Chianti ride from Siena

A weekend of cycling between Siena, Chianti’s ancient towns, and the walled village of Monteriggioni

Enjoy a memorable cycling weekend starting from Siena, the perfect base to explore both the Chianti region and the medieval village of Monteriggioni. Siena is one of Tuscany’s most enchanting cities, a place where history, culture, and cycling come together. Its medieval city center, with narrow streets and brick‑colored palaces, creates an atmosphere that feels suspended in time. It’s also the official starting point of the world‑famous Strade Bianche professional race, making it an ideal destination for anyone who loves riding through the countryside.

From Siena, a series of carefully selected bike routes will lead you deep into the Chianti wine region, a landscape shaped by rolling hills, endless vineyards, and ancient olive groves. This area is celebrated worldwide not only for its wines but also for its breathtaking panoramas and timeless rural charm. Along the way, you’ll have the chance to visit iconic landmarks such as the Castello di Brolio, a historic fortress surrounded by vineyards, and Castellina in Chianti, a medieval town with Etruscan origins that offers sweeping views over the Val d’Elsa.

Your journey also includes a visit to Monteriggioni, one of Tuscany’s most evocative hilltop villages. Encircled by perfectly preserved 13th‑century walls and towers, it feels like stepping into a living postcard from the Middle Ages.

This cycling weekend blends sport, culture, and relaxation, giving you the freedom to ride at your own pace, explore charming towns, and fully immerse yourself in the landscapes and traditions that make Tuscany unforgettable.

  • Duration

  • Length

    109 km - 68 mi

  • Price

  • Level

    Difficult: medium

Day 1 – Welcome to Tuscany

Individual arrival, dinner on your own and accommodation in 3 stars hotel located at Siena. Upgrade in 4 and 5 stars hotel available on request.
At your arrival you will receive all the informations to complete the bike tour in Tuscany.

Day 2 – Chianti region and Castello di Brolio, 56 km – Elevation gain: 760 meters

First stage to discover the Chianti region, very famous wine region.
Castelnuovo Berardenga, Villa a Sesta and San Gusmè, cute towns in Chianti
Castello di Brolio, with its cypress-lined entrance. The breath-taking panorama below the walls, over the vineyards, represents one of the most wonderful parts of the first stage. You can decide also to visit the Castle, owned by the Ricasoli family since 1141, or taste a glass of Chianti Classico at the enoteca.
You’ll be back to Siena riding up and down with the skyline of Siena on the horizon.

Dinner on your own and accommodation in 3 stars hotel.

Day 3 – Castellina in Chianti and Monteriggioni, 53 km – Elevation gain: 750 meters

Long climb direction Castellina in Chianti, passing Fonterutoli and surrounded by beautiful views over the Val d’Elsa.
Castellina in Chianti, interesting medieval town of Etruscan origins and one of the most charming hilltop villages in the Chianti.
Monteriggioni with its walls and the ring of towers that dominate the hill. Enjoy a break or have lunch in the central square.
You’ll be back to Siena riding the Montagnola Senese region, crossing the road of the Via Francigena pilgrimage route.

Dinner on your own and accommodation in 3 stars hotel.

Day 4 – Goodbye Tuscany

Check out and individual departure.
Private transfer available on request.

WHAT’S INCLUDED
  • 4 nights stay with breakfast in double room
  • Baggage transportation between the hotels
  • Informations for your daily stage
  • Maps with altimetry of each stage in PDF file
  • GPX tracks for GPS system or mobile App.
  • Phone assistance

 


NOT INCLUDED
  • Medical baggage insurance
  • Tourist city tax

 


OPTIONAL SERVICES
  • Medical baggage insurance
  • Bike guide
  • Van support during your daily stage
  • Bike rental (MTB, gravel or E-Bikes)
  • GPS rental
  • Transfers from hotels, airport, train station

Book your Tour here

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