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Tuscan Delights: Siena, San Gimignano & Chianti 4-Day Itinerary

Tuscan Delights: Siena, San Gimignano & Chianti 4-Day Itinerary Itinerary

Last updated: 2024 Jun 14

Siena's Splendors and Culinary Beginnings

Morning
Begin your Tuscan adventure with a sumptuous breakfast at La Taverna di San Giuseppe, a local favorite. Afterward, immerse yourself in the grandeur of the Siena Cathedral (Duomo) and the exquisite Piccolomini Library (Libreria Piccolomini). The morning light enhances the beauty of these historic sites.
Afternoon
For lunch, indulge in the authentic Tuscan cuisine at Trattoria La Torre, where the flavors are as rich as the surrounding landscape. Post-lunch, explore the Siena Historic Center (Siena Centro Storico), including the iconic Piazza del Campo and the soaring Mangia Tower (Torre del Mangia). Take in the vibrant atmosphere and the architectural marvels.
Evening
As the day winds down, enjoy a delightful dinner at Enoteca I Terzi, known for its extensive wine selection and delectable dishes. Afterward, take a leisurely stroll through the city, savoring the Tuscan evening ambiance.
Bedtime
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Visit Siena Cathedral (Duomo) in Siena
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Siena Cathedral (Duomo)

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Visit Piccolomini Library (Libreria Piccolomini) in Siena
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Piccolomini Library (Libreria Piccolomini)

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Chianti's Vineyards and San Gimignano's Towers

Morning
Fuel up for the day with a hearty breakfast at Il Pomodorino. Today's adventure takes you to the heart of Chianti. Start with the From Siena Chianti and Castles Tour with Wine Tastings, where you'll visit historic wineries, taste world-renowned wines, and enjoy the rolling vineyard views.
Afternoon
After the tour, enjoy a countryside lunch at San Gimignano Lunch or Dinner at a Winery with Wine Tasting [204433]. Post-lunch, explore the medieval marvel of San Gimignano, known for its well-preserved tower houses. Wander through the cobbled streets and take in the panoramic views.
Evening
Return to Siena and unwind with a dinner at Osteria Le Logge, an establishment that perfectly captures the essence of Tuscan dining. Reflect on the day's experiences as you enjoy the culinary delights.
Bedtime
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Visit From Siena Chianti and Castles Tour with Wine Tastings in Siena
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From Siena Chianti and Castles Tour with Wine Tastings

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San Gimignano

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Montalcino's Elegance and Tuscan Cooking

Morning
Start with a visit to the serene Abbey of Sant'Antimo (Abbazia di Sant'Antimo), where the Gregorian chants create a tranquil atmosphere. Then, head to Montalcino, the land of Brunello wine, for a Montalcino Brunello Wine Tasting Experience in the late morning.
Afternoon
Enjoy a delightful lunch at Antica Trattoria Papei, a place that respects tradition and local flavors. Post-lunch, explore the Montalcino Fortress (Fortezza di Montalcino) and the surrounding vineyards. If time allows, consider a visit to the Monteriggioni fortress town.
Evening
Return to Siena and participate in a hands-on Siena Small Group Pasta and Tiramisu Class at a local cooking school. Learn the secrets of Tuscan cuisine and enjoy the fruits of your labor for dinner.
Bedtime
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Visit Abbey of Sant'Antimo (Abbazia di Sant'Antimo) in Siena
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Abbey of Sant'Antimo (Abbazia di Sant'Antimo)

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Montalcino

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Siena's Art, History, and Farewell

Morning
Begin with a guided Siena Guided City Tour with Cathedral Skip-the-Line Entry, providing insights into the city's history and hidden gems. After the tour, enjoy a light breakfast at a local cafe of your choice.
Afternoon
For your final lunch in Siena, savor the dishes at Ristorante Guidoriccio, where the menu reflects the best of Tuscany. Post-lunch, visit the Siena Palazzo Pubblico Entry Ticket and the Siena Civic Museum (Museo Civico di Siena) to appreciate the art and governance of the region.
Evening
Conclude your Tuscan journey with a farewell dinner at a restaurant of your choice, reminiscing about the flavors, sights, and experiences of Siena.
Bedtime
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Siena Guided City Tour with Cathedral Skip-the-Line Entry

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Siena Palazzo Pubblico Entry Ticket

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