Tuscany shaped by wine

A wine-focused journey through Tuscany's landscape

9 days From €12200 per person
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Introduction

This journey moves across Tuscany’s most significant wine landscapes, from Florence to Chianti, the Maremma, and Montalcino. Visits to wineries, villages, and rural estates are combined with tastings and encounters that reveal how wine, culture, and history are inseparable from the territory.

Day 1: Florence

Arrival in Florence and private transfer to your hotel in the city center. Meet your local guide for an introductory walking tour through Florence’s historic streets and piazzas. Follow the trail of the city’s wine windows, created in the 16th century under Cosimo I de’ Medici, allowing noble families to sell wine directly from their palaces.  

Overnight in Florence.

FLORENCE_OVERVIEW

Day 2: Florence and wine culture

Begin the day with a guided visit to the Uffizi Gallery, where art and political power shaped Renaissance Florence.  

After lunch, explore Florence’s wine culture from a contemporary perspective. Visit a wine museum and continue to a wine bar dedicated to the promotion of natural and small-scale producers, offering tastings guided by an expert who contextualizes wine within today’s sustainability debate.  

Dining at a traditional Enoteca, where haute cuisine meets an extraordinary wine cellar. 

Overnight in Florence. 

FLORENCE2_OVERVIEW

Day 3: Chianti

Depart Florence and travel south into Chianti Classico. Visit a historical estate since 1385, where innovation and tradition meet in a winery renowned for both its wines and its architecture. 

Continue to the countryside near Colle di Val d’Elsa, check in at a wine estate where organic and biodynamic practices reflect a new approach to viticulture. 

Overnight in a family-run wine estate in the hills of San Gimignano, where generations of work, Vernaccia wineyards, and contemporary winemaking come together to tell the story of the land.

CHIANTI_OVERVIEW

Day 4: San Gimignano

Meet your local guide for a walking tour of San Gimignano, a medieval town historically linked to trade and agriculture. Lunch in town, followed by a visit to a family-run organic farm for an olive oil tasting. Learn how natural treatments and local knowledge shape both oil and wine production. A tasting of Vernaccia di San Gimignano and Chianti Classico completes the day.  

Overnight in a family-run wine estate in the hills of San Gimignano, where generations of work, Vernaccia vineyards and contemporary winemaking come together to tell the story of the land.

SANGIMIGNANO_OVERVIEW

Day 5: Siena

Travel to Siena for a guided visit of the historic center and the Duomo, understanding how civic identity and countryside have always been closely linked.  

After lunch and free time, continue south toward the Maremma. Arrive at a local farm for a tasting of Morellino di Scansano, a wine deeply connected to this coastal landscape. 

Overnight in a contemporary wine estate set in the rolling hills of the Maremma, where vineyards, open landscapes, and sustainable viticulture define a modern interpretation of Tuscan wine culture.

SIENA_OVERVIEW

Day 6: Pitigliano

Visit Pitigliano, a dramatic village carved into volcanic rock. Continue to Sassotondo, where you taste Ciliegiolo, a lesser-known grape variety now reinterpreted through sustainable practices.  

Overnight in a contemporary wine estate set in the rolling hills of the Maremma, where vineyards, open landscapes, and sustainable viticulture define a modern interpretation of Tuscan wine culture

PITIGLIANO_OVERVIEW

Day 7: Montalcino

Travel north through some of Tuscany’s most iconic landscapes toward Montalcino. Explore the village before visiting Fattoria dei Barbi, including the Museum of Brunello and a food & wine experience at the estate’s tavern.  

Continue to Borgo Canalicchio di Sopra, a wine resort surrounded by vineyards. Before dinner, enjoy a tasting of the estate’s Brunello di Montalcino.  

Overnight in a historic wine estate immersed in the hills of Montalcino, surrounded by Brunello vineyards and a landscape shaped by centuries of winemaking tradition

MONTALCINO_OVERVIEW

Day 8: Pienza

Visit Montepulciano and Pienza, where wine, cheese, and landscape form a single cultural system.  

Stop at an organic farm for a lunch experience focused on cheese-making, olive oil, and wines from local producers, offering the chance to compare styles and choose personal favorites.  

Overnight in a historic wine estate immersed in the hills of Montalcino, surrounded by Brunello vineyards and a landscape shaped by centuries of winemaking tradition.

PIENZA_OVERVIEW

Day 9: Return to Florence and departure

Private transfer back to Florence Airport for departure.

This is a selected example of our journeys. Contact us to personalize it.

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A wine-focused journey through Tuscany’s landscapes

Wine in Tuscany is a cultural system shaped by centuries of regulation, experimentation, and dialogue with the land. From medieval guilds in Florence to contemporary wineries redefining sustainability, this journey explores Tuscany through its wines, focusing on both historic appellations and innovative producers committed to environmental responsibility. 

Trip Highlights

  • Follow Florence’s historic connection to wine, from medieval guilds to wine windows. 
  • Explore the great classics: Chianti, Brunello di Montalcino, Vernaccia, Morellino di Scansano.  
  • Visit pioneering wineries focused on organic and sustainable practices.  
  • Taste wines alongside olive oil, cheese, and local products.  
  • Discover small villages where landscape, agriculture, and culture remain connected.

This is a selected example of our journeys. Contact us to personalize it.

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