private tour

Private tour to Siena, San Gimignano & Chianti

All health and safety measures are in place. Also keep in mind that booking a private service you will be the only party in the vehicle. The top solution in terms of safety, comfort, privacy and flexibility. Relax and enjoy your experience.



Explore the medieval atmosphere in Siena, San Gimignano and an ancient winery

See the highlights of Siena, walk through the narrow streets of San Gimignano, admire the beautiful Tuscan wine country and visit a typical Tuscan winery. All of this at your own pace and with the maximum comfort you can only get with a private door-to-door service.


Start your private day with a scenic one-hour drive through the Tuscan countryside to reach Siena, the birthplace of the beloved Italian Saint Catherine.

Get lost in this beautiful city made of brown Siena-colored bricks (so that’s how they named the color!). A jumble of narrow streets and delightful squares, medieval towers that make such a spectacular skyline, the spectacular cathedral, the tall and trim Torre del Mangia.

All together create an enticing atmosphere almost like stepping back in time.

Piazza del Campo

Siena was built on three hills and is home to one of the most authentic and important Gothic cathedrals south of the Alps. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration having been seen in numerous films and photographs.

Palio horserace

In this brick-covered square twice a year takes place the famous ‘Palio’ horserace. It involves the entire population and is considered one of the most important events in the life of the local people. Almost anything will be done to win this extremely competitive race and bring home the ‘Palio’, a silk banner proudly displayed in the ‘contrada’ or neighborhood it represents.


Your private day trip will continue with a stop in San Gimignano. A small medieval town in Tuscany famous for its splendid skyline made up of 13 towers.
This 11th-century town rises 334 meters above Elsa Valley along the ancient road ‘Via Francigena’ on which traders and pilgrims traveled to Rome.

Ancient palaces and local crafts

Besides its remaining 13 towers, admire the Duomo and its magnificent frescoes, ‘Palazzo del Popolo’, ‘Palazzo Nuovo del Podestà’ today the town hall. See the church dedicated to Saint Augustine, the Museum of Holy Relics and the infamous Museum of Torture with its macabre displays of early torture instruments.

Wander up and down the main street in San Gimignano and enter the numerous specialty shops. The ceramics are beautiful here and there are also places for buying leather goods and linens.


Continuing the drive through amazing landscapes, reach the heart of Chianti Classico countryside. Stop at a hilltop winery for a visit at the discovery behind excellence then enjoy a tasting of the famous Chianti wine, olive oil and local food. The perfect way to conclude your experience and better understand the Tuscan wine culture.



At the end of your day in Siena, San Gimignano and Chianti,  enjoy a comfortable relaxing drive to your accommodation in Florence

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Can we reserve a local guide directly on site on the day?
Unfortunately, no! If you’d like to add this optional service you must book it at the time of reservation, or at least a few days in advance.



Is this tour, accessible for people with disability?

Yes, it is! We can accommodate people with reduced mobility and foldable wheelchair/scooters users.
Please note: it is mandatory to specify each specific need at the time of booking and in case of wheelchair/scooters, the exact dimensions to be sure they can fit in the trunk of the vehicle.



How much walking is involved on this tour?
It is totally up to you. Our vehicles have special permits/licenses to circulate almost everywhere (pedestrian areas included).
For example in Siena, we can drop you off right in front of the Cathedral or directly in Piazza del Campo. Being a private service you are free to decide your own pace, with no rush.



Are the entrance fees for Siena Cathedral included in the price?
The entrance fees for the Siena Cathedral or any other attraction are not included in the price.
Your driver can give you all the info to buy the admission tickets on-site. Keep in mind that normally in Italy, to enter religious sites it is mandatory to have shoulders and knees covered.



Is a wine tour/tasting included?
Yes, this tour includes a visit to a winery followed by wine tasting.



Do we taste white wines?
The tour includes a winery located in the Chianti Classico, famous for red wines primarily made with Sangiovese grapes. As a plus depending on the time of the year and production, you may also taste some rosé or white wine. If your main interest is in white wine, let us know so we can arrange an itinerary in a different area.



Are meals included?
Meals are not included on this tour, so you are free to decide the option that best suits your needs. Your driver can give you suggestions according to your tastes.



Can I buy/ship wine/olive oil?
Yes. You can buy a few bottles or a larger quantity to ship home. Make sure you know your country’s rules of taking wine back home – every country has different rules.


You may find additional info on our FAQs page, in the Private Tours section.

Free date changes

You can change your service date for free, within 24 hr prior departure.

Credit for future tours

You can convert your existing payments to credit, and use it on your next trip, up to 24 hr prior departure

Gift or transfer

You can transfer your credit to a friend or family member, at no extra cost.

Free Cancellation

– Up to 24 hours prior departure time

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