Wine Trekking In Tuscany

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the heart of the Tuscan countryside, past picturesque castles, villages, vineyards and ruins. Once you reach the medieval walled village of Monteriggioni, reward yourself during a wine tasting session, where you will sip on 3-4 different local, organic wines. Return to Siena at your own leisure by bus (bus tickets provided).

It is not just an E-Bike tour but it is a journey through history and the landscape to discover the native wines of the Island of Elba, personally told by Antonio Arrighi who will accompany us on his bike for 13 hectares around his vineyards, making us discover the organoleptic characteristics and the links with this beautiful territory.

Let the enchanting Chianti region win you over as you trek alongside a pro nature guide through vineyards, olive groves, and a cute little forest. Get ready to inhale the sweet scents of nature as you soak up the beauty of this fantastic route, learning all about Tuscany and its unique quirks along the way. Our adventure kicks off in Florence, where a swanky private ride awaits to whisk you to Montespertoli. Your guide, a walking Tuscany encyclopedia, will lead you on a trekking escapade, up and down hills, offering you panoramic views of the iconic Tuscan landscape. When you hit the halfway mark (7.9 km in), prepare for a pitstop at a wine estate. Take a breather, soak in the vibes, and don't miss the chance to sample some of their best wine – it's practically a must! The journey continues with more delightful paths, weaving through a charming forest and lush vineyards. At the tour's end, your trusty driver is ready to zip you back to Florence. (Hiking path: 3hrs)

Our PRIVAT E-Bike Experience is more than just an adventure—it’s a deep dive into the heart of Tuscany, where every turn tells a story and every moment connects you to something greater. We believe in the power of human connection, in the value of a guide who doesn’t just lead but shares, inspires, and brings the land to life. Our experiences are crafted with passion, blending history, culture, and breathtaking landscapes in a way that feels personal and unforgettable. Riding through this iconic scenery, you’re not just a visitor—you become part of the rhythm of the land, feeling the same rolling hills that have shaped centuries of tradition. And with our brand-new TREK e-bikes, the experience is effortless yet exhilarating.Enjoy a guided visit to a typical winery, where you’ll learn about local winemaking traditions and explore the cellar. The experience ends with a relaxing light lunch sipping wine—a perfect way to soak in the essence of Tuscany.

Discover Montepulciano with a private tour. In 1500 Antonio da Sangallo fortified this town, an ancient settlement of Etruscan origin, which became the important castle on the borders of the Grand Duchy of Tuscany. Montepulciano was the birthplace of Poliziano, poet and secretary of Lorenzo the Magnificent and we will pass under his house. The elegant town is full of noble residences and Renaissance churches. we will visit the Piazza Grande, the natural theater of many artistic, folkloric and oenological events. We will visit its incredible medieval cellars dug into the rock under the noble palaces, for centuries the place of aging of Vino Nobile di Montepulciano DOCG. Let's discover together the surprising beauties of this small city of art – It is also possible to go on an exciting URBAN TREKKING from San Biagio to Porta a Prato and back, with a visit to the medieval cellars. Suggested tour for ART and WINE lovers