Cortona Travel Guide – How to Give, Grow, Dine & Play the Tuscan Way

If you’re dreaming of a charming Tuscan hill town with rich history, stunning views, and unforgettable food and wine—look no further than Cortona, Italy.

We spent extended time in this magical place, fully embracing the wise words of Thomas Merton:

“Take more time, cover less ground.”

Here’s how to make the most of your visit to Cortona—where to go, what to see, and where to eat.

🏛️ Things to Do in Cortona – Give & Grow

Whether you’re hiking ancient stone streets or pausing in sacred spaces, Cortona offers moments to connect, reflect, and grow.

1. Basilica di Santa Margherita: A rewarding uphill walk leads to this beautiful 14th-century church dedicated to Santa Margherita da Cortona. Come for the views—stay for the peace and grandeur.

2. Chiesa San Francesco: Built in 1247 in the distinctive Franciscan style, this church is a quiet treasure. Inside, you’ll find beautiful works of art, including Annunciation by Pietro da Cortona.

3. Duomo di Cortona: Dedicated to the Assumption of the Virgin Mary, this Roman Catholic cathedral features classic Romanesque architecture and is a peaceful place to pause and take in the town’s sacred heritage.

4. Hermitage of Le Celle: Just a few kilometers from Cortona’s old town, this serene retreat feels worlds away. Founded in 1211, the Hermitage is still a “house of prayer” for those seeking quiet reflection and inner peace.

5. La Giostra dell’Archidado:If you’re lucky enough to be in town in June, catch this medieval festival celebrating the 1397 wedding of Francesco Casali and Antonia Salimbeni. Complete with costumes, archery, parades, and flag-flying games—it’s unforgettable.

🍷 Where to Eat in Cortona – Dine & Play

Tuscany is a dream for food and wine lovers, and Cortona is no exception. Here are a few of our favorite stops:

1. Bar 500: A laid-back wine bar in the heart of town. Great for a snack, spritz, or casual meal between exploring.

2. Enoteca Enotria: This Enoteca offers a range of wines, sparkling wines, beer, along with Italian meats and cheeses for a perfect pairing.

3. Ercolani Wines: This shop is the Cortona outpost of the Ercolani family winery from Montepulciano. Stop in for a guided tasting with warm, knowledgeable sommeliers. Don’t forget to say hi to Serina and Sara for us!

4. Locanda al Pozzo Antico: Located in a historic building of 1400, Pozzo Antico (Ancient Well) is a wonderful choice for an authentic Tuscan meal in a casually elegant atmosphere.

5. Trattoria Toscana: Loved by both locals and visitors, this trattoria is a highlight for homemade pasta, seasonal specials, and heartfelt Italian hospitality.

🌿 Why Visit Cortona?

Cortona is a true gem tucked into the Tuscan hills. Take your time, soak in the views, savor the flavors, and embrace la dolce vita—the sweet life!

For more information, check out these links:

Bar 500

Basilica di Santa Margherita

Chiesa San Francesco

Duomo di Cortona

Enoteca Enotria

Ercolani Winery – Cellars in Montepulciano, a wine store, and tastings in Cortona

Hermitage of Le Celle

La Giostra dell’Archidado

Locanda al Pozzo Antico

Trattoria Toscana