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7 Days Exploring Tuscany's Wine Roads Itinerary

Last updated: 2024 Jun 14

Welcome to Tuscany's Vineyards

Morning

Start your Tuscan adventure with a visit to Castle of Meleto (Castello di Meleto). This historic castle offers stunning views of the Chianti region and is renowned for its wine production. Enjoy a guided tour of the vineyards and cellars, followed by a wine tasting session where you can sample some of the finest Chianti wines.

Afternoon

Head to the charming town of Radda in Chianti for lunch at Osteria del Gambero Rosso. This local favorite serves traditional Tuscan dishes made from fresh, locally sourced ingredients. After lunch, explore the town's medieval streets and visit local shops selling artisanal products.

Evening

Conclude your first day with dinner at Buca Lapi, one of Florence's oldest restaurants. Located in the cellars of Palazzo Antinori, this restaurant is famous for its Bistecca alla Fiorentina (Florentine steak) and other Tuscan specialties.

Bedtime

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Castle of Meleto (Castello di Meleto)
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Historic Siena and Its Surroundings

Morning

Begin your day with a visit to Palio of Siena (Palio di Siena). While the famous horse race takes place only twice a year, you can still explore Piazza del Campo where it happens. The square is surrounded by beautiful medieval buildings and is perfect for a morning stroll.

Afternoon

For lunch, dine at Trattoria da Burde, known for its hearty Tuscan cuisine. Afterward, visit Siena Civic Museum (Museo Civico di Siena) located in Palazzo Pubblico. The museum houses an impressive collection of Sienese art and offers insights into the city's rich history.

Evening

End your day with dinner at Enoteca Pinchiorri in Florence. This Michelin-starred restaurant offers an exquisite dining experience with a menu that combines traditional Tuscan flavors with modern culinary techniques.

Bedtime

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Palio of Siena (Palio di Siena)
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Siena Civic Museum (Museo Civico di Siena)
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Exploring Medieval Hill Towns

Morning

Travel to San Gimignano and start your day by visiting Basilica of Santa Maria Assunta (Duomo di San Gimignano). This Romanesque church features stunning frescoes that depict scenes from the Old and New Testaments.

Afternoon

Enjoy lunch at Ristorante La Grotta, located near the town's main square. The restaurant offers delicious Tuscan dishes in a cozy setting. After lunch, take some time to explore San Gimignano's medieval towers and charming streets.

Evening

In the evening, head to Montalcino for dinner at Da Caino. This two-Michelin-starred restaurant is renowned for its innovative take on traditional Tuscan cuisine. Be sure to try their signature dishes paired with local wines.

Bedtime

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Basilica of Santa Maria Assunta (Duomo di San Gimignano)
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The Beauty of Val d'Orcia

Morning

Start your day with a scenic drive through Val d'Orcia, a UNESCO World Heritage site known for its breathtaking landscapes. Visit Pienza, a picturesque town famous for its Renaissance architecture and pecorino cheese.

Afternoon

Have lunch at one of Pienza's charming eateries before heading to Montepulciano. Visit local wineries where you can taste Vino Nobile di Montepulciano, one of Tuscany's most esteemed wines.

Evening

For dinner, dine at La Pergola in Rome if you're up for a short trip or choose another local restaurant in Montepulciano offering authentic Tuscan cuisine paired with excellent wines.

Bedtime

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Pienza
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Discovering Lucca's Charms

Morning

Begin your day in Lucca with a visit to Lucca Clock Tower (Torre delle Ore). Climb to the top for a panoramic view of the city and its surrounding countryside. The tower is one of the most iconic landmarks in Lucca and offers a unique perspective on this historic town.

Afternoon

For lunch, head to a local favorite, , where you can enjoy traditional Tuscan dishes in a cozy setting. Afterward, explore Via Fillungo, Lucca's main shopping street lined with boutiques, cafes, and historic buildings.

Evening

Conclude your day with dinner at , known for its delicious regional cuisine and warm ambiance. Enjoy a leisurely meal as you reflect on the day's discoveries.

Bedtime

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Lucca Clock Tower (Torre delle Ore)
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Via Fillungo
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Art and History in Florence

Morning

Start your day with a visit to Dante House Museum (Museo Casa di Dante). This museum is dedicated to the life and works of Dante Alighieri, one of Italy's greatest poets. Explore exhibits that provide insight into his life and the historical context of his work.

Afternoon

Have lunch at , where you can savor authentic Florentine dishes. Afterward, visit Palazzo Strozzi, an impressive Renaissance palace that hosts rotating art exhibitions. Take your time exploring the galleries and enjoying the beautiful architecture.

Evening

For dinner, dine at , offering a delightful menu that combines traditional Tuscan flavors with modern culinary techniques. End your evening with a stroll along the Arno River, taking in the beauty of Florence by night.

Bedtime

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Dante House Museum (Museo Casa di Dante)
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Palazzo Strozzi
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The Coastal Beauty of Cinque Terre

Morning

Travel to Cinque Terre National Park and start your day by exploring one of its picturesque villages. Visit Cinque Terre National Park (Parco Nazionale delle Cinque Terre) for breathtaking views of the coastline and charming colorful houses.

Afternoon

Enjoy lunch at a seaside restaurant such as , where you can taste fresh seafood while overlooking the Mediterranean Sea. Spend your afternoon hiking along one of the park's scenic trails or relaxing on the beach.

Evening

End your trip with dinner at another local gem like , known for its excellent seafood dishes and stunning views. Reflect on your week-long adventure through Tuscany as you enjoy your final meal in this beautiful region.

Bedtime

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