Exploring Tuscany’s Vineyards and Medieval Palaces on Foot
If Tuscany were a novel, it would be an epic, full of golden landscapes that had a dreamy quality, noble histories, and characters you savor slowly, like a fine Chianti. But, mind you, this isn’t a novel that can be enjoyed fully from a car window. Tuscany begs to be walked. Its true magic unfolds at the pace of your footsteps, revealing vineyard-covered hills, ancient castles, and stories whispered by beautifully cobbled streets.
In addition to spending your days swimming in the shimmering sea, savoring sunsets and enjoying hearty Italian feasts, here’s a list of what else can be on your itinerary to make the most of your trip.
Strolling Through Tuscany’s Renowned Vineyards
Start your journey where the land tastes as good as it looks. Tuscany’s vineyards are the lifeblood of its culture—rolling waves of green that produce world-famous wines like Chianti Classico and Brunello di Montalcino.
Take your time on a guided tour through estates like Antinori nel Chianti Classico, a modern architectural masterpiece rooted in centuries of tradition, or Tenuta San Guido, where the legendary Sassicaia was born. Here, wine tastings aren’t just mere events – they’re more like a pilgrimage for the senses.
Discovering Medieval Palaces and Castles
As you move from vineyard to village, history greets you with open gates and fortified towers. Monteriggioni, with its perfectly preserved medieval walls, looks like it stepped straight out of a Renaissance painting. Poppi Castle, meanwhile, stands proudly on a hill, offering sweeping views of the Casentino valley. Climb its spiral staircases and stroll the ramparts—it’s not just sightseeing; it’s time-traveling with a view.
Hiking Along Historic Trails
To truly tie Tuscany’s charms together, lace up your boots and follow the ancient Via Francigena. Once a pilgrim’s path, it now weaves together vineyards, walled towns, and quiet monasteries. These guided walking tours offer a heady mix of scenic beauty and cultural immersion—perfect for those seeking hiking holidays in Italy that feed both the body and the soul.
Getting Seduced by Tuscany’s Food, Art and Culture
It’s safe to say that Tuscany is Italy’s food paradise. Everything you taste is fresh and delicious, and super indulgent in a refreshing way. So much so that even the dipping olive oil there can transform a simple piece of bread into a gustatory epiphany of earth and sky and arbor. And the pasta? Oh, that’s just divine there.
Of course, no Tuscan journey is complete without standing under the dome of Florence, marveling at Siena’s Gothic architecture, or wandering the turreted skyline of San Gimignano.
Visit the UNESCO World Heritage sites that helped shape the world’s artistic vocabulary—and discover tucked-away Etruscan ruins that predate even Rome. For more inspiration, Condé Nast Traveller’s guide and Sandaya’s top picks are excellent companions.
Experiencing Tuscany on foot can only make the heart grow fonder for the Tuscan beauty and vibe.
