Best of Chianti

Siena Monteriggioni & San Gimignano in one day!

Best of Chianti 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


Depart from Florence and travel out of the city in your air-conditioned coach toward the amazing Siena. Guided tour will include the visit to the most famous monuments and squares: the Cathedral and the Baptistery, Ospedale di Santa Maria della Scala, Palazzo Salimbeni, Palazzo Tolomei, Piazza del Campo and the Sanctuary of Santa Caterina, the patron of the city. Continue on through the rolling hills of the Chianti wine region to Monteriggioni, a fortified hilltop village founded in 1214 by the Republic of Siena to protect its northern territory from the incursions of the rival Florence. Here we'll enjoy an authentic three courses tuscan lunch paired with the most genuine Chianti wine. Next, hop back in your coach and continue onward to San Gimignano, famous for its 13th century "fine" towers, the saffron locally produced since the medieval times, and the local white wine "Vernaccia di San Gimignano". Guided excursion includes a stop to the panoramic view, the visit to the "1300 Ceramic Museum" and the stop to the Dondoli world champion gelato maker. 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 visit to the most notable monuments of Siena

Authentic three courses tuscan lunch in Monteriggioni

Shopping and relax in Monteriggioni

Guided visit to San Gimignano

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.

10:00 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.

1:00 p.m.

We’ll have an authentic tuscan 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. Tuscan delis will be paired to a bottle of the best Chianti wine.

3:00 p.m.

Next stop will be in San Gimignano, one of the most attractive medieval towns in Tuscany. We’ll have the opportunity to walk on the ancient pilgrim route called “Via Francigena”. We’ll stop at “1300 Ceramic Museum” and “Dondoli world champion gelato”. We’ll also visit the panoramic view over the surrounding rolling hills.

05:00 p.m.

On our way back to Florence we’ll stop at the Michelangelo square, the most romantic panoramic view over 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

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: in particular the main street called "Via Francigena", Piazza del Campo, Piazza del Duomo, Ospedale di Santa Maria della Scala and the panoramic view from S.Domenico. A few barriers are still present but easy to skip with the help of our guide.

Accessibility to the castle of Monteriggioni is pretty good by wheelchair.

Accessibility to San Gimignano is very good. Streets and sqaures are nicely paved. All landmarks are easy to reach. Public toilets are difficult to be used.

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

Our Best of Chianti 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 €175

Booking Form - Single Tour
Total 720 €
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Total 1240 €
Total 1300 €
Total 1350 €
Total 1400 €
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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