Tuscany’s renowned Chianti region, Siena, and the walled town of San Gimignano come together in this private tour, offering guests a captivating journey through the heart of Italy. Travelers can explore the picturesque countryside, visit UNESCO World Heritage sites, and discover the area’s rich history and culture. With the flexibility to customize pickup and drop-off, as well as optional wine tastings and a full lunch, this tour provides an immersive experience that delves into the flavors and traditions that make this part of Italy so enchanting. Whether you’re a wine enthusiast or seeking to uncover the region’s hidden gems, this tour promises an unforgettable adventure.
Key Points
- A private tour that visits the renowned Chianti wine region, the historic cities of Siena and San Gimignano, and provides photo opportunities at Piazzale Michelangelo in Florence.
- Includes transportation in a comfortable air-conditioned minivan with the option to add a full lunch and wine tasting experience or a wine tasting only.
- Provides flexibility with pickup and drop-off directly from/to the customer’s accommodation in Florence, with a flexible pickup location confirmed up to 24 hours before the 9:00 am start.
- Explores the picturesque Chianti countryside, traversing rolling hills and charming villages, and offering the opportunity to sample world-class wines.
- Visits the UNESCO World Heritage sites of Siena and San Gimignano, allowing guests to admire the Gothic architecture, vibrant public squares, and iconic medieval towers.
Tour Overview
The private day trip offers the opportunity to experience the stunning Tuscan countryside and visit two UNESCO World Heritage sites. Guests can customize the itinerary, but a typical tour includes a stop at Piazzale Michelangelo to capture breathtaking photos of Florence.
The journey then winds through the renowned Chianti region before visiting the historic cities of Siena and San Gimignano. While no guided tours are provided in Siena, travelers can explore the city’s medieval architecture and famous Piazza del Campo independently.
The tour also features a drive along the scenic Strada 222 wine road on the return to Florence, providing a delightful finale to the day’s adventures.
You can also read our reviews of more private tours in Florence
Inclusions

This private day trip includes private transportation in an air-conditioned vehicle, as well as bottled water for guests.
Lunch and wine tastings are available at an additional cost, with options for a full lunch and tasting experience (€60 per person) or just a wine tasting (€30 per person). This allows guests to customize their experience and indulge in the local cuisine and wines of the Chianti region.
The tour is designed to provide a comfortable and flexible sightseeing experience, with pickup and drop-off directly at the customer’s Florence accommodation. The tour starts at 9:00 am, giving ample time to explore the highlights of Chianti, Siena, and San Gimignano.
Pickup and Drop-off

Pickup and drop-off for this private tour is directly from and to the customer’s accommodation in Florence.
The tour operator offers flexible pickup locations, which can be confirmed up to 24 hours before the activity starts at 9:00 am. This provides customers with convenience and flexibility, allowing them to start their tour from the location most suitable for them.
The tour ends with drop-off back at the original pickup point, ensuring a seamless experience from beginning to end.
This service is an important part of the overall private tour package, allowing customers to focus on enjoying the sights and activities without worrying about transportation logistics.
Chianti Region Exploration
On this private tour, visitors can explore the renowned Chianti wine region, known for its scenic vineyards and picturesque countryside.
They’ll traverse the rolling hills and charming villages that have made this area of Tuscany famous worldwide.
Along the way, they’ll have the opportunity to stop and sample some of the region’s world-class wines. Whether it’s a full-bodied Sangiovese or a crisp white, the Chianti region is renowned for its exceptional vintages.
Visitors can also take in the stunning views and enjoy the rich history and culture of this beloved Italian destination.
With a knowledgeable driver navigating the scenic roads, they’ll be able to fully enjoy the Chianti experience.
Siena Visit

Visitors will then explore the historic city of Siena, a UNESCO World Heritage site renowned for its stunning Gothic architecture and vibrant public squares. They’ll wander through the winding streets, taking in the impressive Duomo cathedral and the iconic Piazza del Campo, home to the famous Palio horse race.
While no guided tour is provided, the tour allows ample time for independent exploration:
Browse the charming shops and boutiques along the narrow lanes.
Admire the intricate façade of the Duomo, featuring striped marble and ornate carvings.
Relax in Piazza del Campo, one of Europe’s greatest medieval squares.
Soak up the lively atmosphere and feel the pulse of this quintessential Tuscan city.
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San Gimignano Walled Town

Exploring the enchanting San Gimignano walled town, visitors marvel at its iconic medieval towers that pierce the Tuscan skyline, a testament to the wealth and power of its former ruling families.
Wandering through its well-preserved historic center, guests discover quaint piazzas, Romanesque churches, and charming shops selling local crafts and delicacies.
Climbing the Torre Grossa, the town’s tallest tower, rewards adventurers with panoramic vistas over the terracotta rooftops and surrounding countryside.
San Gimignano’s UNESCO World Heritage status reflects its cultural significance, as the town’s architecture and traditions have been meticulously preserved.
Whether strolling its narrow streets or sampling its renowned Vernaccia wine, visitors are transported to a bygone era in this captivating Tuscan gem.
Strada 222 Wine Road

As the private tour winds its way back to Florence, travelers get to experience the picturesque Strada 222 wine road, also known as the Chiantigiana.
This scenic byway weaves through the heart of the renowned Chianti region, offering stunning vistas of rolling hills, vineyards, and medieval villages.
The drive along Strada 222 is a highlight of the tour, allowing visitors to:
- Soak in the bucolic Tuscan countryside
- Spot historic castles and churches along the route
- Stop for photos at scenic overlooks
- Anticipate the next wine tasting or culinary discovery in the charming towns ahead
This leisurely return journey provides a perfect cap to a day spent exploring the treasures of Chianti, Siena, and San Gimignano.
Additional Information
This private tour offers flexible pickup and drop-off options, with the ability to confirm the pickup location up to 24 hours before the activity. It’s not wheelchair accessible, but stroller-friendly for those in need. Guests must not have any heart problems or serious medical conditions to participate. Free cancellation is available up to 24 hours prior to the tour’s start time.
| Tour Type | Private |
|---|---|
| Accessibility | Not wheelchair accessible, but stroller-friendly |
| Medical Restrictions | No heart problems or serious medical conditions |
| Cancellation Policy | Free cancellation up to 24 hours before activity start |
This tour provides a customizable and private experience, allowing guests to explore the Tuscan countryside at their own pace while visiting UNESCO World Heritage sites.
Frequently Asked Questions
What Is the Maximum Group Size for This Private Tour?
This private tour is intended for small groups. The group size is flexible, but it is a private tour, so only the participants in one’s own group will take part in the activities.
Can We Request a Stop at a Specific Winery or Vineyard?
Absolutely, travelers can request a stop at a specific winery or vineyard. The tour is private and customizable, so the itinerary can be tailored to include a visit to a preferred winery along the Chianti wine route.
Is There Any Option to Extend the Tour Duration?
Yes, the tour’s duration can be extended. Customers can add more time to visit additional sites or spend more time at the current stops. This is a customizable private tour, so the itinerary can be adjusted to meet individual needs.
Do We Need to Bring Any Special Equipment or Attire?
No special equipment or attire is needed. Wear comfortable walking shoes and dress for the weather. The tour company will provide the necessary transportation and water. Just come prepared to enjoy the sights and experiences of the Tuscan countryside.
Are There Any Age Restrictions or Requirements for This Tour?
There are no specific age restrictions or requirements for this tour. The tour is open to participants of all ages, though it may not be suitable for young children. Parents should use their discretion in determining if the tour is appropriate for their family.
Private Tour of Chianti Siena and San Gimignano by Minivan
Recap
This private tour offers a captivating journey through the heart of Tuscany. Guests can explore the renowned Chianti wine region, visit UNESCO World Heritage sites, and discover the region’s stunning countryside.
The tour includes transportation, with the flexibility to customize pickup and drop-off. Participants can enhance the experience with optional wine tastings and a full lunch, seeing the rich history, culture, and flavors of this enchanting part of Italy.




























