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October 16-21, 2025 | 6 Days, 5 Nights |
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Step into the heart of Tuscany, where harvest season sets the perfect backdrop for an unforgettable wine journey. Staying at the luxurious Castello di Gabbiano, a historic 12th-century estate surrounded by rolling vineyards and olive groves, guests will experience Tuscany at its most vibrant. With visits to charming medieval towns like Siena, Arezzo and Montepulciano, this immersive journey offers the ultimate Tuscan experience. |
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Danielle Callegari is a Wine Enthusiast Tasting Panel Reviewer covering Italy and a Dartmouth Associate Professor specializing in Italian literature, food and beverage studies. As an author on Dante and Italian food history, and co-host of the "Gola" podcast, Danielle brings a wealth of cultural and regional knowledge to the tour experience. Fluent in both English and Italian, she splits her time between New York and Italy. |
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Arrive in Florence and transfer to Castello di Gabbiano. Relax in the afternoon before an evening drive to Panzano. The tour starts with a welcome tasting at Enoteca Baldi, followed by dinner at Dario Cecchini’s restaurant, where Danielle Callegari will discuss wine pairings with the meat-focused menu. |
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Travel to Valdarno, first visiting Tenuta Sette Ponti to explore their cellars and taste Super Tuscans like Oreno and Crognolo. After time in Arezzo, arrive at Il Borro for a tasting of their wines and olive oil. The evening concludes with dinner at this restored medieval estate. |
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Explore Montalcino, beginning at the organic Col d’Orcia estate for a cellar tour and tasting of their Brunello di Montalcino, paired with a Tuscan lunch. The afternoon includes a visit to Argiano to sample their Super Tuscan and Brunello. Dinner will be at a local restaurant. |
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Journey into Chianti Classico, with a visit to the historic Bindi Sergardi estate for a tasting of five wines paired with Tuscan fare. The evening is spent in Siena for an independent dinner and exploration of the medieval city. |
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Discover the Avignonesi estate in Montepulciano, known for its Vino Nobile and organic practices. Enjoy a vineyard and cellar tour followed by a wine-paired lunch. The afternoon offers free time in Montepulciano. Return to Castello di Gabbiano for a farewell dinner, featuring Gabbiano's Chianti Classico Riserva. |
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Following a leisurely morning, bid arrivederci to the Tuscan countryside as you depart from the hotel for your individual flights home, carrying cherished memories of shared moments and the region's romantic allure. |
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Wine Enthusiast’s Cork+Compass Travel is the magazine’s first endeavor into exceptional wine travel and tourism. Our philosophy is rooted in the mission of our parent company, Wine Enthusiast—to enhance the wine experience for all. |
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