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Monroe County, the Upper Keys

Islamorada, Florida: the Sport Fishing Capital of the World

A village of islands where the charter fleet set the rules of modern light tackle fishing. Here is what comes back to the dock, when the sailfish run, and how to cook the mahi in your cooler.

Five JollyGringo'z bottles on the counter of a bait and tackle shop

How a village became a fishing capital

Islamorada, Village of Islands runs from about mile marker 90 down to mile marker 72, four islands strung along 18 miles of the Overseas Highway: Plantation Key, Windley Key, Upper Matecumbe and Lower Matecumbe. The village government describes the place in one line, as the Sport Fishing Capital of the World.

Before the anglers came the farmers. Settlers from the Bahamas arrived in the mid to late 1800s, and the Pinder family opened the area's first pineapple canning factory, while neighbors grew limes, melons and vegetables. Henry Flagler's railroad reached Key West in 1912 and brought fishing visitors with it, and the first road followed in 1928.

Charter fishing took hold in the late 1930s, when Captain Walter A. Starck and his son Buck began running anglers out of the property now tied to Whale Harbor. In the mid 1940s Bud and Mary Stapleton bought the land that became Bud N' Mary's Marina, and in 1950 local guides and captains founded the Islamorada Fishing Club.

The guides who worked these flats changed the sport. Captain Jimmie Albright is credited with the Albright knot and with guiding anglers to early fly caught bonefish and tarpon. Ted Williams spent years learning from them. Decades later Captain Richard Stanczyk and Vic Gaspeny worked out how to catch broadbill swordfish in daylight off Islamorada.

Sailfish in December, mahi in summer

The Islamorada Sailfish Tournament opens the Florida Keys Gold Cup series every December and is the main fundraiser for the Islamorada Charter Boat Association. Its organizers call it one of the oldest fishing tournaments in the United States. Sailfish are released, which is why the food story here is about everything else the boats bring back.

On a summer charter that usually means mahi, the offshore fish the tourism council's calendar puts at its peak from May through September, plus blackfin tuna and snapper off the reef. The tourism council also points out it is possible here to chase a sailfish offshore and then work the backcountry for bonefish, permit or redfish on the same day.

What is in season

What is biting off Islamorada

Fish timing comes from the Monroe County tourism council's fishing calendar, which shows when a species is usually easiest to target, not when it is legal to keep. Check FWC rules before you harvest.

What is in season in Islamorada, by month
WhatWhenMonths
Sailfish at their peak offshoreIn season nowNovember to March
Blackfin tunaIn season nowSeptember to April
Tarpon in the channels and on the flatsIn season nowApril to July
Mahi offshore, the charter cooler fishIn season nowMay to September
Bonefish on the flatsIn season nowMay to July, then September and October
PermitIn season nowApril to October
Islamorada Sailfish TournamentIn season nowEarly December

Festivals and events

The Florida Keys Gold Cup sailfish series

Three Islamorada tournaments make up the Gold Cup. These dates were posted on the tournament site when we checked in October 2026. Dates update every month: confirmed means the organizers posted it, expected means it follows the usual pattern.

The next twelve months in Islamorada

  1. Oct2026Nothing on the calendar
  2. NovNothing on the calendar
  3. Dec4 December: Islamorada Sailfish Tournament, confirmed
  4. Jan202719 January: Islamorada Fishing Club Captain's Cup Sailfish Tournament, confirmed22 January: Cheeca Lodge Presidential Sailfish Tournament, confirmed
  5. FebNothing on the calendar
  6. MarNothing on the calendar
  7. AprNothing on the calendar
  8. MayNothing on the calendar
  9. JunNothing on the calendar
  10. JulNothing on the calendar
  11. AugNothing on the calendar
  12. SepNothing on the calendar

From the lineup

What we would pack for a week of charters

Firm offshore fish and a hot grill at the rental. These three cover it.

Gulf Coast Blackening

Some Heat, 3 oz, $9

Deep, smoky and herby with a pepper build. Mahi and snapper fillets take a dark crust from it in a hot cast iron pan.

Beautiful Sunset

Mild, 3.5 oz, $9

Dried orange peel and ancho, a little sweet. Good on grilled blackfin tuna or a mild white fish for anyone who wants less heat.

Grand Isle Hook Set Sauce

Some Heat, 8 fl oz, $12

Louisiana style hot sauce with roasted red pepper and lime. Built for fried fish and fish sandwiches.

Cook it at home

Blackened mahi from the charter cooler

Mahi is firm and mild, which makes it the right fish for a hard sear. Do this outside on a grill side burner or with the fan on high.

What you need

  • 4 mahi fillets, skin removed, about 6 oz each and an inch thick
  • Gulf Coast Blackening
  • 3 tbsp melted butter
  • Lime wedges and Grand Isle Hook Set Sauce

How it goes

  1. Heat a dry cast iron skillet over high heat for 5 minutes, until it is smoking hot.
  2. Brush both sides of each fillet with melted butter and coat them heavily with Gulf Coast Blackening.
  3. Lay the fillets in the pan and leave them alone for 2 to 3 minutes, until the bottom is dark and crusted.
  4. Turn, add a spoon of butter to the pan and cook 2 to 3 minutes more, until the center is opaque and the fish flakes.
  5. Rest a minute, then serve with lime and a few shakes of Hook Set Sauce.
Worth knowing. Cut out the dark red bloodline before you season. It tastes strong and keeps the fillet from cooking evenly.

Another one from our kitchen: Blackened Redfish

Questions

Questions about Islamorada

Why is Islamorada called the Sport Fishing Capital of the World?

The village uses the title itself. Charter fishing started there in the late 1930s, and its guides helped pioneer backcountry, fly and light tackle fishing, according to the Monroe County tourism council.

When is the Islamorada Sailfish Tournament?

Early December. The 63rd tournament runs December 4 to 6, 2026, with fishing on December 5 and 6. Dates for 2027 had not been posted when we checked.

What is the Florida Keys Gold Cup?

A three tournament sailfish series in Islamorada: the Islamorada Sailfish Tournament in December, then the Islamorada Fishing Club and Cheeca Lodge tournaments in January.

When is the best time to catch sailfish in Islamorada?

The tourism council's fishing calendar shows sailfish at their peak from November through March, which is why the Gold Cup runs in December and January.

Do you ship to Islamorada?

Yes. We ship anywhere in the U.S. Orders go out within two business days, and shipping is free over $45.

Run a shop, market or kitchen in Islamorada? Carry JollyGringo'z by the case. Tell us about the shop and the price sheet, the case packs and a sample bottle come straight back.

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