Tuscany’s enchanting landscapes and rich cultural heritage come alive on this private day trip from Florence. Explore the medieval charms of Siena, marvel at the UNESCO-listed towers of San Gimignano, and indulge in the renowned wines of Chianti. With comfortable transportation, guided visits, and a delightful tasting, this exclusive tour promises an unforgettable adventure. Uncover the treasures that make this region a beloved destination, and discover why so many travelers return to this corner of Italy.
Key Points

- This private day trip from Florence takes visitors to the Tuscan towns of Siena, San Gimignano, and the Chianti Hills, including a wine tasting.
- The tour includes private transportation, guided visits, and a professional driver, with a duration of around 6 hours.
- Highlights of the trip include exploring medieval architecture in Siena, discovering the UNESCO-listed San Gimignano, and enjoying the scenic Tuscan countryside.
- The price for the tour is Kč 15,656 per group (up to 2 participants), with free cancellation up to 24 hours before the tour.
- Comfortable shoes, sun protection, and a camera are recommended for the best experience during the day-long excursion.
Trip Overview and Pricing

The private day trip from Florence to the Tuscany region, including the historic cities of Siena and San Gimignano, as well as the picturesque Chianti Hills, is priced at Kč 15,656 per group (up to 2 participants).
A private day trip from Florence to the Tuscany region, including Siena, San Gimignano, and the Chianti Hills, for Kč 15,656 per group (up to 2 participants).
Travelers can enjoy free cancellation up to 24 hours before the tour for a full refund, and there’s a reserve now, pay later option available.
The tour includes private transportation, wine tasting, guided visits to Siena and San Gimignano, and a professional driver.
Participants should wear comfortable shoes and bring a camera to capture the scenic views of this Tuscan adventure.
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Itinerary and Destinations

Starting from Piazza Adua in Florence, the private tour takes travelers on a scenic drive to the historic city of Siena, approximately 70 minutes away. There, they’ll enjoy a 2-hour guided tour, marveling at Siena’s medieval architecture and narrow streets, culminating in a visit to the iconic Piazza del Campo. The journey then continues to San Gimignano, a UNESCO World Heritage Site known as the "Medieval Manhattan," where guests will have 2.5 hours to explore the town’s charming alleys and towers. Finally, the tour ventures into the picturesque Chianti Hills for a 2-hour wine tasting at a traditional estate.
| Destination | Travel Time | Duration |
| — | — | — |
| Siena | 70 minutes | 2 hours |
| San Gimignano | 45 minutes | 2.5 hours |
| Chianti Hills | 30 minutes | 2 hours |
Highlights of the Tour

Visitors exploring the historic cities and picturesque Chianti region will be captivated by the tour’s highlights.
In Siena, they’ll marvel at the medieval architecture and wander the narrow streets.
San Gimignano, a UNESCO World Heritage Site, offers a glimpse into the past with its iconic towers, earning it the nickname "Medieval Manhattan."
The Chianti Hills provide a scenic backdrop for a wine tasting at a traditional estate, where guests can savor the region’s renowned wines.
Breathtaking vistas and immersion in Tuscany’s rich cultural heritage make this private tour an unforgettable experience.
Inclusions and Exclusions

This private tour includes a range of services to ensure a seamless and enjoyable experience. It covers private transportation, a wine tasting in the Chianti region, and guided visits to the historic cities of Siena and San Gimignano.
The professional driver is also included in the price. However, lunch isn’t provided, so you will have time to dine on their own during the stop in San Gimignano.
Plus, the tour isn’t suitable for those with mobility impairments or wheelchair users, as it requires walking. Visitors should come prepared with comfortable shoes and other essentials for a day of exploring Tuscany.
More Great Tours NearbyPreparation and Recommendations

To make the most of this private tour, visitors are encouraged to bring a few essential items.
Comfortable, supportive shoes are a must for navigating the medieval streets and hills of Siena and San Gimignano. A hat and sunscreen are advisable to protect against the Tuscan sun.
Comfortable, supportive shoes are essential for navigating the medieval streets and hills. A hat and sunscreen protect against the Tuscan sun.
Don’t forget a camera to capture the stunning landscapes and historic architecture. Staying hydrated is key, so packing a water bottle is recommended.
Smoking and drinking aren’t permitted in the vehicle, so visitors should plan accordingly.
With the right preparation, travelers can fully immerse themselves in the beauty and charm of this Tuscan adventure.
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Exploring Siena’s Medieval Charm
As the private tour departs Florence, the drive to Siena offers a captivating preview of the medieval wonders that await. Winding through the Tuscan countryside, the group arrives in the historic center of Siena, greeted by its iconic Duomo and the magnificent Piazza del Campo. Guided through the city’s narrow, winding streets, visitors are immersed in a world frozen in time. The striking architecture and vibrant piazzas evoke a sense of wonder, as if stepping into a living medieval museum.
| Siena’s Highlights | Description |
| — | — |
| Duomo | A stunning example of Italian Romanesque-Gothic architecture. |
| Piazza del Campo | The iconic shell-shaped main square, known for its biannual Palio horse race. |
| Narrow Streets | Winding alleyways that showcase the city’s medieval character. |
Discovering the UNESCO World Heritage Site of San Gimignano

After departing Siena, the private tour group continues its journey through the rolling Tuscan hills, eventually arriving at the UNESCO World Heritage Site of San Gimignano.
Departing Siena, the private tour group journeys through Tuscan hills, arriving at the UNESCO World Heritage Site of San Gimignano.
This medieval town, known as the "Medieval Manhattan," boasts a skyline of iconic stone towers that once served as symbols of wealthy families’ power and prosperity.
The group explores the charming narrow streets, marveling at the well-preserved Gothic and Romanesque architecture.
They visit Piazza della Cisterna, a picturesque square surrounded by historic buildings, and climb to the top of the town’s tallest tower for panoramic views of the surrounding countryside.
Indulging in the Flavors of Chianti Wine Country
The group now departs San Gimignano, continuing their journey through the picturesque Chianti region.
Nestled amidst rolling hills, vineyards, and medieval castles, the Chianti countryside is renowned for its exceptional wines.
At a traditional Tuscan estate, they’ll indulge in a 2-hour wine tasting experience.
Savoring the robust flavors of Chianti Classico, they’ll learn about the region’s winemaking traditions and the unique terroir that gives these wines their distinctive character.
As they sip and swirl, they’ll appreciate the perfect pairing of the region’s wines with the stunning natural beauty surrounding them.
The Sum Up

Enjoy the captivating landscapes and rich cultural heritage of Tuscany on this private day trip. Uncover the medieval grandeur of Siena, marvel at the iconic towers of San Gimignano, and savor the flavors of renowned Chianti wines. With comfortable transportation and expert guidance, this exclusive tour offers an unforgettable opportunity to experience the essence of this enchanting region.
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