📍 Italy

MILAN TO CHIANTI: DESIGN, ARTISTRY AND WINE CULTURE

Northern cities pulsing with fashion, medieval towers piercing Tuscan sky. Italy marries contemporary design with thousand-year artistic soul.

≈ 8
Days
426
Km
6
Stops
📖 4 min read 🔄 Last updated: 2026-01-17

Explore Milan between fashion and design, then savor Parma's art of living and Bologna's arcades. Florence displays its artistic brilliance, while Siena asserts its Gothic elegance. In Radda, Chianti's wine villages blend stone, vine and rolling horizons.

Your day-by-day itinerary

1
Day

Milano

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10 photos
Day 1
🔍

Discover

1
Galleria Vittorio Emanuele II — historic passage and iconic boutiques
2
Milan Duomo terraces — panorama over the city
3
Spazio Dimore (via Solferino) — creative design hub
4
Sofia Zevi boutique-gallery — furniture, glassware, fashion
+2 Places visited
🎯

Activities

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Walking route between historic center and Brera (urban rhythm, shop windows & interior courtyards)
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Next stop
Distance: 126 km
Travel time: 1h45
2
Day

Parma

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10 photos
Day 2
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Discover

1
Caseificio Parmigiano Reggiano (San Prospero) — production & aging tour
2
Atelier Prosciutto di Parma (Capoponte) — discovery of the curing stages
3
Parco Ducale & Cittadella — landscape walk
4
Auditorium Paganini (Renzo Piano) — glass architecture overlooking park
🎯

Activities

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'Food Valley' itinerary around Parma (stops at producers, farm shops)
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Next stop
Distance: 60 km
Travel time: 50min
3
Day

Bologna

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9 photos
Day 3
🔍

Discover

1
Modena — UNESCO ensemble: Duomo, Piazza Grande, Torre Ghirlandina
2
Palazzo Ducale (exterior) — baroque square and perspectives
3
Acetaia Marchi — tour of balsamic vinegar batteries & tasting
4
Bologna — Piazza Maggiore, porticoes and Due Torri
+1 Places visited
🎯

Activities

→
Evening stroll under the historic porticoes of Bologna's center
🚗
Next stop
Distance: 47 km
Travel time: 45min
4
Day

Bologna

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9 photos
Day 4
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Discover

1
Cineteca di Bologna & Manifattura delle Arti — museums, archives and screenings
2
Traditional pasta workshop (tortellini) with local host ('Cesarine' type platform)
3
Neptune Fountain (Giambologna) — nighttime illumination
🎯

Activities

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Themed route 'portici' (covered galleries) in the historic center
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Next stop
Distance: 108 km
Travel time: 1h20
5
Day

Firenze

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10 photos
Day 5
🔍

Discover

1
Piazza della Signoria — Neptune statue ('Il Biancone') & outdoor sculptures
2
Roberto Casamonti Collection (Palazzo Bartolini Salimbeni) — modern & contemporary art
3
Villa Bardini & hanging gardens — views of Brunelleschi's dome
4
Le Murate — rehabilitated wasteland: squares, galleries, literary café, local venues
🎯

Activities

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Walking tour in Oltrarno between Santo Spirito, artisan workshops and viewpoints
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Next stop
Distance: 50 km
Travel time: 1h10
6
Day

Radda In Chianti

wine village anchors tuscan heart

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7 photos
Day 6
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Discover

1
Medici Chapels (San Lorenzo) — funeral chapels & pietra dura
2
Cantina Antinori nel Chianti Classico — contemporary semi-underground architecture & wine tour
3
Chianti scenic route — viewpoints, cypresses and vineyards
🎯

Activities

→
Short hike between vineyards and olive groves (Greti/Greve in Chianti area)
🚗
Next stop
Distance: 35 km
Travel time: 50min
7
Day

Siena Centro Storico

gothic city shells medieval soul

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5 photos
Day 7
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Discover

1
Greve in Chianti — stop at the triangular square & arcades (in transit)
2
Siena — Duomo (Gothic cathedral) & museum complex
3
Siena — Piazza del Campo & Contrade route (museum of a contrada)
🎯

Activities

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Walking loop in the medieval center of Siena (ramp, viewpoints, alleyways)

🗺️ Itinerary map

🗺️ Nearby itineraries

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🛡️ Travel advice - Italy

Check official recommendations

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❓ Frequently asked questions

What weather should you expect?

Spring (April-June): Perfect weather, blooming landscapes, comfortable temperatures, fewer crowds, excellent value, Easter celebrations, ideal touring conditions.

Summer (July-August): Warmest weather, peak tourist season, highest prices, crowded attractions, vibrant atmosphere, beach season, festival time.

Fall (September-October): Excellent weather, harvest season, wine tourism, comfortable temperatures, fewer crowds, beautiful colors, culinary focus.

Winter (November-March): Mild southern weather, Christmas markets, lowest prices, minimal crowds, cultural focus, cozy atmosphere, indoor attractions.

How many days should I plan?

We believe you will enjoy this itinerary best by dedicating between 6 and 10 days. The next step will allow you to adjust the duration of your stay.

What to discover in Italy?

Cultural masterpiece with incredible art, cuisine, and historical heritage from Rome to Venice. Experience Renaissance treasures, regional diversity, and authentic Italian lifestyle. The country offers cultural immersion with culinary excellence and artistic heritage. Italy provides complete cultural experiences with historical significance and natural beauty.