📍 Italy

ROMAGNA FORTRESSES: MEDIEVAL VILLAGES AND ANCIENT STRONGHOLDS

Medieval towers piercing rocky ridges, fortresses commanding panoramas, stone villages drowsing. Romagna's strongholds, medieval soul.

≈ 5
Days
70
Km
5
Stops
📖 3 min read 🔄 Last updated: 2026-01-17

Travel back in time at Rimini between Roman traces and seafront, then climb toward Santarcangelo di Romagna and its hills. Cross Verucchio, approach San Leo and its fortress set upon the void, and let the Middle Ages tell their story in stone. Romagna reveals itself through viewpoints, lanes and stubborn stories.

Your day-by-day itinerary

1
Day

Rimini

roman arch seaside gateway

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

Discover

1
Arch of Augustus - monumental Roman gate with crenellated medieval crown, historic entrance to the city
2
Tempio Malatestiano - Renaissance cathedral with Alberti's white marble façade and decorated chapels
3
Domus del Chirurgo - Roman archaeological site with mosaics and ancient surgical instruments
4
Piazza Tre Martiri - ancient Roman forum in the heart of the historic center
+2 Places visited
🎯

Activities

→
Walk through Borgo San Giuliano - old fishermen's quarter with colorful houses and wall frescoes
🚗
Next stop
Distance: 13 km
Travel time: 15min
2
Day

Santarcangelo Di Romagna

renaissance hilltop winemaking town

Santarcangelo Di Romagna - Photo 1Santarcangelo Di Romagna - Photo 2Santarcangelo Di Romagna - Photo 3Santarcangelo Di Romagna - Photo 4Santarcangelo Di Romagna - Photo 5Santarcangelo Di Romagna - Photo 6Santarcangelo Di Romagna - Photo 7Santarcangelo Di Romagna - Photo 8Santarcangelo Di Romagna - Photo 9Santarcangelo Di Romagna - Photo 10
10 photos
Day 2
🔍

Discover

1
Rocca Malatestiana - medieval fortress dominating the town from the top of Colle Giove
2
Grotte tufacee - underground network of caves carved into tuff rock of mysterious origins
3
Palazzo Cenci - noble palace with Renaissance facade in the historic center
4
Chiesa Collegiata - main church with bell tower visible from the valley
+1 Places visited
🎯

Activities

→
Strolling through the cobblestone alleys lined with historic palaces and artisan shops
🚗
Next stop
Distance: 12 km
Travel time: 14min
3
Day

Verucchio

cliff fortress ancient territory

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

Discover

1
Rocca Malatestiana di Verucchio - fortress on rocky spur with panoramic view over Romagna and San Marino
2
Museo Civico Archeologico - collection of Villanovan and Etruscan remains discovered in the region
3
Torre del Mastio - accessible medieval keep offering 360-degree panorama
🎯

Activities

→
Walk through the stone alleys of the medieval village at the gates of Montefeltro
🚗
Next stop
Distance: 15 km
Travel time: 18min
4
Day

San Leo

stone pillar impossible fortress

San Leo - Photo 1San Leo - Photo 2San Leo - Photo 3San Leo - Photo 4San Leo - Photo 5San Leo - Photo 6San Leo - Photo 7San Leo - Photo 8San Leo - Photo 9San Leo - Photo 10
10 photos
Day 4
🔍

Discover

1
Fortezza di San Leo - Renaissance citadel perched on rocky spur with vertical walls dominating the valley
2
Pieve di Santa Maria Assunta - pre-Romanesque church with ancient columns and carved capitals
3
Cattedrale di San Leo - Roman cathedral in ashlar stone with austere facade
4
Centro storico - compact medieval village with central square and brick buildings
🎯

Activities

→
Walking ascent to the fortress via the panoramic path crossing the fortifications
→
View from the ramparts over the Marecchia valley and surrounding hills
🚗
Next stop
Distance: 30 km
Travel time: 36min
5
Day

Saludecio

inland village romagna heartland

Saludecio - Photo 1Saludecio - Photo 2Saludecio - Photo 3Saludecio - Photo 4Saludecio - Photo 5Saludecio - Photo 6Saludecio - Photo 7Saludecio - Photo 8
8 photos
Day 5
🔍

Discover

1
Mondaino - fortified town with unique circular arcaded square, surrounded by walls
2
Rocca Malatestiana di Mondaino - fortress with viewpoint over the surrounding wooded hills
3
Museo Paleontologico di Mondaino - marine fossils discovered in the region
4
Montegridolfo - small fortified town enclosed by walls with flower-lined streets and clock tower
+5 Places visited
🎯

Activities

→
Walk between the three villages discovering wall frescoes and panoramas over the Romagna coast

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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 4 and 6 days. The next step will allow you to adjust the duration of your stay.

What to discover in Italy?

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