Hiking in Tuscany with Chianti

Arrive in Florence and breathe in the Renaissance city. We recommend arriving early or booking an extra night before the trip to have time for a city walk among magnificent squares and along the famous Arno River. The walk starts and ends at Piazza della Signoria and takes about 3.5 hours.

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

After breakfast, a private transfer takes you to Greve in Chianti, a rustic market town and capital of Chianti's wine-producing region. Check in at the hotel and visit Le Cantine di Greve where you can taste over 50 different Chianti wines in an ingenious tap system. Then choose between two fine circular walks in the area:

Montefioralle
Make the most of the daylight and venture out into this magnificent landscape. Explore the surroundings through forest and dense wild vegetation, past villas, vineyards and olive groves. You pass abandoned farms, ruins and beautiful villas before reaching the panoramic little village of Montefioralle, birthplace of Amerigo Vespucci, the navigator who gave his name to America.

Uzzano
From the main square starts a circular walk through the Chianti Classico area. You pass Villa Calcinaia and several vineyards and aziende agricole (farms/vineyards) where the prestigious Chianti wine is produced.

Today's hike is a circular tour starting in Panzano which lies 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 remind of medieval times. Here there's also the possibility to discover old Roman farms.

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 several hundred-year-old chestnut trees and continue towards the fantastic medieval village of Volpaia, beautifully situated among vineyards and castles. Stop for a glass of red at a fine enoteca, a wine shop, and then continue to Radda in Chianti. The village is known as the birthplace of Chianti Classico wine with its symbol the black rooster.

A scenic hike around the old town center of Radda in Chianti. Stop for lunch in the charming village of Vertine and treat yourself in the afternoon 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 unrealistically well-preserved medieval city of Siena, known for the famous horse race Palio which is arranged twice a year on Europe's most beautiful shell-shaped square, Piazza del Campo. Don't miss a visit to the cathedral, Duomo, an architectural treasure, as well as the city's many impressive medieval palaces. History feels alive when you wander through the narrow alleys of this exceptionally well-preserved Italian gem.

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