May 17-22, 2027 | 6 days, 5 nights

October 21-26, 2027 | 6 days, 5 nights

Dr. Danielle Callegari is a reviewer of Italian wines on the Wine Enthusiast Tasting Panel. Fluent in both English and Italian, Danielle is a Dartmouth Associate Professor specializing in Italian literature, food, and beverage studies. As an author on Dante and Italian food history as well as the co-host of the Gola podcast, Danielle brings a wealth of cultural and regional knowledge to the Cork+Compass Travel experience.

Once a medieval hamlet and now a meticulously restored estate, Il Borro blends centuries of Tuscan heritage with a modern commitment to organic and sustainable winemaking. Explore the estate’s vineyards and historic cellars before tasting a selection of Il Borro’s wines, which reflect the character of the Valdarno di Sopra terroir and the estate’s dedication to crafting expressive, elegant wines.

One of Montalcino’s pioneering estates in organic viticulture, Col d’Orcia has cultivated the character of its land through generations of winemaking. Explore the estate’s historic cellars before tasting six wines, including the elegant Brunello Vigna Nastagio and bold, age-worthy Poggio al Vento Riserva. A traditional Tuscan lunch completes the experience, pairing the estate’s wines with the flavors of the region.

Founded by the Zingarelli family, Rocca delle Macìe brings together generations of family history, Tuscan hospitality, and a deep connection to the land. Walk through Le Macìe, the beating heart of the winery, to discover the family’s winemaking philosophy before settling in for a tasting menu lunch at Oltre Osteria, housed within a beautifully restored medieval village.

With roots stretching back generations in the Chianti Classico region, Bindi Sergardi is a historic estate where Tuscan winemaking tradition remains at the heart of the experience. Taste a selection of the estate’s award-winning wines, including the elegant Chianti Classico La Ghirlanda and the opulent Calidonia Gran Selezione, expressions of the estate’s enduring connection to its land.

Exclusive access to world-class wineries, guided by the Wine Enthusiast Tasting Panel experts.

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