From Florence: Siena & San Gimignano Guided Tour and Dinner

Discover the Charm of Tuscany with the Siena & San Gimignano Guided Tour and Dinner

This highly-rated tour from Florence offers a popular way to experience Tuscany’s best-known medieval towns without the hassle of driving yourself. We’ve reviewed the experience based on extensive feedback, and it seems like a perfect option for travelers craving an immersive, authentic day full of history, stunning scenery, and regional flavors.

What we love about this tour:

• The intimate nature of the small-group format, which allows for a more personal experience and easier interaction with guides.
• The chance to explore two UNESCO World Heritage Sites—Siena and San Gimignano—with expert-guided tours that go beyond just walking around.
• Ending the day with a sunset dinner in the Chianti hills, complete with local wine tasting, making the trip truly memorable.

One potential drawback is that the day can feel quite packed, especially if you’re hoping for a slow-paced exploration. It’s best suited for those who want a comprehensive taste of Tuscany in one day. This experience is ideal for travelers who love history, picturesque landscapes, and regional food and wine, but prefer not to navigate the logistics themselves.

You can check if your dates are available here:

Good To Know

• Small-group size enhances comfort and personalized attention.
• Two UNESCO sites provide a deep dive into Tuscany’s medieval charm.
• Sunset dinner in the hills offers incredible photo opportunities and atmosphere.
• Expert guides and drivers make the day flow smoothly and add insightful commentary.
• Optional upgrade includes Pisa for a full Tuscan itinerary.
• Great value considering the inclusions like guided tours, wine tastings, and a traditional dinner.

An In-Depth Look at the Tour Experience

Starting Point and Transportation

This tour begins at Piazza Mentana in Florence, a central, easily accessible spot. Guests are transported in either a comfortable minivan or a coach, depending on the option chosen—standard or premium small-group Mercedes. The ride through the Tuscan countryside is part of the charm, with knowledgeable guides sharing snippets about the region’s history and landscape.

Travelers often mention the convenience of being picked up without the need to organize their own transport, which is a big plus given the early start and full schedule. The journey usually lasts around 1 to 1.5 hours, with plenty of opportunities to settle in and enjoy the scenery.

Siena: The Timeless Rival of Florence

Your first stop is Siena, a city that offers a different vibe from Florence—less grandiose but equally captivating. The guided walking tour takes you through the UNESCO-listed historic center, where you’ll see the famous Piazza del Campo, a shell-shaped square famous for hosting the Palio horse race.

Guides like Romana, mentioned in reviews, are praised for sharing rich details and personal insights, making the experience more engaging. Reviewers highlight that the small group setting makes it easier to ask questions and get a more intimate feel of Siena’s contrade neighborhoods—each with its own history and proud traditions.

Expect to spend around 2 to 2.5 hours here, exploring cobbled streets, ancient architecture, and hidden corners. Reviewers mention how the guide’s stories made the history come alive, adding depth beyond just the sights.

More Great Thing To Do Nearby

San Gimignano: The Medieval Manhattan

After Siena, the tour continues through rolling hills dotted with vineyards and olive groves toward San Gimignano, often called the “Manhattan of the Middle Ages” because of its skyline of medieval towers.

During free time, you can wander at your own pace, browse artisan shops, enjoy a cone of authentic gelato from local gelaterias, or walk along the city walls to take in sweeping views. Many appreciate the balance between guided and free time, allowing for personal exploration.

Guides emphasize San Gimignano’s well-preserved medieval architecture and its UNESCO listing, making it a highlight for history buffs and photo enthusiasts alike.

The Sunset & Tuscan Feast

The tour’s pièce de résistance is the sunset dinner in a Tuscan countryside farmhouse or winery. As the sun dips behind the hills, the landscape becomes a canvas of gold. Guests are seated outdoors, surrounded by rolling vineyards and olive groves, creating a magical setting.

The dinner features regional dishes sourced locally, paired with Tuscan wines, often including a tasting at the winery. One reviewer describes it as a “delicious and memorable” experience, with the host sharing insights into local wine production. The ambiance, combined with the golden light and regional flavors, makes it more than just a meal—it’s a moment to savor and remember.

Return to Florence

After dinner, the relaxed drive back completes the experience. Travelers often mention feeling full of visual delights, flavorful food, and new knowledge. The overall timing allows for a comfortable, not rushed, end to a full day.

Optional Tuscany Grand Tour

For those wanting more, the upgrade to the Tuscany Grand Tour adds Pisa and its iconic Leaning Tower, plus a full Tuscan lunch. This option turns a day-trip into a comprehensive exploration of Tuscany’s art, architecture, and landscapes, stretching to about 12 hours of adventure.

The Allure of the Experience

This tour excels at combining the essentials of Tuscany—medieval towns, scenic countryside, and regional cuisine—into one well-organized, enjoyable package. The focus on small groups means fewer crowds and more relaxed interactions with guides, which reviewers have consistently praised.

The Value Factor

At $106.54 per person, the package offers an impressive amount of inclusions: guided tours, wine tastings, dinner, and transport. Many reviewers feel the experience is well worth the price, especially considering the personalized service and the quality of the sites visited.

What Could Be Improved?

The main consideration is the duration—around 8.5 to 12 hours—which can feel long for some, especially if you prefer more leisure time or a slower pace. Also, the itinerary involves some quick stops, so it’s best suited for those eager to see a lot without spending too much time in each place.

Who Is This Tour For?

This experience is best for travelers who want an active, engaging day with plenty of highlights. It suits those interested in history, great scenery, and regional food and wine, but who prefer not to plan their own day trip logistics. It’s particularly ideal for small-group lovers who appreciate personalized attention.

Frequently Asked Questions

Does the tour include pickup from my hotel?
No, the tour starts at Piazza Mentana in Florence. You’ll need to make your way there, but the central location makes it easy to access.

Is transportation comfortable?
Yes, depending on your chosen option, you’ll travel in either a mini coach or a Mercedes minibus, both known for comfort and smooth rides.

How long does the tour last?
The tour runs from about 8.5 hours up to 12 hours, depending on the day’s schedule and optional upgrades.

Can I upgrade to include Pisa?
Yes, the Tuscany Grand Tour upgrade adds Pisa and a Tuscan lunch, making for a longer, more comprehensive day.

Are the guides knowledgeable?
Yes, reviews frequently mention guides like Romana, who share engaging stories and personal insights, enhancing the experience.

Is this suitable for children or those with mobility issues?
The tour is not recommended for people with mobility impairments, and children’s suitability depends on their interest and stamina for a long day.

What’s the highlight of the experience?
Many say the sunset dinner in the Chianti hills is the most memorable, thanks to stunning scenery, regional cuisine, and local wines.

Can I expect free time at each stop?
Yes, especially in San Gimignano, where you can explore on your own during the allocated free time.

Is the cost justified?
Considering the guided tours, tastings, dinner, and transportation, reviewers generally agree it offers excellent value for money.

Final Thoughts

This Siena & San Gimignano tour from Florence offers a fantastic way to see some of Tuscany’s most iconic towns with minimal hassle. The combination of guided storytelling, scenic drives, and a sunset dinner creates a memorable experience suited for eager explorers and food and wine lovers alike.

If you’re after a small-group atmosphere, expert guides, and a well-rounded taste of Tuscany, this tour delivers. Just be prepared for a long day, and you’ll leave with plenty of photos, new knowledge, and a full belly of regional flavors.

Perfect for travelers wanting a meaningful, hassle-free introduction to Tuscany’s medieval gems, with the added bonus of a sunset dinner to top it all off.

You can check if your dates are available here: