San Gimignano & Siena Chianti Winery full experience included

This private day trip from Florence promises an authentic taste of Tuscany’s landscape, history, and gastronomy. The tour combines the charm of medieval towns like San Gimignano and Siena with a personalized visit to a Chianti winery, complete with wine tasting and a traditional three-course lunch. With the comfort of private transportation and flexible exploration time, it’s tailored for travelers seeking a more intimate, hassle-free discovery of these iconic spots.

What truly stands out about this experience is the customized approach—you can explore at your own pace, enjoying quiet moments in medieval piazzas or sampling local wines without the rush of a large group. However, the cost might be a consideration for some, as it’s priced per group rather than per person, which can seem steep if you’re traveling solo or as a couple. Still, for those who value privacy, flexibility, and a curated experience, this tour hits the mark.

This tour is ideal for independent travelers who prefer exploring at their own pace, wine enthusiasts eager to learn about Chianti wines, or anyone looking for a seamless way to see Tuscany’s highlights without driving. Now, let’s break down the experience in detail to help you decide if it’s the right fit.

• Private transportation ensures comfort and flexibility throughout the day.
• The itinerary includes free time in San Gimignano and Siena for self-guided exploration.
• An all-inclusive experience with a 3-course lunch and wine tasting at a Chianti winery.
• Designed for up to two guests, making it perfect for couples or small groups.
• The tour operates with full flexibility, pick-up and drop-off at your preferred Florence location.
• Highly rated with a perfect 5.0/5 from one traveler, who called it the “best part of our trip.”

Easy and Comfortable Pickup in Florence

The journey begins with a convenient pickup from your Florence hotel or a nearby location, making this experience accessible and stress-free. The private vehicle ensures a relaxed ride through the Tuscan countryside, setting a tranquil tone for the day ahead. This personalized service means less waiting and more time enjoying the scenery.

First Stop: San Gimignano

Reaching San Gimignano, known as the “Medieval Manhattan” because of its skyline of famous towers, you’re granted ample free time to explore on foot. The town’s narrow cobbled streets and well-preserved towers create a fairy-tale setting, perfect for wandering at your own pace. You might find yourself drawn into artisan shops, tasting local gelato, or simply soaking in the views of rolling vineyards and olive groves.

One reviewer highlights that the flexibility was a key benefit: “This was the best experience of our whole trip! I wanted a private experience to see the Tuscan landscape, and Gianluca made it perfect.” This suggests the tour offers genuine opportunities for spontaneous discoveries, which are often the most memorable parts of Tuscany visits.

The Chianti Winery: A Local Taste

After exploring San Gimignano, the tour continues to a Chianti winery, where you’ll enjoy a guided cellar tour, taste several wines, and indulge in a traditional 3-course lunch. The wine tasting isn’t just about sampling; it’s an educational experience, often led by knowledgeable guides like Gianluca himself, who is praised for his personal touch. Expect to learn about the wine-making process, regional varieties, and how to identify different flavors.

The lunch typically features local dishes that complement the wines, offering a true taste of Tuscan cuisine. The emphasis on quality here means you’ll be savoring fresh ingredients, prepared in a way that highlights the region’s culinary traditions.

Siena: Medieval Charm at Your Own Pace

Next, your private driver takes you to Siena, a city famous for its medieval architecture and iconic Piazza del Campo. With several hours of free time, you can wander through the historic streets, visit the cathedral, or simply relax in one of the many cafes. This flexible schedule allows travelers to tailor their experience—some may want to admire the architecture, while others prefer to soak up the local atmosphere.

A reviewer noted that this freedom to explore independently was a highlight, allowing them to appreciate Siena’s beauty without being hurried or constrained by a group tour schedule.

Comfortable Return and Drop-Off

At the end of the day, you’ll be driven back to Florence, with drop-off at your hotel or another preferred location. This seamless service ensures you can relax after a full day of sightseeing and tasting, without worrying about transportation logistics.

The tour’s price of $1,498.11 for up to two people might seem high at first glance but considering the inclusions—private transport, a private experience, a 3-course lunch, and wine tastings—it offers notable value. The private vehicle means you avoid the crowds and rigid schedules typical of larger tours, gaining the freedom to explore and photograph at your leisure. The personalized touch, with a guide like Gianluca who has received glowing reviews, adds to the overall value.

The duration of approximately 9 hours ensures a full day immersed in Tuscany’s highlights without feeling rushed. You’ll appreciate the flexibility of pick-up and drop-off locations, making this a convenient option for travelers staying in Florence.

One review explicitly mentions how Gianluca tailored their experience, which demonstrates the tour’s adaptability. The guide’s personal approach adds genuine warmth and insights, transforming a sightseeing trip into an authentic encounter with Tuscany.

You’ll love the way the tour balances structured activities—wine tasting, lunch—and free time, allowing for spontaneous moments and personal discovery. Plus, the chance to taste regional wines in a cellar setting gives a unique perspective that larger, less personalized tours can’t match.

This experience is perfect if you desire a luxurious, personalized day in Tuscany. It suits couples, small groups, or solo travelers who prefer the privacy of a dedicated guide and vehicle. Food and wine lovers will appreciate the opportunity to savor local products in an intimate setting, and those wanting an authentic, relaxed pace will find this a perfect fit.

However, if you’re on a tight budget or prefer a larger, more social group experience, other tours might offer better value. This tour’s strength lies in its bespoke nature—a private, flexible day that allows you to explore Tuscany’s highlights on your terms.

This private San Gimignano and Siena tour with a Chianti winery experience offers an excellent way to discover Tuscany’s postcard-perfect towns and legendary wines with a personal touch. The flexibility to explore at your own pace, combined with the comfort of private transportation and a curated winery visit, makes it a standout for travelers seeking quality and intimacy.

While the price may be a consideration for some, the bespoke nature of the experience—guided by knowledgeable locals like Gianluca—justifies the cost for those who value exclusivity and personalized service. Perfect for couples or small groups, this tour delivers a genuine taste of Tuscany, blending scenic beauty, culinary delights, and historical charm in one seamless day.

If you’re after a relaxed, authentic way to absorb the Tuscan vibe without the rush of bus crowds, this private tour could be your ideal choice. Prepare to enjoy the landscape, taste exquisite wines, and create memories in two of Italy’s most iconic towns—at your own pace and with plenty of local flavor.

Is the tour suitable for solo travelers?
This tour is priced for up to two people, which makes it ideal for couples or small groups. Solo travelers might find the cost high compared to larger group tours but can enjoy the personalized experience and flexibility.

What is included in the price?
The price covers private transportation from Florence, a visit to San Gimignano with free time, a wine tasting and cellar tour at a Chianti winery, a 3-course lunch, and drop-off back in Florence.

How long is the tour?
The tour lasts approximately 9 hours, giving plenty of time to explore each location without feeling rushed.

Can I customize my day?
While the itinerary is set, the free exploration time in San Gimignano and Siena allows for personal choices, such as visiting specific sights or enjoying local cafes.

What is the experience like at the winery?
Guests can expect a guided cellar tour, a wine tasting session, and a traditional Tuscan three-course lunch. The guide often shares insights into regional wine-making, making it both educational and enjoyable.

Is transportation comfortable?
Yes, the private vehicle ensures a comfortable ride, with the flexibility to stop for photos or quick breaks along the way.

What if I need to cancel?
The tour offers free cancellation up to 24 hours in advance, providing peace of mind for flexible planning.

Whether you’re after a relaxing day of sightseeing, wine tasting, and culinary delights, or simply looking for an easy way to see Tuscany’s highlights without the stress of driving, this private tour from Florence offers a well-rounded, memorable experience.