Chianti Guided 7 Days Road

difficulty level

Hard

Exp. level

Advanced

route type

Road

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: Bike assembly and saddle position adjustment. 30 km ride with 600 meters of elevation gain.

In the morning, guests will arrive at the airport in Florence. The Slice Adventures staff will take care of transferring them to the accommodation in Gaiole in Chianti, where they will stay for the first night. A test ride will be conducted to check the bikes.

Day 2: Brolio Castel - 50 km ride with 930 meters of elevation gain.

After cycling along stunning roads and enjoying postcard-perfect views, we will visit the Brolio Castel. Of medieval origin, the castle is renowned for being at the center of numerous battles between Florence and Siena. Restored in the 19th century in Neo-Gothic style, it is now owned by the Ricasoli family, who played a key role in the development and global success of Chianti wine. Surrounded by vineyards and woodlands, the castle offers panoramic views of the Chianti hills and hosts a historic winery, a museum, and a chapel, all of which will be open for our visit. Return to Siena.

Day 3: Castellina - Fonterutoli Castle - Radda - 97 km ride with 1,800 meters of elevation gain.

This is the most challenging ride of the tour. You’ll climb to Castellina in Chianti, a charming medieval village located in the heart of the Chianti region. Known especially for the renowned Chianti Classico wine, Castellina offers picturesque landscapes of vineyards and olive groves, ancient Etruscan walls, and quaint alleys. The village is dominated by the Rocca, a medieval fortress with a panoramic tower. Notably, Castellina is also home to the best ice cream shop in the Siena province. From there, you’ll continue on an exhilarating series of rolling hills, fast and fun, until reaching the stunning Badia a Passignano. The route then takes you to Fonterutoli Castle, the villages of Greve, Panzano, and finally, Radda. Like Castellina, Radda is a fascinating medieval village characterized by picturesque views, narrow streets, historic walls, and a central square. In addition to the many wineries offering tastings, highlights include the Palazzo del Podestà and the Church of San Niccolò.

Day 4: Cooking class, guided tour, and dinner in Siena

After breakfast, the day begins with a cooking class where we will prepare a typical Tuscan lunch. After lunch, a guided tour of the historic center will follow, including entries to the Duomo, Museo dell’Opa, Santa Maria della Scala, and the Pinacoteca. The Duomo and Santa Maria della Scala are absolute must-sees. Free time will be available until 7:00 PM. Lunch: Prepared in the villa with the chef. Dinner: At a restaurant in the center of Siena.

Day 5: San Gimignano 95 km ride with 1,600 meters of elevation gain

A fascinating route rich in history, this stage includes visits to Monteriggioni, Abbadia Isola, and San Gimignano. San Gimignano is a picturesque medieval town, famous for its historic towers—once over 70, of which 14 still remain today. A UNESCO World Heritage Site, the town preserves stunning frescoes, ancient palaces, and a network of cobblestone streets that transport you back to the Middle Ages. Return: To the villa for dinner prepared by the chef.

Day 6: Monteluco - Badia a Coltibuono - Gaiole 57 km ride with 1,200 meters of elevation gain

Still in Chianti, this stage features two challenging climbs: Monte Luco and Badia a Coltibuono. The latter is an ancient Benedictine abbey from the 11th century, now converted into a farmhouse, restaurant, and cooking school. A beautiful and fast descent leads us to the center of Gaiole. This small town is the historic home of L’Eroica, a famous vintage cycling event held annually, attracting enthusiasts from around the world. L’Eroica is a journey through time, with cyclists required to use pre-1987 bicycles and wear retro attire, all in a festive atmosphere rich in tradition. A shop dedicated to the event’s memorabilia adds to the charm. Lunch: In town. Transfer: To Siena in the afternoon, followed by bike disassembly and packing preparation.

Day 7 Bye Bye

Breakfast at the accommodation and departure to Florence Airport.