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Tuscan Wine & Medieval Towns Exploration Itinerary

Last updated: 2024 Jun 14

Florence's Art & Culinary Delights

Morning

Begin your Tuscan adventure with a delightful breakfast at Cibrèo Ristorante Firenze, known for its authentic Italian cuisine. Afterward, immerse yourself in the art world with a visit to the renowned Uffizi Gallery, where you can admire masterpieces by artists like Michelangelo and Leonardo da Vinci.

Afternoon

For lunch, head to Osteria La Porta, a charming restaurant in Monticchiello, known for its Tuscan specialties. Post-lunch, take a scenic drive to the medieval town of Montalcino, famous for its Brunello wine. Explore the town and visit the Montalcino Fortress (Fortezza di Montalcino) for panoramic views.

Evening

In the evening, indulge in a gourmet dinner at Il Canto del Maggio, a Michelin-starred restaurant in the heart of Tuscany. Afterward, unwind with a leisurely stroll through the historic streets of Florence, taking in the magical ambiance of the city at night.

Bedtime

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Uffizi Gallery
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Montalcino
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Siena's Rich History & Gastronomy

Morning

Enjoy a traditional Tuscan breakfast at Antica Trattoria Botteganova, a cozy eatery in Siena. Then, delve into the city's history with a visit to the Siena Cathedral (Duomo di Siena), a stunning example of Italian Gothic architecture. Climb the Torre del Mangia for panoramic views of the city.

Afternoon

For lunch, savor the flavors of Tuscany at La Grotta di Montepulciano, a rustic restaurant in Montepulciano. Afterward, explore the town's medieval streets and visit the La Bottega del Nobile, a wine shop where you can taste the famous Vino Nobile di Montepulciano.

Evening

In the evening, enjoy a memorable dinner at La Taverna di San Giuseppe, known for its traditional Tuscan dishes. After dinner, take a leisurely walk through Siena's Piazza del Campo, one of Italy's most famous squares, and soak in the vibrant atmosphere.

Bedtime

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Siena Cathedral (Duomo di Siena)
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Torre del Mangia
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San Gimignano's Towers & Culinary Delights

Morning

Start your day with a delicious breakfast at Ristorante Il Falconiere, a Michelin-starred restaurant in Cortona. Then, explore the medieval town of San Gimignano, known for its iconic towers. Visit the Basilica of Santa Maria Assunta (Duomo di San Gimignano) and climb the Torre Grossa for panoramic views.

Afternoon

For lunch, enjoy a farm-to-table experience at La Torre, a restaurant in San Gimignano. Afterward, join a San Gimignano "Hands in dough" Cooking Class with Lunch to learn the art of Tuscan cuisine. In the afternoon, indulge in a San Gimignano Olive Oil Tasting and Tuscan Snacks.

Evening

In the evening, take a leisurely stroll through the town's medieval streets and enjoy the enchanting atmosphere. For dinner, head to La Bottega del Nobile, a wine shop and restaurant where you can taste a variety of local wines paired with traditional Tuscan dishes.

Bedtime

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San Gimignano
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Basilica of Santa Maria Assunta (Duomo di San Gimignano)
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Chianti's Vineyards & Scenic Beauty

Morning

Enjoy a leisurely breakfast at Enoteca I Terzi, a wine bar and restaurant in Siena. Then, embark on a From Florence Chianti Half-Day Afternoon Tour to explore the picturesque Chianti region. Visit vineyards, taste local wines, and enjoy the stunning countryside views.

Afternoon

For lunch, stop at Osteria Le Logge, a historic restaurant in Siena known for its Tuscan cuisine. Afterward, continue your wine exploration with a visit to Chianti Terre Di Perseto Winery Guided Tasting & Tour, where you can learn about the winemaking process and sample different varietals.

Evening

In the evening, return to Siena and dine at Osteria dell'Orsa, a cozy trattoria with a warm atmosphere. After dinner, take a romantic evening walk along the Mascagni Terrace (Terrazza Mascagni) and enjoy the panoramic views of the city.

Bedtime

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From Florence Chianti Half-Day Afternoon Tour
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Chianti Terre Di Perseto Winery Guided Tasting & Tour
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Pisa's Leaning Tower & Coastal Charm

Morning

Begin your day with a hearty breakfast at Trattoria Mario, a popular restaurant in Pisa. Then, visit the iconic Leaning Tower of Pisa (Torre Pendente), a UNESCO World Heritage Site. Climb to the top for a unique perspective of the city.

Afternoon

For lunch, enjoy a seafood feast at Santa Margherita Basilica (Basilica di Santa Margherita) [18995], a restaurant overlooking the sea. Afterward, take a leisurely walk along the Livorno Aquarium (Acquario di Livorno) and explore the city's maritime history.

Evening

In the evening, return to Pisa and dine at Trattoria Da Burde, a family-run trattoria known for its authentic Tuscan dishes. After dinner, take a romantic stroll along the Mascagni Terrace (Terrazza Mascagni) and enjoy the sea breeze.

Bedtime

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