The Pirate Poker Run drops anchor on Saturday, September 12, 2026, kicking off the Englewood Beach Waterfest with some real character. Think of it as a wild, good-hearted party straight out of the old pirate legends that haunt Florida’s coastline: rum tales, buried gold, and all sorts of mischief.
Start things off at the Captain’s Party, the official registration, on Friday, September 11, from 5 to 7 p.m. at the Sandbar Tiki & Grille.
On Saturday morning, get yourself checked in at The Backyard at Skip’s Marina between 8:30 and 10:00 a.m.
The Poker Run is the main event, and runs from 10:00 a.m. to 3:00 p.m. You’ll hit at least five of seven stops scattered across the area, by boat, by car, or even by motorcycle. Each stop, like Rum Bay, Endzone Bar & Grill, or Sportman’s Pub, hands you a poker chip. Collect at least five, then show your hand at Lighthouse Grill and Tiki Bar from 4:00 to 8:00 p.m., where the tournament and after-party lights up the night.
You’re playing for genuine treasure here: $500 to the top poker hand, $250 for second, $100 for third, and special contests for best pirate costumes and best decked-out boat. Pre-register for $40 or pay $45 if you wait until the day of the event.
It’s not just about cards and costumes, either. Pirates of the Floridian bring the music from 12:30 to 3:30 p.m., then Marker 5 Band takes over from 5:00 to 8:00.
The air hums with stories of gold doubloons, gemstone-laden chests, leather pouches stuffed with diamonds and pearls. Imagine that old Spanish loot spilling across split timbers and silver bars.
History breathes through this event. In 1493, a nineteen-year-old named Juan Ponce De LeÓn sailed with Columbus to the New World. Twenty years later, he led Spanish galleons along Florida’s coast, mapping the land, chasing treasure, and tangling with the Calusa, who fought back hard enough to send him retreating, wounded, to Cuba. Ponce De LeÓn’s death in 1521 didn’t close the chapter; it shifted Florida into the true pirate era.
Back then, pirates were no joke: brutal, desperate, and deadly. The Gulf Coast swarmed with an estimated 5,000 of them during their heyday from 1715 to 1735. They knew these tangled waterways better than anyone, slipping away from pursuers who risked their ships and lives in unfamiliar waters.
“Dana Lutz and the Pirate Poker Run team are so pleased with the overwhelming support from the Englewood community,” says Ray LaBadie. “We look forward to seeing everyone on the water helping us support Englewood Beach Waterfest and our local restaurants and businesses. ARRRRGG!”
If you’re looking for excitement, history, and maybe a taste of treasure, mark your calendar. Register now and join the adventure, matey!
Click here for more information and to register.
