A food-and-wine weekend in Tuscany, among rolling hills, villages, and authentic flavors

Organizing a food and wine weekend in Tuscany is much more than a simple escape from daily routine: it means immersing yourself in one of the regions with the richest identity and tradition in the world. From the vineyards of Chianti to the moon-like landscapes of the Crete Senesi, passing through the olive groves of the Maremma and the gentle hills of the Val d’Orcia, Tuscany offers a mosaic of experiences that weave together taste, culture, and landscape, often with overnight stays in ancient estates or farmhouses nestled among the vineyards.

In this guide, we’ll explore the most fascinating areas, the typical products you shouldn’t miss, and the ideal routes for a two- or three-day stay discovering the most authentic soul of this splendid region.

The must-see destinations for a food and wine weekend in Tuscany

When you write “Tuscany,” you immediately think of bottles and glasses of wine—especially red—along with cured meats, game, cheeses, local produce, and the region’s prized olive oil. As they say, for anyone who wants to combine the discovery of villages and nature walks with a culinary experience, the options are endless

Chianti: wine, villages, and rural tradition

One of the most famous areas when thinking about food and wine tourism is undoubtedly Chianti. The historical heart of Tuscan viticulture, this region stretches between Florence, Siena, and Arezzo, offering a landscape dotted with rows of vines, olive groves, and ancient fortified villages. This is where one of the most renowned and appreciated wines in the world is produced: Chianti DOCG, made mainly from Sangiovese grapes, a symbol of Tuscany’s winemaking tradition.
The area invites visitors to travel along panoramic roads, such as the famous Chiantigiana route, and to stop in small towns like Greve, Gaiole, or Castellina, where taverns serve authentic dishes such as finocchiona, ribollita, and bistecca alla fiorentina, accompanied by glasses of wine that express the deep connection between people and the land.

Val d’Orcia: postcard landscapes and refined flavors

A UNESCO World Heritage site for the undeniable beauty of its landscapes, the Val d’Orcia is synonymous with elegance and harmony. But beyond its gently rolling hills, scenic roads, and charming villages, there is a whole world of culinary and wine excellence to discover: from Montalcino, home of the Brunello DOCG, to Montepulciano with its Vino Nobile DOCG, each town preserves a long-standing winemaking tradition. Between one glass and another, it’s worth savoring Pienza’s pecorino cheese, the Cinta Senese pork, the local extra virgin olive oil, and pici, fresh pasta emblematic of Tuscan peasant cuisine. And finally, for enthusiasts, also the snails typical of the village of San Quirico d’Orcia.

Maremma, between wild nature and the sea

Further south, the Tuscan Maremma offers an authentic, rural, and wild experience, especially ideal by motorcycle: here, between the sea and the Uccellina mountains, vineyards alternate with pastures and olive groves. In particular, the Val di Cornia opens up between gentle hills and the blue of the Tyrrhenian Sea, in a landscape where vineyards breathe the sea breeze. A weekend in Val di Cornia can alternate between tasting local wines and exploring the medieval villages of Campiglia Marittima and Suvereto, wandering through stone streets and artisan shops. The Morellino di Scansano DOCG takes center stage, but typical local products are also abundant, such as the indispensable Maremma pecorino cheese and Orbetello bottarga. Not to be missed are Maremma-style tortelli, acquacotta (a traditional peasant soup), baccalà alla maremmana, as well as eel, wild boar, and fresh fish. Perfect for those who enjoy slow and sustainable tourism, the Maremma also offers cycling routes and visits to Etruscan villages.

Versilia and the Monti Pisani: Tuscany’s green gold

Not just wine: Tuscany is also a land of olive oil. The Monti Pisani Olive Oil Route, between Lucca and Pisa, is a fascinating journey through olive mills, centuries-old olive groves, and small hilltop villages. Here, a DOP extra virgin olive oil is produced with a fruity and delicate flavor, perfect for pairing with the seafood dishes of the coast. An unmissable stop for anyone wanting to discover Tuscany’s olive oil culture and taste zero-kilometer products directly from the producers.

San Miniato and the truffle trail

In the heart of Tuscany, between Pisa and Florence, lies San Miniato, famous for its prized white truffle. From October to December, the village becomes the center of one of Italy’s most renowned fairs, where visitors can taste truffle-based dishes and join excursions into the woods with local truffle hunters. An experience that combines gastronomy, nature, and tradition, perfect for completing an autumn itinerary.

What to do on a food and wine weekend in Tuscany

Every corner of the region invites you to discover the deep connection between the land, its people, and their traditions, turning a stay into a journey of discovery.

Wine tours, complete with guided cellar visits, are certainly the starting point to understand the art of winemaking up close: the scent of the barrels, the silence of the aging rooms, and the stories of those who preserve Tuscany’s wine heritage make every tasting an intimate and authentic experience.

After a glass of wine, nothing is better than a walk among the vineyards or a trek through olive groves and vineyards, to breathe in the region’s rural soul and admire landscapes that change color with the light of the day.

Food enthusiasts can follow the guidance of expert hands in traditional cooking classes, learning to prepare iconic dishes such as ribollita, pappa al pomodoro, or panzanella, paired with a local glass of wine.

For those who love to explore on the move, panoramic routes by e-bike, motorcycle, or car along the Wine and Olive Oil Roads, as well as on foot along the Via Francigena, offer a different way to discover hilltop villages and their traditions, with stops at small mills and artisan shops to taste extra virgin olive oil, cured meats, and Tuscan cheeses straight from the producers.

A weekend like this becomes a complete immersion into the spirit of Tuscany: a perfect balance of taste, landscape, and culture.

Overnight stays in Tuscany with Tenute del Cerro: signature experience

For those looking to experience a food and wine weekend in Tuscany that combines authenticity, elegance, and a connection with nature, the estates of Tenute del Cerro offer an immersive journey through some of the region’s most beautiful landscapes, where every stay becomes a memory to treasure.

In the heart of the Sienese hills, Fattoria del Cerro represents the pinnacle of Vino Nobile di Montepulciano DOCG – though Chianti lovers can also savor Chianti Colli Senesi DOCG. Guests can explore the vineyards and winery, learning about the winemaking and aging processes, and then enjoy themed tasting experiences paired with local specialties, such as the “Nobile tasting”. A stay at the stunning Relais Villa Grazianella becomes a fully immersive experience, complete with vineyard picnics, truffle hunts, or cooking classes.

In Castelnuovo dell’Abate, La Poderina offers breathtaking views over the Val d’Orcia and an up-close encounter with Brunello di Montalcino DOCG, one of Italy’s most iconic wines. Here, visitors can enjoy personalized sensory experiences, taste historic vintages and tour the vineyards by off-road vehicle accompanied by an expert agronomist.

Nestled in the unspoiled nature of Val di Cornia and Val di Cecina, amid ancient woods, Tenuta di Monterufoli welcomes guests in two historic buildings, fully restored to their former glory. The Vermentino Pian di Seta IGT takes center stage, available through tailored tasting experiences. But this estate is not just about wine: it’s ideal for those who love to combine adventure, relaxation, and culinary discovery. Guests can explore the vineyards by e-bike or off-road vehicle, walk through the Nature Reserve, or take cooking classes with Chef Gabriele Rosini from the estate’s restaurant, “La Miniera.” A true refuge where silence and nature become part of the experience.

At each of these estates, Tuscany reveals itself through the landscape, the table, and warm hospitality: an invitation to slow down, savor, and be enchanted by the treasures of this remarkable region.