The Guy Behind Boatsetter’s Luxury Charter Experiences in Anguilla and St. Martin
Last Updated on August 21, 2025 by Boatsetter Team
Boatsetter is made up of people who don’t just work in boating, but live it. Like Jacob Colburn, the Senior Sales Manager on the Global team. From wakeboarding wipeouts as a kid to cruising in the Caribbean, Jacob’s life has always revolved around the water. Those early adventures turned into a career when he joined Boatsetter nearly a decade ago, and today, he’s the reason Guests can book luxury charter experiences in Anguilla and St. Martin, and is working on unlocking more bucket list destinations.
What’s your earliest memory on the water? How did that journey lead you to Boatsetter?
My earliest memory on the water is learning how to wakeboard. I was maybe 7 or 8. I had some trouble initially but finally got it. I had a blast and did not want to stop until I face planted. Took a break after that! After graduating from the University of Miami, a close friend, who worked for Boatsetter then, asked me if I wanted to join the team. I jumped at the chance, and that was nearly nine years ago.
Could you tell us a little bit about your role?
I’m part of the Global team at Boatsetter, where we focus on expanding our presence in international destinations like Mexico, the Bahamas, and other Caribbean destinations including Turks and Caicos, St. Martin, Anguilla, and St. Barths. Growing up, I was lucky to travel to the Bahamas and other parts of the Caribbean by boat, and those early memories are really dear to me. Now, I get to draw on those experiences to help others create their own meaningful moments.
I’m proud that our team was successful in opening up the Anguilla and St. Martin markets. I used to go boating there as a kid and remember the 30-minute cruise through the channel, which felt like an adventure being out in the open sea. I also remember snorkeling with eels and sea turtles, and the crystal-clear underwater visibility. These islands have some of the best boats and waters in the world, but when I started at Boatsetter they weren’t a major focus.
I made it my prerogative to open up these destinations for Boatsetter. The team and I built relationships with local operators, curated a twin-island experience with personalized itineraries, and essentially created a world-class fleet for people looking to explore these islands as they were intended. The market went from virtually non-existent to one of the most popular global destinations beloved by our luxury clientele.
What’s your dream boat destination?
If I had a magic boat pass for 24 hours, I’d cruise around Mykonos and explore some of the nearby Greek islands like Paros and Naxos. It’s perfect: crystal-clear waters, charming harbors, and rich history. I’d bring my wife (might leave the baby at home for this one), and a few close friends. Cruising around Greece has always been a bucket-list experience.
How do you interpret Boatsetter’s mission personally?
For me, it’s about breaking down the barriers that once made boating feel too exclusive and creating a marketplace where we can facilitate a trip in any destination. I interpret our mission as a call to rethink how people interact with boating, not just as a luxury or a hobby but as a lifestyle and culture available to anyone curious about it.
Editor’s note: This interview has been edited for length and clarity.
Jacob Colburn is a member of Boatsetter’s Global team, where he helps open up world-class boating destinations across the Caribbean, Mexico, and the Bahamas. Nearly a decade into his Boatsetter journey, Jacob has played a key role in launching luxury charter experiences in Anguilla and St. Martin, transforming his childhood adventures on the water into opportunities for travelers to explore the world by boat. When he’s not curating unforgettable itineraries, Jacob enjoys spending time on the water with family and friends and dreaming up his next island-hopping adventure.
