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

Exploring Tuscany beyond Florence becomes effortless with this private daytrip to Siena and Chianti wine country. Priced at $452.16 per person, this 8-hour experience offers a personalized journey with the comfort of door-to-door transfers and a dedicated driver. Known for its medieval villages, rolling hills, and world-famous wines, Tuscany invites visitors to indulge in authentic flavors and scenic beauty, all curated for a relaxed and flexible day.

This tour is ideal for those who appreciate customized experiences, delicious wine tastings, and historic towns. While it includes a visit to a family-run winery and a charming hilltop village, it also allows for free time in Siena, giving guests the flexibility to explore on their own or enjoy a traditional Tuscan lunch. The only potential consideration is that lunch is optional and at your own expense, providing room for personal dining preferences.

Key Points

• Private, fully customizable daytrip from Florence with a private driver
• Visit Greve in Chianti, famous for its wine and local shops
• Enjoy a guided wine tasting at Fattoria di Montecchio or a similar estate
• Stop in Panzano in Chianti, a picturesque hilltop village with iconic sights
• Explore Siena’s historic piazzas, including the Piazza del Duomo and Piazza del Campo
• Round-trip transfers are included, making travel seamless
• Optional Tuscan lunch at a family-owned restaurant, with self-paid expenses

From Florence to Greve in Chianti: Starting your Tuscan adventure

This private tour departs from Florence, with a pickup from your accommodation. A Mercedes vehicle ensures comfort during the 45-minute drive to the Chianti region. The driver provides a detailed overview of the day’s schedule and answers any questions, setting a personalized tone for the day.

The first stop is Greve in Chianti, the main village of the Chianti Classico area. Here, the Piazza Matteotti serves as the lively heart of the town, lined with local shops and wine stores. Notably, the famous butcher shop Falorni and Enoteca Le Cantine feature prominently, allowing visitors to browse regional delicacies and wines. The visit offers about 45 minutes to soak in the charming atmosphere and pick up some authentic souvenirs.

Scenic drive through Chianti’s vineyards and olive groves

Following the visit to Greve, the tour continues with a 30-minute drive along one of Italy’s most scenic wine roads. This stretch showcases rolling hills, vast vineyards, and olive groves typical of the Chianti Classico landscape. The views are quintessentially Tuscan, making for excellent photo opportunities or quiet moments of appreciation.

On the way to the winery, travelers pass through Panzano in Chianti, a hilltop village renowned for its Santa Maria Assunta church and imposing castle tower. This stop offers a quick look at a true Tuscan village scene, with its cobbled streets and panoramic vistas.

Wine tasting at Fattoria di Montecchio and olive oil insights

The highlight of the day is the visit to Fattoria di Montecchio, a local estate where a guided tour introduces visitors to wine and olive oil production. Guests learn about the history of the estate and see the wine cellars, gaining insight into the Chianti wine-making process.

The tasting session features a variety of wines, including Chianti Classico, Riserva, and Super Tuscans, alongside local olive oil. This experience lasts approximately an hour and provides a chance to savor the flavors that define Tuscan cuisine. If Fattoria Montecchio is unavailable, an alternative estate in the region offers a similar experience.

Optional Tuscan lunch at La Locanda di Pietracupa

Just five minutes from the winery, there’s an opportunity to sample authentic Tuscan cuisine at La Locanda di Pietracupa, a family-run restaurant. The lunch is not included in the tour price and is paid at your own expense, giving freedom to choose between a leisurely sit-down meal or a quicker option. The restaurant is renowned for offering some of the best local dishes and wines in the area, making it a worthwhile add-on for food lovers.

Guests can also opt to skip the restaurant and find a meal in Siena later, as there is plenty of time allocated for free exploration and dining.

Discovering Siena’s historic squares and landmarks

The drive to Siena takes around an hour. Upon arrival, the driver drops guests directly at Piazza del Duomo, where the imposing Siena Cathedral and its bell tower serve as the focal point. Visitors have about two hours to explore, including sights like Santa Maria della Scala museum and Palazzo Arcivescovile.

A short walk from the cathedral brings visitors to Piazza del Campo, one of Italy’s most famous squares. Known for its brick paving and the Palio horse race, this square features Town Hall, Mangia Tower, Cappella di Piazza, and the Gaia Fountain. The lively atmosphere here offers a perfect setting for photos, people-watching, and soaking in Siena’s unique charm.

Return journey and relaxing drive back to Florence

After a full day of sightseeing and tasting, the return to Florence takes about an hour. The air-conditioned Mercedes vehicle provides a comfortable ride, giving travelers a chance to reflect on the day’s highlights and enjoy the scenic views of Tuscany during the one-hour drive back.

The tour wraps up with a drop-off at your accommodation, leaving guests with memories of authentic Tuscan landscapes, delicious wines, and historic towns.

Who should consider this private Tuscan daytrip?

This private tour is especially suitable for those who value personalized service and flexibility. The dedicated driver ensures a smooth, tailored experience, with plenty of free time in Siena. Wine enthusiasts will appreciate the guided tasting at a local estate and the chance to learn about Chianti wines and Tuscan olive oil.

Food lovers can enhance their trip with the optional lunch at La Locanda di Pietracupa, while history fans will enjoy exploring Siena’s iconic squares and monuments. The comfort and convenience of door-to-door service make this a relaxing way to explore Tuscany’s highlights without the stress of driving or group tours.

Final thoughts on the Tuscany private daytrip

This 8-hour experience from Florence offers a comprehensive taste of Tuscany’s scenic beauty, culinary delights, and historic charm. The private nature of the tour ensures a tailored pace and the opportunity to customize certain aspects, like visiting specific towns or enjoying an authentic meal.

While the lunch is optional and paid separately, the wine tastings, guided visits, and scenic drives are included, delivering excellent value for those seeking a luxurious, flexible day in Tuscany. The positive reviews consistently highlight the knowledgeable guides, beautiful views, and delicious wine experiences.

This tour fits well for travelers who want an intimate, curated Tuscan adventure, especially if they prefer to avoid large groups and enjoy personalized service. For those eager to explore Siena’s historic streets and Chianti’s vineyards comfortably, this private daytrip is a reliable choice.

Frequently Asked Questions

Is this tour suitable for children?
While most travelers can participate, the tour’s focus on wine tastings may not appeal to very young children. The experience is better suited for adults or older teens.

Are guided tours of Siena included?
No, guided tours of Siena are not included. Guests explore the squares and landmarks on their own, with the driver providing a drop-off point.

Can I customize the itinerary?
The tour is private and allows for some flexibility, with an initial briefing to tailor the day according to preferences.

Is lunch included?
No, lunch at La Locanda di Pietracupa or other restaurants is optional and paid separately.

What is the cancellation policy?
Guests can cancel free of charge up to 24 hours before the scheduled start, for a full refund.

How many stops are there during the tour?
There are four main stops: Greve in Chianti, Panzano in Chianti, Fattoria di Montecchio, and Siena.

What transportation is used?
A fully equipped, air-conditioned Mercedes vehicle is used for all transfers.

Are entrance fees included?
Yes, all fees and taxes for winery visits are included, but entrance fees for Siena sites are not.

Is this tour accessible for people with mobility limitations?
The tour requires walking around Siena’s historic squares and some uneven surfaces, so mobility considerations should be taken into account.

How far in advance should I book?
Most bookings are made about 65 days in advance. Early reservations are recommended to secure availability.