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Ultimate 5-Day Tuscany Itinerary Itinerary

Last updated: 2024 Jun 14

Wine and Ancient Fortresses

Morning

Begin your journey with a hearty breakfast at the renowned Ristorante Dopolavoro La Foce, where you'll enjoy local flavors to start your day. After breakfast, take a guided tour of the historic Montalcino Fortress (Fortezza di Montalcino), learning about the region's rich history and enjoying panoramic views of the surrounding vineyards.

Afternoon

For lunch, head to La Porta, a charming eatery known for its Tuscan cuisine. Spend your afternoon visiting the Abbey of Sant'Antimo (Abbazia di Sant'Antimo), where you can witness a stunning example of Romanesque architecture and enjoy the serene atmosphere.

Evening

As the day winds down, savor a gourmet dinner at Trattoria Osenna, offering a menu filled with local specialties. Conclude your evening with a leisurely stroll through the historic center of Montalcino, taking in the ambiance of this picturesque town.

Bedtime

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Art, Cheese, and Idyllic Views

Morning

Start your day with a delightful breakfast at Ristorante La Parolina, known for its innovative dishes. Afterward, take a guided tour of the Pienza Cathedral (Cattedrale dell'Assunta), admiring its Renaissance architecture, and then explore the charming streets of the Pienza Historic Centre (Centro Storico).

Afternoon

Enjoy a sumptuous lunch at Osteria Perillà, which offers a menu showcasing the flavors of the region. Spend your afternoon visiting a local cheese producer, such as Pecorino di Pienza, where you can learn about the cheese-making process and indulge in tastings.

Evening

For dinner, head to Locanda del Loggiato, a cozy restaurant with a menu featuring traditional Tuscan dishes. Cap off your evening with a visit to the Valley of the Orcia (Val d'Orcia), where you can witness the breathtaking landscapes that have earned this area UNESCO World Heritage status.

Bedtime

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Noble Wines and Renaissance Splendor

Morning

Begin your day with a visit to the Montepulciano Historic Centre (Centro Storico), where you can explore the town's medieval and Renaissance architecture. Enjoy a delightful breakfast at a local cafe and take in the panoramic views of the surrounding countryside.

Afternoon

Savor a leisurely lunch at La Grotta, known for its regional cuisine. Afterward, indulge in a wine tasting at one of the renowned wineries in the area, such as Cantina Fattoria della Talosa, where you can sample the Vino Nobile di Montepulciano.

Evening

For dinner, choose Ristorante Il Silene, a Michelin-starred restaurant offering an unforgettable dining experience. Afterward, take a stroll through the Talosa Winery (Fattoria della Talosa), enjoying the vineyard views and the crisp evening air.

Bedtime

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5.00
Montepulciano Historic Centre (Centro Storico)
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Countryside Serenity and Culinary Delights

Morning

Wake up to a delightful breakfast at La Taverna di San Giuseppe, a local favorite. Spend your morning exploring the idyllic landscape with a visit to the Fields of Pienza (Campi di Pienza), where you can enjoy the peaceful countryside and take memorable photos.

Afternoon

Enjoy a leisurely lunch at Osteria del Borgo, known for its rustic charm and traditional dishes. Afterward, take a guided tour of the Podere Il Casale, a local farm where you can learn about organic farming practices and enjoy a farm-to-table cheese and wine tasting.

Evening

For dinner, head back to Pienza and dine at La Bottega del Nobile, a restaurant that celebrates the local flavors. Conclude your evening with a visit to the Podere Santa Maria della Scala, where you can witness a stunning sunset over the Tuscan hills.

Bedtime

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4.87
Podere Santa Maria della Scala
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Medieval Marvels and Culinary Traditions

Morning

Start your day with a visit to the Siena Cathedral (Duomo di Siena), a magnificent example of Italian Gothic architecture. After marveling at the cathedral, enjoy a traditional Tuscan breakfast at a local cafe.

Afternoon

Explore the Siena Historic Centre (Centro Storico), a well-preserved medieval city with narrow streets and historic landmarks. For lunch, indulge in the famous Sienese cuisine at Ristorante Dopolavoro La Foce, known for its local flavors and elegant setting.

Evening

As the sun sets, take a relaxing stroll to the Palio di Siena, the vibrant horse race that has been a tradition in Siena for centuries. For dinner, enjoy the innovative dishes at Ristorante Il Silene, a Michelin-starred restaurant that offers a memorable dining experience.

Bedtime

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