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). ”

Context Travel: Paul Bennett and Lani Bevacqua
Hometown…
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…
- 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.
- 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.
- 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.

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…
- Context, of course! Seriously, we do amazingly immersive tours that expand your mind and give you an invaluable base from which to explore.
- 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.
- 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.

8 word (or less) travel mantra…
“Never go anywhere for one night.”
favorite non-travel website …
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

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.
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Check out McCool Travel’s previous interviews. McCool 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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Wow, what an interesting life the Context Travel family is leading. I bet their tours are fascinating. Never heard of Wait But Why before and I’m having fun checking it out.
Thank you. That might be my favorite interview question, people have some cool non-travel websites they like.
Amazing life this family is living and it is cool to hear about them.
Thank you for the note. It is especially inspiring to hear the story of people who have integrated a desired lifestyle with their work and passion.
Such a fun interview – short, sharp, witty, informative – and inspiring –
Love it 🙂
Glad you stopped in and enjoyed the interview, Linda.
Travel Happy!
Loved this interview! Cool picks for their fave home away from home places. I’ll definitely check out the Beehive Hotel in Rome
Yeah, I know right? That was the first thing I thought after this interview, go stay in Beehive!
Great interview. Paul and Lani would be fun to meet in person and spend some time with. It’s an interesting life they lead.
Seems so, right, Donna? Inspiring to find people who balance their work and personal lives so magnificently.
Donna. Agreed. Reach via email or our Facebook page.
What a Cool interview! I very much enjoyed meeting Paul and Lani from Context Travel. Re. cheap eats, I also had a fabulous street gordita in Mexico that was prepared on a recycled oil can stove.
Excellent, Carole. Mexico street food has a great reputation among serious travelers, for sure.
Great interview – what an interesting family! I love hearing how they make their interesting life “work” – inspiring!
Thank you, Anne. Completely agree!
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.
Ouch. I was demonstrating the importance of proof reading before hitting “submit”. (That’s my story and I’m sticking to it.) “Their” should be “they’re”. Duh.
Indeed, hope y’all meet up in Philly some time. Invite me to that meeting!
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!
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!
Thank you, Jenny. Travel Happy.
Interesting! I had a wonderful Context tour in Athens so it’s good to know something about their founders.