Want to spin again or change your picks? Start over →

This site uses affiliate links. If you book through one, we may earn a commission — at no extra cost to you.
Italy — video preview

Countryside Italy

Your complete guide to Italy's rural regions

You're in Val d'Orcia, Tuscany. Cypress-lined roads wind through golden hills. Medieval town on distant hilltop. Vineyard rows pattern the landscape. This is postcard Italy—slower pace, agriturismo stays, local wine, simple food, genuine interactions. Italian countryside rewards those who skip between famous cities.

Best countryside regions: Tuscany (rolling hills, wine), Umbria (green heart, truffles), Puglia (olive groves, white towns), Piedmont (Barolo wine, Alba truffles), Le Marche (undiscovered hills). Car essential—trains serve cities, not villages.

Tuscany—rolling hills perfection

Val d'Orcia—UNESCO landscape, postcard views. Pienza (cheese), Montalcino (Brunello wine), Montepulciano (Vino Nobile). Drive backroads, stop at every viewpoint. Stay in agriturismo €100-180/night.

Chianti—wine region between Florence-Siena. Vineyards, olive groves, medieval towers. Rent villa or agriturismo. Wine tastings €15-30. Visit Greve, Radda, Castellina. Car essential for exploring.

Maremma—southern Tuscany coast. Less touristy, cowboys (butteri), wild beaches, Etruscan ruins. Pitigliano carved from tufa rock. Wine (Morellino), thermal springs. Authentic, affordable.

Umbria—green and authentic

Perugia, Assisi, Orvieto anchor region. Between these—rolling hills, forests, hilltop villages. Less international tourists than Tuscany. Truffle hunting autumn (€80-150 experience).

Norcia—truffle capital, medieval town, cured meats (norcineria). Mountains backdrop. Earthquake damaged 2016, rebuilding. Real agricultural town.

Spoleto—Roman/medieval mix, annual summer arts festival. Less crowded than Assisi, equally beautiful. Base for exploring Umbrian countryside.

Puglia—Mediterranean countryside

Valle d'Itria—trulli houses (conical stone roofs), whitewashed towns, olive groves. Alberobello (UNESCO trulli), Locorotondo, Martina Franca. Masserie (fortified farms) now agriturismos.

Salento peninsula—baroque towns (Lecce), olive groves stretching to sea, Greek/Norman heritage. Less developed, authentic. Mediterranean agriculture landscape.

Castel del Monte—Frederick II's geometric castle, isolated on hill. UNESCO site. Mysterious architecture, theories abound. Surrounded by wheat fields.

Italy: Book top-rated tours and tickets

Piedmont—wine and truffles

Langhe region—Barolo, Barbaresco wines. Rolling vine-covered hills. Alba for white truffles (Oct-Dec, €200-300/100g). Michelin restaurants hidden in villages.

Agriturismo stays in wine estates—taste house wines, farm dinners, hillside views. €80-150/night. Book harvest season (Sept-Oct) months ahead.

Medieval hilltop villages—Barolo, La Morra, Serralunga. Each has castle, wine bars, restaurants. Drive between villages wine-tasting.

🌟 Top Countryside Experiences

🏡 Tuscan Agriturismo Stay

Farm stay, pool, vineyard views. Home-cooked dinners, wine tastings. €100-180/night. Book week minimum. More info →

🍷 Chianti Wine Tour

Visit wineries, taste Chianti Classico, lunch at estate. €80-150/person guided. Self-drive cheaper. See tours →

🍄 Truffle Hunting, Umbria

Hunt with trained dogs, guide explains. Taste findings. Autumn best. €80-150. 3 hours. More info →

🏛️ Trulli Houses, Alberobello

UNESCO stone houses, conical roofs. Stay in trullo. Explore Valle d'Itria. Unique architecture. More info →

🚗 Val d'Orcia Drive

Scenic driving, cypress roads, hilltop towns. Pienza, Montalcino, Montepulciano. Full day. Free. More info →

🍷 Barolo Wine Region

Piedmont wine villages. Tastings at cantinas. Alba truffles autumn. €15-30 tastings. See tours →

💡 Insider Tips

  • 🚗 Car absolutely essential—villages poorly connected by public transport. GPS + offline maps. Roads narrow, parking limited.
  • 🏡 Agriturismo minimum stays common (3-7 nights). Book months ahead summer. Off-season (Oct-April) has deals, fewer tourists.
  • 🍷 Wine tastings usually free if buying bottle. Appointments often required. Email ahead—better English communication than phone.
  • 🗓️ Harvest season (Sept-Oct) busiest but best atmosphere. Truffle season (Oct-Dec) expensive but worth experiencing once.
  • 🍽️ Dinner at agriturismo often included (half-board). Home-cooked, local ingredients, generous. Worth paying €25-35/person extra.

Found this useful? Share it.

One new way to travel. Every Thursday.

Not deals or destinations — methods. House sitting, night trains, repositioning cruises, and what each one really costs.

Ever thought of travelling this way?

Work Exchange

A few hours a day at a hostel, a guesthouse or a family home, and the bed is yours — in a town with a metro at the end of the street. Our son did it in South America and stayed ten years.

Read article →

Caretaking

House sitting’s long version: a lodge, an estate or a ranch that needs someone for a whole season, and sometimes pays for it. The job is the place, not the cat.

Read article →

Farm Stays

A few hours’ work a day on a farm, and a bed and dinner at the family table in return. Pick grapes in Portugal in September and again in New Zealand in March.

Read article →

All ways to travel →

↑ Back to top

×Psst — thinking about Italy? Ask me anything 🎡