Chianti Guided 7 Days Gravel

difficulty level

Hard

Exp. level

Advanced

route type

Gravel

rec. perdiod

Sep-Jun

The Chianti region is located in the heart of Tuscany, between the cities of Florence, Siena, and Arezzo. The entire area is characterized by rugged hilltop terrain, green hills covered with miles of vineyards and olive groves, medieval walls, and castles. The climate and unique soil make the Chianti region particularly suited for producing exceptionally fine wines and oils. Additionally, the area is rich in castles, medieval villages, and wineries full of history and charm that will instantly captivate you, making your vacation truly unforgettable.

Day 1: 36 km, 825 m

In the morning, guests arrive at Florence Airport, where the Slice Adventures staff will assist with their transfer to the accommodation in Siena, where they will stay for the entire vacation. Later, a professional mechanic will help guests unpack and assemble their bikes or adjust the position for those with rented bikes. Once everyone is ready, a short ride will be conducted to test the bikes. Dinner: At the accommodation.

Day 2: 63 km, 1650 m

A scenic route starts from Siena, crossing the characteristic Tuscan strade bianche—perfect for gravel enthusiasts. From Siena, the route leads to Vagliagli, a charming village nestled among the Chianti hills, surrounded by vineyards and olive groves. The ride continues toward Lecchi in Chianti, a small medieval gem, and then to Pianella, where the landscape opens up to rolling hills and the typical views of the Sienese countryside. The return to Siena offers breathtaking views and the city’s timeless charm. Dinner: At the accommodation.

Day 3: 92 km, 2880 m

An exciting gravel route begins in Siena and winds along the iconic strade bianche. From the city of the Palio, cyclists head toward Castellina in Chianti, a medieval village surrounded by vineyards and stunning views. The route continues to Gaiole in Chianti, the home of L’Eroica, where history, nature, and cycling tradition meet. After traversing hills, woods, and gravel roads, the ride ends back in Siena, offering a perfect mix of challenge and beauty. Dinner: At the accommodation.

Day 4: Cooking class, guided tour of Siena, and dinner in the city center

Cooking class, guided tour of Siena, and dinner in the city center

Day 5: 71 km, 1689 m

A fascinating route starts in Siena and crosses the famous strade bianche. From Siena, you will cycle to Montebenichi, a small perched village that offers spectacular views of the surrounding countryside. The route continues to Castelnuovo Berardenga, the heart of Chianti, where vineyards and olive groves create postcard-perfect scenery. From here, you will reach Montaperti, a historic site tied to a famous battle, before returning to Siena. Dinner: At the accommodation.

Day 6: 67 km, 1585 m

A unique route begins in Siena and crosses the charming strade bianche. From the city, you will cycle to Colonna del Grillo, a historic crossroads immersed in the gentle Sienese hills. The route continues to San Gusmè, an enchanting medieval village that offers a timeless atmosphere and breathtaking views. From here, you will descend to Pianella, surrounded by vineyards and olive groves, before returning to Siena. Dinner: At the accommodation.

Day 7: Bye Bye

Breakfast at the accommodation and transfer to the airport in Florence or Pisa.