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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. This month is November.

  1. Sailfish at their peak offshoreNovember to MarchIn season now
  2. Blackfin tunaSeptember to AprilIn season now
  3. Tarpon in the channels and on the flatsApril to JulyIn season now
  4. Mahi offshore, the charter cooler fishMay to SeptemberIn season now
  5. Bonefish on the flatsMay to July, then September and OctoberIn season now
  6. PermitApril to OctoberIn season now
  7. Islamorada Sailfish TournamentEarly DecemberIn season now

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. Nov2026Nothing on the calendar
  2. Dec4 December: Islamorada Sailfish Tournament, confirmed
  3. Jan202719 January: Islamorada Fishing Club Captain's Cup Sailfish Tournament, confirmed22 January: Cheeca Lodge Presidential Sailfish Tournament, confirmed
  4. FebNothing on the calendar
  5. MarNothing on the calendar
  6. AprNothing on the calendar
  7. MayNothing on the calendar
  8. JunNothing on the calendar
  9. JulNothing on the calendar
  10. AugNothing on the calendar
  11. SepNothing on the calendar
  12. OctNothing on the calendar

Eat and shop local

Where to eat and what to bring home from Islamorada

The places we would send a friend: kitchens locals swear by and shops worth the stop. Every one was open when we checked in October 2026. Hours run seasonal on the coast, so call ahead.

Islamorada stretches across several islands, so places are listed by mile marker (MM) on the Overseas Highway. Morada Way around MM 81.5 is the walkable arts district, with a gallery walk on the third Thursday of each month.

Where to eat 8 picks, 3 on the water

  1. Green Turtle Inn

    1947 Keys landmark restaurant

    A roadside Keys landmark from 1947 with vintage neon and wood paneling, serving breakfast and dinner plus a Roadside BBQ counter. Order the conch chowder or turtle chowder, or the Keys Benedict at breakfast.

    81219 Overseas Hwy, MM 81.2greenturtleinn.com for Green Turtle Inn (opens in a new tab)

  2. Lazy Days Restaurant

    Oceanfront seafood, cook your catch

    An oceanfront seafood restaurant with a raw bar and its own seafood market. Bring your fillets from a charter and they will cook your catch.

    79867 Overseas Hwy, MM 79.8lazydaysislamorada.com for Lazy Days Restaurant (opens in a new tab)

  3. Hungry Tarpon

    Old Florida marina cafeWater view

    A casual seafood cafe under the mangroves at Robbie's Marina, open from breakfast on. Get the Matecumbe fish sandwich or biscuits and gravy, then feed the tarpon off the dock.

    77522 Overseas Hwy, Robbie's Marina, MM 77.5robbies.com for Hungry Tarpon (opens in a new tab)

  4. Chef Michael's

    Upscale local seafood

    A dinner spot built around local catch. Try hogfish Pontchartrain, blackened with crawfish Creole cream, or the Juliette with shrimp chardonnay butter.

    81671 Overseas Hwy, MM 81.6chefmichaels.com for Chef Michael's (opens in a new tab)

  5. Marker 88

    Bayside sunset seafoodBeachfront

    A long-standing bayfront restaurant on Plantation Key with tables in the sand facing the sunset. The fresh fish sandwich and the house Key lime pie are the classic orders.

    88000 Overseas Hwy, MM 88marker88.net for Marker 88 (opens in a new tab)

  6. Morada Bay Beach Cafe

    Bayfront tables in the sandBeachfront

    Tables set right on the sand of Florida Bay with tiki torches at night, known for its monthly full moon parties. Start with conch salad or fried calamari.

    81600 Overseas Hwy, MM 81.6moradabay.com for Morada Bay Beach Cafe (opens in a new tab)

  7. Islamorada Shrimp Shack

    Casual shrimp and seafood

    A relaxed seafood spot for shrimp and grits and blackened fish, and they will cook your own catch.

    81901 Overseas Hwy, MM 81.9islamoradashrimpshack.com for Islamorada Shrimp Shack (opens in a new tab)

  8. Hog Heaven Sports Bar and Grill

    Oceanside barbecue and seafood

    A laid-back oceanside bar known for hearty barbecue and fresh seafood. Brisket burnt ends, fish tacos and blackened mahi salad are good bets.

    85361 Overseas Hwy, MM 85hogheavenbarandgrill.com for Hog Heaven Sports Bar and Grill (opens in a new tab)

Souvenirs and local shops 6 picks

  1. Rain Barrel Village

    Artisan village and galleries

    A cluster of artist studios, galleries and shops behind Betsy, the giant fiberglass spiny lobster. Watch glassblowing at Sculptured Glass and browse work by about 30 Keys artists at Art on a Whim.

    86700 Overseas Hwy, MM 86.7rainbarrelvillage.squarespace.com for Rain Barrel Village (opens in a new tab)

  2. Robbie's Tropical Open Air Market

    Open-air artisan market

    Small vendor shacks at Robbie's Marina selling beads, glass, local photography and art, next to the tarpon feeding dock.

    77522 Overseas Hwy, MM 77.5robbies.com for Robbie's Tropical Open Air Market (opens in a new tab)

  3. Florida Keys Outfitters

    Saltwater fly shop since 1989

    A respected saltwater fly fishing shop with flies, tackle and FKO logo gear, a good place for a fishing cap or tee with real local credibility.

    81219 Overseas Hwy, MM 81.2floridakeysoutfitters.com for Florida Keys Outfitters (opens in a new tab)

  4. Olive Morada

    Olive oil and specialty foods

    A tasting shop for olive oils and balsamic vinegars, including Keys-inspired flavors, plus gourmet foods, spices and gift baskets.

    82245 Overseas Hwy, MM 82.2olivemorada.com for Olive Morada (opens in a new tab)

  5. The Banyan Tree Garden Boutique

    Garden boutique and gifts

    A mother and daughter shop set in a tropical garden under a banyan tree, selling jewelry, home decor and nature-inspired gifts.

    81197 Overseas Hwy, MM 81.2banyantreeboutique.com for The Banyan Tree Garden Boutique (opens in a new tab)

  6. Islamorada Art Gallery by Pasta

    Marine and sportfish art

    The gallery of marine artist Pasta Pantaleo, known for vivid paintings of gamefish and Keys sea life, with originals and limited editions.

    MM 81.5, Morada Wayartbypasta.com for Islamorada Art Gallery by Pasta (opens in a new tab)

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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