Perched atop a hillside in Chianti, Italy, the villa Poggio alle Corti looks like it’s been plucked out of a Tuscan daydream. The 11th-century estate’s olive groves and vineyards produce their own olive oil, balsamic vinegar, wine, and grappa. An ancient Roman road runs through the nearby village. In the distance, the medieval town of San Donato beckons, but so do the villa’s grounds, which feature sprawling terraces, a stone-lined walk-in pool, tennis court, billiard room, bocce court, fitness center, and idyllic walking trails.
What sets Poggio alle Corti apart, however, is not just its beauty, but its connection to Tuscany’s Renaissance heritage. The region was once home to legendary figures like Leonardo da Vinci, Michelangelo, and Dante, whose influence still shapes the landscape. The villa subtly honors this history with guest rooms named for these great minds—including the Galileo Room, where a private terrace opens onto starlit Tuscan skies. The Renaissance spirit is woven into the very fabric of the region, from its artisanal traditions to world-famous masterpieces like Florence’s Statue of David, giving every stay a deeper cultural resonance.
Like many Tuscan villas, Poggio alle Corti is available for visitors to rent. Unlike many villas, though, this one is owned by a North Shore entrepreneur. “The kids just love exploring and running around the gardens, catching lizards,” says Kevin Anderson, CEO of the ghostwriting and book-coaching firm Kevin Anderson & Associates (KAA). “Last time, we found a couple hedgehogs so docile and calm that you could just pick them up and hold them.”
Anderson lives in West Newbury with his wife and four children, who range in age from 10–15. The couple honeymooned in Tuscany and fell in love with the region, visiting frequently for many years until they decided to put down roots there themselves. “It’s not a straightforward or easy process to acquire a villa in Italy, especially when it’s as old as this one,” Anderson says.
But it was worth every challenge. The 9,000-square-foot villa, set on a 35-acre estate, is “an old fortress and noble residence,” with six-foot-thick stone walls and archways that date back to the 11th century. Even the property’s expansions and renovations are centuries old, some completed in the 1500s. Inside, guests find soaring ceilings, fully renovated marble bathrooms, a chef’s kitchen, and grand fireplaces—luxury finishes that blend seamlessly with the villa’s ancient architecture and historic charm.
The estate is surrounded by Etruscan relics and Roman roads that twist through the landscape. “The Romea Sanese is an ancient road between Florence and Siena that goes right through the property,” Anderson says. “It’s magical to think how many cultures have walked that same cobblestone.” Anderson and his family visit several times each year, welcoming extended family and friends as well. But from the beginning, they wanted the villa to be more than a private retreat.
“We didn’t want to have a home that just sits there and does nothing,” he says. “We wanted something that could really bring people together, be a vibrant entity in itself, and be self-sustaining.” Poggio alle Corti has done exactly that. Less than 25 miles from Florence, it has become a gathering place for guests from all over the world. It hosts weddings, corporate events, and vacations, and KAA includes a week-long stay at the villa for its employees and their families as part of its benefits package.
KAA also operates all-inclusive writers’ retreats at the villa, bringing in renowned editors, literary agents, and bestselling authors for immersive weeklong master classes on topics ranging from the craft of storytelling to memoir writing and nonfiction publishing. “The writers’ retreat mentors are truly incredible,” Anderson says. “Every retreat, aspiring writers get to spend a whole week with the highest caliber of talent in the publishing world.” But you don’t need to be a writer or wedding guest to enjoy the magic of Poggio alle Corti. The main villa sleeps 12 comfortably, with room for six more in the onsite cottage—a 400-year-old villa of its own.
Guests are greeted with a welcome basket filled with local cheeses, prosciutto, and the estate’s own wine, olive oil, and balsamic vinegar. Daily housekeeping, concierge services, and an in-house chef who prepares three-course Italian dinners round out the villa’s approach to effortless hospitality across every detail. Beyond the villa’s walls lies a region rich with art, culture, and culinary treasures. From Michelin-starred Osteria di Passignano to the Renaissance masterpieces of Florence, the surrounding area offers endless opportunities to immerse oneself in Tuscany’s history and flavor.
Anderson says in purchasing the villa, he wanted a place where his kids could experience other cultures, become immersed in history, get connected to the land and agriculture, expand their worlds, and have fun doing it. He’s taking others along with him, too “We wanted our kids to have that experience,” he says, “and have a place that we could build memories with friends and family alike.”
Iconic Italian Destinations
Although Poggio alle Corti feels blissfully secluded among Chianti’s hills, it sits in the heart of Tuscany, making it an ideal home base for exploring Italy. Florence is less than an hour away, placing world-class museums within easy reach, while the Leaning Tower of Pisa, the colorful cliffs of Cinque Terre, and the ancient ruins of Rome are all comfortable day trips. Even Venice is accessible for guests who want to experience its canals before returning to the tranquility of the countryside. This central location allows visitors to enjoy the serenity of villa life without sacrificing access to the country’s most beloved cultural destinations.
Chianti Community
Life at Poggio alle Corti is deeply connected to the surrounding community, giving the property an authenticity that extends well beyond its historic walls. The Anderson family walks to the nearby trattoria, where the staff greets them and their children like old friends. Their neighboring winemaker stores his production in the estate’s cantina and, in exchange, helps with the olive harvest each year. Another vintner tends the villa’s vineyards—yielding between 10,000 and 15,000 bottles annually—and receives the majority of the resulting wine as part of a longstanding agricultural partnership. These relationships, rooted in trust and tradition, weave the villa into the rhythm of everyday Chianti life and offer guests a genuine sense of belonging in the region.