From Florence: Siena, San Gimignano & Tuscany – Small Group

Discover Tuscany in a Day: Florence to Siena, San Gimignano & Chianti

This small-group tour from Florence offers a comprehensive taste of Tuscany, covering Siena, San Gimignano, Monteriggioni, and a Chianti winery in just 9 hours. Priced at $290.27 per person, it is designed for those who want to maximize their time and see multiple highlights with ease. The tour is highly rated with a 5.0 out of 5 based on 52 reviews, and 96% of participants recommend it.

The experience includes round-trip transportation in a comfortable 8-seat minivan, a personalized guide, and a well-curated itinerary that balances guided walks and free time. It’s especially suited for first-time visitors eager to explore Tuscany’s iconic towns, enjoy wine and olive oil tastings, and indulge in a traditional Tuscan lunch. A small group size ensures a more intimate experience, avoiding large bus tours and crowded sites.

Key Points

• Full-day exploration of Tuscany’s most famous towns in just 9 hours
• Small-group tour with a maximum of 8 travelers for a more personal experience
• Includes transport, guided walks, wine and olive oil tastings, and a Tuscan lunch
• Visits to Monteriggioni, Siena, San Gimignano, and the Chianti wine region
• Flexible time for independent exploration, with detailed maps and tips provided
• Tour departs from Florence at 9:00 am and ends around 6:00 pm

Convenient Pickup and Return at Porta Romana in Florence

The tour starts in Florence at the Parcheggio Oltrarno near Piazza della Calza, with the meeting at 9:00 am. Travelers are driven in a comfortable 8-seat minivan, making the journey between towns smooth and scenic. The return to the original meeting point is scheduled for 6:00 pm, providing a full day of sightseeing without the hassle of navigating public transport or driving.

The small group size limits the tour to a maximum of 8 participants, ensuring personalized attention and a relaxed pacing. This setup also means there are no large bus crowds, making the experience more enjoyable and intimate. The tour is suitable for most travelers, though it requires a minimum of three participants to run.

Exploring Monteriggioni, the Medieval Fortress Village

The first stop is Monteriggioni, a well-preserved medieval fortress city with history dating back centuries. Known for its intact walls and towers, it served as a strategic defense point and was used as a filming location for “The Gladiator” and an inspiration for the game “Assassins Creed.”

Spending 40 minutes here allows ample time to walk along the fortress walls, admire panoramic views of the Tuscan countryside, and learn interesting facts about its history from the guide. Since the entry is free, visitors can explore at their own pace, enjoying the historic atmosphere and photo opportunities.

Siena: The Artistic Gem with a Famous Piazza

Siena is the second major stop on the tour, with a dedicated 2-hour visit. The guide leads you on an orientation walk, highlighting the town’s famous architecture and artisan shops, before reaching the Piazza del Campo. This iconic square hosts the Palio horse race twice each summer and remains a lively hub of Tuscan culture.

A highlight of the stop is a visit to Siena Cathedral, renowned for its striking façade and intricate interior. The town’s compact size makes it ideal to explore independently, offering the freedom to relax or visit additional sites like shops or cafes. The guide’s insights ensure you appreciate Siena’s unique charm and artistic heritage.

Tasting Tuscan Wines and Olive Oils in Ulignano

A key feature of this tour is the visit to a Chianti winery in Ulignano, set within the Chianti wine region. Here, a scenic drive through the rolling hills introduces you to vineyards and olive groves. During the 1-hour stop, the guide arranges a wine and extra virgin olive oil tasting, featuring seven different wines along with balsamic vinegar.

The tasting experience is complemented by a Tuscan meal, which includes antipasti like bruschetta, pecorino cheese, cured meats, and a traditional Ribollita soup. The meal caters to vegetarian, vegan, and gluten-free preferences upon request, ensuring a flexible dining experience. This is a chance to savor authentic flavors in a relaxed, picturesque setting.

San Gimignano: The Towered Town in Complete Freedom

The next destination is San Gimignano, a UNESCO World Heritage Site known as the “Manhattan of Tuscany” for its medieval towers. The guide provides each participant with a map and tips for exploring the town, giving you an hour of free time.

Stroll through cobblestone streets, explore historic piazzas, and admire palaces and towers at your own pace. San Gimignano’s atmosphere is timeless, and the flexibility of this stop allows visitors to visit artisan shops, take photos, or relax in cafes. The guide’s tips help ensure you don’t miss the most scenic spots.

Scenic Drive Through the Chianti Region

Throughout the day, the tour offers scenic drives across the Chianti landscape, famous for its vineyards, olive groves, and rolling hills. The guide shares insights into Tuscan agriculture and wine production, enriching the experience beyond just sightseeing.

The drive itself provides stunning views, making it clear why this part of Tuscany remains a favorite among travelers. The combination of beautiful scenery and informative commentary creates a more enriching experience than simply visiting towns.

Lunch at a Local Chianti Winery

A highlight of the tour is the Tuscan lunch, included in the package. The meal features antipasti, lasagna with truffle oil, and Ribollita Soup, paired with local wine and olive oil tastings. The lunch takes place at the winery, offering authentic flavors and a chance to relax before heading to the last stop.

The menu is designed to accommodate vegetarian, vegan, and gluten-free options upon request, making it accessible for various dietary needs. The experience combines culinary delight with the scenic beauty of the vineyard setting, creating a true taste of Tuscany.

Final Stop at Porta Romana in Florence

The tour concludes back in Florence at Porta Romana, around 6:00 pm. This straightforward return allows travelers to continue their exploration of Florence or head to their accommodations without concern. The return transfer makes it effortless to end the day on a relaxing note.

The small size of the group and private transportation mean no waiting for large buses or crowded garages, offering a smooth finish to a busy day of sightseeing.

Why Choose This Tour: Strengths and Considerations

This small-group tour shines with personalized attention, expert guides, and carefully selected stops that showcase Tuscany’s diverse beauty. The included private transport, wine tastings, and lunch provide excellent value, especially given the $290.27 price point.

Guides such as Lorenzo and Christina receive praise for their knowledge, flexibility, and friendly approach, making the experience both informative and enjoyable. Reviews mention that the pacing allows enough time to appreciate each location without feeling rushed.

A key limitation is the minimum participation requirement, so the tour may be canceled if fewer than three people sign up. Also, while the itinerary offers a broad overview, some visitors may find the free time in towns like Siena and San Gimignano to be brief but sufficient for a quick exploration.

Perfect for First-Time Visitors to Tuscany

Designed with first-time visitors in mind, this tour offers a rundown of Tuscany’s most iconic towns and landscapes in a single day. It suits those who prefer small groups, guided experiences, and structural convenience to maximize sightseeing and tasting opportunities.

The organized logistics and professional guides ensure a smooth and informative day, ideal for travelers who want a stress-free, immersive introduction to the region’s highlights. The tour balances guided walks, independent exploration, and tastings to give a well-rounded impression of Tuscany.

Frequently Asked Questions

What is included in the tour price?
The price includes transportation in a minivan, guided walks, wine and olive oil tastings, and a Tuscan lunch.

What is the duration of the tour?
The entire experience lasts approximately 9 hours, departing at 9:00 am and returning around 6:00 pm.

Where does the tour start and end?
It begins at Parcheggio Oltrarno in Florence near Piazza della Calza and ends back at the same meeting point.

Is this tour suitable for all ages?
Most travelers can participate, but it requires a minimum of three participants to run, and it’s best suited for those comfortable with walking and moderate travel.

Can dietary restrictions be accommodated?
Yes, the lunch menu can be adjusted for vegetarian, vegan, or gluten-free preferences if requested in advance.

How much free time is there in Siena and San Gimignano?
Each town offers about 2 hours in Siena and 1 hour in San Gimignano for independent exploration.

Is there a guide during the walks in Siena and San Gimignano?
The guide leads the initial walks and provides tips, but the exploration in towns afterward is self-guided.

What is the size of the tour group?
A maximum of 8 travelers ensures an intimate experience and personalized attention from the guide.

Can the tour be canceled?
Yes, free cancellation is available up to 24 hours before the start if needed.

What makes this tour stand out from other Tuscany excursions?
The small-group size, personalized guide, and inclusive wine and lunch experiences make this tour a memorable, well-organized way to enjoy Tuscany’s highlights in one day.