From Florence: Siena & San Gimignano Guided Tour and Dinner

If you’re planning a day trip from Florence to taste the best of Tuscany’s medieval charm, this guided tour offers a thoughtfully curated experience. It’s perfect for travelers wanting a mix of history, stunning landscapes, authentic local food, and regional wines—all wrapped up in a manageable, well-organized package.

We’re impressed by how this tour balances guided sightseeing with enough free time to soak in the atmosphere of Siena and San Gimignano, two UNESCO World Heritage sites. The highlight for many? The sunset dinner in the Chianti hills, offering a memorable end to a day filled with beauty and flavor.

That said, it’s not without some considerations. The tour’s duration can stretch up to 12 hours, so it’s best suited for those comfortable with a full day on the move. Plus, the small-group setting, while intimate and engaging, might not appeal to those seeking a more flexible or independent style of exploring.

If you love history, scenic drives, authentic Tuscan cuisine, and regional wines, this tour is likely to fit your travel style nicely. It works especially well for first-time visitors wanting a curated overview of Tuscany’s iconic towns without the hassle of self-driving.

Key Points

• Intimate Small Group: A maximum of around 24 travelers, ensuring personalized attention and a more relaxed experience.
• Two UNESCO Sites: Guided visits to Siena and San Gimignano, highlighting Italy’s medieval history and architecture.
• Scenic Landscape: Beautiful rides through Tuscan hills, culminating in a sunset dinner in the Chianti countryside.
• Authentic Tuscan Dinner: Enjoy regional dishes paired with local wines at a countryside farmhouse or winery.
• Optional Upgrades: Add Pisa for a full-day Grand Tour, including the Leaning Tower and a Tuscan lunch.
• Convenient Transportation: Comfortable air-conditioned minibus or Mercedes options, depending on your booking choice.

You can check availability for your dates here:

The Itinerary in Detail

Departure from Florence

The tour begins at Via dei Vagellai, a central location just outside the historic city center. From here, the journey into Tuscany’s landscape quickly immerses you in the rolling hills, vineyards, and olive groves that define this region. The transportation is in a comfortable, air-conditioned minibus, which is crucial after a long morning of sightseeing and sitting.

Siena: Italy’s Timeless Rival to Florence

Our first stop is Siena, a city that rivals Florence in beauty and history but has a character all its own. The guided walking tour takes you through the enchanting historic center, a UNESCO World Heritage site. Expect to see the famous Piazza del Campo, where the legendary Palio horse race takes place twice a year. As you stroll the cobbled streets, you’ll discover Siena’s 17 contrade neighborhoods—each fiercely proud and steeped in tradition.

According to reviews, the guide in Siena is knowledgeable and personable, making the exploration lively and engaging. One traveler appreciated the tour for its timing—”It was nice to see Siena in the afternoon when it was cooler and less crowded.” Keep in mind, there’s limited time for shopping or extra exploring, so plan your photo stops accordingly.

San Gimignano: The Manhattan of the Middle Ages

After Siena, the adventure continues with a scenic drive into the hills to San Gimignano, famous for its medieval towers that create a skyline straight out of a storybook. The town’s well-preserved alleyways and ancient piazzas offer plenty of options for wandering independently during your free time.

Travelers rave about San Gimignano’s stunning views and its artisan shops and gelaterias. One reviewer mentioned, “We only had one hour of self-guided time, I would have liked a little more to explore some back streets.” It’s a good reminder to prioritize your must-see spots if time allows.

More Great Tours Nearby

Sunset Dinner in the Chianti Hills

The finale is arguably the most memorable part: a sunset dinner in a countryside farmhouse or wine estate. As the sun dips below the hills, you’ll be enjoying locally sourced Tuscan dishes, paired with regional wines. Several reviews highlight the quality of the food and wine, describing the dinner as a highlight. One guest called it the “best lasagna” they’d ever had, noting the intimacy of dining at a small family-run winery.

This experience isn’t just about the meal—it’s about the atmosphere. The golden light, the rolling vineyards, and the rustic setting make it a moment you’re unlikely to forget.

Return Journey

After dinner, the comfortable minibus whisks you back to Florence, making the long day feel manageable. The group size and friendly guides make for a smooth and engaging ride home, with travelers often sharing their favorite moments and photos.

Transport & Group Size

Depending on your booking, you’ll travel either in a standard coach or a luxury Mercedes minibus. The latter offers a more intimate, plush riding experience, which many reviewers appreciate. The small-group setting tends to foster a more personal interaction with the guide and fellow travelers, making it feel more like a day out with friends than a big tour bus.

Duration & Timing

The tour runs between 8.5 and 12 hours, so be prepared for a full day. Starting times vary, so check availability. The length is ideal for those eager to see multiple highlights without feeling rushed, though it’s a long day for some. The pacing allows enough time in Siena and San Gimignano to enjoy the sights without feeling hurried, according to reviews.

Price & Value

While the exact cost varies, this tour is generally regarded as offering excellent value given the inclusions—guided walks, transportation, a regional dinner, and wine tastings. The additional upgrade to the Tuscany Grand Tour—which adds Pisa and more region-wide sights—costs extra but delivers a more comprehensive experience. Travelers often find the price justified by the quality of guides, the scenery, and the authentic meals.

Authentic Experiences & Highlights

What truly sets this tour apart are the authentic Tuscan moments. From the lively Piazza del Campo to the panoramic view from San Gimignano’s walls, these are the sights that stay with you. The private dinner with regional wine is a rare treat, offering a taste of local life in a relaxed setting.

Guests consistently mention how knowledgeable and friendly the guides are. The driver and tour leader are praised for sharing insights about the region’s culture and landscape, making the entire day educational and fun.

Who Is This Tour Best For?

This tour is ideal for first-time visitors who want a comprehensive, guided look at Tuscany’s highlights without the stress of self-driving. It suits travelers who enjoy small-group intimacy and are happy to spend a full day exploring. It’s also perfect for those who appreciate authentic local food and wine and are looking for an immersive experience in the Tuscan countryside.

However, if you have mobility issues or prefer a more flexible, less structured day, this might not be the perfect fit. The tour involves walking on cobblestones and a long day on the road, so comfort and stamina matter.

Frequently Asked Questions

How early does the tour start?
Check the availability for specific start times; generally, it begins in the morning, with the exact time depending on the season and booking.

Is transportation comfortable?
Yes, the tour features air-conditioned minibuses, with options for Mercedes luxury vehicles, ensuring a comfortable ride through the Tuscan hills.

How much free time is there in Siena and San Gimignano?
You’ll have a guided tour in Siena, and then a few hours in San Gimignano for independent exploring, shopping, or sampling gelato, but time is limited, so plan accordingly.

What does the dinner include?
The dinner at a countryside farmhouse or winery features locally sourced dishes and regional wines, providing an authentic Tuscan meal experience.

Can I upgrade to the Tuscany Grand Tour?
Yes, the full-day Grand Tour adds Pisa and a Tuscan lunch, giving a broader regional perspective. It is an extra cost but offers a more comprehensive experience.

Is this tour suitable for children or kids?
While not explicitly stated, it’s a full day with walking and lengthy drives, best suited for older children or teenagers comfortable with long hours.

Are pets allowed?
Pets are not permitted on this tour.

Is there any flexibility if I have special requirements?
It’s advisable to inform the supplier in advance about any mobility issues or special needs so they can accommodate you as best as possible.

Will I need to make my own way back to Florence?
No, the tour includes round-trip transportation back to the starting point in Florence.

Final Thoughts

This guided tour from Florence offers a wonderful way to experience some of Tuscany’s most iconic sites, scenic landscapes, and culinary delights all in one day. It’s well-suited for travelers who seek a balanced mix of guided sightseeing, free time, and authentic regional experiences. The small group size fosters a friendly atmosphere, and the sunset dinner in the Chianti hills is a highlight many travelers remember long after returning home.

Ultimately, the tour delivers on its promise of a comprehensive, enjoyable, and memorable Tuscan adventure—whether you’re a first-timer or a seasoned traveler revisiting Italy’s heartland. If you value expert guides, beautiful scenery, good food, and a relaxed pace, this could be your perfect day in Tuscany.

You can check availability for your dates here: