Grand Tour Chianti & Val D'Orcia

Arrive in Florence and take a moment to breathe in the air of the Renaissance.

We suggest you to arrive early to go for a city walk around the magnificent squares and by the illustrious Arno River.

Taste the local cuisine and enjoy the variety of Tuscan dishes! You wont' be disappointed!

Travel uphill on a 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.

Distance: 14 km

Elevation Gain: +535/-535 m

After breakfast you will be transferred 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.

Greve Loop via Montefioralle, 8 km:
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.

Distance: 8 km
Elevation Gain: +300/-300 m

Greve Loop via Uzzano, 8 km:
A rural undulating walk with great vistas through forests and wine fields. Leaving the town of Greve in Chianti the walks leads uphill through the countryside and past the castle of Uzzano.Great views of the classic Chianti landscape with vineyards and olive groves all around, and the Appenine mountains in the distance.

Distance: 8 km
Elevation Gain: +245/-245 m

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.

Distance: 11 km

Elevation Gain: +330/-330 m

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele.
You will be dropped off in the village of Badiaccia a Montemuro where you start the walk, descending through a forested valley of century old chestnut trees.

A short climb brings you to the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red at a fine Enoteca (wine shop).
The last part of the walk is through the typical Chianti landscape woods and vineyards, passing by the Pieve di Santa Maria, on the other side of the valley you can already see Radda in Chianti, one of the most renowned villages of the area.

Distance: 13,5 km

Elevation Gain: +430/-610 m

After breakfast, a pre-arranged private transfer will take you to the marvelous city of Siena. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy.

Situated along three ridges at the southern end of the Chianti hills, Siena is another UNESCO city not to be missed. The town explodes with excitement during the famous Palio horse race run several times over summer in Piazza del Campo. The striking Duomo is jam-packed with artworks by Bernini, Michelangelo and Donatello and is only one of many fascinating sites to explore during your stay. Today is free to explore this exciting town; art galleries, museums, atmospheric squares, churches, boutiques, gelaterias – the choice is endless!

After breakfast take start off on your wonderful Via Francigena trip along the astonishing Tuscan countryside. Walking alongside cultivated meadows, with its colours changing from the greens and yellows of spring and summer to ochre’s of Autumn, you will pass through the medieval village of Cuna, just a few hundred meters before entering the town of Monteroni d’Arbia, with its famous watermill. The last part of the walk leads you to the fortified hamlet of Lucignano d’Arbia, along its characteristic cypress tree-lined entrance.

Distance: 21 km

Elevation Gain: +165/-325 m

Today’s walk is through a series of rolling hills and wheat-cultivated meadows in the heart of the “Crete Senesi”, a clay area that never ceases to amaze the passer by, with its distinctive grey coloured soil that makes it look like you’re on the moon. Your destination for today is the walled town of Buonconvento, rightly considered one of the most beautiful villages in Italy.

Distance: 14 km

Elevation Gain: +70/-100 m

Today you detour off the main route of the Francigena as you climb through the amazing landscape of the Val d’Orcia, with its gentle, rolling hills and the cypress-lined dirt roads leading to solitary farmhouses. The climb through groomed wineyards is one of the trip’s highlights: the world-famous fortified town of Montalcino, “capital” of the exquisite red wine “Brunello”. 

Distance: 16 km

Elevation Gain: +470/-195 m

A day at leisure in Montalcino is a journey into the heart of Tuscany’s serene countryside. Mornings begin slowly, perhaps with a stroll through the charming medieval streets, where stone buildings and quiet piazzas invite reflection. For wine lovers, a visit to a local vineyard offers a tasting of the famed Brunello di Montalcino, paired with breathtaking views over rolling hills. The afternoon can drift by with a relaxed lunch of Tuscan specialties, a visit to the imposing fortress, or simply sitting at a café, watching village life unfold. As the sun begins to set, the golden light bathes the countryside, creating the perfect backdrop for a gentle walk or a quiet moment of contemplation, making the day a seamless blend of relaxation, culture, and natural beauty.

After breakfast, a pre-arranged private transfer will take you to Chiusi Chianciano train station from where you will take a direct train to Rome. 

The trip and our services end after breakfast unless you have booked extra services with us.
 

For our trips, we always choose accommodation with private rooms and private bathrooms. In rare cases, shared accommodations or shared bathrooms may be provided, so we recommend carefully checking the inclusions section to understand the type of accommodation included in the trip you are interested in.  

We place great importance on the choice of accommodations and select hotels with care and attention. We understand how essential it is to rest well after a day of walking. We always prefer cozy and characteristic establishments, preferably family-run, that fully embody the spirit of the place and offer hospitality with courtesy and comfort.  

Where, due to the nature of the route, accommodation options are limited, we choose the one that best aligns with our standards.

This trip is perfect if you want to immerse yourself in the iconic beauty of Chianti and the Tuscan countryside.

Explore famous towns like Montalcino, Siena, Pienza, and hidden gems such as Bagno Vignoni and Buonconvento. It’s a long but quite easy walking trip suitable for beginners, with the option to add extra days and guided tours in Florence and Siena. With a bit of preparation, even first-time hikers can enjoy the rolling Tuscan hills.