Exploring the enchanting beauty of Tuscany on a private tour from Florence is an opportunity we shouldn’t miss. We’ll visit the historic cities of Siena and San Gimignano, along with the renowned Chianti wine region, all while savoring exquisite wines and discovering the region’s rich cultural heritage. With personalized guidance and comfortable transportation, this tour promises an unforgettable day in one of Italy’s most captivating provinces. Shall we delve deeper into the details?
Key Points

- This private tour from Florence covers the highlights of Tuscany, including the historic cities of Siena and San Gimignano, as well as the Chianti wine region.
- The tour includes transportation in a private Mercedes vehicle, local guides, and wine tasting, providing an immersive experience of Tuscan culture and cuisine.
- Travelers have praised the knowledgeable and professional guides, as well as the customized itinerary and secluded winery visits.
- The tour offers free time for exploring the Siena historical center and wandering in the medieval town of San Gimignano.
- Some travelers have mentioned a rushed pace due to the multiple stops, but overall, the tour provides an engaging journey through Tuscany.
Tour Overview

Though this private Tuscany tour from Florence allows you to visit the highlights of Siena, San Gimignano, and the Chianti wine region, it’s important to note that the pricing is per group, with a maximum of 8 people.
The tour includes hotel pickup and drop-off, and features a 4.6-star rating based on 103 reviews, earning it a Badge of Excellence.
During the day, you’ll have free time to explore Siena’s historical center, Piazza del Campo, and Duomo, as well as wander the charming town of San Gimignano and its 13 towers.
The Chianti region also offers optional winery visits.
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Itinerary Highlights

Let’s start our journey by exploring the itinerary highlights of this private Tuscany tour. Our day begins with a morning pickup from your centrally located hotel in Florence. First, we’ll head to the historical city of Siena, where we’ll have 2 hours to freely explore the charming Piazza del Campo and the magnificent Duomo di Siena. Next, we’ll venture to the medieval town of San Gimignano, known for its iconic 13 towers. After 1 hour of wandering, we’ll continue to the Chianti region for additional free time and an optional winery visit. Finally, we’ll return to Florence after our memorable Tuscan adventure.
| Location | Duration |
|---|---|
| Siena | 2 hours |
| San Gimignano | 1 hour |
| Chianti Region | Free time |
Inclusions
The private Tuscany tour includes a private Mercedes vehicle with a knowledgeable driver, bottled water, and Wi-Fi throughout the journey.
We’ll also have local guides in San Gimignano and Monteriggioni to share their expertise and insights. A wine tasting is included, allowing us to sample the region’s renowned Chianti offerings.
Lunch is provided, so we can refuel during our full-day adventure. With confirmation at booking and a maximum group size of 8, we’ll enjoy a personalized experience.
While the tour isn’t wheelchair accessible, dietary requirements can be accommodated with advance notice.
Traveler Experiences

According to the reviews, travelers have had overwhelmingly positive experiences on this private Tuscany tour. Guides like Placido and Cristian receive praise for their knowledge, professionalism, and ability to customize the itinerary.
Highlights include exploring secluded wineries, engaging in wine tastings, and receiving personalized recommendations. While some note a rushed pace due to multiple stops, the overall consensus is that this tour provides an immersive journey through the region’s historic towns and renowned Chianti vineyards.
Travelers leave with a deeper appreciation for Tuscan culture and cuisine, making this a must-do experience.
Tour Pickup and Departure

When booking this private Tuscany tour, we’re picked up from our centrally located hotel in Florence in the morning.
The tour begins with:
- A scenic drive through the Tuscan countryside
- A stop in the historic city of Siena for two hours of free time
- A visit to the charming town of San Gimignano, known for its picturesque towers
- An optional winery tour and tasting in the renowned Chianti wine region
After exploring the highlights of Tuscany, we’re dropped off back at our hotel in Florence, having experienced the region’s rich history, architecture, and renowned winemaking.
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Exploring Siena

After our scenic drive through the Tuscan countryside, we arrive in the historic city of Siena. With 2 hours of free time, we’re eager to explore Siena’s charming medieval center.
| Top Sights in Siena | |
|---|---|
| Piazza del Campo | Siena Cathedral |
| Palazzo Pubblico | Torre del Mangia |
| Basilica of San Domenico | Fonte Gaia |
The Piazza del Campo, Siena’s iconic shell-shaped main square, captivates us with its stunning architecture. We wander the narrow streets, admiring the Gothic Siena Cathedral and its intricate façade. As we climb the Torre del Mangia, panoramic vistas of the city’s red-tiled roofs unfold before us.
Discovering San Gimignano

Next, we board our private vehicle and make our way to the enchanting town of San Gimignano. This medieval hilltop town is renowned for its 13 original towers, which once numbered 72 and served as symbols of the town’s wealth and power.
As we explore the charming streets, we’ll:
- Marvel at the stunning architecture and iconic skyline
- Discover hidden piazzas and quaint shops
- Sample the local Vernaccia wine and other Tuscan delicacies
- Climb to the top of the Duomo for panoramic views of the surrounding countryside
After an hour of free time to soak in the atmosphere, we head to our next destination.
Taking in the Chianti Region

As we continue our journey, we’re immersed in the captivating Chianti region, renowned for its picturesque vineyards and world-class wineries.
We’re granted additional free time to explore this storied wine country, with the option to visit a local winery for a traditional Tuscan experience.
Savor the region’s renowned Chianti wines, learn about the centuries-old winemaking process, and gain a deeper appreciation for the Tuscan way of life.
This immersive stop offers a perfect blend of culture, history, and indulgence, rounding out our unforgettable private tour of Tuscany.
The Sum Up
Exploring Tuscany’s historic cities and renowned wine region on a private tour is the perfect way to learn about the region’s captivating charm. With ample time to discover Siena and San Gimignano, as well as savor Chianti wines, this personalized experience offers an unforgettable day filled with Tuscan enchantment. Don’t miss the opportunity to indulge in the beauty and flavors that make this corner of Italy so special.
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