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. Whether you're visiting as a couple, a group of friends, or a family with kids in tow, the season offers something for everyone — from waterside festivals to open-air music events the whole family can enjoy.
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 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
One of the most family-friendly events of the season, Island Fest brings two days of live music, local food, art booths, and kids' activities to Founders Park — an easy way to experience authentic Keys culture. Held at Founders Park, this annual festival offers a relaxed way to experience island culture beyond the water.
March 28–29, 2026
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
A signature local event bringing anglers and spectators together for competition, camaraderie, and coastal festivities on Islamorada waters.
May 1–2, 2026
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
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
