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5-Day Historical and Wine Exploration in Cortona, Italy

Viewed by 74 travelers

Day 1: Arrival and Town Exploration

Cortona, Italy on August 1, 2025

9:00am

Breakfast at Bar Pasticceria Vannelli

Start your day with fresh pastries and excellent Italian coffee in the heart of Cortona.
EUR10, 1h0m

10:00am

Walk around Cortona Historical Center

Explore pedestrian streets, medieval architecture, and quaint shops of this hilltop town offering panoramic views of the Val di Chiana.
Free, 2h0m

12:30pm

Lunch at La Bucaccia

Enjoy traditional Tuscan cuisine including homemade pastas and local meats in a rustic and cozy setting.
EUR30, 1h30m

2:00pm

Visit the Diocesan Museum of Cortona

Discover important Renaissance art and the famous Cortona School paintings housed in Palazzo Vagnotti. Open 9:30am-1:00pm and 3:00pm-7:00pm.
EUR5, 1h30m

4:00pm

Relax at Piazza della Repubblica

People-watch and enjoy a gelato while soaking in the lively atmosphere of Cortona’s main square.
EUR5, 1h0m

7:30pm

Dinner at Osteria del Teatro

Savor authentic Tuscan dishes paired with excellent local wines in an intimate setting near the central square.
EUR40, 2h0m
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Day 2: Etruscan History and Museums

Cortona, Italy on August 2, 2025

8:30am

Breakfast at Pasticceria Pulcino

Fresh breads and pastries with cappuccino to start the day before exploring.
EUR8, 0h45m

9:30am

Visit Etruscan Academy Museum (Museo dell'Accademia Etrusca)

Explore one of Italy’s best Etruscan collections featuring artifacts, tomb exhibits and ancient inscriptions. Open 8:30am-1:00pm and 3:30pm-7:00pm.
EUR6, 2h0m

12:00pm

Lunch at Trattoria Dardano

Enjoy classic Tuscan dishes amid a charming traditional setting, perfect to recharge before afternoon explorations.
EUR25, 1h0m

1:30pm

Walk to Roman Theatre Ruins and Panorama

Visit the archaeological remains of the ancient Roman theatre and enjoy sweeping views of the valley from the nearby viewpoint.
Free, 1h30m

3:30pm

Relax coffee break at Caffè Poliziano

Located in Piazza della Repubblica, it offers a great spot for a rest and to sample regional wines and coffee.
EUR5, 1h0m

7:30pm

Dinner at Ristorante Il Falconiere

Dine at a Michelin-starred restaurant that boasts an incredible farm-to-table menu paired with local Cortona wines.
EUR70, 2h30m
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Day 3: Wine Tasting Tour

Cortona Countryside, Italy on August 3, 2025

8:00am

Breakfast at Hotel or Local Cafe

Light breakfast to prepare for a full day of wine tasting and countryside exploring.
EUR10, 0h45m

9:00am

Half-day wine tasting tour with Guia Cortona

Visit top Cortona wineries such as Avignonesi and Tenuta di Gracciano della Seta. Tours include vineyard walks, wine production explanations, and tastings of red and white wines.
EUR60, 4h0m

1:30pm

Lunch at Winery Osteria Le Logge

Enjoy locally prepared dishes paired perfectly with wine from the vineyard, an excellent way to taste true regional flavors.
EUR35, 1h30m

3:30pm

Free time walk in Cortona town

Explore artisan shops, book stores, and discover artisan crafts in Cortona’s charming side streets.
Free, 2h0m

7:30pm

Dinner at La Loggetta

Relaxed dining experience offering fresh Tuscan ingredients and house wines in a peaceful courtyard.
EUR30, 1h45m
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Day 4: Churches and Art

Cortona, Italy on August 4, 2025

8:30am

Breakfast at Siribuono!

Organic and healthy Italian breakfast offerings to energize your morning.
EUR12, 0h45m

9:30am

Visit Basilica di Santa Margherita

Discover this important religious site that holds the remains of the town’s patron saint and features beautiful Renaissance art. Open daily 9:30am-6:00pm.
EUR3, 1h0m

10:45am

San Francesco Church

Explore this historic church known for its serene ambiance and frescoes by Luca Signorelli, the renaissance master.
Free, 1h0m

12:00pm

Lunch at Osteria del Teatro

Return for a casual meal with seasonal specialties perfect for any palate.
EUR28, 1h30m

2:00pm

Visit local artisan workshops

Experience authentic Cortona craftsmanship including pottery, leather, and textiles with opportunities to purchase unique souvenirs.
Free, 2h0m

7:30pm

Dinner at Enoteca La Torre

Taste a broad selection of Tuscan wines paired with regional small plates in this cozy wine bar setting.
EUR35, 2h0m
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Day 5: Farewell Morning and Departure

Cortona, Italy on August 5, 2025

8:30am

Breakfast at Caffè Brittle

Enjoy a relaxed breakfast with fresh Italian espresso and pastries before your last walk.
EUR10, 1h0m

9:30am

Leisure walk and photos at Fortezza del Girifalco

Take in sweeping panoramic views of Cortona and the Tuscan countryside from this historic fortress before departure.
EUR3, 1h0m

11:00am

Farewell lunch at La Loggia del Saracino

Enjoy a final Tuscan meal featuring the best local ingredients paired with established favorites from Cortona’s celebrated wine region.
EUR40, 1h30m
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