Discover Cortona: A Hilltop Gem for All Seasons

Introduction to Cortona

Nestled in the heart of Tuscany, Cortona is a charming hilltop town that offers breathtaking views, rich history, and a vibrant culture. Whether you're a history buff, a nature lover, or someone looking to unwind, Cortona is a destination that promises something for everyone.

Immersed in History

Cortona's origins date back to the Etruscans, and its long history is evident in its architecture and museums. The town's narrow streets are lined with medieval buildings, each telling a story of its past. Visit the Etruscan Academy Museum to explore artifacts and learn about the town's ancient roots.

The grandeur of the Diocesan Museum cannot be overlooked, showcasing works by renowned artists. Here, you can find the famous Annunciation by Fra Angelico, a masterpiece that draws art enthusiasts from around the world.

Natural Beauty

Surrounded by rolling hills and lush landscapes, Cortona is a paradise for nature lovers. The town offers numerous hiking trails that lead to panoramic viewpoints, perfect for capturing stunning photos. The nearby Lake Trasimeno is ideal for a day trip, offering opportunities for boating and picnicking.

Spring and autumn are particularly beautiful, when the countryside bursts with color, making it the perfect time for outdoor activities or simply enjoying a leisurely stroll through the town.

Culinary Delights

Cortona is a haven for food enthusiasts. The local cuisine is a delightful blend of traditional Tuscan flavors, featuring fresh, seasonal ingredients. Don't miss trying the pici pasta, a local specialty, or savoring the rich flavors of the region's olive oil and wines.

Numerous trattorias and restaurants offer authentic dining experiences, where you can enjoy everything from simple, rustic dishes to gourmet meals. Be sure to explore the local markets, where you can find fresh produce and artisanal products.

Cultural Events

Throughout the year, Cortona hosts a variety of cultural events that bring the community and visitors together. The Tuscan Sun Festival is a highlight, celebrating music, art, and film, while the Cortona Mix Festival offers a mix of literature, music, and culinary arts.

These events provide a wonderful opportunity to experience the local culture and engage with the community. Whether you're attending a concert in the historic town square or participating in a local workshop, Cortona's events are not to be missed.

Special offer: Villa Alessandra, Cortona

Sleeps 18 | 9 bedrooms | 13 bathrooms | Air-conditioning | Billiard table
4.5km from historic Cortona | Restaurant within 1.5km

Villa Alessandra is a perfect for larger groups seeking space, elegance and authenticity. Grand interiors, extensive gardens and even a private chapel -

Only 4.5 Km from Cortona — the romantic hilltop town made famous by Frances Mayes’ Under the Tuscan Sun — it is an exceptional choice for weddings, family celebrations or a truly memorable Tuscan retreat. The villa benefits from air-con, a billiard table and there is a restaurant within 1.5 Km. Lovely, kind owners who look after their property & guests well.

2026 Exclusive offer on remaining weeks

• 5% off remaining weeks in 2026 and earlybird bookings for 2027
• A complimentary basket of fresh seasonal fruit on arrival

Spring in Tuscany
Available: 9 April – 9 May 2026

Late Summer Sunshine
Available: 15 August – 26 September 2026

Autumn in Tuscany
Available: 3 October – 14 November 2026

Prime dates in Tuscany are booking quickly — these are some of the final remaining weeks at this beautiful property.  (Minimum stay 7 nights – offer ends 28 Feb 2026)

Contact us for Cortona villa rentals

Plan your visit to Cortona and discover why this Tuscan town is a favorite among travelers. With its welcoming atmosphere and endless attractions, Cortona is truly a year-round destination. Contact us with your villa rental requirements: [email protected] +44 (0) 161 787 8587