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Ultimate 5-Day Tuscany Adventure Itinerary

Last updated: 2024 Jun 14

Florence's Treasures and Tuscan Flavors

Morning

Start your day with a delightful breakfast at Cibrèo Ristorante Firenze, known for its delectable Tuscan cuisine. Afterward, head to the iconic Ponte Vecchio for a leisurely stroll and to admire the jewelry shops. Then, visit the impressive Duomo - Cattedrale di Santa Maria del Fiore and climb to the top for panoramic views of the city.

Afternoon

For lunch, savor the flavors of Tuscany at Osteria dell'Orsa, a charming trattoria known for its authentic dishes. In the afternoon, take a guided tour of the renowned Uffizi Gallery to admire masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci.

Evening

In the evening, indulge in a gourmet dinner at the Michelin-starred Il Canto del Maggio, where you can enjoy innovative Italian cuisine in a picturesque setting.

Bedtime

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Duomo - Cattedrale di Santa Maria del Fiore
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Uffizi Gallery
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Siena's Rich Heritage and Chianti Wines

Morning

Enjoy a delightful breakfast at La Taverna di San Giuseppe, a charming restaurant known for its warm hospitality. Then, explore the medieval streets of Siena, including the magnificent Siena Cathedral and the historic Piazza del Campo.

Afternoon

For lunch, head to La Bottega del Nobile, a hidden gem offering a selection of Tuscan specialties. Afterward, embark on a wine tasting tour in the picturesque Chianti region, visiting local wineries and savoring the renowned wines of the area.

Evening

Conclude your day with a sumptuous dinner at Ristorante La Torre, located in a historic villa with panoramic views. Enjoy the flavors of Tuscany in an elegant and romantic setting.

Bedtime

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Siena
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Siena Cathedral
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San Gimignano's Towers and Culinary Delights

Morning

Start your day with a visit to the iconic San Gimignano, known for its medieval towers and well-preserved architecture. Climb the Torre Grossa for breathtaking views of the surrounding countryside.

Afternoon

For lunch, enjoy a traditional Tuscan meal at Antica Trattoria Botteganova, a family-run restaurant with a warm and welcoming atmosphere. Afterward, join a cheese and wine tasting tour at a local farm, such as San Gimignano Cheese and Wine Tasting Tour, to sample the region's specialties.

Evening

In the evening, take a leisurely stroll through the town and savor a gelato from one of the local gelaterias. For dinner, head to Osteria Acquacheta, a popular eatery known for its hearty Tuscan dishes and lively ambiance.

Bedtime

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San Gimignano
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4.88
San Gimignano Cheese and Wine Tasting Tour
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Montepulciano's Elegance and Wine Heritage

Morning

Enjoy a leisurely breakfast at La Grotta di Montepulciano, a charming restaurant offering a selection of local delicacies. Then, explore the beautiful town of Montepulciano, known for its Renaissance architecture and the famous Cantina del Redi.

Afternoon

For lunch, indulge in a gourmet meal at Osteria Le Logge, a Michelin-starred restaurant known for its creative cuisine. Afterward, visit a local winery for a wine tasting experience, such as Montepulciano Winery Tour with Wine Tasting and Lunch, to sample the renowned Vino Nobile di Montepulciano.

Evening

Conclude your day with a romantic dinner at Il Falconiere, a historic restaurant located in a charming villa. Enjoy the elegant ambiance and exceptional cuisine, accompanied by fine wines from the region.

Bedtime

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Montepulciano
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Montepulciano Winery Tour with Wine Tasting and Lunch
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Chianti's Scenic Beauty and Gastronomic Delights

Morning

Start your day with a visit to the picturesque Chianti region, known for its rolling hills, vineyards, and olive groves. Enjoy a scenic drive through the countryside and stop at a local farm to learn about the production of olive oil and wine.

Afternoon

For lunch, savor the flavors of Chianti at Trattoria Da Burde, a family-run restaurant known for its traditional Tuscan dishes. Afterward, visit a renowned winery for a guided tour and wine tasting, such as Organic Wine Tasting at Fattoria Majnoni Guicciardini, to sample the region's finest wines.

Evening

Conclude your Tuscany adventure with a farewell dinner at Enoteca I Terzi, a popular restaurant in the heart of Chianti. Enjoy a memorable dining experience with a selection of local and international wines.

Bedtime

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