Florence: Chianti Villages, San Gimignano and Winery Tour

If you’re dreaming of a day exploring Tuscany’s lush landscapes, winding roads, and centuries-old villages, this tour promises just that. It’s a well-rated experience, with a 4.7 out of 5 from nearly 100 reviews, and it’s designed for those who want a taste of authentic Chianti without the hassle of planning their own trip.

What we love about this tour is its small-group vibe, which keeps things cozy and personal, and the opportunity to explore San Gimignano’s famous medieval towers—a UNESCO site that truly feels like stepping back in time. The wine tastings at two vineyards and the local, farm-fresh lunch are also major highlights, giving you a genuine sample of Tuscan flavors and hospitality.

One thing to keep in mind is that the itinerary might shift due to weather, which is typical for outdoor experiences, but it’s worth considering if you’re visiting in a time when weather could impact the day’s flow. This tour is ideal if you’re after a relaxed, informative day with beautiful scenery, tasty wine, and enough free time to wander and soak in the atmosphere. It suits travelers who want a curated experience but still a touch of independence.

Key Points

• Small-group tour offers a more intimate, relaxed setting
• San Gimignano provides iconic medieval architecture and photo opportunities
• Wine tastings at two local vineyards include organic olive oil sampling
• Light lunch at a family-run farm showcases authentic Tuscan cuisine
• Flexible pickup options make planning easier
• Knowledgeable guides enhance the experience with local insights

You can check availability for your dates here:

A Closer Look at What You Can Expect

The Journey into Tuscany’s Heartland

Starting from Florence, your day begins with a comfortable minivan ride along the famous Chiantigiana Road. This route is a highlight itself, offering views of rolling hills, lush vineyards, and tiny villages that seem pulled right from a postcard. The drive takes about 45 minutes to Greve in Chianti, a charming town that’s a perfect first stop to stretch your legs and take in the scenery.

Wine Tasting in Greve in Chianti

Once in Greve, you’ll visit a local winery for a tour of their cellars and a tasting session. This part of the tour, spanning about two hours, is where you’ll really get a sense of the region’s wine craftsmanship. Many reviewers praise the knowledgeable guides, like Kelley who said, “Luigi was a wonderful and knowledgeable guide,” emphasizing how much added value a good guide brings.

During this stop, you also have the option to purchase organic extra virgin olive oil—something many guests find exciting. You’ll learn about the local production methods and get a chance to take home a bottle, which makes for a lovely souvenir.

Exploring San Gimignano

Next, you’ll head to San Gimignano, a UNESCO World Heritage site famous for its 13 medieval towers that pierce the skyline. You’ll have about an hour to walk through the narrow streets, snap photos of the towers, and perhaps pick up some souvenirs or gelato from Dondoli’s renowned shop, as Jil recommended.

Many reviews highlight the charm of San Gimignano: “The town is beautiful and quaint,” and “We loved the way the towers stood out in the skyline.” The free time allows you to explore at your own pace, whether you want to pause for a coffee, shop for local crafts, or simply soak in the views.

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A Traditional Tuscan Lunch with Wine

After your exploration, you’ll enjoy a light lunch at a family-run farm or a typical restaurant producing organic wine. The meal is paired with a wine tasting, lasting around 1.5 hours, and many guests say the food is delicious—think simple, hearty, and fresh. From reviews, it seems the experience is both authentic and satisfying, with plenty of generous pours that let you really appreciate the wines.

One reviewer, Michelle, mentions how the wines and foods were delicious, and the lunch included local products like bread, meats, cheeses, and truffle-infused oils, giving a real taste of Tuscany’s culinary simplicity and quality.

Return Journey with Scenic Stops

The drive back to Florence takes about an hour and 15 minutes, but many guides like Francesco or Aladdin go the extra mile by making scenic stops—such as Piazzale Michelangelo—for panoramic city views, weather permitting. Several reviews highlight how guides go out of their way to make the trip memorable, sharing stories and local tips along the way.

How This Tour Fits Different Travelers

Many reviews speak to the friendly, insightful guides (like Luigi and Christian), which really enhance the experience. The small-group setup ensures everyone feels engaged and gets personalized attention. If you’re someone who enjoys wine, good scenery, and authentic local food, this tour hits the right notes.

It’s also a good pick for those who want to combine sightseeing with a laid-back day of tasting and exploring. The itinerary provides a nice balance of structured activities and free time, allowing you to relax and soak up the atmosphere at your own pace.

However, the tour is quite full for a single day, so expect to be on the move and in the van quite a bit—about 45 minutes to an hour each way, plus the stops. If you prefer a more leisurely, unhurried day, you might find this a bit packed. Also, if you’re on a strict budget, consider the value—comparing the included tastings, lunch, and transportation—many find it reasonable for a full day of Tuscany experience.

The Real Deal from Reviews

One of the most praised aspects is the guides. Kelley and Melanie both mention how guides like Luigi, Aladdin, and Christian made the day feel special, offering insights and making the experience more personal. Many reviews also appreciate the quality of the wine tastings and the authentic, hearty lunch.

Some guests, like Sandra, mention the second winery could be disappointing if the staff were rude or the food wasn’t up to par. That’s the risk with any tour—expect some variability—but overall, the experience tends to be well-received.

A recurring theme is how scenic and picturesque the stops are, whether it’s at the vineyards or in San Gimignano, making it a perfect day for photos and memories. The small-group size means you won’t feel lost in a crowd, and you’ll get more personalized recommendations and stories.

Detailed Breakdown of the Day

Pickup and Travel

Starting from Florence, you’ll be picked up from designated locations or your accommodation, making logistics simple. The minivan ride, about 45 minutes, gets you into the heart of Chianti smoothly. The vehicle is comfortable, and guides are often friendly and engaging, setting the tone for the day.

Greve in Chianti and the First Winery

Your first real taste of Chianti takes place in Greve. The winery tour is about two hours and includes a cellar visit, wine tasting, and olive oil sampling. Many guests appreciated the expertise of the guides—they often share stories about local traditions and wine-making techniques.

San Gimignano’s Medieval Charm

The highlight for many is the free time in San Gimignano. The town’s famous towers create a dramatic skyline, and the narrow streets invite exploration. You can stop for gelato at Dondoli’s or browse local shops. The town is a perfect mix of history and leisure, allowing you to enjoy its timeless appeal.

Lunch and Wine Tasting

The lunch, typically at a family-run farm or a traditional Tuscan restaurant, pairs well with the wines you’ve sampled earlier. Many guests find the food simple but delicious, often with locally sourced ingredients and a focus on organic produce.

The Return and Scenic Stops

Back in Florence, many guides like Francesco or Aladdin take scenic routes or stop at viewpoints like Piazzale Michelangelo, weather permitting. This offers a lovely final moment to reflect on the day and snap some more photos.

Who Is This Tour Best For?

This experience is perfect if you’re after a well-rounded taste of Chianti and San Gimignano without the stress of organizing multiple arrangements. It’s especially suited for those who enjoy wine, scenic drives, and small-group intimacy. History buffs get a bonus from San Gimignano’s medieval towers, and food lovers will appreciate the authentic Tuscan lunch.

It’s a good choice for travelers who want a full, yet manageable day—not too rushed but enough to see the key highlights. Families with older children might enjoy it, especially if they appreciate wine and history, but younger kids should be prepared for a fair bit of sitting and moving around.

FAQ — Practical Questions Answered

How long is the total tour?
The entire experience lasts about 6.5 to 7 hours, starting from pickup in Florence and ending with drop-offs at your accommodation.

Is transportation comfortable and private?
Yes, the tour takes place in a comfortable minivan, with private groups ensuring a relaxed atmosphere. The vehicles are designed for small groups, making it easier to move around and chat with your guide.

What’s included in the lunch?
Guests enjoy a light, traditional Italian lunch, often at a family-run farm, with wines served alongside local dishes like bread, meats, and cheeses. The meal is paired with wine tasting at the same location.

Can I buy wine or olive oil to take home?
Absolutely. Many wineries offer the chance to purchase organic extra virgin olive oil and wine, which they can ship to your home if you prefer.

Are there any age restrictions or is it family-friendly?
The tour is mainly suited for adults and older children who can appreciate wine tastings and walking around towns. It’s not explicitly family-focused, but older kids with an interest in wine or history might enjoy it.

What happens if the weather is bad?
The itinerary might change depending on weather conditions, but the core experiences—vineyard visits, San Gimignano, and lunch—are generally adaptable, sometimes with indoor options.

How much free time do I get in San Gimignano?
You have about an hour to explore, shop, or take photos. It’s enough to get a good feel for the town but not to see everything in detail.

Is this a guided tour throughout?
Yes, you’ll have an English-speaking driver or guide with you the entire day, providing insights and commentary at each stop.

Wrapping It Up

This tour offers a well-paced, authentic taste of Tuscany’s Chianti countryside, medieval towns, and wine culture. With expert guides, comfortable transport, and delicious local food and wine, it’s a solid choice for anyone wanting a manageable yet memorable day outside Florence.

Ideal for wine lovers, history enthusiasts, and travelers seeking a relaxed but enriching experience, this tour strikes a good balance between guided discovery and free time to explore on your own. Keep in mind the weather, and be ready to enjoy some truly stunning scenery, flavorful wines, and a touch of medieval magic.

Whether you’re celebrating a special occasion or just craving a day in Italy’s most iconic landscapes, this trip is likely to leave you with lasting memories—and maybe a bottle or two of wine to bring home.

You can check availability for your dates here: