Labor Day weekend, St. Croix was buzzing with the roar of powerful engines and sleek boats cutting through its azure waters. What was going on, you ask? It was none other than the 8th annual St. Croix Poker Run! As someone deeply passionate about boating and water adventures back in the States, where I’ve enjoyed numerous poker runs in Michigan and Florida, I was thrilled to discover that St. Croix had its very own poker run. When I learned it coincided with Labor Day weekend, I had to go experience this Caribbean event and see how it measured up to the ones I knew from home.

With eager anticipation, I reached out to the event organizers to uncover the details of this event. I couldn’t wait to capture snapshots of the fast and stylish boats that would grace St. Croix’s pristine waters. To my delight, the organizers, Davidson Charlemagne and Anton Kuipers, not only promptly provided me with the event’s particulars but also extended a warm and generous invitation to see things firsthand. They invited me not just to be a spectator but to climb aboard one of their vessels and become a participant in the poker run itself!
Can you believe it? I was about to immerse myself right in the middle of all the action of the St. Croix Poker Run. Special shout out to Charlemagne’s wife Sasha for the connections. Thank you!

So, just what is a Poker Run?
Let’s start with what it is not…A poker run is NOT a race. A poker run is a social event for fast boats that involves a long cruise with several stops. Participants pick up a playing card at each stop and try to have the best poker hand at the end of the run. In our case, we made stops at Rainbow Beach, Ann E. Abramson Pier (Frederiksted Dock), Cramer’s Park (lunch stop), Deep End (Green Cay Marina), and finally Shupe’s for the final playing card and party.
A Poker Run is a game of luck and only the boat with the best poker hand wins. It’s all in the cards. Whether your boat goes 50 mph or 100+ mph, speed has no bearing on the winner.
Poker Run organizers usually develop a unique or scenic route covering a 30-75-mile radius with 5 stops along the way. The ride should take approximately 3-4 hours to complete. In our case, we made stops around the island of St. Croix.

Are there any Charities involved?
Poker runs can give participants a chance to explore new territory and discover new lands. They can also be used to raise money for charity. The affiliated charity for the St. Croix Poker Run is the St. Croix Dolphins. This is an organization that teaches people of all ages how to swim.
This makes this charity a natural partner as boats, water, and swimming go hand in hand. The event raises money to put a group of kids through a 3-month swimming program that teaches them how to swim. It is a difference maker in these kids’ lives and will serve them their whole life. It also helps break the cultural stigma of islanders not learning how to swim.
How do I win in a poker run?
As mentioned earlier, it’s essential to clarify that a poker run isn’t a traditional race, despite the speedy boats in the mix. Instead, it’s a game of chance, with victory awarded to the boat or team holding the strongest poker hand, which might surprise you—it’s not necessarily the fastest boat that wins. Typically, the winning boat reaps rewards in the form of prizes and cash, and the St. Croix Poker Run certainly didn’t hold back in delivering both to its lucky winners.

The cash prizes are pretty substantial: (The entry fee was only $150 per person)
1st Prize = $9,000 – The winner was Brian Alexander with a 4 of a Kind.
2nd Prize = $5,000 – Second place was Tomas Corcino with an Aces High Full House.
3rd Prize = $1,500 – Third place went to Michael Powell with a Kings High Full House.
Best Dressed Team – Big Pressure won prizes donated by Cardow Jewelers and their Extra Virgin Rum.
The run’s sponsors graciously donated much of the cash and prizes.

Some of the notable sponsors include:
B20
Italia Marble and Granite
Luxury SUV Rental Service
A9 Trucking
Government of the Virgin Islands – Department of Parks and Recreation
Yacht Club
A special thanks to all the volunteers that made the event successful.
Also, a special shout-out to the Virgin Islands Royal Police and Local Coast Guard who provided marine safety support as well as a super cool Midnight Express that kept up with some of the fastest boats in the poker run.

In conclusion, the St. Croix Poker Run embodies the magic that truly comes alive on the water. It’s not just about the boats, the speed, or the breathtaking scenery—although those are undeniably spectacular—it’s about the people. It’s about the passionate souls who call the water their second home, the ones who’ve fallen head over heels in love with St. Croix and its unrivaled beauty. It’s about safety, ensuring every participant enjoys the rush while staying secure. It’s about networking, forging connections with fellow water lovers, and creating memories that last a lifetime. It’s about meeting new friends from all corners of the globe, united by a shared love for adventure and the open sea. But most importantly, it’s about boating—an exhilarating, heart-pounding affair that unites us all in the pursuit of the perfect wave.
So, next time you find yourself in St. Croix, don’t miss the chance to experience the magic of a poker run. It’s not just a race; it’s a celebration of everything that makes this island paradise and the boating community so special.
Great story and pictures