Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Exploring Tuscany’s iconic towns becomes effortless with the Siena and San Gimignano: Small-Group Tour with Lunch from Florence. Priced at $171.76 per person, this 10-hour journey offers a well-balanced mix of guided sightseeing, free exploration, and delicious local cuisine. The tour is highly recommended, with a 5.0-star rating based on 1,478 reviews, and is perfect for those looking for a comprehensive yet relaxed day out.

This tour departs from Piazzale Montelungo in Florence at 8:00 am, and the group size is limited to 25 participants, ensuring a more personal experience. Travelers appreciate the luxurious, air-conditioned transport, which features complimentary Wi-Fi. One of the key strengths is the combination of guided visits to Piazza del Campo and Siena Cathedral, along with free time to discover San Gimignano at your own pace. The inclusion of a Tuscan winery lunch with seasonal dishes and local wines makes this trip both scenic and flavorful.

Key Points

• Small-group tour from Florence to Siena and San Gimignano, with a maximum of 25 travelers
• Guided walking tour of Siena’s highlights, including Piazza del Campo and Siena Cathedral
• Free time in San Gimignano for gelato, shopping, or sightseeing
• Tuscan winery lunch with seasonal dishes and wines, hosted at a family-owned estate
• Flexible options to visit Siena Cathedral (additional fee) or explore towns at your own pace
• Convenient transport in air-conditioned minivans with free Wi-Fi and professional guide

Departure from Florence: Central Pickup and Comfortable Transport

This tour starts at Piazzale Montelungo, right next to Florence’s train station, making it easy to access via public transportation. An air-conditioned minibus or minivan with complimentary Wi-Fi takes you into the Tuscan countryside, providing a comfortable ride for the 10-hour journey. The group size is limited to 25 people, which helps maintain an intimate atmosphere and allows guides to give more personalized attention.

The transportation is operated by Prestige Rent, which ensures professional driving, and most travelers find the experience smooth and stress-free. This setup suits those who appreciate a relaxed pace and want to avoid large, crowded tours.

Exploring Siena’s Medieval Heart with a Guided Walk

Upon arrival, a guided walking tour leads through the medieval historic center of Siena. This includes visits to Piazza del Campo, known for its shell shape and lively atmosphere, and the Siena Cathedral, celebrated for its striking black-and-white striped façade and stunning interior. The guide shares insights into Siena’s history and architecture, bringing the city’s past to life.

Guests have about one hour at each site, enough to take photos and soak up the atmosphere. An optional tour of Siena Cathedral is available for €15 per person, payable directly to the guide, but it is not available on Sundays. This flexibility allows visitors to tailor their experience based on interests and time.

The Unique Stop at Monteriggioni

A highlight of the trip is a stop at Monteriggioni, a small medieval fortress town perched on a hill. While the data does not specify the exact duration, this stop offers a chance to appreciate the town’s well-preserved walls and picturesque views. It provides a quiet break and an authentic taste of medieval Tuscany outside the larger towns.

Wine Tasting and Lunch at a Tuscan Winery

The tour continues with a visit to Agriturismo Tenuta di Mensanello, a family-owned estate renowned for its wine production. Here, a light lunch features seasonal Tuscan delicacies, such as local cheeses, bread, and other regional specialties. During this 1 hour and 30 minutes stop, guests can explore the cellars and see the process of wine-making.

The meal is paired with local wines, including reds that showcase the estate’s craftsmanship. The setting is idyllic, often described as a highlight, and offers a chance to appreciate Tuscany’s culinary traditions in a relaxed atmosphere. The light lunch and wine tasting are included in the tour price, with the estate providing a genuine taste of the region’s wine culture.

Discovering San Gimignano’s Towered Skyline

The final sightseeing stop is San Gimignano, famously known for its medieval towers and skyline. Guests have approximately one hour and fifteen minutes to explore at their own pace. This free time is perfect for visiting the main street, browsing local shops, or admiring the Collegiata church.

The town’s compact size makes it ideal for a relaxed stroll or enjoying a gelato—a must-do activity here. Visitors often praise the opportunity to soak in the stunning views and authentic atmosphere without feeling rushed.

Flexibility and Free Time for Personal Exploration

This tour’s design offers ample free time in both Siena and San Gimignano, allowing guests to customize their experience. Whether it’s visiting additional landmarks, shopping for souvenirs, or simply relaxing with a coffee, the schedule balances guided discovery with personal exploration.

For those interested in local architecture or regional specialties, this freedom enhances the overall experience. It’s a practical way to see two of Tuscany’s most famous towns comfortably and without the rush of larger group tours.

Practical Details: Booking, Cancellation, and Accessibility

Most travelers book this tour 73 days in advance, reflecting its popularity. It is suitable for most, with most travelers able to participate. Special dietary needs, such as vegetarian or gluten-free options, can be accommodated if advised at booking.

The tour is not inclusive of hotel pickup and drop-off, but the meeting point is near public transportation, making it easy to join from most central locations in Florence. The return to Florence is scheduled around 6:00 pm, providing a full and satisfying day.

Cancellation is straightforward—full refunds are available if canceled at least 24 hours in advance—making it a flexible choice for travelers with uncertain plans.

Guides and Overall Experience: Highly Praised

The guides and drivers earn high praise, with many reviews mentioning knowledgeable guides, professional drivers, and friendly service. Guides like Lorenzo, Susie, and Gemma are noted for their engaging storytelling and local insights.

Guests appreciate the small-group atmosphere, which fosters more personal interactions and a relaxed pace. The wine tasting and lunch are frequently highlighted as delightful surprises, offering authentic regional flavors.

Who Will Enjoy This Tour Most?

This trip appeals to those who want a comprehensive day in Tuscany without the hassle of planning. The combination of guided tours, free time, and delicious food makes it ideal for history lovers, foodies, and photographers alike. It suits travelers who prefer a small, comfortable group and enjoy local experiences.

However, those with limited mobility should note that Siena Cathedral is not accessible on Sundays or during celebrations, and the tour involves walking through historic streets, which may be uneven.

Siena and San Gimignano: Small-Group Tour with Lunch from Florence (Final Summary)

This tour offers a well-rounded taste of Tuscany’s most iconic towns, combining guided sightseeing, free time, and regional cuisine in a comfortable and intimate setting. The professional guides make the history come alive, while the lunch at a family-run winery provides a genuine culinary experience.

The well-organized schedule and small group size help create a relaxed and personal atmosphere, making it perfect for those seeking depth and flexibility. While the Siena Cathedral is optional and the walking can be physically demanding for some, the overall experience provides a rich and satisfying day out in Tuscany.

Frequently Asked Questions

What’s included in the tour price?
The small-group transportation, guided walking tours, lunch at the winery, and free time in San Gimignano are included. An optional Siena Cathedral tour can be purchased on-site for €15.

How long is the travel time?
The total duration is approximately 10 hours, with the departure at 8:00 am and return around 6:00 pm.

Is this tour suitable for all mobility levels?
Most travelers can participate, but walking in Siena and extensive roaming in San Gimignano may pose challenges for those with limited mobility.

Can dietary restrictions be accommodated?
Yes, vegetarian and gluten-free options can be arranged if advised at the time of booking.

What are the main highlights of this tour?
Piazza del Campo, Siena Cathedral, wine tasting at a Tuscan estate, and San Gimignano’s towers and shops are the key sights.

Is the tour family-friendly?
Yes, it suits families, especially those interested in history, food, and scenic towns. However, young children should be prepared for walking.

What is the maximum group size?
The tour has a maximum of 25 participants, ensuring a more personalized experience.

How do I cancel if my plans change?
You can cancel for free up to 24 hours before the tour starts for a full refund. Cancellations less than 24 hours before are non-refundable.

What is the weather policy?
The tour generally proceeds rain or shine; check the weather forecast and dress appropriately, especially for outdoor walking.

How do I book this tour?
Booking is available through the linked provider, Prestige Rent, with the convenience of mobile tickets and easy rescheduling if needed.

This Siena and San Gimignano tour delivers a meaningful glimpse into Tuscany’s medieval charm, complemented by local flavors and a relaxed pace, making it a top pick for visitors wanting to experience the region’s essence without rushing.