Siena and Montalcino

exploring the Brunello wine region!

Siena and Montalcino by Fun in Tuscany Tour
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Departure 8:00 a.m.
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Duration 10h
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Offered in english or italian
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Private tour
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All year round
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Family and kids friendly


Montalcino and the DOCG wine region of Brunello are located about 50 Km south of Siena. According to some historians the name of the town comes from the roman goddess Lucina, for others it most likely refers to Mons Ilcinus, that in latin stand for "the mount of the holm oaks", a special variety of oak threes still very common in the area. The production of wine around Montalcino is documented since the Middle Age: the period of the harvest was strictly regulated by the governament. Along the centuries many important visitors had mentioned the high quality of the wines produced in Montalcino. But it's only in the XIX century that farmers begun to experiment with a native grape variety cultivated in the surrounding territory and called Brunello. It was a special variety of Sangiovese. Brunello di Montalcino, originated as delicacy of an elite of wine experts, got its popularity in the second half of the XX century: it was registered as DOC wine in 1966 and it was the first wine to become DOCG in 1980. Since then it has been considered one of the best italian wines in a worldwide ranking. Our daytrip is a wonderful opportunity to discover and explore the region and the town of Montalcino. Departing early in the morning from our meeting place in Florence we'll be in the Brunello region arond 10:30 am. Our first stop will be in a local family-owned winery where we'll have a guided tour of the vineyards and cellar. An expert winemaker will inform us about the history of the family, with a description of the estate and its wine production. Under his guidance we hope to unveil some of those secrets that made the legend of the Brunello wine! We'll then enjoy a lovely wine tasting, to appreciate their wines and possibly buy them. After this fantastic wine experience, we'll visit the town of Montalcino where we'll have a typical tuscan lunch at a local restaurant. Back to the car we'll be on our way to Siena. In Siena we'll enjoy the panoramic view of the city from the "secret path" of San Domenico, we'll then stop by at the Santa Caterina Sanctuary, and we'll visit the Duomo and Ospedale di Santa Maria della Scala. Following the ancient pilgrims road "Via Francigena" we'll go to Piazza del Campo, the main square of Siena where twice a year the famous horse race called "Palio" takes place. In the shell-shaped square we'll see "Torre del Mangia", the city tower, "Palazzo Pubblico", the town hall, and "Fonte Gaia", the marbled fountain sculpted in the XV century by Iacopo della Quercia. On our way back to the car we'll also see Palazzo Tolomei and Palazzo Salimbeni, some of the most prestigious palaces of Siena. We'll be back to Florence around 6pm. Families and kids are more than welcome!

Comfortable roundtrip transportation by AC car or minivan

Informative english speaking tour guide/driver

Visit to a family-owned winery in the Brunello wine region with tour of the cellar and wine tasting

Visit to the town of Montalcino

Authentic tuscan lunch at a local restaurant

Guided walk to the most notable monuments of Siena

DEPARTURE 8:00 a.m.

Via Curtatone 9, outside cafe Gamberini, just a five min walk from S.M.Novella train station in Florence

RETURN 6:00 p.m.

Returns to original departure point


10 hours (Approx.)


Private pick up at your accomodation in Florence or Tuscany available upon request at an extra charge. Please contact us before booking.

8:00 a.m.

Meeting point and check in will be on Via Curtatone n.9, outside cafe Gamberini, a few minutes walk from the main Florence train station. Departure by 9:30am. Upon request and at an extra charge we can organize pick up at your villa in Tuscany or at your hotel in Florence. It is also possible to customize the time of departure. Please contact us with your requests.

9:30 a.m.

On our way to Valdorcia we’ll have a short stop in Buonconvento for a coffee in a nice cafe’ inside the walled town.

10:30 a.m.

Visit to the cellar and vineyards of a winery located in the famous Brunello wine region, the small DOCG area where this top premier wine is produced. Wine tasting will combined to a generous plate of tuscan snacks.

1:00 p.m.

We’ll reach Montalcino for a typical tuscan lunch at a local restaurant and a walk of the cozy alleys of this medieval town.

3:30 p.m.

Visit to the most important landmarks in Siena. We’ll walk from San Domenico to the House and Sanctuary of Santa Caterina. After visiting the Duomo and Ospedale di Santa Maria della Scala, we’ll reach Piazza del Campo with Torre del Mangia and the Town Hall. Along the ancient Via Francigena we’ll have a stop at Palazzo Tolomei and Palazzo Salimbeni.

06:00 p.m.

Back to Florence.


Note: All scheduled times are an approximation and can vary slightly based on situations out of our control (traffic, weather, etc.)

Online booking is required

Confirmation will be received at time of booking

Infant seats available

Vegetarian, vegan and gluten-free meals available upon request

Please advise any specific dietary requirements at time of booking

Private tour

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8 people
Free cancellation up to 24 hours in advance

Regular transportation is provided by 8-seater minivan. For private tours 4-seater car is available too.

Wheelchairs and other lugguage may be stored in the trunk of the vehicle.

Wineries we visit are well accessible to differently abled persons, with a few barriers easy to skip with help of our guide.

We'll visit the accessible area of the town of Montalcino.

We reach Siena by car. The city tour will be personalized to include an accessible area. This area covers the panoramic view from San Domenico, the "via Francigena", Piazza del Campo, Piazza del Duomo and Ospedale Santa Maria della Scala.

Single Tour Age Restrictions Family Icon
No age restrictions
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No experience required

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From €245

Booking Form - Single Tour
Total 1070 €
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Total 1960 €
Free Cancellation up to 24 hours in advance

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Read some of our reviews

Leave us a review on Tripadvisor!
18 Luglio 2023

Great day out

Great experience, loved the horse riding, the town we visited was beautiful, unfortunately I was too hungover to do the wine tasting and lunch but the staff were so friendly and accomodating of my self inflicted illness which was much appreciated ! Would definitely come back to experience the whole day as per the actual plan..

Ehren Q
Ehren Q
5 Febbraio 2013

Vespa Tour

The vespa tour was an absolute blast. Unfortunately the equipment supplied to Fun in Tuscany by a third party was not the most reliable, however, the scenery and ride was worth any trouble that may have been caused by said equipment.

Andrew Y
Andrew Y
29 Giugno 2023

Loved this trip

Lorenzo is the guide and driver. He is so nice and informative. Loved the trip. The horse riding sure is wonderful!

17 Maggio 2023

A totally enjoyable day.

A totally enjoyable experience. Our guide, Guido, the self-proclaimed King of Tuscany did a great job. Our visit to the two wineries, that included lunches were both great. Also, the visit to San Gimignano was a pleasant time. One of the best memories of our stay in Florence.

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