The Context Story: Our Origins in Rome & Beyond

On Context’s 20th anniversary birthday month, we’re taking some time to pause and celebrate the remarkable successes we’ve had in the last two decades. This milestone marks years of providing immersive travel experiences that allow travelers to connect with local culture on a deeper level. We’re especially reflecting on the mission that led to the founding of Context, its lasting values, our commitment to being a B Corp company, and the vision of its founders, Paul Bennett and Lani Bevacqua.

It all started in Rome

It all started in Rome for Paul Bennett and Lani Bevacqua, and for Context. We talked to the founder about why he sought out to establish Context. Through his story, we’re able to see how the company was born with values of global connection, deep local learning, and sustainable travel.

Paul and Lani founded Context after a two-year sailboat journey from New York City to Rome, passing through Central America and the North Atlantic. During this journey, Paul worked as a journalist, which led them to seek out local expertise everywhere they landed. They soon realized that the key to a meaningful and potentially life-changing travel experience was to connect with locals who had deep expertise in the places they visited. This expertise could include an architect who could explain the built environment, an art historian who could contextualize local art within the wider movement of art history, or a theologian who could show them local churches and monasteries and explain how they shaped local history. When they arrived in Rome, they knew they wanted to share this sense of deep local learning to unlock the city's rich history, enrich the lives of travelers, and leave the city unscathed by developing a more sustainable means of tourism.

And what better city to start in? The Eternal City is the perfect backdrop for experiential learning from locals who are passionate about the history, culture, cuisine, and art dating 2,000+ years of civilization. Ruins of the past mark every street corner with more discoveries unearthed every day. Rome’s history combined with centuries of popularity as a tourist destination made it the perfect place to begin. This realization led them to found Context with the mission of providing travelers with meaningful experiences that go beyond surface-level tourist attractions by connecting them with local historians, archaeologists, curators, and more who could provide a deeper understanding of the places they visit.

Paul, with his knowledge of history, garden, and landscape, was actually one of Context’s first experts — leading tours out to Tivoli Gardens. From there, Paul and Lani’s network of experts grew with the connections they had from their days of journalism. In the next couple of years, with a few challenging setbacks here and there that only make the company grow stronger, Context expanded to Florence, Paris, and beyond.

An early commitment to sustainability

In one of Context’s biggest milestones in the past 20 years, our groundbreaking commitment to sustainability began in 2009. We were one of the first companies to develop a sustainable business in that time. In fact, we were the second travel business to become B Corp certified, a recognition that we take seriously to this day. From 2003 to 2023, we have sought to connect intentional travelers to local ways of living, going deeper into the history and culture of a city, and leaving a memorable impact on both traveler and place.

Creating a Global Community of Learners

Intentional travel is at the root of what we do every single day, a fact that has remained true since our founding 20 years ago. Since then, we’ve grown to 60+ destinations around the world, fostered a network of 3,000 experts and counting, and launched online lectures to create an even more accessible world of learning.

As we reflect on our 20th anniversary, it’s apparent that our milestones and foundations show a clear commitment to our values and shared interests. By creating experiences that prioritize local culture and history and by emphasizing sustainable tourism, we’ve set a standard for what responsible, intentional travel can look like.

Both our company culture and our travelers share an uncanny likemindedness about learning and wanting to know as much as we can about the world around us. As true as ever, Paul muses that “We are a bunch of culture nerds who read too many books and love to argue over whether Borromini or Bernini are the better artists.” At 20 years, we’re proud of our foundations, who we are, and our global community of learners.