Top Things to Do in Cortona, Tuscany – Plus Where to Stay in Style

Cortona, Tuscany: Discover the Hilltop Town Made Famous by Under the Tuscan Sun

Cortona is one of those magical places in Italy where the light seems to hit just right, the views go on forever, and every winding alley invites you to slow down and savor life. Set high above the Val di Chiana, this historic Tuscan hilltown gained worldwide fame through the book and film Under the Tuscan Sun, but locals and well-traveled visitors have long known that Cortona is far more than a movie set.

Whether you're planning a romantic escape, a family holiday, or a once-in-a-lifetime group trip, Cortona offers the best of Tuscany — Renaissance architecture, ancient Etruscan roots, vibrant local culture, and access to both iconic destinations and quiet countryside corners.

And now, you can experience it all from the rare comfort of a luxury villa located within the town walls.

👉 View this exceptional villa in Cortona – Palazzo Cortona, 7 bedrooms, 7 bathrooms:
https://classicvillavacations.com/collections/villas-in-tuscany/products/palazzo-cortona-luxury-villa-in-town-7-bedrooms-7-bathrooms

Why Visit Cortona?

·       Etruscan walls and archaeological sites dating back to the 4th century BC

·       A beautiful Piazza della Repubblica with cafés perfect for people-watching

·       The MAEC Museum — one of Tuscany’s best-kept cultural secrets

·       Artisan boutiques, wine bars, and local trattorie at every turn

·       The Basilica of Santa Margherita and the sweeping views from Fortezza del Girifalco

·       The Franciscan Hermitage Le Celle — a serene monastic complex carved into the hillside

Off-the-Beaten-Track Things to Do in Cortona

·       Walk the old stone road (Via Crucis) up to the fortress for sunrise or sunset

·       Visit on market day (Saturday mornings) when locals come in from the countryside

·       Take a cooking class in a private home or learn about local olive oil production

·       Follow the locals to the town’s hidden wine bars and late-night gelato shops

·       Hike or e-bike through the nearby Val di Chiana hills and discover ancient farmhouses and vineyards

The Ultimate Place to Stay: A 7-Bedroom Luxury Villa Inside the Town Walls

Most villas in Tuscany are set in the countryside — and while they offer space and seclusion, you’ll often need a car to get anywhere. That’s what makes this property so exceptional.

Palazzo Cortona is a fully restored, grand 7-bedroom villa that offers the comfort and privacy of a high-end estate, but with a location that lets you walk to everything.

Highlights include:

·       Private pool, garden terraces, and panoramic views over the valley

·       Elegant interiors with soaring ceilings, curated art, and cozy living spaces

·       A chef’s kitchen perfect for family meals or private dinners

·       All bedrooms with en-suite bathrooms and air conditioning

·       Just steps to Cortona’s main piazza — no car required

Note: We also have many lovely villas in the surrounding countryside within a 10–20 minute drive of Cortona — from beautifully restored rustic farmhouses and charming agriturismo stays to elegant luxury estates with pools and vineyard views. If you'd prefer something just outside of town, contact us directly and let us know what you’re looking for — we’re happy to make personalized recommendations. check it out - https://classicvillavacations.com/collections/villas-in-tuscany

Nearby Day Trips and Activities

·       Montepulciano – wine tasting in one of Italy’s most scenic hill towns (45 min)

·       Lake Trasimeno – enjoy lunch by the lake or ferry to Isola Maggiore (30 min)

·       Pienza & Val d'Orcia – famous for pecorino cheese, rolling hills, and picture-perfect landscapes (1 hr)

·       Perugia & Assisi – medieval towns filled with history, art, and authentic Umbrian culture (1  hr)

·       Florence – world-class art and architecture, just over an hour by train or car

Plan Your Tuscan Escape

If you’re dreaming of living like a local in Tuscany while enjoying all the space and luxury of a grand villa, this might be your perfect match. You won’t just be visiting Cortona — you’ll be part of it.

👉 Explore the villa here:
https://classicvillavacations.com/collections/villas-in-tuscany/products/palazzo-cortona-luxury-villa-in-town-7-bedrooms-7-bathrooms

Need help planning your stay? I’ve visited Cortona and this villa personally and would love to help you customize your itinerary. From vineyard visits and private chefs to cultural experiences and transfers — everything is possible.

📩 Get in touch anytime at info@classicvacationrental.com

📱 Or follow us on Instagram: @classicvacationrental or DM or directly from IG