Curator’s statement
When clients dream of Tuscany, they envision romantic cobblestone streets, centuries-old churches, warm trattorias brimming with local flavor, and, of course, world-class wine, but are sometimes disappointed with the hecticness of the region as they pass through. However, tucked into the rolling hills of eastern Tuscany near Umbria, the lesser known area of Cortona delivers on these expectations. Picture-book perfect and rich in character, Cortona offers all the charm of its more famous neighbors, yet retains a sense of intimacy and authenticity that’s increasingly rare in the region.
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Trip overview
Quintessential Cortona
Though it may not carry the immediate name recognition of Chianti or Lucca, Cortona is every bit as captivating—perhaps even more so. With fewer crowds than the more touristed parts of Tuscany (though it still buzzes with visitors), it manages to feel both lively and serene. And with a handful of exceptional luxury properties either within or just outside the historic center, it’s the perfect base for a sophisticated yet soulful Italian escape.
Stay in the heart of town: Monastero di Cortona
The view from Monastero di Cortona
For those who prefer to immerse themselves in the heart of the action—steps from artisan shops, tucked-away cafes, and the energy of local life—Monastero di Cortona is an exceptional choice. As the name suggests, this unique property is housed in a former monastery, and its sense of history is woven throughout the guest experience.
No two rooms are alike, but all feature thoughtful design, a refined color palette, and a seamless blend of classical architecture with contemporary comfort. Some rooms preserve original frescos, while others open onto terraces overlooking the iconic Tuscan hills—several even come with private loungers beside the in-room plunge pools, allowing guests to soak in the views without ever leaving their suite.
Look at that fresco!
The hotel’s spa is a true sanctuary, complete with an indoor pool, hydrotherapy jets, and holistic treatments. Dining here is another highlight: the light lunch menu is surprisingly elevated (don’t miss the stracci al ragù), but the real standout is Gli Affreschi, the on-site fine dining restaurant. Refined, creative, and beautifully presented, it’s ideal for a celebratory meal that goes beyond traditional Tuscan fare.
Warm, professional service rounds out the experience—staff members are genuinely welcoming and committed to crafting the perfect stay, whether you’re here for romance, relaxation, or a bit of both.
A countryside escape: Relais Il Falconiere
Aperitivo at Il Falconiere
Just a short drive from Cortona’s city center lies Il Falconiere, a luxury country estate that redefines the agriturismo experience. This is not a rustic farmhouse stay—it’s a refined, deeply romantic retreat with soul.
Our Junior Suite, overlooking one of two serene outdoor pools, exuded timeless Tuscan elegance. Though the accommodations were newly built in 2018, they honored the design and ambiance of historic villas—with antique-style furnishings, a plush king-sized bed, and double balconies that framed postcard-worthy views of the countryside.
The most relaxing pool
The spa here is a true jewel, with a third indoor-outdoor pool and an atmosphere of tranquil seclusion. As I floated in the warm water, the sound of chickens clucking and roosters crowing outside the spa reminded me that this luxurious property remains deeply connected to the land and local life.
Culinary experiences are where Il Falconiere truly shines. The resort’s Michelin-starred restaurant, helmed by Chef Silvia, is one of the most exquisite dining experiences I’ve had in Italy. With soaring windows that frame the vineyard-draped hills, the dining room is as visually breathtaking as the food itself. Every plate is a masterpiece—and while the cuisine is refined, the ambiance is relaxed and welcoming (yes, even with our 18-month-old in tow!).
The most beautiful Michelin Star meal
Wine lovers will appreciate the family’s own label, which guests can enjoy throughout the property or explore further through cellar tours and guided tastings.
Despite the elevated atmosphere, there’s a warmth and soulfulness to Il Falconiere that makes it feel like home. It’s the kind of place you’ll long to return to the moment you leave.
Dining like a local: Locanda al Pozzo Antico
More scenes from beautiful Cortona
Beyond the elegant hotel restaurants, Cortona also offers wonderful opportunities for casual, homestyle Tuscan dining. Just a short stroll from the town center, Locanda al Pozzo Antico is a hidden gem—unpretentious, authentic, and bursting with flavor.
Run by a charming local nonna who radiates warmth and hospitality, this cozy trattoria specializes in seasonal vegetables, homemade pastas, and a perfectly grilled bistecca alla Fiorentina. The dining room feels like an inviting country home, while a quiet garden patio adds a layer of rustic romance. It’s simple, soulful, and absolutely delicious.
What to do in Cortona (besides eat your way through town)
Quintessential Cortona
While food and wine are at the heart of the Cortona experience, the town offers plenty to see and do between meals.
Climb to the Fortezza del Girifalco, perched above the town, for some of the most spectacular views in all of Tuscany.
Explore local artisan boutiques tucked around the main piazzas—perfect for discovering handmade ceramics, textiles, and antiques.
Visit the Basilica di Santa Margherita, a church that houses the remains of Saint Margaret, Cortona’s patron saint, and still hosts regular services.
The magic of Cortona lies in its contrasts: ancient yet vibrant, luxurious yet grounded, lively yet tranquil. It invites you to slow down, savor every moment, and immerse yourself in the Tuscan way of life.
Need to know
Cortona is a challenging city to drive through, but it’s helpful to have a car to see the surrounding countryside. Travelers should consider this when deciding whether or not to rent a car.
For more inspiration and insider recommendations, visit our Tuscany page.
Travel Advisor
Jennifer Coppolino
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