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Photo ©Shutterstock.com / Claudio Giovanni Colombo

6 days in the Chianti, wine in hand and nature all around

Spend a week visiting the best of the Chianti, from wine to castles to endless greenery

Have you always dreamed of visiting those postcard-perfect destinations of Tuscany, with their rolling hills and cypress-lined lanes, dotted with medieval villages and historic castles? Look no further than the Chianti, the famous area where some of Italy’s best wines are made and nature offers no shortage of opportunities for outdoor excursions. Follow our itinerary to explore the best of Chianti wine and nature. 

Day 1

Greve in Chianti

We head to Greve in Chianti, where we’ll spend the next few nights. You can reach this small town in about an hour from Florence by car, winding through the start of the Chianti hills along the way. We recommend spending the first part of your day wandering these medieval streets and piazzas, especially Piazza Matteotti, the centre of town life. We won’t have to wait long to dive into the “wine-ier” aspects of our holiday: visit the Wine Museum, where you can learn about the traditions and history of the Chianti through artefacts and materials collected from the surrounding territory.

Armed with this new knowledge, let’s move on to a winery to see how wine is made first-hand. A quick internet search of places around Greve in Chianti offering winery tours with a tasting included will reveal endless possibilities – we suggest checking one out that’s housed in a former castle for a bit of fun and history rolled into one.

Day 2

Hiking from Greve to Panzano

You came for the nature too, right? There many trekking and biking routes that leave from Greve, winding through the countryside before looping back into town. This ring route will take you all the way to Panzano in Chianti and back: 14 km of gravel and asphalt roads that even slightly inexperienced hikers can tackle. The first stretch of the route passes through Montefioralle, a charming hamlet built atop a high plain and said to have a house that once belonged to Amerigo Vespucci. If you’re visiting in March, be sure to enjoy the Festa di Fritelle!
As you continue the walk to Panzano, you’ll cross through rows and rows of vineyards, alternated with the foliage of olive groves. We recommend taking a break in Panzano, where you can have lunch in a typical trattoria and explore the historic castle. Fortunately, the walk back to Greve is downhill, so you can take the road back at a leisurely pace.

Day 3


Our hike for the next day is admittedly strenuous, so the journey is best suited for experienced hikers and/or bikers. With an early start, we head to Radda in Chianti by car, from where we will hike a circular route that passes through the medieval village-turned-winery Volpaia, with a quick stop in Panzano and other small hamlets before returning to Radda. We recommend eating lunch or a light meal upon arriving in Volpaia, where you can taste wine made directly on the premises: 0km at its best!

Day 4

Gaiole in Chianti

While the northern Chianti is sure to have met all your expectations, there’s still so much beauty to be explored! Head down the Chianti Classico Wine Road until Gaiole in Chianti, where we’ll set up camp for the next few nights. We suggest spending some time exploring this gem of a town, home to Romanesque churches with fragments of splendid Renaissance frescoes. In the afternoon, pay a visit to Brolio Castle, 20 minutes away by car. Home to what is said to be the oldest winery in Italy, the castle sits atop a hill and has belonged to the same family since 1141 – that’s nearly 900 years! Spend the afternoon exploring the castle and strolling through its vast gardens. Money permitting, why not end the day with a luxury meal? After all, how often can you say at you’ve dined in a castle?

Day 5

Crisscrossing Chianti hills

After all the wine consumed yesterday, you might be looking for a bit of exercise. Why not spend another day crisscrossing the Chianti hills? Our map of all the hiking trails surrounding Gaiole in Chianti can give you an idea of the level of expertise needed to embark on your chosen hike through the countryside. The OXFAM trail may be long, but the sites are sure to be worth the effort: with stops at the Meleto Castle, Castello di Ama, the fortified town of Vertine and castle in Montegrossi, you’ll come across all the best aspects of the Chianti territory.

Day 6

Castelnuovo Berardenga

For your last day in the Chianti, why not take it at an ultra-slow pace, exploring the wild, funky world of contemporary art at the Chianti Sculpture Park. Just 15 minutes by car from Gaiole, wake up with ease before hitting the quaint provincial roads that wind through open fields and shaded stretches. If you’re here in July and August, be sure to catch a concert, part of the park’s annual summer program. 

After the park, have lunch in Castelnuovo Berardenga. The town is thought to have Etruscan origins, but its most prosperous time came in the Middle Ages, when it was ruled over by Count Berardo and his descendants. While here, make sure to visit the Landscape Museum, a unique institution that invites visitors to reflect on the various meanings given to the word “landscape”. 

And if time permits, we recommend hopping in the late afternoon for a visit to the Certosa di Pontignano, a historic Carthusian monastery with artworks by artists like Bernardino Poccetti, Giuseppe Nicola Nasini and Domenico Atticciati. Of course, in a place like the Certosa, a perfect end to the day just might be a glass of Chianti in hand, as you gaze at the hills around you. 

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