Private daytrip to Siena & Chianti wine country, with wine tasting from Florence

Planning a trip to Italy often means dreaming of scenic vineyards, charming villages, and centuries-old piazzas — and Tuscany delivers on all counts. This private daytrip from Florence to Siena and Chianti promises to bring those dreams to life, with the comfort and flexibility of a personalized experience. While we haven’t personally taken this exact tour, the glowing reviews and detailed itinerary suggest it’s a fantastic option for those looking to explore Tuscany beyond Florence without the hassle of driving.

What we love about this tour is how it balances guided visits with free time—perfect for soaking up the atmosphere at your own pace. The private driver ensures a smooth day, and the chance to taste excellent wines and local foods adds a delicious touch. On the flip side, an important consideration is that lunch isn’t included in the price, meaning you’ll need to plan for that separately. This experience seems best suited for travelers who want a curated glimpse of Tuscany’s highlights, with the option to customize along the way.

Key Points

• Private driver, personalized experience offers convenience and flexibility.
• Includes a guided wine tasting at a reputable Tuscan estate, plus free time in Siena.
• Scenic drive through Chianti’s iconic hills makes for memorable views and photo ops.
• Not including lunch means you can choose to dine where you prefer or skip it altogether.
• Highly rated for knowledgeable guides and authentic experiences.
• Book well in advance, as this tour tends to fill quickly, often booked about 65 days ahead.

An In-Depth Look at the Itinerary and Experience

Starting in Florence: Comfortable Pickup and Personalized Planning

Your day kicks off with a pickup from your Florence accommodation in a fully equipped Mercedes vehicle. The driver, who doubles as your guide, offers a warm initial briefing, explaining the day’s options so you can tailor your experience. This personal touch is a real bonus, especially if you have specific interests or want to spend more time in certain spots.

First Stop: Greve in Chianti — The Heart of the Chianti Classico

The drive to Greve in Chianti takes about 45 minutes, giving you a chance to enjoy the rolling Tuscan landscapes. This town is famous for being the birthplace of Giovanni da Verrazzano, the explorer who discovered New York Harbor — a fun fact that adds some extra flavor to your visit. Once there, you’ll have some free time to stroll around Piazza Matteotti, the lively square that’s the hub of local life. It’s a charming spot to soak in the atmosphere, browse local shops, or even pick up some Italian leather or wine.

According to reviews, visitors appreciated the opportunity to explore at their own pace: “Stopped in Siena, bought beautiful Italian leather products,” shared one traveler. The town’s simple yet authentic vibe makes it a lovely start to the day.

The Scenic Drive and Panzano in Chianti

Next, a 30-minute drive takes you along some of Italy’s most picturesque wine roads, dotted with vineyards and olive groves—classic Chianti scenery. The drive itself is a highlight, setting the scene for the wine and food adventures ahead.

En route, you’ll pass through Panzano in Chianti, a picture-perfect hilltop village known for its Santa Maria Assunta church and impressive castle tower. The charm here is palpable, with panoramic views that showcase Tuscany’s rolling hills.

The Winery Visit: Fattoria di Montecchio

The highlight for many is the visit to Fattoria di Montecchio (or an equivalent estate if unavailable), where you’ll learn about the estate’s history and wine-making process. The guided tour of old cellars and explanation of how Chianti and Tuscan olive oil are produced add a layer of appreciation for what’s in your glass.

After the tour, you’ll get to taste a selection of wines — from Chianti Classico and Riserva to Super Tuscans — alongside their high-quality olive oil. Reviewers rave about the wine quality and the friendly, expert guidance: “Taste different wines and olive oil, one of the most important ingredients of Italian cuisine,” one reviewer mentions. It’s a genuine chance to enjoy wines that are well-regarded around the world, paired with locally produced olive oil.

Optional Lunch at La Locanda di Pietracupa

Just five minutes from the winery, you’ll find the family-run restaurant, La Locanda di Pietracupa. Guests have described the food as “genuine Tuscan,” with some saying it’s among the best local food they’ve had. You can choose to indulge here, pairing your meal with local wines, or opt to skip lunch and explore Siena instead. Keep in mind that lunch is at your own expense, which offers flexibility depending on your appetite and timing.

Free Time in Siena: A Medieval Marvel

The afternoon is reserved for Siena, a city that’s a feast for the senses. Your driver will deliver you directly to Piazza del Duomo, where you can admire the majestic cathedral and its bell tower. With about two hours, you’ll have enough time to absorb the atmosphere, visit Santa Maria della Scala museum if you wish, and marvel at the Piazza del Campo, one of Italy’s most iconic squares.

Standouts include the Gothic Town Hall with its tower, the Gaia Fountain, and the stunning palaces surrounding the square. If you’re a fan of history, architecture, or simply people-watching in lively squares, Siena’s atmosphere will not disappoint.

Return to Florence

After exploring Siena and its sights, your driver will take you back to Florence for a relaxing one-hour drive. Many reviews highlight how smooth and comfortable this part of the journey is—making the entire day feel like a well-organized, enjoyable escape.

What Makes This Tour Stand Out?

This trip’s strength lies in its private, customizable approach. Having your own driver means you’re not just stuck with a set itinerary; you can ask to linger longer in places you love or skip those that don’t catch your interest. The reviews consistently mention knowledgeable guides and attentive drivers, which elevates the experience from just sightseeing to a personal journey.

The wine tasting at a reputable estate adds a tangible, flavorful element that makes the day memorable. Travelers describe the wines as high quality, with some noting the “great selection,” and the olive oil is described as “famous all over the world,” adding authenticity to the tasting experience.

The free time in Siena is another highlight. For many, wandering the narrow streets and soaking in the medieval charm of Siena is a perfect way to round out the day. The city’s lively squares, historic buildings, and vibrant atmosphere make it a favorite among visitors.

How Does the Price Stack Up?

At $452.16 per person, this tour isn’t cheap, but considering it includes private transportation, a guided winery visit, tastings, and door-to-door service, many find it offers good value. The convenience of avoiding a crowded group tour, plus the flexibility to customize your day, makes it worth the investment for those who prioritize comfort and personalized experiences.

Who Would Enjoy This Tour?

This experience caters well to couples, small groups, or friends who want a seamless, immersive day in Tuscany. It’s particularly suited for those who appreciate wine, local food, and scenic drives, and prefer not to navigate public transport or drive themselves. If you’re traveling with family or friends and want a day tailored to your interests, this private tour fits the bill.

FAQs

• What is included in this tour?
  The tour includes a private English-speaking driver, a guided visit and wine tasting at a Tuscan winery, private transportation, and all fees and taxes.

• Are entrance fees to Siena included?
  No, entrance fees to Siena are not included. You’ll have free time to explore the city on your own.

• Is lunch included?
  No, lunch is not included. You can choose to eat at the nearby family-run restaurant or elsewhere, at your own expense.

• How long is the total tour?
  The tour lasts about 8 hours, including travel time, winery visit, free time in Siena, and return to Florence.

• Can I customize the itinerary?
  Yes, the driver provides an initial briefing to help tailor the day according to your preferences.

• Is this tour suitable for children?
  While not specifically tailored for kids, the tour is generally family-friendly, especially if your children enjoy scenic drives, wine tasting (adults only), and exploring historic towns.

• How do I book this tour?
  It’s best to book in advance—most travelers book about 65 days ahead—through the provider’s website or your preferred booking platform.

Final Thoughts

This private daytrip to Siena and Chianti offers a well-rounded taste of Tuscany’s best features—vineyard landscapes, historic towns, and good food. The personalized touch of a private driver, combined with high-quality wine tastings and free time in Siena, makes it stand out from larger, less flexible tours.

It’s ideal for travelers who want a comfortable, curated experience with the freedom to explore at their own pace. Whether you’re a wine lover, history buff, or simply after a scenic escape from Florence, this trip promises a memorable day in Italy’s most celebrated region.

If you’re after a hassle-free, intimate look at Tuscany with plenty of opportunities to savor local flavors and enjoy stunning views, this tour could be just what you’re looking for.