Hiking in Tuscany with Chianti

Arrive in Florence and breathe in the city of the Renaissance. We recommend arriving early or booking an extra night before the trip so you have time for a city walk among magnificent squares and along the famous Arno river.

After breakfast, you take the local bus up the hills for about 25 minutes to the village of Settignano, where the trip's first walk begins. Along the way, you'll enjoy magnificent views of cypresses, olive groves, Renaissance villas, and all of Florence spreading out below you. Stroll through charming Fiesole and visit the Etruscan ruins, the Roman amphitheatre, and the Franciscan monastery.

After breakfast, a private transfer takes you to Greve in Chianti, a rustic market town and the main hub of Chianti's wine-producing region. Check in to your hotel and visit Le Cantine di Greve, where you can taste over 50 different Chianti wines with an ingenious card-based tasting system. Then choose between two lovely walking routes in the area:

Montefioralle
Make the most of the daylight and head out into this magnificent landscape. Explore the surroundings through forests and dense wild vegetation, past villas, vineyards, and olive groves. You'll pass abandoned farms, ruins, and beautiful villas before reaching the panoramic little village of Montefioralle, birthplace of Amerigo Vespucci, the seafarer who gave America its name.

Uzzano
From the main square, a walking route begins through the Chianti Classico area. You'll pass Villa Calcinaia and several vineyards and aziende agricole (farms/vineyards) where the prestigious Chianti wine is produced.

Today's walk is a round trip starting in Panzano, located above Greve. A local celebrity in the village is the butcher Dario Cecchini, who saved the fiorentina (T-bone steak) from EU regulation. You walk through the hills surrounding the village, in the classic Chianti landscape where forests and vineyards are reminiscent of the Middle Ages. There's also an opportunity here to discover old Roman farmsteads.

After breakfast, a short car transfer takes you up to Monte San Michele, the highest of Chianti's hills. From Badiaccia, you walk down through a forested valley with chestnut trees that are several hundred years old, and continue towards the fantastic medieval village of Volpaia, beautifully situated among vineyards and castles. Stop for a glass of red wine at a lovely enoteca, a wine shop, and then continue on to Radda in Chianti. The village is known as the birthplace of Chianti Classico wine, with its symbol, the black rooster.

A scenic walk around the old town centre of Radda in Chianti. Stop for lunch in the charming village of Vertine, and in the afternoon treat yourself to a glass of Chianti at Colle Bereto, a well-known local vineyard that you pass on the way back to Radda.

After breakfast, a private transfer takes you to the unbelievably well-preserved medieval city of Siena, known for the famous horse race Palio, held twice a year on Europe's most beautiful shell-shaped square, Piazza del Campo. Don't miss a visit to the cathedral, the Duomo, an architectural treasure, as well as the city's many impressive medieval palaces. History feels alive as you walk through the narrow alleys of this outstanding, well-preserved Italian gem.

The trip ends after breakfast. However, we highly recommend booking extra nights in Siena to continue exploring the historic city centre, exquisite museums, fine galleries, and magnificent churches. A visit to the top of the bell tower is also an experience in itself.