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5 Days of Chianti Charm Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chianti

Morning

Start your journey in the heart of Chianti with a visit to Castello di Brolio. This historic castle offers stunning views of the surrounding vineyards and a fascinating history dating back to the 12th century. After exploring the castle, take a leisurely stroll through its beautiful gardens. For breakfast, enjoy a delicious meal at Barone Ricasoli. Their pastries and coffee are highly recommended.

Afternoon

In the afternoon, head to Greve in Chianti, one of the most charming towns in the region. Explore the picturesque Piazza Matteotti, lined with quaint shops and cafes. Don't miss the chance to visit the Wine Museum to learn about Chianti's rich winemaking history. For lunch, dine at La Cantina, known for its traditional Tuscan dishes and excellent wine selection.

Evening

As evening falls, make your way to Montefioralle, a medieval village near Greve in Chianti. Wander through its narrow streets and enjoy the peaceful atmosphere. For dinner, savor a meal at Ristorante Il Guerrino, which offers stunning views of the surrounding countryside and delicious local cuisine.

Bedtime

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4.68
Castello di Brolio
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4.85
Greve in Chianti
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Wine Tasting and Scenic Views

Morning

Begin your day with a visit to Verranzzano Castle. This historic site not only offers breathtaking views but also provides an opportunity for wine tasting. Learn about the winemaking process and sample some of their finest wines. Enjoy breakfast at Castello di Verrazzano Restaurant, where you can indulge in fresh pastries and coffee while taking in panoramic views.

Afternoon

In the afternoon, take a scenic drive through the rolling hills of Chianti to reach Panzano in Chianti. This charming village is known for its vibrant food scene and stunning landscapes. Visit local artisan shops and enjoy lunch at Officina della Bistecca, famous for its mouthwatering steaks prepared by renowned butcher Dario Cecchini.

Evening

Conclude your day with a visit to Badia a Passignano, an ancient abbey surrounded by vineyards. Take a guided tour of this historic site and learn about its significance in Chianti's history. For dinner, dine at Osteria di Passignano, located within the abbey's grounds, offering exquisite Tuscan cuisine paired with fine wines.

Bedtime

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4.52
Verranzzano Castle
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4.63
Panzano in Chianti
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Cultural Immersion in Chianti

Morning

Start your day with a visit to Radda in Chianti. This picturesque town is known for its medieval architecture and charming streets. Explore Palazzo del Podestà and enjoy breakfast at Bar Dante Alighieri, where you can savor freshly baked goods and aromatic coffee.

Afternoon

In the afternoon, head to Castellina in Chianti, another beautiful town in the region. Visit Rocca di Castellina, an ancient fortress offering panoramic views of the countryside. Enjoy lunch at Taverna Squarcialupi, known for its delicious Tuscan dishes made from locally sourced ingredients.

Evening

End your day with a visit to Volpaia, a well-preserved medieval village surrounded by vineyards. Take a leisurely walk through its cobblestone streets and soak in the serene atmosphere. For dinner, dine at La Bottega di Volpaia, offering traditional Tuscan cuisine paired with exceptional wines.

Bedtime

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Art and History in Chianti

Morning

Begin your day with a visit to Gaiole in Chianti. This quaint town is known for its rich history and beautiful architecture. Start with a tour of the Church of San Sigismondo, a stunning example of Romanesque architecture. For breakfast, stop by Caffè le Logge, where you can enjoy freshly baked pastries and a cup of aromatic coffee.

Afternoon

In the afternoon, head to Castello di Meleto, a magnificent castle surrounded by vineyards. Take a guided tour to learn about its history and explore its beautifully preserved interiors. Don't miss the chance to taste some of the estate's wines. For lunch, dine at Ristorante Il Celliere, known for its delicious Tuscan cuisine and scenic views.

Evening

As evening approaches, make your way to San Donato in Poggio, a charming village with medieval roots. Wander through its narrow streets and visit the Church of Santa Maria della Neve. For dinner, savor a meal at La Locanda di Pietracupa, which offers traditional Tuscan dishes made from locally sourced ingredients.

Bedtime

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4.56
Castello di Meleto
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4.27
San Donato in Poggio
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Relaxation and Farewell

Morning

Lamole is your first stop today. This small village offers breathtaking views of the surrounding vineyards and hills. Start your day with breakfast at Ristoro di Lamole, where you can enjoy fresh pastries and coffee while taking in the stunning scenery.

Afternoon

Castello di Volpaia awaits you in the afternoon. This historic castle is not only an architectural gem but also home to some of Chianti's finest wines. Take a guided tour to learn about its history and enjoy wine tasting sessions. For lunch, dine at Osteria Volpaia, known for its exquisite Tuscan dishes.

Evening

Pieve di San Leolino is your final destination for this trip. This ancient church is renowned for its beautiful frescoes and serene atmosphere. Spend some time exploring the church and its surroundings before heading to dinner at Ristorante La Castellana, which offers delicious local cuisine paired with fine wines.

Bedtime

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