Today we’d like to introduce you to Adam Bailie.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
Tropical Sailing had humble beginnings — just a few small Hobie Cats gliding over the turquoise waters off Deerfield Beach. But even in those early days, we had a big dream: to share the beauty and spirit of South Florida with as many people as possible.
Not long after, we took a major leap forward by acquiring the Spirit of Lauderdale, a 49-passenger sailing catamaran that we proudly docked at the legendary Bahia Mar Marina. That move put us right at the heart of Fort Lauderdale’s vibrant waterfront. Soon opportunity knocked again — this time in Miami — and we expanded our fleet with the Tranquility, operating out of Bayside Marketplace.
As we grew, so did our guests. We discovered that South Florida wasn’t just a paradise for vacationers — it was also a hot spot for corporate incentive groups, reunions, and large celebrations. The weather, the energy, and the world-class infrastructure made it a magnet for planners from around the globe. Before long, our 49-passenger catamarans were filling up fast, and we found ourselves splitting large groups between multiple boats — sometimes run by outside vendors who didn’t always share our high standards.
That’s when we decided to take control of the experience from bow to stern — and bring in something truly extraordinary: The Caribbean Spirit. At 125 passengers, she was not only the largest day-sailing catamaran in South Florida — but the largest in all of North America at the time.
And talk about timing! Her arrival coincided perfectly with the 2009 NFL Pro Bowl and Super Bowl — right here in South Florida. Suddenly, we weren’t just sailing guests anymore — we were hosting celebrity events, NFL players, and major corporate functions under the sun and stars.
From a few beach-launched Hobies to one of the largest sailing operations in the country, Tropical Sailing’s journey has always been driven by one thing: creating unforgettable experiences on the water — with the wind in our sails and a smile on every guest’s face..
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The catamaran business, much like the seas upon which we sail, isn’t always calm and predictable. We’re at the mercy of many forces beyond our control — weather, machinery, shifting tourism trends, and of course, the economy itself.
Within months of making a major investment in our first beachside concession, the world changed overnight. The events of 9/11 brought tourism in Florida to a near standstill. Like many small business owners, our founders did whatever it took to keep the dream afloat — from delivering pizzas to cleaning pools — anything to stay above water, literally and figuratively.
Over the years, we’ve weathered nearly every kind of storm — from the back-to-back hurricanes of 2004 and 2005 that chased tourists away for seasons at a time, to the economic crash of 2008, to red tide, Zika, and of course, the global shutdown of COVID-19. Each challenge tested our resolve, but also revealed our strength. With careful planning, adaptability, and a deep love for what we do, we’ve always managed to come through stronger than before.
Today, Tropical Sailing isn’t just surviving — we’re thriving. Our eyes are on the horizon as we expand into new markets, both international and domestic. Because if there’s one thing we’ve learned from years at sea, it’s that calm waters never made a skilled sailor — and we’ve become very skilled indeed.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I am not sure how well I understand this question. Is it asking what category my work falls under? Choices provided don’t quite capture what my work embodies. I would say I am an entrepreneur by spirit, Captain by profession, and running this company luck.
Where do you see things going in the next 5-10 years?
I gave up trying to predict the future of this industry years ago — the ocean and the economy both have a funny way of reminding you who’s really the captain. What I do see is a generational shift: younger people seem to value experiences over possessions. They’d rather collect memories than things — which is great news for a business built on sunshine, salt air, and a good splash of adventure.
AI will no doubt play a big role in shaping what’s ahead. We might be heading into a golden age of leisure, where robots handle the spreadsheets and everyone finally has time to go sailing. Or, who knows, maybe we’re on a fast tack toward a full-on Blade Runner future — flying taxis, holographic dolphins, and all.
Either way, technology can change how people book a trip, but it’ll never replace the feeling of wind in your hair, salt on your skin, or a captain who can steer a catamaran, tell a bad joke, and hand you a cold drink — sometimes all at once. As long as that’s true, I think we’ll stay afloat just fine
Contact Info:
- Website: tropical sailing..com
- Instagram: https://www.instagram.com/tropicalsailingcatamarans/
- Facebook: https://www.facebook.com/tropicalsailingfl
