From Florence: Siena & San Gimignano Guided Tour and Dinner

The From Florence: Siena & San Gimignano Guided Tour and Dinner offers an engaging way to explore some of Tuscany’s most iconic towns in a single day. For around 8.5 to 12 hours, this tour takes travelers from Florence into the heart of Tuscany, with a focus on history, scenic views, and regional flavors. It’s perfect for those who want a comprehensive day trip that combines cultural sights, countryside scenery, and a memorable Tuscan dinner — all in a small-group setting.

The tour features visits to Siena, a UNESCO World Heritage Site, and San Gimignano, known for its skyline of medieval towers. An unforgettable sunset dinner in the Chianti hills is a key highlight, along with the option to upgrade to the Tuscany Grand Tour which adds Pisa and a Tuscan lunch. With positive reviews praising the guides, the scenery, and the food, this experience suits travelers looking for a well-organized, intimate way to experience Tuscany’s best.

Key Points

• Visits to Siena and San Gimignano—two of Tuscany’s most celebrated medieval towns
• Sunset dinner in the Chianti hills with regional wines and local dishes
• Small-group tours available, including a luxury Mercedes minibus option
• Optional upgrade to include Pisa and a full-day Tuscany adventure
• Expert English-speaking guides lead the walking tours and provide interesting insights
• Meeting point at Piazza Mentana in Florence, with flexible cancellation policies

You can check availability for your dates here:

From Florence to Siena and San Gimignano in Comfort

Starting from Via dei Vagellai, 22 R in Florence, this tour departs in a comfortable, air-conditioned minibus. Travelers can choose between a standard coach or premium Mercedes small-group ride, which offers a more intimate experience. The tour duration is flexible, lasting from 8.5 to 12 hours, depending on the selected options and timing.

The logistics are straightforward, with the meeting point located at Piazza Mentana, opposite the Arno River in Florence. The group size remains small, ensuring personalized attention and a relaxed atmosphere. The tour is led by an English-speaking guide, who shares stories, history, and interesting details about each location along the way.

Exploring Siena’s Historic Heart

Once in Siena, the guided walking tour begins in the enchanting historic center, a UNESCO site filled with medieval charm. The Piazza del Campo is the centerpiece, famous for hosting the Palio horse race twice a year. Visitors walk through cobbled streets, discovering Siena’s contrade — its 17 fiercely proud neighborhoods with deep-rooted traditions.

The guide leads you through the fascinating streets and piazzas, explaining Siena’s history, architecture, and local customs. Though the guided tour lasts around 5.5 hours including sightseeing, shopping, and optional walking, the main focus remains on experiencing Siena’s timeless ambiance and vibrant cultural life.

San Gimignano’s Medieval Skyline and Artisan Streets

After leaving Siena, travelers enjoy a scenic drive through the Tuscan hills to reach San Gimignano. Known as the “Manhattan of the Middle Ages,” San Gimignano is famous for its medieval towers that rise above the town. The town’s well-preserved alleys and piazzas invite exploration at your own pace.

During approximately 3 hours in San Gimignano, visitors can stroll along its ancient streets, take in sweeping views from the city walls, and browse artisan shops and gelaterias. The free time allows for an authentic experience of the town’s medieval architecture and lively local scene, though some reviews suggest one hour might feel limited for a full exploration.

Sunset in the Chianti Hills and Tuscan Dinner

The day’s highlight is an unforgettable sunset dinner in a countryside farmhouse or wine estate within the Chianti hills. As the sun dips, the landscape turns golden, providing a stunning backdrop for a traditional Tuscan feast. The meal features locally sourced dishes, regional wines, and regional specialties, making it more than just a dinner — it’s a culinary memory.

Travelers enjoy the relaxed atmosphere, with many reviews praising the passionate hosts and the quality of the food and wine. The dinner is not just a meal but an experience that captures the essence of Tuscan hospitality. The experience ends with a peaceful return trip to Florence in the quiet comfort of the minibus.

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Optional Tuscany Grand Tour: Pisa Included

For those seeking a fuller taste of Tuscany, the upgrade to the Tuscany Grand Tour adds a visit to Pisa, including its famous Leaning Tower. This extension turns the day into a 12-hour adventure that includes a Tuscan lunch and more sightseeing. It’s perfect for travelers eager to see another iconic Tuscan city and get a broader sense of the region’s art, history, and landscapes.

Practical Details and Group Experience

This tour is designed to provide a personalized experience with a small group size, making it easier to ask questions and enjoy a more relaxed pace. The live guide speaks English throughout, sharing insights and anecdotes that enrich the experience.

The tour is flexible with free cancellation up to 24 hours in advance, and you can reserve now and pay later, giving travelers peace of mind when planning their trip. Notably, the tour does not allow pets and is not suitable for travelers with mobility impairments.

Highlights According to Positive Feedback

Many reviews praise the knowledgeable guides, especially highlighting Romano for his excellent commentary and Micky (Michele) for her liveliness and energy. The scenery along the drive, the quality of the dinner, and the small-group intimacy are consistently mentioned as standout features.

The dinner at a small family winery receives particular praise, with some calling it the best lasagna ever and emphasizing the authentic atmosphere. The sunset vineyard experience is frequently described as a highlight of the trip.

Limitations and Considerations

While most reviews are highly favorable, some mention limited time in San Gimignano, feeling that more time to explore would be ideal. Also, the timing means that seeing San Gimignano or Siena at night isn’t always possible, which could limit the ambiance if travelers prefer evening visits.

Final Thoughts on This Tuscany Day Trip

This small-group tour from Florence offers a well-balanced mix of sightseeing, culture, and culinary delights. It’s a great choice for those who want to see Siena and San Gimignano comfortably and indulge in a memorable sunset dinner in the Tuscan countryside.

The upgraded Tuscany Grand Tour broadens the experience further, perfect for travelers with an extra day to spare. The combination of expert guides, scenic drives, and regional food and wine makes this an appealing option for history, culture, and wine lovers alike.

Frequently Asked Questions

How long is the tour?
The tour lasts between 8.5 and 12 hours, depending on the selected option and timing.

Where does the tour depart from?
From Via dei Vagellai, 22 R in Florence, at Piazza Mentana, opposite the Arno River.

What is included in the dinner?
The dinner features locally sourced dishes along with Tuscan wines and regional specialties, served at a countryside farmhouse or wine estate.

Can I upgrade to include Pisa?
Yes, there is an optional upgrade called the Tuscany Grand Tour that adds a visit to Pisa and a Tuscan lunch.

What size are the groups?
Small-group options are available, with personalized attention, especially on the luxury Mercedes minibus.

Is the tour accessible for travelers with mobility issues?
No, the tour is not suitable for travelers with mobility impairments.

How flexible is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund.

How do I book and pay?
Reservations can be made now with the option to pay later, providing flexibility.

Are pets allowed?
No, pets are not permitted on this tour.

What do reviews say about the guides?
Guides are praised for their knowledge, friendliness, and passion, with notable mentions of Romano and Micky for their engaging commentary.

What is the main highlight of the tour?
Most agree that the sunset dinner in the Chianti hills and the scenic visits to Siena and San Gimignano are the key memorable moments.

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