
Italy · Easy
13 Hidden Gems in Italy: A Complete 14-Day Road Trip
A 14-day in-depth self-drive tour through Italy’s most beautiful and lesser-known destinations—from medieval hilltop towns in the north to ancient cave dwellings in the south, and on to historic towns in Sicily—offering a comprehensive glimpse into Italy’s diverse charm along the way.
- Days
- 14
- Stops
- 11
- Mapped stops
- 11
- Mapped distance
- 2,660.8 km
Share this itinerary
Trip
Day-by-day route
Day 1
1 stopsDay 2
1 stops · 136.8 km · 1 hr 30 minDay 3
1 stops · 222.1 km · 2 hr 40 minDay 5
1 stops · 300.7 km · 3 hr 30 minDay 6
1 stops · 92.2 km · 1 hr 30 minDay 7
1 stops · 81.4 km · 1 hr 20 minDay 9
1 stops · 364.4 km · 4 hr 0 minDay 10
1 stops · 232.7 km · 3 hr 10 minDay 11
1 stops · 67.7 km · 1 hr 10 minDay 12
1 stops · 225.4 km · 3 hr 20 minDay 14
1 stops · 937.4 km · 11 hr 30 minMap explore
Map explore
Related reading
Discover places worth the detour
Italy
13 Hidden Gems in Italy: A Complete 14-Day Road Trip
Day 1
Bergamo Old City
Bergamo's Città Alta (Upper City) is one of the finest preserved medieval walled towns in northern Italy, perched 250 meters above the modern city on a dramatic hilltop accessible by historic funicular. Its Venetian defensive walls, a UNESCO World Heritage Site since 2017, enclose a beautiful medieval streetscape of churches, piazzas, and palaces. Le Corbusier described Piazza Vecchia, at the city's heart, as the most beautiful piazza in Italy.
View in Google Maps
Day 2
Borromean Islands
View in Google Maps
Day 3
Sirmione
Sirmione is a named place of interest that can add local context, scenery, or culture to a travel itinerary. It is best used as a focused stop when exploring nearby neighborhoods, landmarks, or regional routes.
View in Google Maps
Day 5
San Gimignano
San Gimignano is a named place of interest that can add local context, scenery, or culture to a travel itinerary. It is best used as a focused stop when exploring nearby neighborhoods, landmarks, or regional routes.
View in Google Maps
Day 6
Pienza
Pienza is a perfectly preserved Renaissance ideal city in the Val d'Orcia, Tuscany, designated a UNESCO World Heritage Site. Commissioned by Pope Pius II in the 15th century as his model humanist city, its compact historic center features a harmonious cathedral piazza and elegant palazzi. The town is also famous for its Pecorino di Pienza cheese and offers sweeping views over the rolling Tuscan countryside.
View in Google Maps
Day 7
Orvieto
Orvieto is a notable point of interest, offering visitors an opportunity to experience the distinctive character and appeal of this destination. Whether for its natural beauty, cultural significance, or unique atmosphere, it provides a rewarding experience as part of a broader exploration of the area.
View in Google Maps
Day 9
Ravello
Ravello is a notable point of interest, offering visitors an opportunity to experience the distinctive character and appeal of this destination. Whether for its natural beauty, cultural significance, or unique atmosphere, it provides a rewarding experience as part of a broader exploration of the area.
View in Google Maps
Day 10
Matera
Matera is a notable point of interest, offering visitors an opportunity to experience the distinctive character and appeal of this destination. Whether for its natural beauty, cultural significance, or unique atmosphere, it provides a rewarding experience as part of a broader exploration of the area.
View in Google Maps
Day 11
Alberobello
Alberobello in the Apulia region of southern Italy is a UNESCO World Heritage Site famous for its extraordinary concentration of trulli — traditional dry-stone huts with conical roofs unique to this area of Italy. The hilltop Rione Monti district contains over 1,500 trulli packed into a magical whitewashed village that appears to have emerged from a fairy tale. The trulli's conical roofs are painted with mystical symbols representing astrological, pagan, or Christian beliefs.
View in Google Maps
Day 12
Vieste
Vieste is a named place of interest that can add local context, scenery, or culture to a travel itinerary. It is best used as a focused stop when exploring nearby neighborhoods, landmarks, or regional routes.
View in Google Maps
Day 14
Erice
Erice is a medieval hilltop town perched at 750 meters on the summit of Mount Erice above Trapani in northwestern Sicily, offering panoramic views over the Aegean-blue salt flats and Mediterranean Sea. Founded by the Elymians, Phoenicians, Greeks, and Romans, its cobblestoned streets and Norman castle are shrouded in clouds and medieval mystery. The town is famous throughout Italy for its traditional almond pastries (genovesi) and the stunning descent through the fog-wrapped medieval lanes.
View in Google Maps





