From Florence: PRIVATE Siena and San Gimignano with wine tasting

A Full-Day Private Tour from Florence: Siena, San Gimignano & More

This private excursion from Florence offers a well-rounded taste of Tuscany’s medieval charm without the hassle of renting a car. For around $640 per person, you’ll spend roughly 9.5 hours exploring Siena’s stunning Piazza del Campo, wandering the towers of San Gimignano, and soaking up the history at Monteriggioni Castle. It’s a small-group, personalized experience with guided visits, a gourmet Tuscan lunch, and wine tasting—all in the comfort of a plush minivan.

What we really love about this tour is how it balances guided insights with free time, giving you space to soak in each town at your own pace. Plus, the inclusion of a wine tasting and lunch in an atmospheric setting elevates the day from merely sightseeing to a true taste of Tuscany’s local flavors.

One potential consideration is the price—while the tour offers a lot, it does come at a premium compared to self-guided options. However, the comfort of private transportation and expert guides often makes it worth the extra cost. This tour is perfect if you appreciate historical towns, want easy logistics, and enjoy sampling local wines and cuisine—all in one seamless day.

If you’re a traveler who values expert local guides, authentic small-town atmospheres, and a good mix of cultural and culinary experiences, this tour will likely suit you perfectly. It’s especially well-suited for those who prefer comfort, convenience, and a bit of guided storytelling to enhance their understanding of Tuscany’s highlights.

Key Points

• Comfortable Transportation: Round-trip in a luxury minivan with air conditioning and water.
• Expert Guides: Knowledgeable local guides lead the Siena visit, enriching your understanding.
• Authentic Experiences: Free time in Siena, San Gimignano, and Monteriggioni allows personal exploration.
• Gourmet Lunch & Wine Tasting: Indulge in Tuscan cuisine and learn about local wines in a scenic setting.
• Balanced Itinerary: Carefully curated stops highlight Tuscany’s medieval architecture and landscape.
• Intimate Group Size: Private tour with a maximum of 8 guests for a personalized experience.

The Itinerary in Detail: What You Can Expect

Starting Point and Transportation

Your day begins early, meeting at Cantinetta Antinori in Florence at 8:00 am. From there, you’ll hop into a premium minivan, which is a far cry from the cramped, noisy buses some tours offer. The driver, who also acts as your guide, is friendly, helpful, and dedicated to making your journey smooth. With air conditioning and plenty of water, you’ll be comfortable as you travel through the Tuscan countryside—famous for its rolling hills, vineyards, and olive groves.

Siena: Medieval Majesty

The first stop is Siena, one of Tuscany’s crown jewels. Here, a local guide named Maria (according to reviews) will take you through the heart of the city for about an hour. Expect to walk through Piazza del Campo, renowned for its shell shape and vibrant daily life. You’ll also visit Piazza del Duomo and the stunning Siena Cathedral, an architectural marvel with intricate marble floors and impressive facades.

The guided portion provides insights into Siena’s unique history and medieval atmosphere. Afterward, you have roughly an hour of free time. This is your chance to explore the Duomo’s interior, browse local shops, or simply enjoy the lively street scenes. Several reviews mention that Siena’s charm and beauty got high praise—one reviewer called it “very interested and beautiful,” highlighting how the city’s authentic medieval vibe rings true.

Monteriggioni Castle: A Walled Wonder

Next, you’ll drive to Monteriggioni, a tiny, walled hilltop town built in 1213. Its compact size and ramparts make it feel like stepping into a medieval film set. Dante Alighieri even mentions Monteriggioni in the Divine Comedy, underlining its fame. You’ll have about an hour and a half here, which is enough to walk the ramparts, enjoy the panoramic views, and absorb the castle’s storied past.

Then, comes the highlight for many—lunch in a scenic location with local wine. The reviews emphasize the quality and atmosphere, noting that the lunch is not just a meal but a true taste of Tuscany’s culinary tradition. The included wine tasting here is a real treat, offering a chance to learn about vineyard techniques, wine aging, and how to appreciate different varieties.

San Gimignano: Towering Medieval Town

The journey continues through the scenic Chianti landscape, dotted with vineyards and olive groves. Arriving in San Gimignano, you’ll get about 1.5 hours to explore the “Town of Beautiful Towers.” The skyline, dominated by medieval towers, is a UNESCO World Heritage site, and the narrow streets are perfect for wandering at your own pace.

Many travelers praise the free time here, citing the town’s charm and photogenic appeal. You might visit the Collegiate Church of Santa Maria Assunta or just soak in the views from one of the many viewpoints. The town’s history as a medieval trading hub adds to its authenticity and allure.

Wine Tasting & Final Return

The tour culminates with a visit to a local winery, where you’ll spend about 75 minutes learning about the wine-making process. You’ll taste different wines and olive oils, gaining appreciation for Tuscany’s renowned products. The reviews highlight this part as particularly enjoyable, with guides explaining vineyard techniques and helping you understand how to savor each glass.

After the tasting, your driver will bring you back to Florence, just in time for sunset. The comfortable ride and scenic views make the return trip relaxing, and many reviews note how the experience’s overall value made it well worth the price.

Why This Tour Offers Great Value

While $640 per person might seem steep at first glance, consider what’s included — private, air-conditioned transport, guided tours, a gourmet lunch, and wine tasting. Without the stress of navigating or making multiple bookings, you get a seamless day that covers significant highlights in a manageable, intimate setting. The reviews underscore how knowledgeable guides, especially in Siena, enrich the experience, turning sightseeing into storytelling.

Plus, the flexibility of time in each town lets you avoid rushed visits. You can explore at your leisure, whether that means browsing shops, taking photos, or just sitting with a glass of local wine and soaking up the atmosphere.

Who Will Love This Tour?

This trip is ideal for travelers who want to see Tuscany’s key medieval towns without the complications of self-driving. If you value expert guides, authentic small-town experiences, and culinary delights, you’ll find this tour hits the mark. It’s especially suited for families, couples, or small groups who enjoy a personalized touch and the comfort of private transportation.

If you’re the type of traveler who appreciates historical context and local flavors in a relaxed, well-organized setting, this trip will likely become a highlight of your Italian journey.

FAQ

Is hotel pickup and drop-off included?
No, the tour begins and ends at the designated meeting point in Florence.

What is the maximum group size?
A maximum of 8 people ensures a more personal experience and attentive guides.

Can children participate?
Yes, there’s no minimum age requirement, but children must be accompanied by adults.

How long is each stop?
Siena: about 2 hours (guided plus free time), Monteriggioni: 1 hour 30 minutes, San Gimignano: 1 hour 30 minutes, wine tasting: 1 hour 15 minutes.

What is included in the price?
Guided tours in Siena, lunch, wine tasting, private transportation, and a professional guide.

Is the tour suitable for those with mobility issues?
Since walking is involved in towns like Siena and San Gimignano, travelers with mobility concerns should consider this before booking.

What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund.

To sum it up, this private tour from Florence offers a rich blend of history, scenery, and culinary delights in Tuscany’s most famous medieval towns. The flexible schedule, expert guides, and inclusion of delicious food and wine make it an excellent choice for travelers eager for an authentic, hassle-free Tuscan experience. Whether you’re a history buff, a wine lover, or simply want to enjoy Italy’s landscape without the stress of driving, this day trip will leave you with lasting memories—and plenty of photos.