2026-2027 Islamorada Sailfish Tournament Schedule

Sailfish season is not that far off, and the new 2026-2027 tournament calendar is out.

That means it is time to start building teams, blocking dates, lining up bait plans, and getting serious before every good boat in Islamorada is already spoken for.

DirtyBoat will be available for select sailfish tournament charters this season, and we are also looking for sponsor partners who want their name riding with a hard-fishing Islamorada program.

Tournament Charters

If you want to fish one of these events with a crew that knows the local water, the winter sailfish bite, and the tournament routine, now is the time to get on the calendar.

Tournament weeks move fast. Practice days, bait, lodging, registrations, anglers, and weather windows all stack up at once. Waiting until the week before is how you end up watching the fleet leave without you.

DirtyBoat can help with:

• Tournament charter availability
• Practice and scouting days
• Private sailfish trips around tournament week
• Angler teams looking for a boat
• Sponsor visibility on the boat, online, and through DirtyBoat media

2026 Schedule

December 4-6, 2026

Islamorada Sailfish Tournament

First leg of the Florida Keys Gold Cup Championship. The 2026 event is listed with a new 2-day fishing format and a non-professional angler team division.

Website: islamoradasailfishtournament.com

December 11-13, 2026

Islamorada Junior Sailfish Tournament

A junior angler sailfish tournament to get the next generation into the winter bite.

2027 Schedule

January 5-7, 2027

Islamorada Sailfly Tournament

Fly tackle. Sailfish. Islamorada. Not for the faint of heart.

January 8-9, 2027

Fish For Holly Sailfish Tournament

Website: fishforholly.com

January 19-20, 2027

Islamorada Fishing Club Sailfish Tournament

Second leg of the Florida Keys Gold Cup Championship.

Website: theislamoradafishingclub.com

January 22-24, 2027

Cheeca Lodge Presidential Sailfish Tournament

Third leg of the Florida Keys Gold Cup Sailfish Championship.

Website: cheeca.com

January 29-30, 2027

Keys Kids Sailfish Tournament

Free to all kids 16 and under.

Website: tacklecenterislamorada.com

January 31-February 1, 2027

Bartenders Sailfish Open

One of the classic local winter sailfish events. Usually a good one.

February 2-3, 2027

Poor Girls Sailfish Tournament

Another women-led sailfish tournament in the Florida Keys winter run.

February 5-7, 2027

Islamorada Women’s Sailfish Tournament

Website: ladiesletsgofishing.com

February 9-10, 2027

Al Flutie Over the Hill Tournament

For anglers 50 and over. Still mean enough to pull on sails.

March 2-6, 2027

Jimmy Johnson’s Quest for the Ring

Website: questfortheringfl.com

April 1-3, 2027

Key West Sailfish Tournament

Website: profishingtournaments.com

April 15-17, 2027

Marathon Premier Sailfish Tournament

The Marathon Premier Sailfish Tournament returns with expanded boundaries.

Website: marathonsailfish.com

Sponsors Wanted

Tournament season is a clean way for a brand to get seen by the right crowd: anglers, boat owners, charter customers, dock crews, tackle shops, local businesses, and offshore fishing people who actually buy gear, fuel, food, rooms, and trips.

DirtyBoat sponsor packages can be built around:

• Boat and tournament-week visibility
• Social media posts and short-form fishing content
• Fishing report features
• Website placement
• Photo and video coverage during tournament season

We are not looking for random logo clutter. We are looking for sponsors that make sense for the boat, the fishery, and the people who follow DirtyBoat.

Lock In Early

The sailfish calendar is stacked from early December through mid-April. If you want to fish, sponsor, or build a tournament week around DirtyBoat, get in early.

Looking for tournament charters or sponsor opportunities? Contact DirtyBoat here ->