At the end of May, I attended my third TBEX conference (Travel Blog Exchange) and was introduced to Paul Bennett and his wife Lani, the founders of Context Travel. Context Travel is a network of Ph-D level scholars and experts living in cultural capitals around the world who take tourists on small or private guided tours of their cities. Paul and Lani founded the company in 2003 after two years of sailing across the Atlantic with their young children. They were so inspired by the experiences while traveling that they wanted to create something authentic and unique. A kind of travel company that would enable travelers to get a rare behind the scenes view of what a place is like while also promoting sustainable travel. There are no tour buses or tour guides; instead you are swept away on a walking “seminar” with a local expert.

The Context vision is to create an atmosphere—a context, if you will—for curious travelers to engage with local experts; to give them access to places and cultures that might otherwise remain out of sight to the casual visitor; to invite them off the tourist track and into the real life of the people, history, and culture that makes these cultural capitals amazing.

Paul and Italo on a drive through Venice's canals.

Paul and Italo on a drive through Venice’s canals.

Fast forward 13 years, and Context Travel now operates in over 35 cities around the world, inspiring travelers to see a city through local, knowledgeable eyes. Context Travel is recommended by such acclaimed sources as the New York Times, Travel and Leisure, and National Geographic (to name a few) as well as a growing number of highly satisfied customers. I was so inspired by Paul and Lani’s story that I asked to do an interview to learn more. Here is what Paul had to say.

Where did you and Lani meet?  Lani and I met at Macalester College in Existentialism class. Seriously.

What did you study in college?  We both majored in English.

Did you both travel internationally before starting Context Travel?  A little. We both did post-college trips through Europe and some basic Caribbean and Mexico travel. I worked as a journalist for several years, and that took us to places like Rome and Ecuador. Just before we started Context we sailed a 38-foot boat from New York to Italy via Central America, on a voyage that took nearly 2 years and included stops in places like the Azores (highly recommended).

Where was your first trip? My first international trip was as a teenager. I went on a school trip to China in 1987. It blew my mind.

What inspired you to start Context Travel? When we arrived in Italy after sailing for two years we realized that the single most important ingredient to our travels was being able to connect with some local expert who some kind of specialized knowledge of the place and could get us access beyond what we could glean from a guidebook. For example, in the Azores I had an assignment for Islands magazine to interview a master scrimshaw artist. This guy was amazing and taught us so much about the heritage of whaling in the islands—much more powerful than what we got from Lonely Planet. And so this became the impetus for Context: To connect curious travelers with local experts when they arrive in destination.

When did you start Context Travel and in what country? We started in Rome in 2003.

What has been the most challenging part of starting and running the business  Geez. Everything. Bootstrapping a business requires wearing a lot of hats. We’ve had to become effective recruiters, storytellers, financial managers, digital marketers… and so on. Getting technology right has been our biggest struggle.

What has been the biggest reward? The quality of what we do. There’s a common arc among Context experiences. It goes like this. A traveler finds us, perhaps through a post like this. They come to our website and compare us to other companies and usually pick a Context tour because it seems like the best quality. Maybe they like the credentials of our docents, who mostly have Ph.D.s. Or, maybe they like the small group size (6 max). Whatever. But, they show up at the tour thinking that it will be a good tour. Three hours later they are amazed. We’ve completely changed their thinking about art, history, or heritage, and given them a much deeper travel experience than they expected. They’re transformed. Hearing this story day in and day out is the biggest reward.

What makes your tours different from others on the market today?  Small groups, expert docents, and a commitment to creating immersive experiences.

Context New York MOMA Seminar, led by art historian Ara Merjian

Context New York MOMA Seminar, led by art historian Ara Merjian

Give me a few examples of what visitors will experience on one of your tours?  In Paris one of my favorite tours is Immigration and the Changing Face of Paris, which is led by a local sociologist and explores the history and present situation of Arabs and North Africans in France. We visit some neighborhoods that most tourists never see, and talk about the headlines. But, because the guide is actually a specialist in this area with a degree in sociology, you get a much deeper, more nuanced approach than what you read in the media.

I also love our Birth of the Cocktail walk in New York, which looks at the history of American cocktail making from Prohibition through the speakeasy revival movement of the early 2000s. The drinks are good, but the narrative is even better.

In Asia, I’m crazy for our Anime and Manga walk in Tokyo. It’s just super cool.

Of course, we also do the Louvrethe Vatican, and the Tower of London; and those are pretty mind-blowing, especially in a small group with a highly knowledgeable, Ph.D.-level docent.

Where are your tours offered?  Rome, Florence, Venice, Milan, Tuscany, Naples, Paris, Barcelona, Madrid, London, Dublin, Edinburgh, Amsterdam, Berlin, Prague, Vienne, Budapest, Athens, Istanbul, Bangkok, Hong Kong, Shanghai, Beijing, Tokyo, Kyoto, Melbourne, Sydney, Buenos Aires, Rio de Janeiro, Cartagena, Washington D.C., Philadelphia, New York, Boston, Montreal and Vancouver.

Tell me about the guides. How do you find them and what kinds of backgrounds/expertise do they have?  In academic subjects we look for people with a Ph.D. in the topic and some experience teaching. In non academic topics we look for experience in the field—practicing architect, chef, e.g. During the interview process we test their ability to craft a narrative and tell a story. We also look at their emotional intelligence and whether they will be the consummate host. We have a bunch of training designed around this.

How long do tours run and how much do they cost? 3 hours is our sweet spot, and the average price is $90 pp for a group walk or about $350 flat fee for a private walk.

What have past participants said about your tours?

“Our tour was fabulous. Our docent knew the history and food of Barcelona and her knowledge was unbelievable.

Amazing, simply amazing. 10 out of 10!”

“Be careful. Once you’ve taken a Context tour you’ll be spoiled. Not only will you never want to use any other tour company, but you’ll be very hesitant to visit any city where Context doesn’t offer their services. It’s that good.”

Where do you hope to see Context Travel in the next ten years?  I see us operating in 100 cities and known as THE tour company for the culturally curious.

Finally, tell me more about your sustainability practice and why it is important. This is really baked into our DNA. We run a nonprofit that supports local initiative like a scholarship program for apprentice artisans in Florence and a youth center in Cartagena. Our docents are trained to talk about sustainable travel practices like flashes in museums and how to invest your travel dollars wisely with local businesses.

About Paul and Lani, founders of Context Travel

Lani Bevacqua, Paul Bennett and one of their children, Jade.

Lani Bevacqua, Paul Bennett and one of their children, Jade.

Paul Bennett
Co-founder, Context

Paul spent the first part of his career as an award-winning writer for National Geographic and National Geographic Adventure. He holds an MA from St. John’s “Great Books” program and has written four books for Princeton Architectural Press about architecture and landscape. He founded Context with life/business partner, Lani Bevacqua, in 2003 after having spent 18 months sailing a 38-foot boat from New York to Rome.

Paul oversees strategy, finance, and bad jokes. When he is not helping run Context, Paul lectures on travel and sustainability, and works on the Context Foundation for Sustainable Travel.

Lani Bevacqua
Co-founder, Context

Lani co-founded Context with life/business partner, Paul Bennett, after having sailed to Rome from New York on a small boat. That experience deeply informs everything she does at Context.

In a previous life Lani was a graphic designer and art director in New York City. She worked in-house for Artforum, Dance Theater Workshop, and Gartner Group. Her agency clients included Gillette, Compaq, Computer Associates, IBM, and PeoplePC. She won awards for her digital advertising and web animation. Along with being the creative director and designer for the Context websites and publications, she is home-schooling three small children and is the impetus behind Context’s much-lauded Family Program.

About Context Travel’s sustainable tourism and social responsibility commitment

Context adheres to the precepts of sustainable travel. We invest in programs that mitigate the effect of tourism. Learn about the Context Foundation for Sustainable Travel. Context is also a certified B Corporation. B Corporations are a new kind of company which uses the power of business to solve social and environmental problems. Learn more about B Corporations.

To learn more about Context Travel and their tours, visit their website here.


  1. You know, I’ve thought of doing some posts like this, but just don’t seem to get around to it. This is a nice diversion, and interesting concept for travel. I might look them up! Or get a job!

    1. They have the tours in DC and I am going to do one next time I visit. The tours sound amazing! I love to learn and I’m sure the DC tour would teach me things I don’t know .

  2. Interesting concept. My parents used to travel with Elder Hostel which sounds like a similar idea and tgey too loved it. The problem I have with organised activities is the stickng to a schedule which I sm not very good at doing, especially when travellng.

    1. Wonderful! I would love to hear back on how it went! If you remember can you let me know? I’m hoping to do one in DC or NYC next time I’m there. Cartagena sounds fabulous!

  3. I love the idea of a more intimate tour, especially from a locals perspective! Next time I visit a new city I’ll have to look these guys up. Sounds like something special

  4. I love the idea of going on an in-depth tour of a single subject in a city to help gain new perspective and understanding of it. I’ve been on a few tours, one in Europe, which was great but very need-to-know basic. Then, in South Africa, we had locals who took us through some spots and it made a difference in hearing their stories and perspectives to add more context. I’ll have to try to check one out next time I travel to one of their cities.

  5. I absolutely love Context Travel. I have been in touch with Paul and would love to work with them some day. I have pitched so many of their tours to my Indian clients, but unfortunately do find them very steep as they do not see the value. I shall not quit though. I have recently pitched their Tokyo & Kyoto walks. Fingers crossed!

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