Captain Howie has saltwater in his veins and a lifetime of adventure behind the helm. He’s been boating since before he could walk, and by the age of 13 — before he could even drive a car — he was already working as a commercial fisherman. While other kids were getting dropped off at soccer practice, Howie was getting dropped off at the docks by his dad.

After growing up in Rhode Island (and getting tired of shoveling snow), Howie took off to explore the Caribbean, spending five years traveling through St. Thomas, Cozumel, St. Croix, and even Alaska. His retail career took him across the islands and eventually brought him to Key West — where he bought a home in 1997 and never looked back.

Strangely enough, it wasn’t until nearly a decade later that he bought his first boat. It took a call from his mom — who couldn’t believe he was living in the best boating destination in the country without a boat — to finally push him over the edge. The very next day, Howie picked up a boat (already named Make It So), and his love affair with the waters of Key West began in full force.

He spent every free moment on the water, exploring, relaxing, and racing to the sandbars on his days off. Eventually, he earned his captain’s license and began running private charters part-time. As demand grew, so did his passion — until he found himself using personal days just to get more guests out on the water.

When the 2020 pandemic closed the local retail business, Howie already had one foot out the door. He seized the opportunity, went all in on charters, bought a second boat, and struck gold by bringing the amazing Captain Amanda on board.

Today, Captain Howie runs one of the most loved private charter operations in Key West — not just because of the boats or the sunsets (though they’re unreal), but because of the experience he creates for every guest. For Howie, this isn’t just a job. It’s a way of life — and he’s never happier than when he’s out on the water, sharing it with people who come as guests and leave as friends.