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Cycling tour in Italy | The Gravel Roads of Chianti
Bike Tour Tuscany | The Gravel Roads of Chianti
The Departure of the Chianti Wine Tour
Chianti's Alluring Views
Wine Tasting at Ricasoli Winery
Brolio Castle
The View to the Brolio Castle
Panoramic View from the Brolio Castle
White Dirt roads of Chianti, near San Gusmé
Lunch at San Gusmé - Glass of Wine
Orange Tart - Dessert
Il Vin Santo - Typical Tuscan Sweet Wine
Chianti-1.png
2025 Bike Tours and Hiking Excursions Discover the Chianti Classico on a Scenic Tuscany Bike Tour

Discover the Chianti Classico on a Scenic Tuscany Bike Tour

€165.00

Explore Tuscany’s Chianti Classico on an assisted electric bike that'll take you to its fascinating hills, cycling along iconic gravel roads of the Eroica, thus revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting of one glass included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. Furthermore, the aim of this experience is going beyond the façade by getting in touch with the local culture of Siena and proposing an immersion into Siena’s and the Chianti Classico history. It includes a guided tour (only in the morning tour option) in one of the most iconic castles of Tuscany where you’ll deepen the knowledge about one of the most traditional tuscan families (more than 1000 years old), and take in a breathtaking view of the city of Siena from the castle’s terrace. We propose the lunch break at a small, local trattoria, located in a charming hamlet where you, in addition to enjoying the tranquility and warmth of the tuscan welcome, will be able to enrich your exploration of the Tuscan flavours. Developed in partnership with Ebike Siena.

Duration: 6-7 hours

Tour Language: English/Italian/Portuguese

Group Size: Minimum of 02 participants (Possibility of Private Groups - contact us)

Free cancellation: as long as it is carried out within 24 hours of the departure time

Meeting point: Address: Via Mentana, 38, 53100 Siena SI (Click here for GPS navigation)

Available times: 08.30 am / 2.00 pm*

*afternoon option avaible only during summer time: it doesn’t include the guided visit to the Castle keep - being substituted by an orientation tour through the castle’s main outside areas and chapel offered by the tour leader; and instead of a pause for lunch there will be a pause for a snack or chopping board at a local bar

Add To Cart

Discover the Chianti Classico on a Scenic Tuscany Bike Tour

€165.00

Explore Tuscany’s Chianti Classico on an assisted electric bike that'll take you to its fascinating hills, cycling along iconic gravel roads of the Eroica, thus revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting of one glass included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. Furthermore, the aim of this experience is going beyond the façade by getting in touch with the local culture of Siena and proposing an immersion into Siena’s and the Chianti Classico history. It includes a guided tour (only in the morning tour option) in one of the most iconic castles of Tuscany where you’ll deepen the knowledge about one of the most traditional tuscan families (more than 1000 years old), and take in a breathtaking view of the city of Siena from the castle’s terrace. We propose the lunch break at a small, local trattoria, located in a charming hamlet where you, in addition to enjoying the tranquility and warmth of the tuscan welcome, will be able to enrich your exploration of the Tuscan flavours. Developed in partnership with Ebike Siena.

Duration: 6-7 hours

Tour Language: English/Italian/Portuguese

Group Size: Minimum of 02 participants (Possibility of Private Groups - contact us)

Free cancellation: as long as it is carried out within 24 hours of the departure time

Meeting point: Address: Via Mentana, 38, 53100 Siena SI (Click here for GPS navigation)

Available times: 08.30 am / 2.00 pm*

*afternoon option avaible only during summer time: it doesn’t include the guided visit to the Castle keep - being substituted by an orientation tour through the castle’s main outside areas and chapel offered by the tour leader; and instead of a pause for lunch there will be a pause for a snack or chopping board at a local bar

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  • 08.30 - Arrival at the meeting point. Presentation of the Staff, Introductory and Orientation Talk

    09.00 - Bike Fitting and Safety talk

    09.15 - Start cycling

    09.50 - We reach the hamlet of Geggiano

    10.30 - Pass through the vineyards of the Vallepicciola winery. From here, the landscape switches onto hilly shapes, dotted with cypress trees decorating the streets, and castles reigning over the territory. It's time for the famous white roads of Chianti Classico, known for the Eroica race.

    10.45 - We cycle along the white gravel roads, with time for shooting some photos and listening to stories until we reach Monti in Chianti.

    11.10 - We make a stop at the borough of Monti in Chianti, to stretch and freshen up before climbing to Cacchiano Castle.

    11.30 - Check point at the Cacchiano Castle

    12.00 - Guided tour of the Brolio Castle with a local guide (only available in the morning tour).

    13.00 - We will pop into the Ricasoli wine shop tasting one glass of wine

    13.30 - Lunch time (not included): we propose a local, no-frills trattoria where you’ll will taste the delights of typical Tuscan gastronomy, in the surroundings of the Brolio Castle (the afternoon tour includes a short pause at a local cafè for a light lunch or refreshments)

    14.30 - Return to Siena. Through secondary tarmac roads, making short pauses for for storytelling and, if necessary, a stop for a coffee or toilet, we’ll get back to Siena

    16.30 / 17.00 - Estimated Time of Arrival at the starting point

  • Together with our cycling guides, this bike tour starts in the fascinating Siena to enter the territory known as Chianti Classico. Equipped with our comfortable Assisted Electric Bikes we will use the famous Tuscan gravel roads to reach one of the most iconic medieval castles in the area, that of Brolio. As we cross territories rich in grape and olive cultivation, we will have the opportunity to stop at panoramic points to take some photos and for storytelling. We'll get off of our bikes for a guided tour of the castle installations with a local guide, learning in detail about the events linked to the internal wars between Siena and Florence, and the life of the Ricasoli family. Afterwards, we will pop into the winery to learn about and go for the chianti wine tasting, in which you'll get to choose among various kinds of the Chianti Classico produced by Vinicola Ricasoli (one glass comprised). Afterwards, we'll get back on our bikes and head to the restaurant where you will taste the delights of typical Tuscan gastronomy (attention: the afternoon tour does not include a lunch break and does not pass through San Gusmé: there will be a stop in the bar in front of the cellar). The tour ends by returning to Siena.

    *During the entire route you will be accompanied by a cycle tour guide certified by the National MTB Academy and the Italian Association of Environmental Hiking Guides (card no. 712).

    • Approximate Tour Duration: 6-7 hs

    • Total Approximate distance : 49 km / 30 mi

    • Accumulated Ascents: 855 m / 2,821 ft

    • Terrain: 15% dirt / 85% asphalt (mostly secondary roads)

    • Maximum Climb Steepness: 12 %

    • Difficulty level: medium

    • Technical ability required: good technical ability (you must be able to turn and brake on inconsistent terrain such as the gravel roads)

    • Physical effort: medium (you must be used to covering a similar distance in a bike, and reasonably fit)

    • Cycling guide certified for the National MTB Academy with total knowledge of the area

    • Tour Leader Third party civil liability insurance (in force in accordance with the terms of the RC 70346 policy)

    • Emergency mechanical assistance in the event of a breakdown

    • Rental of Electrical Bike (MTB kind)

    • Helmets

    • Guided visit in the Brolio Castle (not included in the afternoon option - instead we offer an orientation tour through the castle main outside areas and chapel with the tour leader)

    • 1 Glass of Wine: to be chosen in the moment in the winery (Chianti Classico or others)

    • Water or food to consume during the bike ride

    • Shuttle o transfer

    • Meals

    • Personal Accidents Insurance (possible to be added under request)

    • In the event of cancellation of the tour due to bad weather, it will be rescheduled. If participation on the new proposed date is impossible, the amount will be refunded (depending on the payment method, management costs may be withheld)

    • As long as the cancellation is requested within 48 hours of the start time of the chosen tour, the refund will be granted in full, with management costs relating to the payment method being withheld.

    • Refund won't be granted if the cancellation request arrives in less than 48 hours prior the tour meeting time.

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