Palm-fringed tropical beach with lounge chairs, a rocky jetty, and calm blue water at sunset; a tranquil island paradise.

Spring and Summer Events in The Florida Keys

Published on February 24, 2026

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Spring and summer are when The Florida Keys fully come to life. The season brings a steady rhythm of events rooted in the region’s fishing heritage, outdoor culture, and love of time on the water. From multi-day tournaments to live music gatherings and open water swims, these moments shape the pace of the islands and add depth to any visit.

Staying at The Islands of Islamorada places you in the heart of it all. With a relaxed island setting and easy access to events throughout The Keys, it’s a natural home base for travelers who want to experience the season while still enjoying the space, privacy, and comfort of a private villa or suite.

A person in sunglasses examines jewelry at a colorful outdoor market, surrounded by various items on display on a table.

Morada Way Third Thursday Art Walk

A lively monthly evening event showcasing local galleries, artists, live music, and food along Islamorada’s Morada Way Arts District. This community favorite offers a relaxed cultural experience and an easy way to enjoy the island after sunset.

Third Thursday of each month
6-9pm

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A large sandcastle on the beach with colorful kites and sails, people playing nearby, and the ocean in the background.

Islamorada 34th Annual Island Fest

A two day community celebration featuring live music, local food vendors, art booths, and family friendly activities. Held at Founders Park, this annual festival offers a relaxed way to experience island culture beyond the water.

March 28–29, 2026

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A close-up of a person strumming an acoustic guitar, fingers plucking the strings near the soundhole, wood grain visible.

Key West Songwriters Festival

A beloved music festival featuring live performances at waterfront venues throughout Key West, easily paired with a stay in the Upper Keys.

April 29–May 3, 2026

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Two people are fishing from a boat on calm turquoise coastal waters under a clear blue sky.

ABC-FEC Islamorada Backcountry Fishing Tournament

A signature local event bringing anglers and spectators together for competition, camaraderie, and coastal festivities on Islamorada waters.

May 1–2, 2026

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Logo reading “Golden Fly Tarpon Tournament” over a grayscale photo of a large fish (tarpon) on a boat or water.

Golden Fly Tarpon Tournament

A respected fly fishing competition drawing anglers to Islamorada waters for three days of skill, strategy, and friendly rivalry. Known for its strong local participation and long standing presence in the Keys fishing community.

May 18–20, 2026

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A lighthouse tower rises above the waterline as waves splash around, with a diver or swimmer visible underwater near the bottom, in clear blue seas.

Swim for Alligator Lighthouse

A renowned open-water swim held each year in the Keys, drawing participants and spectators from around the world for a challenging and unforgettable journey to the historic Alligator Lighthouse.

September 12, 2026

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