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![Tuscan Countryside Escape: Chianti and Beyond](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f6a1d-51fe-74f0-814f-5d2950779953/location8.jpg)
Tuscan Countryside Escape: Chianti and Beyond Itinerary
Last updated: 2024 Jun 14Chianti Wine Tasting and Relaxation
Morning
Start your day with a scenic drive through the vineyards of Chianti. Arrive at Castello di Brolio, where you can take a guided tour of the historic castle and enjoy a wine tasting experience.
Afternoon
For lunch, savor traditional Tuscan dishes at Osteria di Brolio, known for its local cuisine. Afterward, visit the charming town of Gaiole in Chianti and explore its picturesque streets.
Evening
Return to your accommodation for a relaxing evening, perhaps with a glass of Chianti wine overlooking the sunset.
Bedtime
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![Visit Brolio Castle (Castello di Brolio) in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/ae/27.jpg)
4.97Castello di Brolio
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![Visit Brolio Castle (Castello di Brolio) in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/ae/27.jpg)
Castello di Brolio
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![Visit Brera in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/a8/69/d8.jpg)
4.69Gaiole in Chianti
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![Visit Brera in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/a8/69/d8.jpg)
Gaiole in Chianti
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Exploring San Gimignano and Lucca
Morning
Depart early for San Gimignano, known for its medieval towers. Wander through the town and visit the Fortezza di Montalcino for panoramic views.
Afternoon
Enjoy a leisurely lunch at Ristorante Dorando, a local favorite. Afterward, continue to the charming city of Lucca and take a bike ride along the ancient city walls.
Evening
Dine at Buca San Giovanni, a hidden gem in Lucca, before heading back to Chianti for the night.
Bedtime
Find amazing hotels in Chianti, Tuscany, Italy.
![Visit Montalcino in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f6/a7.jpg)
4.86San Gimignano
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![Visit Montalcino in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f6/a7.jpg)
San Gimignano
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![Visit Montalcino Fortress (Fortezza di Montalcino) in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/dd.jpg)
4.78Fortezza di Montalcino
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![Visit Montalcino Fortress (Fortezza di Montalcino) in Chianti, Tuscany, Italy](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/dd.jpg)
Fortezza di Montalcino
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Siena and Departure
Morning
Visit the historic city of Siena and explore the Siena Cathedral and the Piazza del Campo. Climb the Torre del Mangia for panoramic views.
Afternoon
Enjoy a traditional Tuscan lunch at Osteria Le Logge in Siena. Afterward, take a leisurely stroll through the city's medieval streets.
Evening
Return to Florence to drop off your car and catch your onward journey, taking with you the memories of your Tuscan countryside escape.
Bedtime
Find amazing hotels in Chianti, Tuscany, Italy.