Day Trip to Siena, San Gimignano and Chianti

Everyday except on Christmas Day and New Year's Eve

9 hours

Private Tour

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Reviews

Day Trip to Siena, San Gimignano and Chianti

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

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9 hours

Private Tour

Everyday except on Christmas Day and New Year's Eve

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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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 to Siena and tuscan countryside. 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

FAQ

Cancellation policy

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

Please noteĀ 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 daysĀ 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

Values

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— 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

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

Reviews

FAQs

Yes, all our Rome private tours include Skip-the-Line tickets. You will bypass the general admission queues and enter directly with your private guide, saving up to 2 hours of waiting time.

Yes, the itinerary can be adapted: wheelchair users follow an alternative route inside the Vatican Museums, assisted by an accompanying person and our guide while the rest of the group continues on the standard route. Access to St. Peter’s Basilica is not included due to architectural barriers. If you travel with a wheelchair, please contact us in advance so we can arrange the best possible accommodations.

Our tours are strictly private, meaning the experience is exclusive to your group only. There is no fixed maximum — whether you are traveling as a couple, a family, or a small group, the tour is tailored entirely to you.

Absolutely. Our guides are experienced in making history engaging for younger visitors. We adapt the pace, language and storytelling to suit families with children of all ages.

Yes. When visiting religious sites such as the Vatican Museums, St. Peter’s Basilica or churches, shoulders and knees must be covered. We recommend bringing a light scarf or shawl. Comfortable walking shoes are also strongly advised.

The exact meeting point is confirmed in your booking confirmation email. Your guide will be holding a Vivicos Travel sign and will contact you directly before the tour to ensure a smooth meeting.

Yes. Our private tours are available in English, Italian, Spanish, French and German. Please select your preferred language at the time of booking. Availability may vary by date.

Our tours operate rain or shine. Rome’s main attractions are largely indoors, so weather rarely affects the experience. In the unlikely event of extreme weather conditions, you will be offered a free reschedule or a full refund.

Yes, one of the main advantages of a private tour is full flexibility. If you have specific interests — art, history, architecture, food — simply let us know at the time of booking and your guide will tailor the experience accordingly.

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