Arrive in Florence and take a moment to breathe in the air of the Renaissance. We suggested arriving early to go for a city walk around the magnificent squares and by the illustrious Arno River. This walk starts and ends in the Piazza della Signoria and takes about 3,5 hours.

Travel uphill on a twenty-five minute local city bus ride to the village of Settignano where the walk begins. On the walk, you have magnificent views of cypress trees, olive groves, Renaissance villas and the whole city of Florence at your feet. Stroll through the charming town of Fiesole and tour its Etruscan ruins, Roman amphitheater and Franciscan monastery.

Challenge: 3/6 hours, 8/16 km, 347/567m ascent, 224/566m descent

After breakfast, take the local bus (with your luggage) or book a private transfer to Greve in Chianti, a rustic market village and the capital of the Chianti wine producing region. Check in to the hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines. Take advantage of the daylight to walk around this gorgeous scenery by choosing between two routes

Walk A: Greve in Chianti loop via Uzzano

In the afternoon, make a round walk north of the attractive main square of Greve in Chianti, through a picture perfect landscape. From the main square a round walk starts and takes you through the Chianti Classico area passing by the Villa Calcinaia and numerous vineyards with “aziende agricole” (farms) where the prestigious Chianti wine is produced.

Walk B: Greve loop via Montefioralle

Explore the wonderful surroundings through the forest, among dense wild vegetation, villas, vineyards and olive groves. You will be passing by abandoned old farms, ruins and beautiful villas before reaching the panoramic hamlet of Montefioralle.

Challenge: 2.5/3.5 hours, 11.4/10 km, 425/358m ascent, 447/355m descent

The walk is made up of a loop out of Panzano. You walk through the hills surrounding the village, in the classic Chianti landscape that alternates forests with vineyards, offering you the possibility to discover ancient Roman farmsteads.

Challenge: 4 hours, 11.7 km, 385m ascent, 384m descent

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. From Badiaccia you descend through a forested valley of century old chestnut trees and continue towards the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red at a fine Enoteca, wine shop, and then continue on to Radda in Chianti.

Challenge: 5/3 hours, 14/12 km, 506m ascent, 668m descent

A quiet, relaxing day awaits you. Bask under the Tuscan sun and go for a scenic walk around the old centre of Radda in Chianti. Wind along the narrow alleyways and visit the church of Santa Maria Novella. As you head out of town through the vineyard covered slopes stop to treat yourself to a glass of Chianti Gallo Nero wine at a celebrated local vineyards.

Challenge: 5 hours, 15.8 km, 586m ascent, 586m descent

After breakfast, take the local bus (with your luggage) or with a prearranged private transfer, to the marvelous city of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy.

Our services end after breakfast, however we highly recommend you to book extra nights in Siena to continue exploring the old centre, exquisite museums, lush galleries and marvelous churches. A visit to the top of the bell tower is also quite a sight.