From Florence: Siena, San Gimignano & Chianti

Planning a trip to Tuscany and wondering how to soak up its essence without being dragged around in a big tour bus? This private day trip from Florence to Siena, San Gimignano, and Chianti offers an intimate, relaxed way to experience some of Italy’s most iconic towns and landscapes. While it’s not the cheapest option, the personalized attention, curated itinerary, and tasting experiences make it well worth considering—especially if you want a mix of culture, scenery, and wine without the hassle of self-driving.

We particularly like that this tour keeps driving to a minimum, allowing you more time to explore and absorb the atmosphere. The chance to walk through medieval streets and piazzas, while sampling world-class wines, makes for a memorable day. One thing to keep in mind is that this is a full-day excursion, so it’s best suited for those prepared for a long, active day. If you’re after a personalized, in-depth look at Tuscany’s highlights with a knowledgeable guide, this tour might be just the ticket.

However, some travelers might find the price a bit steep given the inclusion of only one scheduled wine tasting and no lunch. Also, if you’re not a fan of guided tours or want more free time in each town, you might prefer a different format. But for couples, small groups, or travelers hungry for a deep, authentic experience with a focus on wines and medieval towns, this tour hits many sweet spots.

Key Points

• Private group experience offers personalized attention and flexibility.
• In-depth visits to Siena and San Gimignano provide authentic local atmosphere.
• Wine tasting at a Chianti winery delivers a true taste of Tuscany’s renowned wines.
• Limited driving time maximizes exploring and minimizes travel fatigue.
• Cultural highlights include piazzas, medieval towers, and scenic views.
• Pricing is based on a per-group fee, making it good value for a private experience.

You can check availability for your dates here:

An Authentic Taste of Tuscany: The Tour Experience

What Sets This Tour Apart?

This is a private guided day trip from Florence that focuses on quality over quantity. Instead of rushing from one place to another, you’ll spend meaningful time in each location, with your own driver/guide tailoring the experience. The tour promises limited driving—a real plus given Tuscany’s scenic but winding roads—so you can enjoy the view and learn about the region without feeling hurried.

Starting Point and Logistics

You’ll meet your guide at Piazza Adua, near a Burger King—an easy, central spot in Florence. From there, your journey begins with a comfortable private vehicle, oriented towards making the most of your time. The tour is scheduled for roughly 10 hours, but check the availability for your preferred start times, ensuring it fits your travel plans.

Siena: Medieval Majesty

First stop is Siena, a city that looks like a living museum with its narrow streets, Gothic architecture, and famous Piazza Il Campo. Your guide will take you through the historic center, explaining Siena’s unique medieval heritage, including the Palio horse race and the stunning Duomo di Siena. Expect about 105 minutes here, enough to appreciate the grandeur and take some photographs, but not so long that you miss other highlights.

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San Gimignano: The Town of Towers

Next, you’ll visit San Gimignano, often called the “Medieval Manhattan” for its skyline of medieval towers. With about 1.5 hours to explore, you’ll walk through its cobblestone streets, browse artisan shops, and soak in the views from the walls. The guided tour here offers insights into its history as a bustling medieval trading hub, and you’ll get a chance to sample local treats like Panforte and gelato, which are highly recommended by past travelers for their authentic flavors.

Chianti: Wine and Scenic Vistas

The highlight for many is the visit to a Chianti winery. With a guided tour of the cellars and a wine tasting session, you’ll discover why Tuscany’s wines are world-famous. The tour includes tasting big-brand Chianti Classico, giving you a chance to savor classic flavors and learn about the grape cultivation—mainly Sangiovese—an essential part of the region’s identity.

Past guests have noted that the scenic views en route are spectacular, with rolling hills, vineyards, and olive groves creating a perfect backdrop for your day. The winery visit lasts about 75 minutes, giving enough time to appreciate the wine-making process and enjoy some tastings.

End of the Day

Your day concludes back at Piazza Adua, giving you ample time to reflect on your Tuscany experience or plan the rest of your evening in Florence. Since the tour is private, your guide can offer tips or accommodate any specific interests you might have.

What’s Included and What’s Not

Included are the essential experiences like wine tasting, guided cellar tours, and a dedicated guide, all of which add value to the cost. Keep in mind that lunch is not included, so you might want to pack a snack or plan to dine in Siena or San Gimignano after your sightseeing.

Transportation is private, comfortable, and tailored to your group, which enhances the overall experience. It’s also a flexible option—able to cater to your pace and interests—making it a good choice for those seeking a more personalized day.

The Cost and Value

At $739.65 per group, this tour is on the higher end, especially considering that it covers just the main sights and a single winery visit. However, for a private experience with dedicated guide service, the value lies in the convenience, personalized attention, and quality of visits. If you’re traveling as a couple or small group, splitting the cost makes this a compelling option compared to larger group tours that can feel rushed.

Price Analysis

Compared to other similar experiences, the inclusion of guided tours, wine tasting, and private transport justifies the price. Travelers consistently mention the value of having a dedicated guide who enriches the visit with stories and historical context, which can be hard to glean on your own.

Who Will Love This Tour?

This experience is ideal for travelers who appreciate culture, wine tasting, and small-group intimacy. Perfect for those who want to avoid the crowds and enjoy a deeper, more relaxed exploration of Tuscany’s highlights. If your schedule is tight and you want to see Siena, San Gimignano, and Chianti in one day, this tour offers a comprehensive package.

Who Might Not Find It Suitable?

If you’re on a tight budget or prefer a more flexible, independent approach, you might find the price steep. Also, if you dislike guided tours or wish to spend more time exploring each town at your leisure, this might feel a bit regimented.

This private tour from Florence to Siena, San Gimignano, and Chianti offers a well-balanced mix of history, scenery, and wine—all in one day. The focus on personalized attention and limited driving makes it a relaxing yet informative way to experience Tuscany’s best. It’s especially suited for those who value authentic experiences, good storytelling, and the chance to taste some of Italy’s finest wines.

While the cost might seem high at first glance, the value is in the quality of the experience—small groups, expert guides, and carefully curated stops. If you’re looking for a day that combines cultural sights with wine and stunning landscapes, this tour delivers on all fronts.

Is this a private group experience?
Yes, this tour is designed for your private group, providing personalized attention and flexibility.

Where do I meet the tour?
You will meet your guide at Piazza Adua, near Burger King in Florence.

How long is the tour?
The tour lasts approximately 10 hours from start to finish, but check availability for specific starting times.

What does the tour include?
It includes guided visits to Siena and San Gimignano, a wine tasting at a Chianti winery, and private transportation. Lunch is not included.

Can I cancel this tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Are there language options for the guide?
Yes, the tour guide speaks English, Italian, and Spanish.

Is there any luggage storage?
If you are traveling with luggage, you should communicate this prior to booking, as it might affect arrangements.

What is the price for the group?
The cost is $739.65 for the entire group, making it a good value for a private, guided experience.

Is there free time in the towns?
Yes, in San Gimignano you will have some free time to explore, shop, or enjoy local treats.

This private tour blends scenic beauty, cultural richness, and wine indulgence into one memorable day. Perfect for those looking to experience Tuscany authentically without sacrificing comfort or depth.

You can check availability for your dates here: