Category Archives: Sailfishing

The thrill of seeing a sailfish jump like crazy is one of the best sights in the waters around Key West. Sailfish are one of the best fighting gamefish that we have here in The Keys. They are beautiful creatures with an iridescent blue sail that seems to “light up” when they get ready to strike a bait.

We have many methods of fishing for sailfish. We specialize in live bait sailfishing on the RELENTLESS we hook many more fish due to our versatility with live bait and trolling.

Al Flutie Over the Hill Rip-Off Sailfish Tournament.

Jan. 21-22: Islamorada. Entering its 24th year, this event is “almost too much fun for old guys to handle.” Locally called the Flutie, the tournament has donated $420,000 to local and national charities. Anglers age 50 and over are welcome. … Continue reading

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Cheeca Lodge Presidential Sailfish Tournament

Jan. 17-19: Cheeca Lodge Presidential Sailfish Tournament. Islamorada.  Now in its 23rd year, the contest is a facet of the World Billfish Series and the second leg of the three-tournament Florida Keys Gold Cup Sailfish Championship. The event kicks off … Continue reading

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Islamorada SailFly Championship

Jan. 9-10: Islamorada. In this fly-fishing, all-release boat team tournament, captains, mates or anglers can tease, but only the registered anglers can cast, hook and play the fish. The 13th annual invitational challenge is limited to 20 teams, with no … Continue reading

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Key Largo Sailfish Challenge

Jan. 4-6 Key Largo Sailfish Challenge. Key Largo. At the height of the sailfish season this event follows a boat-tournament format, and prizes and trophies await first-, second- and third-place teams. Proceeds help benefit the Coral Shores High School Band … Continue reading

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Junior Sailfish Tournament.

Dec. 14-16: Islamorada Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates how to tie a bimini or rig ballyhoo. One weekend each year, anglers age 16 and younger can apply such lessons … Continue reading

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Don Gurgiolo Sailfish Classic

Dec. 7-9: Islamorada. Part of the acclaimed Redbone at Large series of tournaments, this all-release challenge offers anglers a chance to pursue sailfish in Captain Don’s memory. Up to four anglers can fish per boat. Contact Tammie Gurgiolo at 305-240-9337 … Continue reading

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IFC Captain’s Cup Sailfish Tournament.

Dec. 5-6 IFC Captain’s Cup Sailfish Tournament. Islamorada. A $25,000 winner-take-all prize, along with the prestigious Captain’s Cup, go to the top boat team. The cash prize is guaranteed if a minimum of 20 boats registers for the tournament. Once … Continue reading

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