Race Day in ChiantiThis 3-day itinerary is your ticket to an action-packed adventure centered around the popular Chianti ultra marathon trail race. Whether you're a seasoned runner looking for a new challenge or simply craving a getaway filled with nature and culture, this trip has something for everyone.Authorsrachelhelsby
DestinationsTuscanyItinerary

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Bellavista - Castello di Bossi
Nestled in Chianti's rolling vineyards, Castello di Bossi is a timeless retreat. Wake up to panoramic views, savor world-class Chianti wines, and explore lush gardens and olive groves. With its blend of modern comfort and Tuscan charm, every moment here is a celebration of la dolce vita.
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Prep Day

Torre del Mangia
Start your day with a visit to the iconic Piazza del Campo, the heart of Siena. Marvel at the stunning medieval architecture, including the Palazzo Pubblico and the Torre del Mangia. Climb to the top of the tower for panoramic views of the city and surrounding countryside.
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Siena’s Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
After exploring the city, I highly recommend joining a guided food tour. These tours offer a fantastic opportunity to explore the city's food scene in depth, led by local experts who know all the best spots. You'll get to taste a variety of traditional Tuscan dishes, from freshly made pasta to artisanal cheeses and wines.
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Siena Private Walking Tour: Traditions, Streets & Cathedral
Whether you're a history buff, an art enthusiast, or simply curious about Siena's cultural treasures, this guided tour is sure to leave you inspired and amazed.
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La Taverna di San Giuseppe
Now it's time to carb load! Indulge in authentic Tuscan flavors at Taverna di San Giuseppe in Siena. With its cozy ambiance and traditional dishes, like hearty ribollita and tender bistecca alla Fiorentina, it's the perfect spot to experience the culinary delights of Tuscany.
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Race Day

Sandy
Before the race starts grab a quick espresso from Pasticceria Gelateria Sampoli & Lapis, who open early for the race start.
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Chianti Ultra Trail by Utmb
Get ready for a wild ride at Chianti Ultra Trail in the charming town of Radda in Chianti! With breathtaking views of the Tuscan countryside, this trail race offers a challenging course for all levels of runners. Lace up those sneakers and get ready to conquer the hills and vineyards of this beautiful region. Don't forget to refuel with some delicious Chianti wine afterwards!
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Ristorante Enoteca di Colle Bereto
You did it!!! Now time to celerbate and eat at Ristorante Enoteca di Colle Bereto! Indulge in local Chianti wines paired with delicious Tuscan dishes, all while enjoying the picturesque views of Piazza IV Novembre.
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Rest Day

Pasticceria Chianti
It's the day after the race, so it's time to explore more of Tuscany. Head to Greve in Chianti for a morning cappucino and cornetto at Pasticceria Chianti.
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Montefioralle
Next, visit the delightful village of Montefioralle, where you can meander through its cobblestone streets and soak in the breathtaking views of the Chianti countryside.
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Fontodi
Indulge in the quintessential Tuscan experience with a wine tasting at Fontodi. Nestled in the heart of Tuscany, Fontodi is renowned for its exquisite wines and stunning vineyard views.
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Osteria Le Panzanelle
Enjoy a delicious dinner at Osteria Le Panzanelle in Tuscany. With its cozy atmosphere and authentic Tuscan dishes, it's the perfect spot to unwind after a day of exploring.
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