Article overview: Explore the 2026/2027 South Florida sailfish tournament calendar, discover upcoming events, and find sportfishing yachts for sale with HMY Yacht Sales.
As sailfish season arrives, passionate anglers are taking to South Florida's waters for a chance to claim a tournament title or fill their riggers with release flags. These events offer a unique mix of competition and camaraderie: more than a test of angling skill, they're a celebration of the sport shared by everyone who takes part.
The 2026/2027 season brings an abundance of tournaments to choose from. Whichever you plan to fish, the most important tool is your vessel. HMY has an extensive inventory of sportfishing yachts for sale to put you into the heart of the action. Our Yacht Sales Professionals, many of them sportfishing enthusiasts and tournament participants themselves, are ready to help equip you for the season.
This guide offers a comprehensive look at South Florida’s tournament calendar. Dates and event details are subject to change; check out each tournament’s official website or social media for the latest updates.
Mark your calendars with the following list for 2026/2027:
Dust 'Em Off Sailfish Warmup | December 2-6, 2026 | Pompano Beach, Florida
Get ready for the months of sailfishing ahead with this early season event! Join fellow anglers, connect with sponsors, and get geared up for the season. The Dust ’Em Off Sailfish Warmup takes place December 2nd through 6th, 2026, in South Florida, giving anglers an affordable opportunity to get back on the water ahead of the sailfish season. The event features north and south captain’s meetings, one day of competitive fishing, and a family friendly awards brunch to kick off the season.
Florida Keys Gold Cup Sailfish Championship
This trifecta invites anglers and teams to compete for the Gold Cup Trophy across three events:
Islamorada Sailfish Tournament | December 4-6, 2026 | Islamorada, Florida
The first leg kicks off at the Whale Harbor banquet facility on December 4th, followed by two days of fishing. The awards ceremony will be held on Sunday, December 6th.
IFC Captain's Cup Sailfish Tournament | January 19-20, 2027 | Islamorada, Florida
The second leg kicks off with a cocktail hour and dinner on Tuesday, January 19, followed by a day of fishing and the awards ceremony on Wednesday, January 20.
Cheeca Lodge Presidential | January 22-24, 2027 | Islamorada, Florida
Hosted by Cheeca Lodge & Spa in Islamorada, the 37th Annual Cheeca Lodge Presidential Sailfish Tournament returns to Islamorada, Florida, January 22nd through 24th, 2027. As the final leg of the Florida Keys Gold Cup Sailfish Championship, the tournament brings together anglers for competitive sailfishing, awards, and a weekend of festivities at Cheeca Lodge.
Pirate's Cove Sailfish Classic | December 9-12, 2026 | Stuart, Florida
This action-packed event hosted by Pirate’s Cove Resort and Marina brings together premier sailfish anglers, with elite fishing spots just 30 minutes from the Stuart docks.
The captains’ meeting is hosted on Wednesday, December 9th at Pirate’s Cove Resort and Marina, followed by three days of fishing. Saturday is concluded with an award ceremony by the Pirate’s Cove Restaurant.
Staying nearby? Check out Pirate's Cove Resort and Marina.
Stuart Sailfish Club Light Tackle | December 16-19, 2026 | Stuart, Florida
This three-day catch-and-release tournament offers awards for multiple species and participants, with prize categories for top boats overall as well as daily winners.
60 Day Sail | December 31, 2026-February 28, 2027 | South Florida
The 60 Day Sail is a sailfish release tournament hosted out of Jupiter, Florida, giving anglers the flexibility to fish from their own boats on any four days during a 60 day window. With every release recorded and verified through ReelCam, the tournament combines flexible fishing schedules with live standings and a video verified format across the waters from Fort Pierce to the Palm Beach Inlet.
As tournament season approaches, check our events page for the latest updates and behind-the-scenes recaps. And if you're looking to upgrade your battlewagon before your next tournament, browse our full inventory of yachts for sale.
Fish for Holly Sailfish Tournament | January 8-9, 2027 | Islamorada, Florida
Fish for Holly has grown into one of the largest tournaments in the Florida Keys, with record-breaking sailfish release numbers. Held in honor of community treasure Holly Given, the event supports domestic abuse prevention and educational scholarships.
Pelican Yacht Club Invitational | January 4-9, 2027 | Fort Pierce, Florida
This five-day billfish tournament lets teams choose three fishing days before returning to the Pelican Yacht Club in Fort Pierce for libations and first-rate cuisine. HMY Yacht Sales Professional Mark Mitchell is a longtime fan and recalls catching 30 to 40 fish in a single day one year.
Silver Sailfish Derby | January 6-9, 2027 | West Palm Beach, Florida
Dating to 1935, the Silver Sailfish Derby is the longest-running sailfish tournament in the world and was once sponsored in part by Ernest Hemingway. Non-pro participants of all skill levels have a chance to claim an award, making it a favorite of HMY Yacht Sales Professional Luke Davis. The fleet is limited to 50 boats which has been filled for the year but a waitlist is available. to join the waitlist email the West Palm Beach Fishing Club at wpbfc@westpalmbeachfishingclub.org.
Quest for the Crest Sailfish Series
Three high-stakes legs give anglers multiple chances to test their skills:
Operation Sailfish | January 13-17, 2027 | West Palm Beach, Florida
Operation Sailfish kicks off the 2027 Quest for the Crest Sailfish Series January 13th through 17th in West Palm Beach, Florida. The tournament features two days of competitive sailfishing and the Take a Hero Fishing event, honoring our nation’s military and supporting military families through Operation Homefront.
Buccaneer Cup | January 19-23, 2027 | Palm Beach Shores, Florida
The 64th Annual Buccaneer Cup Sailfish Tournament returns to Palm Beach Shores, Florida, January 19th through 23rd, 2027. The event kicks off with a captains’ meeting before teams compete across two of three fishing days, followed by an awards celebration dinner at Jupiter Beach Resort & Spa.
Annual Gold Cup Team Fishing Tournament | January 26-30, 2027 | Palm Beach, Florida
The 55th Annual Sailfish Club Gold Cup takes place January 26th through 30th, 2027, in Palm Beach, Florida. This prestigious invitational team tournament brings together experienced anglers to compete in catch and release sail fishing, with teams vying for the honor of having their names engraved on one of sportfishing’s most coveted trophies.
The Cove Billfish Tournament | February 4-6, 2027 | Deerfield Beach, Florida
The Cove’s Annual Billfish Tournament takes place February 4th through 6th, 2027, in Deerfield Beach, Florida. This annual event brings anglers together for competitive fishing and waterfront festivities, with all proceeds benefiting the Boys & Girls Clubs of Broward County.
Islamorada Women's Sailfish Tournament | February 5-7, 2027 | Islamorada, Florida
The Islamorada Women’s Sailfish Tournament returns February 5th through 7th, 2027, in Islamorada, Florida. Hosted by Ladies, Let’s Go Fishing, the tournament welcomes lady anglers of all experience levels to compete in sailfishing while supporting charitable causes and encouraging more women to get involved in the sport.
Sailfish Challenge | February 17-21, 2027 | Pompano Beach, Florida
The Sailfish Challenge returns February 17th through 21st, 2027, in South Florida as the second leg of the Quest for the Crest Sailfish Series. Featuring two days of competitive fishing, teams can fish out of three inlets: Government Cut, Hillsboro Inlet, or Lake Worth Inlet, as they compete for the coveted Burgundy Jacket and support billfish conservation through The Billfish Foundation.
Jupiter Billfish Classic | February/March 2027 | Jupiter, Florida
The Jupiter Billfish Classic takes place in Jupiter, Florida. This two day, all release billfish tournament brings together competitive fishing teams to target sailfish, white marlin, and blue marlin, with video verified releases and additional meat fish weigh ins. Dates and additional details for the Jupiter Billfish Classic are still to come. Follow along on Instagram at @jupiterbillfishtournaments for the latest updates!
Jimmy Johnson's Quest for the Ring | March 2-6, 2027 | Hollywood, Florida
Hosted at the Seminole Hard Rock Hotel and Casino in Hollywood, FL, this lavish event boasts one of the richest purses in the sport and the chance to fish multiple locations from Palm Beach to the Florida Keys.
Final Sail | April 6-10, 2027 | Ft. Lauderdale, Florida
Final Sail wraps up the 2027 Quest for the Crest Sailfish Series April 6th through 10th in Fort Lauderdale, Florida. As the final leg of the series, teams make their last push for the coveted Burgundy Jacket, bringing the season to a close with two days of competitive fishing and a championship celebration.
Viking Key West Challenge | April 14-17, 2027 | Key West, Florida
The 13th Annual Viking Key West Challenge takes place April 14th through 17th, 2027, in Key West, Florida. Exclusive to Viking and Valhalla owners, the event brings together boating families for two days of competitive fishing, 4 days of dockside gatherings, family-friendly activities, and celebrations throughout the week.
Quick Links:
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