Private Tour of Chianti Siena and San Gimignano by Minivan

If you’re dreaming of a day exploring the timeless charm of Tuscany, a private tour through Chianti, Siena, and San Gimignano could be just what you need. These guided trips promise personalized attention, stunning scenery, and the chance to experience some of Italy’s most iconic spots without the hassle of navigating on your own.

What we really like about this particular experience is how flexible and personal it feels—your guide is dedicated to crafting a day that suits your interests, whether that’s focusing on breathtaking views or indulging in local wines. Plus, the scenery along the wine route, especially between Florence and Siena, is a sight to behold.

On the flip side, the price is not exactly pocket change, and optional extras like wine tastings or meals can add up. This tour best suits travelers who appreciate comfort, a bit of customization, and the opportunity to see multiple highlights in one day without feeling rushed. It’s ideal for those who want a relaxed, private experience—perfect for couples, friends, or small groups.

Key Points

• Private, air-conditioned transportation makes for a comfortable day of sightseeing.
• Flexible itinerary that can be tailored to your interests, with knowledgeable guides.
• Stunning scenic drives along Tuscany’s famous wine route, with breathtaking views.
• Visits to historic towns like Siena and San Gimignano, both UNESCO sites with medieval charm.
• Wine tasting options at Chianti wineries, with the chance to sample local wines and explore cellars.
• Round-trip convenience from Florence, with pickup and drop-off included.

What’s Included in the Tour

This private tour offers a lot of value for those who want a hassle-free experience. You’ll travel in your own air-conditioned minivan, which means plenty of space, comfort, and climate control—crucial for Tuscan summer days. Bottled water is on hand, so hydration isn’t a concern as you explore.

The actual transportation is exclusive to your group, which can be up to six people. Since it’s private, you won’t be sharing with strangers, and that means more flexibility with timing and stops. The meeting point is typically arranged for a 9:00 am start, with the tour lasting approximately 8 to 9 hours, giving you ample time to soak in the sights.

The Itinerary: What You Can Expect

Stop 1: Piazzale Michelangelo – The Viewpoint Over Florence

Your day kicks off with a quick jaunt to Piazzale Michelangelo. This spot is famous for panoramic photos of Florence’s skyline, including the Duomo and Ponte Vecchio. It’s a crowd favorite for good reason, and 15 minutes here give you a taste of the city’s beauty before heading into the countryside.

Stop 2: Piazza del Campo in Siena

Next, you’ll spend around two hours exploring Siena’s historic center, centered around the iconic Piazza del Campo. This square is a marvel—sloped, shell-shaped, and lined with medieval buildings. It’s the heart of the city and a perfect place to soak in Siena’s atmosphere. You’ll have the chance to wander at your own pace, check out shops, or just sit back and enjoy the scenery.

Stop 3: Farm Sant’Appiano & Optional Wine Tasting

A highlight for many is the visit to Farm Sant’Appiano, where you can peek inside a working cellar and see how wine is made. If you choose to, you can indulge in a tasting of six local wines and enjoy a meal—though this costs an additional €60 per person. Many reviews praise this stop, with comments like “the wine was incredible” and “the owners were very involved and informative,” making it a memorable experience.

Stop 4: San Gimignano – The Medieval Town with Towering Charm

In San Gimignano, you’ll have about two hours to explore this UNESCO World Heritage Site. Known for its medieval towers and well-preserved walls, it’s a fairy-tale setting. The Piazza della Cisterna, flanked by medieval houses, and the local cathedral with Ghirlandaio frescoes are prime attractions. Think cobblestone streets, panoramic views, and a real sense of stepping back in time.

Stop 5: Scenic Drive Along Strada in Chianti

The return journey includes a leisurely drive along the Strada 222 wine route. This stretch of road is famous for its breathtaking views of rolling vineyards, lush hills, and charming villages. Many reviews mention how this drive alone makes the tour worthwhile—an experience of Tuscany’s landscape that’s hard to beat.

How the Experience Comes Together

The reviews consistently highlight how this tour’s success lies in the guides’ flexibility and knowledge. Francesco and Gino, the standout guides, are praised for their warm, engaging manner and their ability to adapt the day to your interests. One reviewer notes, “Francesco was helpful and flexible,” while another appreciates Gino’s kindness and care, especially when accommodating mobility issues or rainy weather.

The transportation itself receives high marks for comfort and safety, with many reviewers mentioning how much they appreciated having their own space without the crowd of a larger bus. The vehicle’s wifi, as noted by one guest, adds convenience, especially when staying connected or sharing photos during the trip.

The Value of the Tour and Extra Costs

The base price of around $719.87 per group (up to six people) covers transportation, bottled water, and the core itinerary. However, the optional wine tasting and lunch at Farm Sant’Appiano cost about €70 per person, which many consider a worthwhile splurge given the quality of wines and the lovely setting.

While the price might seem steep for a day trip, many reviews point out the value in having a private, personalized experience. You won’t be rushed, and the flexibility allows you to spend more time at places that resonate most with you. For travelers seeking a relaxed yet comprehensive way to see Tuscany’s highlights, this tour offers a good balance of sightseeing and comfort.

The Downsides to Keep in Mind

Some reviews mention minor setbacks—like one guest feeling the Siena visit was a bit brief or that the tour didn’t include a full Siena-specific guided experience. Also, the optional wine tasting and meal are additional expenses, so budget accordingly.

A few guests noted that the itinerary covers a lot, and time in each location is somewhat limited—an unavoidable trade-off when trying to see so much in one day.

Who’s This Tour For?

This experience suits travelers who value comfort, flexibility, and a private setting. If you want to avoid crowded tours and prefer a personalized approach, this is a strong choice. It’s ideal for those who want to enjoy scenic drives, explore medieval towns, and sample local wines without the hassle of planning every detail.

It’s also perfect for small groups, couples, or friends who want a day of relaxation and discovery. Families with older children may also appreciate the laid-back vibe and scenic stops, but check with the provider if traveling with kids under 6.

Frequently Asked Questions

Is this tour suitable for families?
Yes, especially for families with older children or teenagers who enjoy scenic drives and exploring historic towns.

What’s the duration of the tour?
The tour lasts approximately 8 to 9 hours, starting at 9:00 am.

Can I customize the stops?
Yes, the tour is private and can be tailored to your interests, including extra time at certain locations or skipping optional activities.

Are meals included?
Lunch is not included in the base price but can be added at an extra cost (€60 per person at Farm Sant’Appiano). The tour includes bottled water and transportation.

What is the price?
It’s around $719.87 per group (up to 6 people), making it a good deal for a private experience covering multiple highlights.

What’s the best part of the tour?
Many guests rave about the scenic drive along the wine route and the personalized service from knowledgeable guides like Gino and Francesco.

Is there a wine tasting?
Yes, optional tastings are available at the Chianti winery, costing about €30 per person. Many reviews praise the quality of wines and the cellar visits.

What if it rains?
The tour is private and offers flexibility. Guides like Francesco and Gino are praised for their helpfulness in bad weather, such as greeting guests with umbrellas.

Are there any hidden costs?
Optional activities like wine tasting and meals cost extra. The main price covers transportation, bottled water, and the core itinerary.

What should I bring?
Comfortable shoes for walking in towns, a camera for the views, and maybe a hat or sunscreen for sunny days.

Final Thoughts

If you’re after a relaxed, personalized way to experience Tuscany’s most iconic sights, this private tour offers a well-planned, scenic, and engaging day. The ability to customize your experience, combined with the comfort of private transportation and expert guides, makes it a standout choice for small groups or couples wanting in-depth exploration without the crowds.

You’ll love the way this tour balances sightseeing, scenery, and tasting experiences—each stop carefully chosen to give you a taste of Tuscany’s essence. Though it costs a bit more than standard group tours, many travelers find the private, tailored approach worth every euro.

For those who want to see the best of Chianti, Siena, and San Gimignano in one day, with a guide who acts more like a host than just a driver, this tour ticks all the boxes. It’s a fantastic way to deepen your Tuscan experience with comfort, flexibility, and authentic charm.

Hope this helps you decide if this private tour is right for your Tuscan adventure. Feel free to ask if you want more tips or insights about exploring Italy!