Photo of Bob RossLandscape architect and culinary enthusiast Bob Ross is crafting an intimate journey that marries Renaissance gardens with traditional Tuscan cuisine—and he’s inviting just six fortunate travelers to join him.

This isn’t your typical “book now, figure it out later” vacation. Instead, Ross has designed a thoughtful preparatory journey that unfolds over four seasonal cooking classes, culminating in an October week in the heart of Tuscany—a time he notes is “a beautiful time to be there.” The preparation is part of the experience, as participants gather in the Culinary Arts Studio to master dishes spanning centuries of Tuscan tradition.

The culinary curriculum reads like a history book brought to life. There’s the legendary Peposo dell’Impruneta, a robust beef stew whose origins trace back to the craftsmen who built Brunelleschi’s magnificent Duomo in Florence. According to Ross, workers would cook the stew in ovens adjacent to those firing the cathedral’s bricks—bricks crafted by families whose descendants continue the terra cotta tradition to this day. Students will also tackle the lesser-known but beloved Gnocchi alla Romana, pulled from the pages of Pellegrino Artusi’s 1891 cookbook, and the renaissance-era Arista alla Fiorentina, a succulent pork shoulder stuffed with rosemary, marinated figs, and sage.

But what sets this program apart is its connection to modern-day Tuscany. “You feel a real strong connection to history there, and it’s the same way with the food—the tradition of Tuscan food is really connected to the local landscape and what’s available in the different seasons,” Ross explains. Participants will engage in Zoom sessions with local Florentine chefs, garden experts, and cultural guides who will later become their hosts. A married chef couple, Mirella and Stefano, will welcome the group into their family home—built by her grandfather—for an intimate pasta-making workshop. Meanwhile, specialized guides will unlock the secrets of Florence’s historic gardens, offering a perspective that few tourists ever glimpse.

Ross brings a unique perspective to this cultural immersion. As a Loeb Fellow at Harvard’s Graduate School of Design and a traveler who has spent significant time in North Africa and Europe, he has developed a passionate connection with central Italy. “When you’re in Florence, just because of the way the city is put together, there are lots of narrow walkways and old, old buildings made of brick and stone. You feel like you’re walking through history,” he says. This authenticity is no accident—Florence, like Paris, was largely spared from mass destruction during World War II and the German occupation, preserving its Renaissance character.

“The whole idea is to build and plan a trip that’s not just a trip you buy off a website, but that you’re involved in planning it,” Ross emphasizes. For those seeking to move beyond superficial tourism into deep cultural connection, this small-group journey offers a chance to experience Tuscany as insiders rather than observers. It’s an opportunity not just to visit Italy but to arrive knowing its flavors, understanding its gardens, and feeling connected to its people.

After all, isn’t that how travel should be?

Trip to Tuscany (Oct 12-18, 2025) with Bob Ross

4 meetings, beginning Saturday, Jan. 18