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Tuscan Countryside Escape: Wine, Villages, and Gastronomy Itinerary

Last updated: 2024 Jun 14

Chianti Wine Tour and Tuscan Countryside

Morning

Start your day with a scenic drive to the heart of the Chianti region. Enjoy the rolling hills, vineyards, and olive groves as you make your way to the first winery. Visit the Organic Wine Tasting at Fattoria Majnoni Guicciardini and learn about the organic winemaking process. Sample a selection of their best wines and enjoy the peaceful surroundings.

Afternoon

After the wine tasting, continue your journey through the countryside and stop for a traditional Tuscan lunch at La Grotta di Montepulciano, a family-run restaurant known for its homemade pasta and local specialties. Take your time to savor the flavors and relax in the charming atmosphere.

Evening

In the late afternoon, head to San Gimignano, a UNESCO World Heritage site famous for its medieval towers. Explore the historic center and visit the Duomo with its beautiful frescoes. Climb the Torre Grossa for panoramic views of the town and the surrounding countryside. For dinner, enjoy a cheese and wine tasting experience at Osteria La Porta, where you can sample the region's best cheeses paired with local wines.

Bedtime

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5.00
Organic Wine Tasting at Fattoria Majnoni Guicciardini
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4.11
Duomo
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Florence Exploration and Wine Tasting

Morning

Start your day with a visit to the Accademia Gallery to see Michelangelo's famous statue of David. After the museum, wander through the Mercato Centrale and sample local cheeses, meats, and wines. For a light lunch, try the truffle panini at Da Nerbone.

Afternoon

In the afternoon, take a short drive to the Chianti countryside for a wine tasting experience at Castello di Verrazzano. Learn about the winemaking process and sample some of the region's best wines. Enjoy the picturesque vineyard views.

Evening

For dinner, head back to Florence and dine at Osteria dell'Orsa, a cozy trattoria known for its authentic Tuscan dishes. After dinner, take a romantic evening stroll along the Arno River and enjoy the city lights.

Bedtime

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Accademia Gallery
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Siena Day Trip and Palio Experience

Morning

Depart for Siena, a charming medieval city known for its beautiful cathedral and the famous Palio horse race. Explore the Piazza del Campo, one of Europe's greatest medieval squares, and visit the Siena Cathedral with its stunning facade and interior.

Afternoon

For lunch, try the traditional Tuscan dishes at La Taverna di San Giuseppe, a family-run restaurant in the heart of Siena. After lunch, take a guided tour to learn about the history and traditions of the Palio, Siena's most important event.

Evening

Enjoy a special dinner at Ristorante Il Falconiere, located in the countryside near Siena. The restaurant offers a unique dining experience with a focus on local and seasonal ingredients. After dinner, relax and enjoy the peaceful surroundings.

Bedtime

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4.64
Palio horse race
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4.63
Piazza del Campo
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San Gimignano and Wine Tasting

Morning

Travel to San Gimignano, a UNESCO World Heritage site famous for its medieval towers. Explore the historic center and visit the Duomo with its beautiful frescoes. Climb the Torre Grossa for panoramic views of the town and the surrounding countryside.

Afternoon

For lunch, enjoy a picnic at a local winery, paired with some of the region's best wines. After lunch, take a guided tour of the winery and learn about the winemaking process. Sample different varietals and enjoy the peaceful atmosphere.

Evening

Return to Florence and have dinner at Enoteca I Terzi, a wine bar and restaurant known for its extensive wine list and creative dishes. After dinner, take a leisurely walk through the city and enjoy the vibrant nightlife.

Bedtime

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4.11
Duomo
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4.89
Torre Grossa
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Montepulciano and Pienza Day Trip

Morning

Depart for Montepulciano, a hilltop town known for its Renaissance architecture and the production of Vino Nobile wine. Visit the Piazza Grande and the Duomo, and take a walk along the city walls for panoramic views of the countryside.

Afternoon

For lunch, try the local specialties at La Grotta di Montepulciano, located in a historic wine cellar. After lunch, continue to Pienza, a charming town known for its pecorino cheese. Visit the Palazzo Piccolomini and the Pienza Cathedral, and stroll through the historic center.

Evening

Return to Florence and have dinner at Osteria Le Logge, a Michelin starred restaurant known for its refined Tuscan cuisine. After dinner, take a walk to the Piazzale Michelangelo for breathtaking views of the city at night.

Bedtime

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4.71
Pienza Cathedral
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4.81
Piazzale Michelangelo
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Florence Free Day and Cooking Class

Morning

Enjoy a leisurely morning in Florence. Visit the Boboli Gardens and the Pitti Palace, or take a walk to the San Lorenzo Market for some shopping. For lunch, try the famous lampredotto sandwich at Trattoria Da Burde.

Afternoon

In the afternoon, take a cooking class to learn how to prepare traditional Tuscan dishes. Visit the Mercato di Sant'Ambrogio to buy fresh ingredients, and then head to the kitchen to create a delicious meal. Enjoy the fruits of your labor with a glass of Chianti wine.

Evening

For dinner, try the modern Tuscan cuisine at Il Canto del Maggio, a restaurant located in the countryside near Florence. After dinner, relax and enjoy the peaceful surroundings.

Bedtime

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4.78
Boboli Gardens
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Chianti Wine Tour and Balloon Flight

Morning

Start your day with a hot air balloon flight over the Chianti countryside. Enjoy the breathtaking views of the vineyards, olive groves, and medieval villages from above. After the flight, celebrate with a glass of Prosecco and a traditional Tuscan breakfast.

Afternoon

After the flight, visit a local winery for a wine tasting experience. Learn about the different varietals and the winemaking process, and sample some of the region's best wines. Enjoy a light lunch with a glass of Chianti.

Evening

Return to Florence and have dinner at La Bottega del Nobile, a restaurant known for its extensive wine list and the focus on local ingredients. After dinner, take a walk through the city and enjoy the lively atmosphere.

Bedtime

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Florence Museums and Artisan Workshops

Morning

Spend the morning visiting the Palazzo Vecchio and the Bargello Museum. After the museums, take a walk to the Santa Croce Church and visit the tombs of Michelangelo, Galileo, and Machiavelli.

Afternoon

For lunch, try the traditional Tuscan dishes at Antica Trattoria Botteganova, a historic restaurant located near the Ponte Vecchio. After lunch, visit the Oltrarno and explore the artisan workshops in the area. Watch the craftsmen at work and buy some unique souvenirs.

Evening

For dinner, try the modern Tuscan cuisine at Il Canto del Maggio, a restaurant located in the countryside near Florence. After dinner, relax and enjoy the peaceful surroundings.

Bedtime

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4.72
Palazzo Vecchio
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4.67
Bargello Museum
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Artisan Workshops and Ceramic Class

Morning

Visit Montelupo Fiorentino, a town known for its ceramics. Take a guided tour of the Museum of Ceramics and learn about the history and techniques of ceramic production. Visit some of the local workshops and see the craftsmen at work.

Afternoon

Take a ceramic class and create your own piece of art. Learn how to shape the clay, decorate the piece, and glaze it. Enjoy a light lunch with a glass of local wine. After the class, visit the Ceramics Market and buy some unique souvenirs.

Evening

Return to Florence and have dinner at Osteria Acquacheta, a traditional restaurant known for its grilled meats and the lively atmosphere. After dinner, take a walk through the city and enjoy the vibrant nightlife.

Bedtime

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Florence Free Day and Sunset Wine Tasting

Morning

Afternoon

In the afternoon, take a guided tour of the Palazzo Pitti and the Boboli Gardens. Learn about the history of the palace and the Medici family, and enjoy the beautiful gardens with their fountains and sculptures.

Evening

For dinner, try the modern Tuscan cuisine at Il Canto del Maggio, a restaurant located in the countryside near Florence. After dinner, relax and enjoy the peaceful surroundings.

Bedtime

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4.78
Boboli Gardens
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5.00
Boboli Gardens
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Florence Museums and Artisan Workshops

Morning

Spend the morning visiting the Palazzo Vecchio and the Bargello Museum. After the museums, take a walk to the Santa Croce Church and visit the tombs of Michelangelo, Galileo, and Machiavelli.

Afternoon

Evening

For dinner, try the modern Tuscan cuisine at Il Canto del Maggio, a restaurant located in the countryside near Florence. After dinner, relax and enjoy the peaceful surroundings.

Bedtime

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4.72
Palazzo Vecchio
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4.67
Bargello Museum
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Florence Departure and Farewell Dinner

Morning

Afternoon

Evening

For your farewell dinner, experience the elegance of Cibrèo Ristorante Firenze, known for its innovative Tuscan cuisine. Savor the flavors of the region and toast to the end of your Tuscan adventure.

Bedtime

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