Mile Marker 82 · Islamorada, FL

From our archive · Summer 2026

Florida Keys Festivals and Events: Summer 2026

Key lime pie contests, Hemingway look-alikes, and lobster season — a look back at Summer 2026 in the Keys.

The famous lobster statue in Key Largo, Florida

Key Takeaways

  • The Key Lime Festival (July 1–5) returns to the birthplace of Key lime pie, with pie-eating championships, tasting tours, live music, and Fourth of July festivities woven in.
  • Hemingway Days (July 22–26) is the Florida Keys’ most iconic summer literary event, drawing crowds to Sloppy Joe’s Bar for the legendary look-alike contest, fishing tournaments, and more.
  • Key West Lobsterfest (Aug. 5–9) marks the opening of Florida’s spiny lobster season with five days of feasting, live music, and a massive Duval Street fair.
  • The Florida Keys History & Discovery Center in Islamorada is the perfect complement to any summer festival visit, offering interactive exhibits, aquariums, and a theater that bring Keys history to vivid life.

Summer in the Florida Keys comes with a packed calendar of festivals, food events, and only-in-the-Keys traditions. From literary tributes to crustacean feasts and citrus showdowns, here’s your guide to the best Florida Keys summer festivals and events.

Key Lime Festival | July 1–5, 2026

The Key Lime Festival rolls into Key West — the birthplace of Key lime pie — for five citrus-soaked days spanning the Fourth of July weekend. Highlights include the World Famous Key Lime Pie Eating Championship on July 4, the gravity-defying Key Lime Pie Drop from atop the historic lighthouse, and the Key Lime Pie Hop, a downtown tasting tour through Old Town. Cocktail Sip & Strolls, rum tastings, artisan vendor markets, and live music round out the week.

Pair your trip with a stop at the Florida Keys History & Discovery Center in Islamorada. Our exhibits on the Keys’ agricultural and maritime heritage add rich context to the culinary traditions you’re celebrating.

Hemingway Days | July 22–26, 2026

Now in its 45th year, Hemingway Days honors the legacy of Ernest Hemingway, who called Key West home throughout the 1930s, with five days of literature, sport, and spectacle. The beloved Look-Alike Contest at Sloppy Joe’s Bar is the centerpiece, but the week also includes marlin fishing tournaments, book signings at the Hemingway Home & Museum, rum tastings, and a tongue-in-cheek “Running of the Bulls.” Book accommodations early; this is one of the Keys’ busiest weekends of the year.

For a deeper dive into the era that shaped Hemingway’s Key West, the Florida Keys History & Discovery Center is a natural companion stop. Exhibits on the Overseas Railroad and the catastrophic 1935 Labor Day Hurricane bring this chapter of Keys history to life. General admission is $15; military admission is free.

Key West Lobsterfest | Aug. 5–9, 2026

Key West Lobsterfest returns for its 28th year, celebrating the opening of Florida’s spiny lobster season with five days of feasting, live music, and a sprawling Duval Street Fair. The kickoff Lobster Boil sets the tone, and the street fair keeps the energy going with lobster prepared every imaginable way and local bands playing into the night. Proceeds benefit the Key West High School Scholarship Fund.

Whether you’re chasing pie-eating contests or Papa Hemingway look-alikes, the Florida Keys has plenty to offer this summer. Make time for the Florida Keys History & Discovery Center along the way; it’s the one stop that makes every other stop more meaningful.

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