Private tour Siena, San Gimignano and Monteriggioni, lunch in the cellar

5 (3)
Florence, IT
5 (3)
Florence, IT
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Experience the beauty and charm of Tuscany with a private tour to Siena, San Gimignano, and Monteriggioni. With an English-speaking driver as your guide, you'll have the freedom to create your own itinerary and explore at your own pace. Begin in Siena, where you can marvel at the stunning Basilica of San Domenico and visit the famous Piazza del Campo. Continue to Monteriggioni, a picturesque village that feels like stepping into a fairytale. Enjoy a wine tasting and lunch at a family-run winery in Sant'Appiano (not included in price), immersing yourself in the authentic flavors of the region. Finally, explore the medieval streets of San Gimignano and take in the panoramic view of the Tuscan countryside. This private tour is the perfect way to experience the rich history, breathtaking scenery, and delicious cuisine of Tuscany.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Admission Included
  • 8 hours - 9 hours
  • Suitable for 1-7 Participants
  • Private Tour
  • Guided Experience
  • Walking through the historic center of Siena
  • Visiting the castle of Monteriggioni
  • Wine tasting and lunch in a family-run winery
  • Exploring the medieval village of San Gimignano
  • Admiring the view of the Tuscan countryside
  • Private transportation
  • Bottled water
  • Wifi on board
  • Air-conditioned vehicle
  • English speaking driver
  • Lunch
  • Gratuities
  • Tourist guide only on request (paid separately)
  • Admission tickets (for the duomo of siena at about € 7 per person)

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More about this experience


Escape to the picturesque region of Tuscany on a private tour of Siena, San Gimignano, and Monteriggioni. This full-day adventure offers a personalized experience, led by a friendly English-speaking driver who will ensure that your journey is flexible and tailored to your preferences. Immerse yourself in the rich history and cultural treasures of these enchanting destinations, as you stroll through the iconic streets of Siena, visit the medieval castle of Monteriggioni, and explore the charming village of San Gimignano. Along the way, you'll also have the opportunity to indulge in the renowned Chianti wine and savor the flavors of Tuscany during a delightful lunch at a family-run winery (please note that tasting and lunch are not included in the price). To top it all off, admire the breathtaking panoramic views of the Tuscan countryside from San Gimignano and make a stop at Piazzale Michelangelo in Florence before returning, creating memories that will last a lifetime.

What to expect:

Embark on a journey that spans 480 to 540 minutes, allowing you ample time to fully immerse yourself in the beauty and charm of Siena, San Gimignano, and Monteriggioni. Discover the architectural wonders of Siena, including the Basilica of San Domenico and the iconic Piazza del Campo. Marvel at the majestic Duomo of Siena and meander through the labyrinthine streets of the UNESCO-listed historic center. Next, venture to the medieval fortress of Monteriggioni, relishing in the fairy tale-like ambiance of this enchanting castle. Indulge in a wine tasting and lunch at a family-run winery in Sant'Appiano, savoring the authentic flavors of Tuscany. Continue your adventure to the captivating village of San Gimignano, known for its medieval towers and stunning views of the Tuscan countryside. Finally, make a final stop at Piazzale Michelangelo in Florence, where you can enjoy panoramic vistas of this Renaissance city.

Who is this for?

This private tour is perfect for those seeking a personalized and immersive experience of Tuscany. Whether you're a history enthusiast, a wine lover, or simply someone who appreciates the beauty of picturesque landscapes, this tour caters to a wide range of interests and preferences. It is suitable for individuals, couples, families, and small groups who want to explore these iconic destinations at their own pace, without the constraints of a large tour group. With the guidance of an experienced English-speaking driver, you can fully customize your itinerary and enjoy the flexibility of spending more time in the places that captivate you the most. This tour is designed to accommodate both seasoned travelers looking to delve deeper into the rich cultural heritage of Tuscany, as well as those experiencing the region for the first time.

Why book this?

Indulge in the ultimate Tuscany experience with this private tour of Siena, San Gimignano, and Monteriggioni. Unlike conventional group tours, this personalized excursion allows you to set the pace and focus on the aspects that interest you the most. Delve into the captivating history, art, and architecture of Siena as you explore its medieval streets. Wander through the enchanting castle of Monteriggioni, feeling as though you have stepped into a fairy tale. Taste the renowned Chianti wine and savor authentic regional cuisine at a family-run winery. Immerse yourself in the charm of San Gimignano, with its medieval towers and breathtaking views of the Tuscan countryside. Throughout the journey, a friendly English-speaking driver will share their insights and recommendations, offering a unique perspective on the region. By booking this tour, you can create unforgettable memories, appreciate the beauty of Tuscany, and explore these iconic destinations with ease and flexibility.

Good to know:

Please note that this tour does not include tasting and lunch at the winery, allowing you the freedom to choose your own dining experience. The duration of the tour is approximately 480 to 540 minutes, providing ample time to explore each destination at a leisurely pace. Comfortable walking shoes are recommended as you will be strolling through historic centers and picturesque streets. Additionally, it is advisable to bring a camera to capture the scenic beauty of Tuscany. The tour begins and ends in Florence, with convenient meeting and end points. Throughout the journey, your experienced English-speaking driver will provide valuable insights and recommendations, ensuring a seamless and enjoyable experience. Discover the magic of Tuscany on this private tour and create memories that will last a lifetime.


Travelers who have experienced this private tour of Siena, San Gimignano, and Monteriggioni have been captivated by the beauty and authenticity of Tuscany. They have praised the flexibility and personalized approach of the tour, allowing them to explore each destination at their own pace. Many have been charmed by the rich history and cultural treasures of Siena, immersing themselves in the vibrant atmosphere of the UNESCO-listed historic center. The enchanting castle of Monteriggioni has left a lasting impression on visitors, with its fairy tale-like ambiance and breathtaking views. Wine lovers have delighted in the opportunity to taste the renowned Chianti wine at a family-run winery, savoring the flavors of Tuscany. The medieval village of San Gimignano has mesmerized travelers with its towers and panoramic vistas of the Tuscan countryside. Overall, individuals who have embarked on this private tour have expressed their satisfaction and gratitude for the incredible experiences and memories created along the way.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary

Centro Storico di Siena

After about an hour's journey from Florence you get to Siena. - Internal visit of the Basilica of San Domenico, one of the most beautiful Gothic churches of Siena, famous above all because it is here preserved the head-relic of Santa Caterina, patron saint of the city and co-patron of Italy. - Visit on foot of Piazza del Campo, a UNESCO World Heritage Site since 1995. Piazza del Campo is also the place where every year, on July 2nd and August 16th, the Palio, the most famous race of horses in the world. - Visit from the outside of the Duomo of Siena (Metropolitan Cathedral of Santa Maria Assunta) with possible internal visit of the Duomo (not included in the price). - Walk in the center. Getting lost in its streets is one of the most beautiful things that can happen. Wandering aimlessly through the streets, alleys and squares of the UNESCO's historic center, following what from time to time suggests instinct.

Admission Included

Castello Monteriggioni

After about 25 minutes from Siena you get to Monteriggioni. It takes just a few minutes to get around Monteriggioni. The village is small and with few streets. The impression that remains in the memory, however, lasts forever. One notices that he has discovered a magical place, almost an enchanted castle like those that are known in fairy tales, as children

Admission Included


Wine tasting and lunch in the cellar, here they have lunch in a family-run farm (not included in the price).

Historic Centre of San Gimignano

After about 40 minutes from Monteriggioni you arrive in San Gimignano, followed by a visit to one of the most characteristic and fascinating medieval Tuscan villages: San Gimignano, a UNESCO heritage site, is a town that has remained almost intact from the end of the fourteenth century to today.

Admission Included



5 (3)


Our driver and guide Florian was very professional and informative. We enjoyed our day very much. Lunch was good and entertaining at a winery. He brought us to a great place for a photo.


Great personal experience for the 4 of us! We had requested English-speaking driver but didn’t get one. However Leo’s friendliness and promptness at every stop made up for the English he did not understand. Would totally do it again!


The tour was fantastic, Florian, our driver/guide was punctual, friendly and an excellent person, i recomend this tour to all
Collected by Evendo & our supplier partners
2024-07-19 21:45