📍 Italy

CASENTINO: ART, MEDIEVAL VILLAGES AND SANCTUARY MOUNTAINS

Renaissance frescoes with colors intact, crenellated towers crowning hills, monastery bells ringing through mountains. Casentino, artistic and sacred soul.

≈ 11
Days
224
Km
11
Stops
📖 7 min read 🔄 Last updated: 2026-01-17

Explore Arezzo and its Renaissance frescoes, then reach Anghiari and its crenelated towers. Discover Sansepolcro and Piero della Francesca's heritage, before reaching La Verna sanctuary clinging to wooded summits. This land unites art, silence and spiritual elevation.

Your day-by-day itinerary

1
Day

Castiglione Del Lago

lakeside fortress commands water view

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4 photos
Day 1
🔍

Discover

1
Lake Trasimeno: natural paradise in the heart of Umbria, with reed beds and white water lilies
2
Castiglione del Lago: ancient town on the shores of the lake
3
Passignano sul Trasimeno: picturesque village by the water
🎯

Activities

→
Panoramic ferry tour to the three islands of Lake Trasimeno
🚗
Next stop
Distance: 38 km
Travel time: 46min
2
Day

Cortona

hilltop etruscan town terra cotta

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8 photos
Day 2
🔍

Discover

1
Historic center: Etruscan and medieval town surrounded by walls, picturesque alleys with views of Valdichiana
2
Medieval and Renaissance palaces: monumental architecture of the center
3
Historic churches: numerous buildings of artistic and religious importance
🎯

Activities

→
Panoramic viewpoints over the Tuscan hills and valley
🚗
Next stop
Distance: 22 km
Travel time: 27min
3
Day

Lucignano

spiral village concentrically perfect

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10 photos
Day 3
🔍

Discover

1
Elliptical medieval village: exceptional example of medieval urbanism with concentric ring layout
2
Intact historic center: appearance preserved for centuries
🎯

Activities

→
Stroll through the narrow streets following the unique elliptical layout of the town
🚗
Next stop
Distance: 50 km
Travel time: 1h
4
Day

Castiglion Fiorentino

tower-crowned town overlooking valleys

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6 photos
Day 4
🔍

Discover

1
Fortified medieval center: hilltop town between Cortona and Arezzo, surrounded by walls and towers
2
Torre del Cassero: imposing tower offering a magnificent panorama over the Valdichiana
🎯

Activities

→
Stroll through the historic center surrounded by medieval ramparts
🚗
Next stop
Distance: 12 km
Travel time: 14min
5
Day

Arezzo

renaissance city where frescoes gleam

Arezzo - Photo 1Arezzo - Photo 2Arezzo - Photo 3Arezzo - Photo 4Arezzo - Photo 5Arezzo - Photo 6
6 photos
Day 5
🔍

Discover

1
Piazza Grande: one of Italy's most beautiful squares, site of numerous annual events
2
Basilica San Francesco: frescoes by Piero della Francesca depicting The Legend of the True Cross
3
Chiesa di San Domenico: houses the famous Crucifix by Cimabue
4
Duomo d'Arezzo: remarkable example of Italian Gothic architecture
🎯

Activities

→
Discovery of the filming locations of Roberto Benigni's film La Vita è Bella, winner of three Oscars
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Copies of the Etruscan Chimera: fountains near the station and Porta San Lorentino (original in Florence museum)
→
Giostra del Saracino: medieval tournament in June and September with knights representing the four districts
+2 Optional activities
🚗
Next stop
Distance: 18 km
Travel time: 22min
6
Day

Monterchi

village where madonna del parto

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8 photos
Day 6
🔍

Discover

1
Museo della Madonna del Parto: famous fresco by Piero della Francesca in a dedicated museum
🎯

Activities

→
Discovery of the surrounding countryside: pievi, ancient castles and rural hamlets
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Next stop
Distance: 13 km
Travel time: 15min
7
Day

Anghiari

battlement towers pierce hilltop sky

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6 photos
Day 7
🔍

Discover

1
Fortified village: classified among the most beautiful villages in Italy, perched on a hill overlooking the Valtiberina
2
Medieval center: stone houses, narrow streets, stairs and picturesque small squares
🎯

Activities

→
Discovery of the preserved medieval atmosphere of the village
🚗
Next stop
Distance: 10 km
Travel time: 12min
8
Day

Sansepolcro

piero della francesca hometown treasures

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6 photos
Day 8
🔍

Discover

1
Renaissance City of Piero della Francesca: birthplace of the painter in the early 15th century
2
Museo Civico: masterpieces by Piero della Francesca and terracottas by the Della Robbia
3
Medieval and Renaissance architecture: majestic buildings from the Middle Ages to the 16th century
🎯

Activities

→
Walk through the historic center preserving its character as a city of art
🚗
Next stop
Distance: 30 km
Travel time: 35min
9
Day

La Verna

monastery monastery clinging sacred peaks

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6 photos
Day 9
🔍

Discover

1
Santuario de La Verna: large monastic complex clinging to the rock of Sacro Sasso, place where Saint Francis received the stigmata
🎯

Activities

→
Spiritual immersion in the forest of firs and beeches of Casentino
→
Discovery of the site where Saint Francis spent his last years
🚗
Next stop
Distance: 18 km
Travel time: 21min
10
Day

Poppi

castle village commanding forested views

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6 photos
Day 10
🔍

Discover

1
Castello dei Conti Guidi: 12th-century castle dominating the village and a large part of Casentino
🎯

Activities

→
Discovery of the architectural jewel perched at the top of the hill
11
Day

Camaldoli

hermitage monastery forest solitude

Camaldoli - Photo 1Camaldoli - Photo 2Camaldoli - Photo 3Camaldoli - Photo 4Camaldoli - Photo 5Camaldoli - Photo 6Camaldoli - Photo 7Camaldoli - Photo 8Camaldoli - Photo 9Camaldoli - Photo 10
10 photos
Day 11
🔍

Discover

1
Monastery of Camaldoli: complex including monastery, church, old forestry and historic pharmacy
2
Hermitage of San Romualdo: hermitage founded by Saint Romuald 3 km from the center, place of high spirituality
🎯

Activities

→
Hiking in the heart of the Casentino Forests National Park
🚗
Next stop
Distance: 13 km
Travel time: 15min

🗺️ Itinerary map

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🛡️ Travel advice - Italy

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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 9 and 13 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.