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Tuscan Delights: Siena and Val d'Orcia 5-Day Itinerary

Tuscan Delights: Siena and Val d'Orcia 5-Day Itinerary Itinerary

Last updated: 2024 Jun 14

Siena City Exploration and Culinary Delights

Morning
Start your day with a delightful breakfast at Il Pomodorino, known for its fresh pastries and great coffee. Afterward, immerse yourself in the beauty of the Siena Cathedral (Duomo) and the Piccolomini Library (Libreria Piccolomini) with your Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS).
Afternoon
For lunch, savor the traditional Tuscan flavors at Trattoria La Torre, a local favorite. In the afternoon, take a Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets to discover the Piazza del Campo, the Mangia Tower (Torre del Mangia), and the Siena Historic Center (Siena Centro Storico).
Evening
Enjoy a memorable dinner at Osteria Le Logge, known for its authentic Tuscan cuisine. Afterward, take a leisurely stroll through the charming streets of Siena.
Bedtime
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Siena Cathedral (Duomo)

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Piccolomini Library (Libreria Piccolomini)

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Siena Cathedral Complex Pass with Audio Guide (OPA SI PASS)

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Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

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Piazza del Campo

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Mangia Tower (Torre del Mangia)

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Siena Historic Center (Siena Centro Storico)

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Wine and Dine in Chianti

Morning
Indulge in a delicious breakfast at Antica Trattoria Papei, a historic restaurant in Siena. After breakfast, embark on a Total Immersion Wine Tour in Chianti to experience the best of the region's wines.
Afternoon
Enjoy a gourmet lunch at a Tuscan castle during the wine tour. In the afternoon, continue your wine exploration with a visit to an Organic Winery Tour and Wine Tasting in Siena.
Evening
For dinner, head to Ristorante Guidoriccio, a renowned restaurant in Siena. Relax and enjoy the evening in the heart of Tuscany.
Bedtime
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Total Immersion Wine Tour in Chianti

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Organic Winery Tour and Wine Tasting in Siena

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Cultural Immersion in Siena

Morning
Start your day with a delightful breakfast at Enoteca I Terzi, known for its excellent wine selection and Italian cuisine. After breakfast, visit the Siena Civic Museum (Museo Civico di Siena) and the Baptistery of San Giovanni (Battistero di San Giovanni).
Afternoon
For lunch, enjoy the local specialties at La Taverna di San Giuseppe. In the afternoon, take a Siena Walking Tour with Cathedral and Crypt & Museum Option to delve deeper into the history of Siena.
Evening
Dine at Trattoria La Torre, known for its panoramic views of the city. After dinner, take a leisurely evening walk through the enchanting streets of Siena.
Bedtime
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Siena Civic Museum (Museo Civico di Siena)

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Baptistery of San Giovanni (Battistero di San Giovanni)

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Siena Walking Tour with Cathedral and Crypt & Museum Option

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Montalcino Wine Paradise

Morning
Enjoy a scenic drive to Montalcino and have a relaxing breakfast at a local cafe. Then, experience a Montalcino Brunello Wine Tasting Experience in the heart of this renowned wine region.
Afternoon
Delight in a leisurely lunch at one of the local trattorias. Afterward, visit the Montalcino Fortress (Fortezza di Montalcino) and take a stroll through the charming streets of the town.
Evening
Conclude your day with a memorable Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle experience. Enjoy the sunset over the vineyards before heading back to Siena.
Bedtime
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Montalcino Brunello Wine Tasting Experience

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Montalcino Fortress (Fortezza di Montalcino)

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Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle

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Siena Countryside and Farewell

Morning
For your last day, enjoy a peaceful morning with a Siena 2 hour Horseback Riding Tour in the Siena Countryside. After the ride, have a relaxed brunch at a local farmhouse.
Afternoon
Spend the afternoon at leisure, exploring the Siena Highlights Self-Guided Scavenger Hunt and City Tour. Visit any sites you may have missed and take in the beauty of the city.
Evening
End your trip with a special dinner at La Taverna di San Giuseppe, savoring the flavors of Tuscany. Raise a glass to a wonderful time in Siena and the Val d'Orcia.
Bedtime
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Siena 2 hour Horseback Riding Tour in the Siena Countryside

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Siena Highlights Self-Guided Scavenger Hunt and City Tour

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