Tournament Fishing
Compete against the best in the Sportfishing Capital of the World.
Enter The Arena
Tournament fishing isn't just about catching fish; it's about strategy, precision, and adrenaline. It's the moment the drag screams and the radio lights up.
On the Miss Penny, we shift gears from "Charter Mode" to **"Tournament Mode."** This means specialized tackle prep, competitive kite spreads, and a crew that is 100% focused on putting you on the podium.
Names engraved on trophies and checks in hand.
High pressure. High reward. Pure sport.
Sailfish Season
2025 - 2026 Confirmed Dates
Islamorada Sailfish Tournament
1st Leg of the Florida Keys Gold Cup Championship.
New 2-day fishing format & Non-Professional Angler Division.
Islamorada Junior Sailfish Tournament
The future of the sport.
Islamorada Sailfly Tournament
Fly fishing only.
Fish For Holly Sailfish Tournament
Charity tournament.
Islamorada Fishing Clubs Sailfish Tournament
2nd Leg of the Florida Keys Gold Cup Championship.
Cheeca Lodge Presidential Sailfish Tournament
3rd Leg of the Florida Keys Gold Cup Championship.
Luxury meets hardcore sportfishing.
Islamorada Women’s Sailfish Tournament
Ladies, Let's Go Fishing!
Bartenders Sailfish Open
Local favorite.
Poor Girls Sailfish Tournament
Charity event.
Al Flutie Over the Hill Tournament
For anglers 50 and over.
Keys Kids Sailfish Tournament
Free to all kids 16 and under.
Jimmy Johnson’s Quest for the Ring
High stakes, big payouts.
Key West Sailfish Tournament
Southernmost showdown.
Marathon Premier Sailfish Tournament
Expanded boundaries.
Mahi & Meat
Projected 2026 Dates.
Please contact event organizers to confirm exact days.
Jeff Leoni Reel and Steel Classic
Grouper & Hogfish / Fishing & Diving.
Hosted at Angler House Marina. Prizes for rod & reel, freediving, and scuba.
Marathon Offshore Bull and Cow
Big Money Dolphin Tournament.
$10,000 guaranteed cash plus prizes.
Nick Sheahan Dolphin Rodeo
Benefits Coral Shores HS Seniors.
Held out of Tavernier Creek Marina.
Skippers Dolphin Tournament
Major Prize Money Event.
Over $50,000 awarded historically. Combined weight & individual prizes.
Ladies Dolphin Tournament
Presented by Florida Keys Elks Club.
Combined weight of three fish determines winners.
UM Sports Hall of Fame Celebrity
Celebrity-filled Dolphin Tournament.
$10,000 in prize money plus Calcuttas.
Islamorada Fishing Clubs Dolphin Tournament
One Day Shootout.
Chance at up to $25,000 in prize money.
Bartenders Dolphin Tournament
Industry Fun Day.
For bartenders and restaurant employees. Weigh in at Florida Boy.
Secure Your Boat
Tournament dates book fast—often a year in advance. To compete on the Miss Penny, you need to lock in your dates immediately.
*Tournament entry fees are separate from charter costs.