Siena & Tuscany

a wonderful day in art history and wine!

Siena & Tuscany by Fun in Tuscany Tour
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Departure 8:30 a.m.
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Duration 8h
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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


Our first stop will be in Siena. Medieval atmosphere and stunning surrounding landscapes make Siena a favorite destination for a vast number of visitors from all over the world. Siena with its monuments and art treasures is considered a world heritage site protected by UNESCO. We'll start our walk in Siena from Basilica di San Domenico, we'll continue to the panoramic viewpoint over the city, next we'll stop at the house and Sanctuary of Santa Caterina, to reach the square with the Duomo and the medieval Hospital of Santa Maria della Scala. Then we'll visit Piazza del Campo with the white marbled Fonte Gaia and Torre del Mangia for more photo ops. On our way back to the car we'll see the beautifull Palazzo Tolomei and Palazzo Salimbeni located along the ancient "Via Francigena", the legendary pilgrim route still leading to Rome. After Siena, we'll direct to the countryside and stop in Monteriggioni for a typical tuscan lunch. Next we'll visit a local cozy winery for a guided wine tasting. On the way back to Florence we will stop at "Piazzale Michelangelo" which is considered one of the most romantic spots of the city.

Comfortable roundtrip transportation by AC car or minivan

Informative english speaking tour guide/driver

Guided walking tour to the most notable monuments of Siena

Authentic three courses tuscan lunch in Monteriggioni

Guided visit to vineyards and wine cellar of a Chianti winery

Opportunity to buy top Chianti wines

Stop at Michelangelo Square, the best panoramic view over Florence

DEPARTURE 8:30 a.m.

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

RETURN 5:00 p.m.

Returns to original departure point


8 hours


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

8:30 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 8:45 am. 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.

10:30 a.m.

Our first stop will be in Siena, one of the most celebrated and beautiful medieval town of the Tuscany region. We’ll park the vehicle and walk along the ancient “Via Francigena”, the ancient pilgrim road connecting Rome and the north of Europe since the VIII century a.C. We’ll enjoy the magic atmospehre of the city and its monuments: Basilica di San Domenico, House and Sanctuary of Santa Caterina, Duomo and Baptistery, Spedale di Santa Maria della Scala, Piazza del Campo and Fonte Gaia, Torre del Mangia, Palazzo Tolomei and Palazzo Salimbeni.

1:30 p.m.

We’ll stop for lunch at a typical italian restaurant located inside the stunning castle of Monteriggioni, built by Siena in 1213 to protect the region by the incursions of the florentines. Lunch will be paired to a bottle of the best Chianti wine!

3:00 p.m.

Next stop will be at a local winery, top winery located in the Chianti Classico region, the oldest area of the Chianti region. We’ll enjoy a tour of the cellar and you will have the pleasure to taste some of their best wines: Chianti Classico, Chianti Classico Riserva and Chianti Classico Superiore, will be on the list! All around the winery you will have the chance to take amazing pictures of the magnificent landscape offered by the Chianti Classico region. And after the tasting if you like you will have the opportunity to buy and ship worldwide.

05:00 p.m.

On our way back to Florence we’ll stop at the fantastic panoramic view of “Piazzale Michelangelo”. Tour lasts approximately 8 hours. Upon request it is possible to skip the visit to the winery to make it shorter. Another available option is to skip the restaurant in Monteriggioni and enjoy a typical tuscan lunch combined to a wine tasting class at a different winery in the area of San Gimignano. Do not hesitate to contact us for more details.


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

Vegetarian, vegan and gluten-free meals available upon request

Please advise any specific dietary requirements at time of booking

Infants and children are welcome

Private tour

1 person
2 people
3 people
4 people
5 people
6 people
7 people
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.

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

Tour of the main monuments of Siena will be personalized to include accessible areas and panoramic views.

Tour also includes a stop at the Michelangelo square in Florence. Accessibility to all this area is very good.

Our Siena & Tuscany private tour is differently abled persons friendly.

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No age restrictions
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No experience required

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From €166

Booking Form - Single Tour
Total 620 €
Total 790 €
Total 930 €
Total 1050 €
Total 1160 €
Total 1250 €
Total 1330 €
Total 1380 €
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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