Visit Siena and San Gimignano with lunch at a family farm

If you’re dreaming of wandering through the postcard-perfect streets of Tuscany, this private tour offers a well-rounded taste of what makes this region so special. Designed for those who want to combine history, scenic landscapes, and delicious food, it’s a package that promises a memorable day without feeling rushed.

What we really like about this experience is how smoothly it’s arranged—your driver picks you up directly from your accommodation, cutting out the hassle of navigating on your own. Plus, the focus on authentic experiences, like a homemade farm lunch paired with Chianti wines, really captures the spirit of Tuscany.

On the flip side, the full day can feel quite packed, especially if you’re not used to moving between several sites in one go. It’s important to come prepared for a fair amount of walking and a busy schedule. This tour will suit travelers who enjoy a mix of sightseeing, culinary delights, and scenic drives, especially those with an appreciation for local craftsmanship and history.

Key Points:

• Seamless pickup and drop-off directly from your accommodation
• Authentic Tuscan food and wine experiences that highlight regional flavors
• Visit UNESCO sites in Siena and the iconic towers of San Gimignano
• Beautiful scenic drives through Chianti hills and countryside
• Flexible language options including English, French, and Spanish-speaking guides
• A well-curated itinerary balancing history, scenery, and food in about 7 hours

You can check availability for your dates here:

Why This Tour Stands Out

This tour offers a genuine taste of Tuscany’s most charming highlights in one day. We liked that it’s a private experience, which means you get personalized attention and a flexible schedule. It’s a great way to explore if you prefer to avoid crowded group tours and want to enjoy the sights at your own pace with a knowledgeable guide.

The pick-up service is especially convenient. Instead of worrying about taxis or public transport, your driver, speaking your preferred language, will come straight to your door, saving you time and effort. That’s a big plus if you’re traveling with a lot of luggage or just want a hassle-free start to your day.

Discovering Siena: A Medieval Gem

Your journey begins in Siena, a city often overshadowed by Florence but equally captivating. We loved how the city’s historic center is a UNESCO World Heritage site, with its stunning Piazza del Campo at the heart. It’s the perfect place to soak in medieval architecture, with its curving streets and stone buildings.

You’ll have about an hour and a half to explore on your own—this is enough time to admire landmarks like the Duomo di Siena, take some photos, or simply enjoy the lively atmosphere. According to reviews, guides are well-informed and friendly, adding context to the sights without overwhelming you.

Tasting Tuscany: Lunch at a Family-Run Farm

One of the highlights of this tour is the lunch at a traditional family farm in the Chianti hills. We found the idea of a farm-to-table meal really appealing—fresh, homemade, and full of local flavors. You’ll savor homemade pasta paired with a curated selection of Chianti wines, including Chianti Reserva and Super Tuscan varieties.

The farm offers a genuine look at regional food traditions, with five types of olive oil and three different balsamic vinegars to sample. Plus, the guide will walk you through the wine-making process, making the tasting both educational and enjoyable.

Guests have raved about the food and wine, with one reviewer calling the experience “fabulous” and mentioning the high-quality olive oils and wines. The farm setting adds a peaceful, rustic touch to the experience, far from touristy restaurants.

Exploring San Gimignano: The Town of Towers

In the afternoon, you’ll visit San Gimignano, known for its impressive medieval skyline of fifteen towers. It’s easy to see why it’s called the “Town of Fine Towers.” The historic center is compact enough to stroll in an hour but packed with plenty of photo-worthy spots.

You’ll love wandering through artisan shops and taking in panoramic views over the countryside from the towers. According to reviews, the guide helps you make the most of your visit, pointing out highlights and sharing stories that bring the town’s history to life.

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Scenic Drive and Photo Stops

The drive through the Chianti Hills offers stunning views of rolling vineyards, olive groves, and quaint farmhouses. There’s a quick 20-minute photo stop to appreciate the landscape and capture some memorable shots. This part of the trip is a great chance to relax and enjoy Tuscany’s natural beauty.

Timing and Pacing

The entire experience lasts around 7 hours, with the driver arriving at your accommodation in Florence around 4 pm. The schedule is quite full but well-structured, giving you enough time at each stop to enjoy without feeling hurried.

The tour is ideal for travelers who want a comprehensive, yet relaxed, overview of Siena and San Gimignano, combined with good food and wine. The group size is private, ensuring a more intimate experience—a plus if you prefer personalized attention.

Real Experiences from Other Travelers

Many reviewers have praised the guides for their knowledge and friendliness. One said, “Stefano was over the top amazing,” highlighting the personal touch guides bring to the experience. Others appreciated the quality of the wine and olive oil tastings, describing them as “fabulous” and “delicious.”

A family particularly appreciated the flexibility and attentiveness of the driver, who helped with logistics and made sure everyone, including babies, felt comfortable. The overall consensus is that this tour delivers excellent value, especially for those who love combining scenery, history, and culinary delights.

Practical Details & Considerations

The tour includes hotel pickup and drop-off, and the driver can pick up at private addresses or B&Bs, provided you specify the location. The small group size (private group) means you get personalized service, but it also requires good weather, as most of the day involves outdoor walking and scenic drives.

The cost reflects the private, curated nature of the experience, which many find worthwhile given the hassle-free logistics, personalized attention, and high-quality activities.

Who Is This Tour Best For?

This experience is perfect if you’re looking for a relaxed yet comprehensive day trip that combines sightseeing, local food, and wine tasting without the chaos of a large tour group. It works well for couples, small families, or friends who enjoy a mix of history, scenic landscapes, and culinary exploration.

While it isn’t specifically tailored for children, the relaxed pace and engaging food experiences could be enjoyable for those traveling with teenagers or older children. However, younger kids should be prepared for some walking and outdoor time.

Final Thoughts

All in all, this tour offers a well-rounded taste of Tuscany’s highlights in a way that feels intimate and authentic. The highlight for many is the personalized guide, who makes the experience informative and fun without overloading you with facts. The lunch and wine tasting elevate the day from sightseeing to a true regional immersion.

If you’re after a convenient, private way to experience Siena and San Gimignano, combined with top-quality food and wine, this trip is definitely worth considering. Just remember to come ready for a full day and some walking—it’s a busy but rewarding adventure.

FAQ

Is hotel pickup included?
Yes, your driver will pick you up directly from your accommodation in Florence, whether it’s a hotel, apartment, or B&B, with no extra charge.

How long is the total tour?
The entire experience lasts about 7 hours, including transport, sightseeing, lunch, and tastings.

Can I customize the pickup location?
Pickup is available in the indicated province or at private addresses if you specify the location in advance. Make sure it’s in a paved area and not within restricted traffic zones.

What languages do guides speak?
Guides are available in English, French, and Spanish.

What’s included in the farm lunch?
Expect homemade pasta, five types of olive oil, three balsamic vinegars, and a curated selection of wines including Chianti, Chianti Reserva, Super Tuscan, and Vernaccia.

Is this tour suitable for families?
While not specifically marketed as family-friendly, the relaxed pace and engaging tastings could appeal to older children and teenagers. Parents should consider the walking involved.

What about the scenery?
You’ll enjoy scenic drives through the Chianti hills, with photo stops to capture the stunning landscapes of vineyards and olive groves.

How does the wine tasting work?
You’ll sample a curated selection of regional wines, guided by knowledgeable staff, in an authentic farm setting. It’s educational and enjoyable.

This tour balances scenic beauty, cultural richness, and culinary delights, making it a fantastic way to experience Tuscany if you want a bit of everything in one day.

You can check availability for your dates here: