When true Milanese local, DOCG certified, as she likes to joke, Rebecca Alessandra first met David Leibowitz in a cozy wine bar in Milan, she was stunned by how much the Connecticut native knew about her homeland, Northern Italy.

“There’s so much to see and explore within just a couple of hours. You can be in the Alps or down on the Mediterranean coast!” David enthused. As the evening unfolded, the two delved deep into conversation about the region’s astonishing diversity, its culture, history, art, dialects, food, wine, and breathtaking landscapes. David spoke passionately about how dramatically everything can shift from one valley to the next, even from one hilltop village to another.

Rebecca was intrigued. How does this Yankee know more about my country than I do? She wondered.

And the rest, as they say, is history. One sip of local wine at a time, Rebecca and David, now co-owner of Adventures in Italy & Adventures in Jewish Italy, have been exploring and sharing the rich and varied treasures of Italy’s northern regions ever since.

One of the company’s core missions is to connect people, what Rebecca and David like to call “building cultural bridges”, between Italians and travelers from around the world. Despite the speed and ease of modern communication, they believe that genuine understanding across cultures remains surprisingly rare. Stereotypes often persist, even between countries as seemingly close as Italy and the United States. Through immersive, culturally rich tours, Adventures in Italy & Adventures in Jewish Italy aims to foster a deeper mutual understanding between locals and visitors alike.

Another guiding principle is to share the Italian approach to life, where, no matter how hard one works, Sundays are sacred for family, friends, leisurely walks, and shared meals. It’s a rhythm of life that prioritizes connection over hustle.

Finally, the team is passionate about uncovering both the iconic destinations and the hidden gems of each region, places so off the beaten path that even many Italians don’t know they exist. It’s a rewarding mission, made easier by the fact that most travelers still flock to the same famous spots, leaving countless marvels just waiting to be discovered.