Florence: San gimignano tour + Tasting Chianti Wines &Cheese

Travelers looking for a taste of authentic Tuscany will find this private tour from Florence to San Gimignano and Chianti an appealing mix of history, scenery, and flavors. With a focus on small-group comfort, expert guides, and a well-rounded culinary experience, it promises a day full of memorable sights and delicious bites.

Three things we particularly love about this experience are the personalized transport in a private vehicle, the chance to explore San Gimignano’s legendary towers, and the generous tasting of regional cheeses, cured meats, and Chianti wine. That said, it’s a full-day trip, so those with limited mobility or a tight schedule might want to plan accordingly.

This tour is best suited for travelers who appreciate good food and wine, enjoy exploring historic towns at their own pace, and want an intimate, guided experience rather than a crowded bus tour. If you’re after a relaxing, immersive day in Tuscany, this might just be your perfect match.

Good To Know

• Private, comfortable transport from Florence ensures a relaxed start and end to your day.
• San Gimignano’s UNESCO-listed medieval architecture is a highlight, with entry to the main tower included.
• Tastings of Pecorino, cured hams, and balsamic vinegar showcase Tuscany’s culinary craftsmanship.
• A traditional Tuscan dinner in a historic Chianti winery pairs local wines with regional dishes.
• Options to buy and ship local products at discount prices make for great souvenirs.
• Flexible timings and personalized experience with live guides in English or Spanish.

You can check if your dates are available here:

Exploring Tuscany: What This Tour Offers

This tour gives you a comprehensive taste of what makes Tuscany so beloved. From the scenic drive out of Florence to the ancient streets of San Gimignano, each step feels designed to show you the best of this region’s culture, architecture, and cuisine. The fact that it’s a private group means you’re likely to get a more tailored experience with fewer interruptions, allowing you to absorb the surroundings at your own pace.

Comfortable Transport & Scenic Journey from Florence

Your adventure begins with a pickup from your Florence accommodation, or a designated central location like Piazza Ognissanti or Piazza Adua. The ride in a private, air-conditioned vehicle guarantees a comfortable journey, giving you the chance to sit back and enjoy the rolling hills and vineyards that define Tuscany’s landscape.

Travel time varies between 6.5 and 10 hours, depending on your chosen options and pace. The drive itself is a highlight, offering a peaceful transition from the bustling city to the tranquil countryside. Since the group size is limited to four, you’ll avoid the typical crowded coach experience, making for more meaningful conversations and a personalized touch.

San Gimignano: Medieval Marvel with a View

Once in San Gimignano, the medieval town’s skyline, dotted with its famous towers, instantly transports you to another era. The visit includes a professional tour guide who will take you inside the main tower, offering stunning panoramic views of the Tuscan hills.

The town’s charm lies in its cobbled streets, artisan shops, and historical buildings. You’ll have around two hours for free exploration, which is ample time to wander, browse local shops, and take photos of the iconic skyline.

According to reviews, visitors loved the opportunity to explore at their own pace, with one noting, “The view & the atmosphere was something that we’ll never forget.” The free time also allows for a relaxed lunch or quick shopping—perfect for picking up local specialties.

Tuscan Tastings: Cheeses, Cured Meats, and Vinegars

One of the tour’s real highlights is the tasting experience, which showcases some of Tuscany’s finest products. Expect to sample up to 10 types and combinations of Pecorino cheeses, alongside balsamic vinegars, truffle sauces, and cured hams. These tastings provide a direct taste of regional craftsmanship and flavor profiles that are difficult to find outside Italy.

A guest review describes the cheese and food experience as “such a cool experience,” emphasizing the quality and authenticity of the offerings. The tasting is not just about eating but about understanding the region’s culinary traditions—an essential part of Tuscan culture.

More Great Thing To Do Nearby

The Winery Experience & Tuscan Dinner

After San Gimignano, the journey continues to an historic Chianti winery. Here, you’ll enjoy a full meal—either lunch or dinner, depending on your option—paired with a selection of at least 8 local wines, including the renowned Chianti varieties.

The winery visit isn’t just about tasting wines; it’s about understanding the craftsmanship behind them. The chef prepares three courses of regional dishes, all crafted to complement the wines. Many reviewers mention the “delicious” food and the “excellent” wine selection, which elevate this part of the tour into a true culinary celebration.

One guest recounted, “The wine & the food were so good. We didn’t want to leave,” highlighting how memorable the experience can be, especially for wine lovers. Plus, if you’re interested, there’s the possibility to buy and ship wines and local products at a discount, making it easier to bring a taste of Tuscany home.

Return Journey & Scenic Stopover

After the winery, the return to Florence includes a scenic stop at a panoramic view of the city—best on clear days, as one reviewer noted. This offers a perfect photo opportunity and a moment to reflect on the day’s highlights before heading back to your accommodation.

The total duration of the tour allows for a leisurely, unhurried experience, giving ample time to enjoy each site without feeling rushed.

Pricing & Value

At $914.68 for a private group of up to four, this tour might seem on the higher end, but it reflects the personalized service, private transport, and immersive experiences included. Visitors consistently find the value in the exclusive access, expert guides, and the quality of tastings and meals.

Compared to larger group tours, the intimacy and flexibility can make all the difference, especially if you’re seeking a special, stress-free day in Tuscany. Plus, the ability to reserve now and pay later adds flexibility for your travel plans.

Who Should Consider This Tour?

If you’re traveling in a small group, seeking an authentic and private experience, and love wine and food, this tour is a great choice. It also suits travelers who appreciate good scenery and the chance to explore at their own pace, with expert guidance.

However, if mobility is a concern or you prefer a shorter, less involved trip, this might be more than you need. The full-day commitment and walking in San Gimignano require a certain level of comfort with being on your feet.

FAQs

Is this a private tour or a group experience?
It’s a private group experience for up to four people, ensuring a more personalized and intimate atmosphere.

What’s included in the price?
Transport in a private car, guided tour in San Gimignano, tastings of cheeses and local products, and a Tuscan meal with wine tasting are all included. Optional wine tastings and additional visits can be added.

How long does the tour last?
The duration ranges from 6.5 to 10 hours, depending on your chosen options and timing. Check availability for specific start times.

Can I buy products during the tour?
Yes, you can purchase and have products shipped home at a discounted rate, perfect for souvenirs or gifts.

Is this tour suitable for children or non-drinkers?
While primarily focused on food and wine, non-drinkers can still appreciate the cultural and scenic aspects. However, it’s best suited for adults.

What should I bring?
Comfortable shoes are recommended for walking around San Gimignano’s cobbled streets and the winery grounds.

The Sum Up

This private tour from Florence offers a well-rounded taste of Tuscany, combining stunning medieval architecture, authentic culinary experiences, and exquisite wines. Its personalized nature makes it ideal for couples, small groups, or anyone seeking a relaxed yet comprehensive day in Italy’s heartland.

The combination of expert guides, scenic drives, and high-quality tastings ensures a memorable experience that captures the essence of Tuscany’s charm. If you’re eager to enjoy Italy’s food, wine, and history in a small-group setting, this tour is a fantastic choice.

For travelers who value quality over quantity, and who want a day filled with beautiful sights and delicious bites, this experience delivers on all fronts — making your Tuscany visit truly special.

You can check if your dates are available here: