Flexibility and Review Highlights

While the tour is praised for its knowledgeable guides and beautiful scenery, some reviews note a variation in experience. For instance, one review mentions that the guide’s role is primarily to drive and provide information about the sights, with limited guided commentary during free time.

Others appreciate the flexibility in spending extra time in favorite towns or adjusting the schedule. The small group size fosters a relaxed atmosphere, and the wine tasting at Casa Emma is consistently highlighted as a memorable highlight.

Who Will Appreciate This Tour?

This private tour is ideal for those seeking a personalized experience with wine and culture. It’s suited for small groups who want to enjoy scenic drives, historic towns, and wine tastings without the hassle of independent planning.

Travelers who prefer a balance of guided sightseeing and free time will find this tour appealing. However, those expecting a deeply guided historical tour of each city might find this experience more relaxed and taste-focused.

Final Thoughts on the Siena, San Gimignano, and Chianti Tour

This 10-hour private experience offers a well-rounded taste of Tuscan culture, wine, and scenery. The inclusion of wine tastings at a local winery and visits to iconic towns like Siena and San Gimignano make it a rewarding choice for culinary and scenic lovers.

While the price point is higher than some group tours, the private setting and hotel drop-off add convenience and a more personalized touch. The moderate pace and flexibility suit those who want a relaxed yet comprehensive Tuscany day trip.

If you value small groups, scenic drives, and wine experiences, this tour is a solid pick—just keep in mind that it emphasizes cultural highlights and taste-testing over detailed guided tours of every location.

Frequently Asked Questions

Is the tour suitable for those with mobility issues?
The tour involves walking around towns like Siena and San Gimignano, which have cobblestone streets and some uneven surfaces. It is best suited for visitors comfortable with walking.

Does the tour include lunch?
No, lunch is not included in the tour price, so participants should plan to bring a snack or make arrangements for a meal.

Can I get hotel pick-up instead of drop-off?
Yes, hotel drop-off is available at select hotels, providing extra convenience at the end of the day.

What should I bring for the wine tasting?
Participants should bring identification if required and may want to carry a small bag or wine bottle carrier if purchasing bottles.

How flexible is the schedule?
The tour offers some flexibility in spending time at each stop, especially in Siena and San Gimignano, based on individual interests and the guide’s discretion.