Ultimate Italy wine tours

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Turn your dream of tasting authentic Italian flavors into a beautifully crafted journey through Tuscany. This experience brings together the richness of local vineyards, the charm of artisan producers, and the warmth of rustic cuisine, all curated with the help of a dedicated local specialist.

Every moment is shaped around your tastes and interests, so you can enjoy meaningful encounters and memorable meals in thoughtfully selected settings that celebrate the spirit of Italy wine tours.

Start planning one of the most rewarding trips to Italy and create food and wine memories that stay with you long after you return home.

 Italy wine tour highlights

  • Chianti tasting with local experts: Enjoy an intimate introduction to the region’s character as you sample elegant Chianti wines in welcoming family estates.
  • Tuscan flavors experience: Discover the traditions behind regional dishes through a relaxed culinary session.
  • Vineyard exploration and sensory walk: Wander through rolling vines with a local guide who brings the stories of the land to life.
  • Sunset aperitivo among the vines: Settle into a peaceful evening at a boutique estate where you enjoy small bites and thoughtfully selected wines.
  • Tailored cultural discoveries: Visit hilltop towns, artisan studios, and atmospheric historic sites chosen to complement your interests.
DayLocationActivityOvernight
1Tuscany (Colle Val d’Elsa area)

• Arrival in Tuscany with relaxed private transfer

• Light Chianti Classico tasting and vineyard walk

• Check-in and stroll through Colle Val d’Elsa

Tuscany
2Chianti / San Gimignano / Tuscany

• Vespa or vintage Fiat 500 tour through Chianti Colli Fiorentini

• Wine and olive oil pairing lunch at a boutique winery near San Gimignano

• Relaxed evening at your hotel

Tuscany
3Bolgheri / Tuscany

• Private tour and gourmet pairing lunch at a Bolgheri Super Tuscan estate

• Boutique winery tasting

• Optional sommelier-led regional wine comparison

Tuscany
4Montalcino / Tuscany

• Visit a Brunello di Montalcino winery with guided cellar tour

• Sunset vineyard aperitivo or blending workshop

• Final Tuscan dinner or quiet evening at the hotel

Tuscany
5Tuscany → Airport

• Farmhouse breakfast and short vineyard walk

• Private transfer to the airport

• Departure

Places you'll visit

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Colle di Val d'Elsa
Colle di Val d'ElsaColle di Val d'Elsa
Day01

A warm welcome to Tuscany

Your arrival in Tuscany sets the stage for a relaxing beginning as you settle into the gentle pace of the countryside. A private scenic transfer gives you time to unwind and absorb the views that make this region so inviting. Later, you visit a Chianti Classico estate for a light tasting and an easy walk among the vines, which offers a calm introduction to local flavors.

As the afternoon softens into evening, you stroll through Colle Val d’Elsa and enjoy the peaceful atmosphere of this charming town. This opening chapter becomes a lovely start to your Italy wine trip and begins shaping your Italy itinerary in a very natural way.

Chianti Region
Day02

Chianti’s hills and local tastes

Your morning takes you through the rolling beauty of Chianti Colli Fiorentini in a Vespa or vintage Fiat, creating a joyful sense of immersion in the rural landscape.

When you reach a boutique winery near San Gimignano, you settle in for a long and flavorful pairing lunch that highlights the connection between wine, food, and local culture.

The afternoon invites you to relax and enjoy the serenity of the estate before returning to your hotel. This gentle rhythm allows you to experience the warmth and pleasure that make Italy travel so rewarding.

Vespa in Tuscany
Day03

Tuscan secrets in Bolgheri

Your journey continues toward the coast as you explore the celebrated Bolgheri region, known for its elegant Super Tuscan wines and memorable estate traditions. This part of your Tuscany tour introduces you to a landscape shaped by sea breezes and golden light that reveals the character of each vineyard.

A private tour followed by a gourmet lunch helps you appreciate how the coastal terroir influences the depth and balance of these wines. Later, you visit a small boutique winery that celebrates expressive local varieties and shares the personal stories behind every bottle.

A relaxed, optional tasting in the evening invites you to compare different styles and expands your understanding of what makes Italy wine tours so special.

Bolgheri
Day04

Brunello traditions

Your morning brings you to the hills of Montalcino, where the celebrated Brunello wines are created with remarkable patience and devotion. A guided cellar experience reveals the artistry behind this tradition and the strong sense of identity that defines the region.

In the afternoon, you enjoy your signature moment as you settle into a sunset aperitivo in the vineyards or join a blending session that highlights the uniqueness of local grapes. Each part of the day reflects the emotional richness found in Italy wine tours and leaves you with a sense of meaningful connection to the land. The evening is yours to celebrate or unwind quietly.

Poggio Stenti
Fabio

Tips from Fabio

Italy Travel Expert

quotes

Ask for a Brunello “di annata” (from a recent vintage) and a “riserva” to taste side by side. It’s the best way to understand what makes Montalcino’s wines special, without committing to a full bottle.

Day05

Farewell to Tuscany

Enjoy one last leisurely morning in the fascinating Tuscan countryside, a landscape that sits at the heart of any trip to Tuscany, with options like a farmhouse breakfast, a stroll through vineyards, or a relaxed coffee overlooking rolling hills.

It is one last chance to soak in the flavors and atmosphere of a region that gives Italy wine tours their charm. At the scheduled time, your private driver will transfer you to the airport for your flight home.

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