> Walk from village to village through Chianti Classico
> Enjoy Tuscan wine and cuisine straight from the source
> We book your boutique stays in Chianti's best towns
Golden hills, old stone farmhouses, and vineyards as far as the eye can see. Tuscany isn't just beautiful, it’s absurdly beautiful. And walking is the best way to drink it all in. On this 5-day trek through Chianti, you’ll go from Greve to Radda to Gaiole, through the heart of Italy’s most iconic wine country. It’s a journey made for food lovers, wine dreamers, and anyone who believes slow travel is the best travel.
This is the shorter version of our full 7-day Chianti route. You’ll cover the most scenic stretches and still get your fill of Tuscan views, tagliatelle, and local vino. The walking is relatively easy and the elevation changes are kind to your knees. Perfect for hikers who want the Chianti experience without the hustle.
Your day begins in the heart of Greve, with more than half the walk gradually ascending through classic Tuscan countryside. The trail climbs steadily toward Montegonzi, offering sweeping views of the Chianti Hills and the ancient hamlet of Montefioralle.
From there, continue to Panzano in Chianti, a charming village that makes the perfect spot for a mid-hike pause. Grab a coffee, enjoy a light lunch, or simply soak in the scenery before tackling the next stretch.
The trail continues uphill through olive groves and vineyards, leading you over a gentle ridge before a rewarding descent. Surrounded by rolling hills and timeless landscapes, you'll cross a tranquil river valley before facing the final climb up to Radda in Chianti, one of the most picturesque and historically rich villages in the region.
On this final day of hiking, you’ll leave Gaiole and make your way to the majestic Castello di Brolio, perched atop a hill and surrounded by rolling vineyards. Here, take a guided tour and enjoy a tasting of Chianti wines, immersing yourself in the rich history of the region.
From the castle, continue your scenic walk through the tranquil Tuscan landscape to La Madonna, where you’ll spend a relaxing evening in the heart of nature. This is the perfect ending to your Chianti journey—a chance to unwind, take in the peaceful surroundings, and enjoy the starry sky as you reflect on a week of discovery and unforgettable moments.
