Siena
Private Experiences

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Our most recommended Siena Private Experiences

Siena Half-Day Tour from Florence

1. Siena Half-Day Tour from Florence

Visit Siena on a guided half-day tour from Florence. Drive you through the gorgeous countryside of Tuscany. Your professional guide is officially licensed, meaning they can give you ample information about art, history, wine, food and local traditions. The traditional rival of Florence, Siena has been one of the most important and richest cities in Europe and is hometown of Saint Bernardino and Saint Catherine. Visiting Siena is like stepping back in time. The architecture, the roads, the churches - really everything - will remind you of the 13th and 14th century. This tour will view the Siena Cathedral, probably the most precious of Tuscan churches. You will also visit Campo Square, which is home to the famous “Palio” horse race.

Antinori Winery & Brolio's Castle: Private Tour

2. Antinori Winery & Brolio's Castle: Private Tour

Start your day at the office of the local partner, perfectly positioned in the city center. You will meet your personal driver with an exclusive car and your local private guide as well as wine expert. Leaving the city center, the first stop of your visit to Chianti will be Antinori's cellar in Bargino, a wonderfully innovative winery located in the green Chianti hills. Inside the cellar you can taste different types of wine, listening to stories and anecdotes about the Antinori family told by the guide who will accompany you on this wonderful journey. After this visit, you will have lunch in a typical Tuscan restaurant "La Cantinetta di Rignana", halfway between the Antinori vineyard and Brolio's Castle. Here you can taste local salami, cheeses, Tuscan crostini, extra virgin olive oil, pasta or meat dishes, accompanied by wines and local products. Ending the lunch, you can enjoy some free time inside the restaurant, which is also a farmhouse. The last stop of the visit will be the Castle of Brolio and the Barone Ricasoli vineyard. Here, you will privately visit the castle and the vineyard, discovering the cellars and the finest quality wines, tasting most of the local production, tasting every single glass, accompanied by the guide's explanation. When you're ready, you will return to Florence in your exclusive car.

Siena: Civic Museum Private Tour

3. Siena: Civic Museum Private Tour

With this 1.5-hour guided tour of the Civic Museum you will discover one of the major Italy museums. Inside Palazzo Pubblico an expert guide will explain you the frescoes, created by some of the most important 14th-century artists, such as Simone Martini, Duccio di Buoninsegna and Ambrogio Lorenzetti. Within the exhibitions, you will see artistic works from the 14th up to the 19th century, offering you a complete overview of the evolution of Sienese art. Your guide will lead you to discover the heart of Sienese Art — the Civic Museum inside the Sienese town hall. Once inside the Civic Museum you will be introduced to the beautiful 19th-century frescoes in the first room of the museum, dedicated to Italy’s Risorgimento (unification), and you'll discover the medieval World Map Room, with the masterpieces of Simone Martini, la Maestà, and il Guidoriccio da Fogliano. Finishing your visit in the Peace Room, where you'll find the famous depiction of Siena, and the Allegory of Good and Bad Government, by Ambrogio Lorenzetti, one of the first examples of civil art. The subject of the painting is not religious, but rather represents Utopia in Siena and explains the difference between the good and the bad government.

Siena: Private Family-Friendly Treasure Hunt Walking Tour

4. Siena: Private Family-Friendly Treasure Hunt Walking Tour

Try to beat the clock and find the right clues that will lead you to the treasure on this guided scavenger hunt walking tour, perfect for everyone in your group or family. Discover the sights and history of Siena in a fun, learning environment for all ages. Thanks to this treasure hunt, children will discover the history of Siena, its legends, its myths and many nice anecdotes related to the city. Visit the most significant monuments and find out the importance that Siena had in the past. The tour will start with your guide in front of the Basilica San Domenico, where you can admire Siena from breathtaking views, see an ancient castle now incorporated into modern buildings, and hear about the symbol of Siena, the she-wolf, which looks down on visitors and protects them. From there, kick off your scavenger hunt with your tour guide giving a quiz to the children and parents that needs to be solved during the whole tour. You'll learn about 17 districts called Contrade. Children will find the symbols and colors that represent the Contrade all over the city. You’ll pass by a Contrada stable and look for the little fountains hidden through the streets. Along the way, visit the main points of the city and the lesser-known but characteristic alleys. The walk will take you to the last stop of the tour, where the youngest participants will find a treasure to keep.

Siena San Gimignano Private Full-Day Tour by Deluxe Car

5. Siena San Gimignano Private Full-Day Tour by Deluxe Car

Explore Tuscany on this tour of quaint towns and cities. After pick-up from your hotel, the tour will make its first stop in Monteriggioni. Here you can explore a medieval walled town built by the Sienese in the early 13th century. The tour continues to Siena where you will discover one of the most beautiful cities of Tuscany. Siena is famous for its annual historic horse-race, the "Palio," and for its Duomo, an art-filled cathedral that features works by Michelangelo and Donatello. Make your final stop in San Gimignano, one of the most charming and picturesque Tuscan hill towns. Medieval towers dominate the landscape of this UNESCO World Heritage town in a manner that is strikingly similar to the skyscrapers of our modern cities. During the day, you will have the option to stop in a local restaurant for lunch.

From Florence: Siena, San Gimignano & Chianti Private Tour

6. From Florence: Siena, San Gimignano & Chianti Private Tour

Amongst the vineyards and olive groves of Chianti, lie medieval towns and UNESCO heritage sites. Explore them all on a private, 8-hour tour of the Chianti countryside, Siena and San Gimignano. A truly private tour, you will begin your day with complimentary pick-up at your Florence hotel by chauffeured private vehicle. Your English-speaking driver is at your disposal for a maximum of 8 hours. Your first stop will be in Siena, a medieval town. Here you will meet with your private tour guide, who is at your disposal for a maximum of 2 hours. Your guide will take you through the historic city center, where you may admire the splendid palaces and other points of interest. Your tour of Siena will conclude in the Piazza del Campo, one of the most beautiful piazzas in the world. Here, you will find the Palazzo del Comune and have some free time to enjoy lunch. The journey to your next stop, San Gimignano, will take you through Chianti territory. Along the road you will find panoramic vistas, as well as lush vineyards and olive groves. Along the way to San Gimignano you may wish to stop and admire the fortified hamlet of Monteriggioni. This hamlet is a small jewel built in the 13th-century and still embraced by ancient walls. San Gimignano you will find is a UNESCO designated world heritage site. Here you will be given free time to take in the historically interesting medieval town planning, as well as the numerous towers. You will soon find out why this place is called the “Manhattan of the Middle Ages”. Touring this extraordinary region of Italy is a wonderful experience and the fact that this tour is entirely private makes it even more special.

Chianti: Wine and Olive Oil Tasting with Cellar Tour

7. Chianti: Wine and Olive Oil Tasting with Cellar Tour

After arriving at the Fattoria Santa Stefano, your tour begins with an introduction to the grounds and history of this charming farmhouse. After learning about the building’s construction and local food and wine production, you’ll enter the farmhouse’s large wine cellar, featuring stainless steel and cement tanks used for the fermentation of their delicious Chianti wines. Then, it's time to visit the small and rustic 18th century cellar, home to the large barrels of French oak where the wine gets transferred and remains for six months to develop its rich and vibrant flavors. In the same cellar, you’ll also find the little barrels used for the production of Vinsanto, a delicious, amber-colored local dessert wine. To finish off the tour, see the farmhouse’s impressive “Orciaia”, where the extra-virgin olive oil is stocked directly after harvesting and pressing. From there, head back into the small wine shop to enjoy a tasting of some of the excellent local wine varieties and delicious extra-virgin olive oil, along with some great local food.

Siena: Private Tour Ideal for Families with Children

8. Siena: Private Tour Ideal for Families with Children

Enjoy a private tour that takes into account children’s attention spans, not one where the young are dragged by their parents on exhausting journeys. With the help of a local guide, keep your children’s attention alive with language that is colorful and lively, and where history is mixed with art, legends, and traditions. By encouraging children to make observations, answer questions, and solve riddles, your guide will reveal the history and secrets of Siena’s monuments in a pleasant way that is sure to prevent children becoming impatient, bored, and complaining. From the meeting point in front of the Basilica Cateriniana San Domenico, you’ll learn about the traditions of the Palio di Siena horse race and admire the magnificent front of the Duomo di Siena cathedral. Next, walk the Via Banchi di Sopra — the former route of pilgrimage to Rome — that will you lead to Piazza del Campo, the principal public space of the historic center of Siena where the tour will end with a souvenir and great memories.

From Florence: Private Full-Day Jewels of Tuscany Tour

9. From Florence: Private Full-Day Jewels of Tuscany Tour

Be seduced by the eternal charm of Tuscany’s jewels on this 12-hour tour. What are Tuscany’s jewels? The beautiful cities and villages, as well as art and the historical monuments that call this unique region of Italy home. Falling in step with the more ‘human’ way of life in Tuscany, this relaxed tour begins when you want it to. You determine the pick-up time from your centrally-located Florence hotel. You will also enjoy the transportation, which is provided by a private vehicle operated by an English-speaking driver. After pick-up, you will drive through the Tuscan countryside until your first stop, Siena, is reached. Siena is a medieval city known for its artistic treasures, which have been recognized by UNESCO. In Siena you will visit the shell-shaped Piazza del Campo. Here you will find the Palazzo Comunale flanked by the Torre del Mangia. Every year the famous Palio takes place here. You will also have free time to visit the cathedral, built in the Middle Ages and admire the splendid buildings and narrow streets. From Siena, you will enjoy a drive through Chianti territory on your way to Monteriggioni. The drive boasts a panoramic view of the vineyards and olive groves. Monteriggioni is a small 13th-century town which is still surrounded with its original town walls. Here you will take a walk within the restricted perimeter of the walls, which have eleven towers with spectacular views. This is a Tuscan gem that will transport you back in time. Only a short distance away, in a pleasant country estate you will be served a typical Chianti-region lunch. You will also enjoy a guided tasting of Chianti and Vernaccia wines. After lunch you will leave the estates and go to San Gimignano, another beautiful town and UNESCO world heritage site. Famous for its signature medieval town planning, it is called the “Manhattan of the Middle Ages”. On a stroll through the town center you will discover the Piazza della Cisterna, the Dome, the Palazzo del Podestà and the Church of Saint Agostino. Your final stop will be at the famous town of Pisa, which is also a UNESCO world heritage site. In the Piassa dei Miracoli the masterpieces in marble rise from the green lawn, including the famous Leaning Tower of Pisa, the magnificent Baptistery, the stunning Cathedral and the Monumental Graveyard Tuscany is a one-of-a-kind region of boundless natural and cultural beauty. This small, personalized tour is an authentically Tuscan experience.

Siena: Palio Walking Tour

10. Siena: Palio Walking Tour

Learn about the unique history of Sienna on a walking tour of the medieval old town with an informative guide. Get to know the different "contrade" or districts that make up the city and hear how they date back to medieval times. Stroll through the Piazza del Campo, where the famous Palio horse race takes place every year on July 2nd and August 14th, featuring a contestant from each of the contrade. Visualize the colorful banners and crests of the competing contrade and learn how the competition has defined civic life in the city for centuries. Hear stories about the life and culture of the city from locals and visit the Museum of the Contrada for a more official account. Then head to the Duomo of Siena and check out the characteristic black and white marble interior of the cathedral designed to symbolize the black and white horses of the city's founders. Afterwards, switch gears and enjoy a local tasting experience at a traditional cafe. Try Panforte, Ricciarelli, and Cavallucci, typical sweets famous around the world. Wash them down with a glass of Vin Santo del Chianti.

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What people are saying about Siena

We had a wonderful day and a great tour with our tour guide Massimo. We were picked up very close to our hotel in the center of Florence on time with a comfortable V-class and were dropped off there again in the evening. The whole day was great and Massimo was a superb driver and a great guide. We can really recommend this tour for everybody who wants to see the most important sights of Tuscany. Thanks Massimo for this great day in the Tuscany!

This was a fantastic experience for our family! Sylvia was a very knowledgeable and engaging tour guide. She tried to connect with our kids, asking them questions along the way. We visited eight different cities on our trip to Italy, and our children liked Siena the best because of the tour we had with Sylvia. Highly recommend this tour for families with kids, you will all learn a lot and enjoy seeing this beautiful city!

Fantastic experience !! Alessandro provided solid communication before, during & after our tour. He was on time, provided great information during the different visits and was very attentive to all our questions. As someone that has completed many tours like this, I particularly appreciated the patience with the family (when you have kids!!!) as well as the good driving. Highly recommended !!!

Massimo was absolutely excellent. Very friendly. Arrived on time and let us know some background and history of all the locations we went to. The drive was very scenic and the locations were picturesque. Massimo also gave us suggestions on where to have some of the best gelato in Italy and he was not wrong, it was absolutely delicious. 10/10 would absolutely do it again.

We greatly enjoyed our day tour to Tuscany. Our guide, Arran, was very knowledgeable and friendly. We loved hearing all the history and seeing so many beautiful sights. The rolling hills and wineries are fantastic. This was a wonderful addition to our honeymoon!