5 Minutes With Context Travel

For McCool Travel’s 121st travel profile, I am happy to introduce you to Lani Bevacqua and Paul Bennett the founders of Context Travel. I recently saw an interview with them in Forbes and thought it would be cool to interview them myself. They said Yes!

Context Travel‘s bio: “Paul Bennett and Lani Bevacqua are the founders of Context Travel, which organizes small-group, expert-led tours for the intellectually curious all over the world. They spend a lot of their time traveling, and often by boat. They’ve sailed throughout Central America, across the Atlantic, and through the Mediterranean; and on their last trip (2014-15) they sailed from the Caribbean to Australia with their three daughters, Stella (14), Cleo (12), and Jade (9). ”

McCool Travel interview with Context Travel: founders Lani Bevacqua and Paul Bennett
Context Travel: founders Lani Bevacqua and Paul Bennett

Context Travel: Paul Bennett and Lani Bevacqua


We are currently based in Philadelphia, where we own a house now. However we’ve spent more time on the road or living abroad in the last 20 years. 18 months ago we returned from a 2-year sailing trip, in which we sailed a 40-foot sailboat from the Caribbean to Australia with our daughters; and we’re currently planning our next escape. Philadelphia is a great East Coast city, but the road (er, water in our case) calls.

Always in my luggage…

Well, on a boat you have a lot of space. Probably our most critical piece of equipment was our Iridium 9575 and Redport optimizer that allows us to send/receive email from the middle of the ocean. When we travel normally (by plane) our only critical pieces of equipment are an iPhone and a hat. We’re minimalists.

3 favorite home-away-from-home places…

  1. Fulaga – A remote island in the Lau group, off Fiji. We spent a month here and fell in love with the villagers and their way of life. Plus the surrounding lagoon is pretty spectacular.
  2. Hong Kong – This is one of the newest Context cities, and an amazing place for food, culture, and the steady thump of a real city.
  3. Rome – We lived here for 5 years and our two oldest daughters were born here. It’s a magical city despite its challenges, and will always be home.
McCool Travel interview with Context Travel: founders Lani Bevacqua and Paul Bennett
Context Travel: founders Paul Bennett and Lani Bevacqua and daughters

A favorite travel memory is…

For Paul, it’s visiting climate scientist Konrad Steffen’s camp on the Greenland ice cap for National Geographic. He spent a week with him in a place that feels like Mars learning the ins and outs of what’s happening to our planet.
For Lani it’s eating oysters on the beach of Los Roques, Venezuela before the country collapsed.

3 favorite travel brands…

  1. Context, of course! Seriously, we do amazingly immersive tours that expand your mind and give you an invaluable base from which to explore.
  2. When in Rome we stay at the Beehive Hotel, hands down one of the coolest hotels in the world. Steve and Linda, the proprietors, do a great job.
  3. We’re also Uber devotees because it saves time and gives you a chance to meet a local. It’s also indispensable in places like Mexico City where taxis are a disaster.

3 money-saving travel tactics I use are…

Our main overall tactic is living like a local, which is easy when you rock up in a sailboat. If you’re not in a hotel and avoid tourist zones, you generally find prices are about half. Roaming charges are often our biggest expense, so getting a local chip for internet—which is often a glorious adventure in itself—is usually our first item of business when we arrive somewhere. We’ve started getting our children to do it for us. They hate it, but it’s good for them.

3 ways that I have fun while traveling are …

Eating street food. It’s a great way to immerse yourself in a place, and—Montezuma’s revenge notwithstanding—usually better than restaurant fare. We love meeting people. The best for us if staying some place for a long time and getting to know the locals, which then leads to all sorts of adventures. We stayed a month on a little island west of Bora Bora called Maupiti, anchored off the beach of a great family. They taught us how to weave reed baskets, gather snails, and catch lobsters with our bare hands. That was a lot of fun.

McCool Travel interview with Context Travel: founders Lani Bevacqua and Paul Bennett
Context Travel: founders Lani Bevacqua and Paul Bennett

8 word (or less) travel mantra…

Never go anywhere for one night.

favorite non-travel website …

Wait but Why?

most memorable souvenir …

Our daughter Stella. We had her on our first sailing trip.

favorite cheap eat …

The gorditas we ate today in the market in Queretaro, Mexico. They were great.

recent discovery …

Mexico City

McCool Travel interview with Context Travel: founders Lani Bevacqua and Paul Bennett
Context Travel: founders Lani Bevacqua and Paul Bennett and daughters

I am fortunate to have met …

Each other

I would like to meet …

Elon Musk, Michelle Obama, and Yoda

Thank you so much, Paul and Lani, for taking a few minutes to share travel inspiration and tips.
Follow Context Travel on TwitterInstagramFacebook, Pinterest, Google+, and ContextTravel.com.

Check out McCool Travel’s previous interviewsMcCool Travel presents tips from travel experts in our 5 Minutes interview series—featuring travel industry giants, super frequent travelers, and adventurous persons. Previous 5 Minutes post: Power Couple Life.

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5 Minutes With Context Travel was originally published on McCool Travel.com on Jan 13, 2017.

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22 thoughts on “5 Minutes With Context Travel”

  1. If I want to meet them IRL, it sounds like I need to find them the next time their in our mutual home town—Philly. Our last Context Travel tour was in Edinburgh. That sailing across the Pacific thing from the Caribbean—yikes. I find flying across the Pacific (as a passenger) to be challenging enough.

  2. I’ve always admired their story and how they make it work for their family, really admirable! The Context Tours I’ve taken in Spain and Boston were all top notch!

  3. What an interesting interview. It’s great to learn a little about the founders of such wonderful tours. I can’t wait to check out their favourite non travel website!

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