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Day Trip to Siena, San Gimignano and Chianti

Tuscan Treasures & Wine Tasting: Private Day Trip to Medieval Gems from Florence

This full-day private tour from Florence is the ultimate experience for combining culture and relaxation. You will journey through the iconic Tuscan countryside with a dedicated private driver, enjoy an in-depth 3-hour private tour in the UNESCO World Heritage city of Siena and indulge in a memorable wine-tasting experience in the Chianti region.
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Itinerary Highlights

  • Siena: A 3-hour private walking tour takes you through this historic city. Admire the magnificent Duomo and uncover the deep traditions behind the iconic Palio di Siena horse race.

  • Chianti Winery: Visit the heart of the wine region for an unforgettable wine-tasting and a delicious light lunch featuring authentic local specialties.

  • San Gimignano: Discover the charm of this stunning hilltop village, famous for its medieval towers, where you’ll have free time to wander and shop.

Why book this tour

  • Personalized Service: A dedicated English-speaking private driver ensures a seamless and comfortable travel.

  • In-Depth Exploration: Gain deep insights into Siena’s history with a dedicated local private guide.

  • Gourmet Experience Included: Enjoy a complimentary wine-tasting and light lunch at a traditional Chianti estate.

  • Total Relaxation: Stress-free day trip with convenient hotel pick-up and drop-off in central Florence.

  • Perfect Blend: A comprehensive tour encompassing Medieval history, Renaissance architecture and authentic Tuscan wine culture.

Description

Leave the hustle of Florence behind and delve into the authentic charm of Tuscany with this exclusive private day trip. This tour perfectly balances historic immersion and relaxing countryside enjoyment, accompanied by your own knowledgeable private driver.

Your journey starts in the spectacular city of Siena. Here, you will meet a local private guide who will lead you through its historic core, revealing the secrets of the incredible Duomo and the city’s celebrated heritage, including histories and anecdotes about the famous “Palio” horse race. Next, we travel through the picturesque scenery to the Chianti wine region. This is your chance to unwind and savor an authentic wine-tasting experience paired with a light lunch at a traditional Chianti winery.

The final stop is the iconic skyline of San Gimignano. With its striking medieval towers still intact, this charming hilltop town offers a step back in time. You’ll have ample free time to wander its ancient streets, discover local artisan shops and capture unforgettable views before your private driver safely returns you to Florence.

Things to know before the tour

This tour includes pick up and drop off at your hotel in Florence: please let us know your hotel’s name and address at the time of booking.

Important information

Dress Code: in order to enter religious sites, such as Churches, every participant must make sure they cover their shoulders and knees.

We also suggest you wear comfortable shoes, as a moderate amount of walking is involved in this tour.

Pleasenote: the order of the sites visited could change.

This tour operates in all weather conditions: please dress appropriately

Cancellation policy

Cancellations 4 days or earlier prior to the scheduled tour are subject to a penalty.

Please note Tickets and reservation are strictly not refundable. If you cancel 4 days or earlier prior to the tour we will refund you partially for the price of guide only.

No refund will be provided if you cancel your tour within 4 days prior to the scheduled tour.

Meeting point

Your hotel in central Florence

Included

  • 9 hours private driver
  • 3 hours private guide in Siena
  • Wine-tasting with light lunch in Chianti

Excluded

Tickets for Siena Cathedral

Tips

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About the Tour

Offered in English, Spanish, French or German

Duration

9 hours

Level

Easy

Access

Audio

Private Tour

Dates and departures

Everyday except on Christmas Day and New Year's Eve

Values

— What you won’t miss

You Will See

san gimignano

San Gimignano

San Gimignano is a spectacular medieval hill town often referred to as the "Manhattan of the Middle Ages," famous for its remarkable skyline of surviving stone towers that dominate the Tuscan landscape. Step back in time within its perfectly preserved walls, where you can climb the Torre Grossa for stunning views and explore its magnificent central squares and frescoed churches.
siena cathedral at sunset

Siena

Siena is an exquisite Tuscan hill town and a UNESCO World Heritage site, famous for its perfectly preserved Gothic cityscape of winding, narrow streets and warm, terracotta-toned buildings. Experience the deep-seated pride of its 17 historic contrade (neighborhoods) and the unique civic passion that culminates in the thrilling, world-famous Palio horse race held in its spectacular main square.

— About Us

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