Cortona is in a great position, overlooking some of the most beautiful views of Tuscany spread out in all directions below it. Cortona's streets are steep and narrow, so this is a town best explored on foot. Some of the our Guru's recommendations for the best places to stay in Cortona are actually outside the town, but they offer similarly wonderful views over vineyards, olive groves and more beautiful hilltop towns. And that's the really incredible thing about Cortona, there are just so many beautiful rooms with views.
The Piazza della Repubblica is probably the most famous square in Cortona, and a good place to start your explorations. The Piazza Signorelli is right next door, and this is where you'll find the wonderful Sunday flea market and antiques fair, and Cortona's theatre.
You should also see the churches, but that's really a given in Tuscany, the main ones being the Duomo, the Eremo Le Celle a Franciscan hermitage, the Basilica de Santa Margherita - right at the top of the town, and the Chiesa de San Domenico, a 15th Century church home to some wonderful artworks.
Cortona is a great place for walkers - especially those who enjoy a hilly challenge. In the surrounding region you can stroll the old Roman roads of Torreone or Monte Maestrino, or just walk among the vines, and stop for a glass of Chianti in the vineyards dotted around the hills.
Don't forget to book early if you want a bed in one of best places to stay in Cortona during the busy summer months - the town is absolutely heaving in July and August. But if you plan your visit in May, June or September, you'll still have lovely weather (probably better because it won't be so hot), but the streets will be your own.
Still not sure which to book? Browse through our list of all the best places to stay in Cortona, or contact one of our friendly Gurus for advice. Alternatively widen the net and check out all our recommendations in Tuscany.
A stunning country house set in the hills of Chianti. Traditional and cosy interiors have wooden beams, brass bedsteads, stone floors, and antiques. A selection of rooms, suites, and apartments. Fabulous views from the pool area, restaurant, and bar. Cooking lessons and a large wine list.
A striking country house hotel just outside Cortona. Plenty to do; expert cooking lessons, wine tasting, sunbathing by an enormous pool, or strolling through the gardens. Dreamy rooms and suites are traditional and decorated with romance. A great choice for a couple as well as foodies.
This former Medici hunting lodge is now a magical Tuscan family-run hotel. Retreat to the romantic rooms, relax by the pool, stroll around the beautiful gardens, and feast on delicious Tuscan food and wine. The perfect country escape for all to explore Tuscany. Foodies will love the cooking classes.
Pozzo della Chiana Arezzo, Tuscany
Attractive red brick Tuscan villa with stunning views. Sun-soaked walls and terraces, contemporary designed rooms and suites, plus swimming pool and tennis court. Great for couples or for groups to rent exclusively.
Romantic setting for food lovers. Dine at a Micehlin-starred restaurant in a stunning 17th Century Tuscan manor. Beautiful, spacious rooms are a perfect blend of homely meets luxury. Relax by the pool or at the spa. Dining is top class plus you can take part in cooking classes and wine tasting.