What’s Happening From Key Largo to Key West This Summer

by Noreen Kompanik
Last updated: 10:00 AM ET, Sat May 30, 2026

Florida Keys & Key West is turning up the heat with a summer of local traditions, world-class culinary festivals and landmark America250 celebrations.

Memorial Day weekend kicked off with the 36^th Annual Schooner Wharf Minimal Regatta along with the Murph Challenge at Big Pine Key Memorial Park. The rest of the summer months through Labor Day weekend offer more exciting local-inspired events.

June Events

Key West Pride (June 3 – 7) — With the theme “Color the Island: A Celebration of Identity Through Color & Creativity,” the island transforms into a vibrant, living work of art filled with music, performances, and community connection, culminating in a joyful Key West Pride parade.
Coralpalooza (June 7) — Divers from across the globe join the Coral Restoration Foundation for reef restoration dives during this internationally recognized ocean conservation event.
Summer Solstice Celebration (June 8 – 21) — celebrates the longest days of the year at Mallory Square, featuring live performances, artisan demonstrations and interactive experiences.
CFK Swim Around Key West & Swim Meets (June 12 – 14) — Adventure seekers can dive into the 12.5-mile Swim Around Key West, the only sanctioned, insured, and U.S. Coast Guard-permitted race of its kind. The event includes additional swim meets and festivities celebrating endurance, ocean adventure, and the spirit of competition.
Truman’s Tropical Fruit Festival (June 13) — Sample sweet flavors and exotic fruits of the tropics at the historic Harry S. Truman Little White House. Learn fascinating fruit lore, purchase tropical trees and enjoy local food, cocktails and family-friendly activities in a lush garden setting.

July Events

Key Lime Festival (July 1 – 5) — a vibrant celebration honoring the island’s signature citrus and quirky spirit that includes a lineup of pie tastings, gastronomic events, contests, live music, and creative activities.
Key West Mermaid Festival (July 2 – 5) — Mythical aquatic creatures come to life for several days of whimsical fun highlighting ocean conservation with an imaginative twist, family friendly events at the Florida Keys Eco-Discovery Center, and mermaid-themed pool parties.

America 250 Celebrations

Monroe County is proud to celebrate America’s 250th anniversary with community-wide experiences that honor our nation’s history while showcasing the unique spirit of The Florida Keys. Independence Day weekend events include:

Declaration of Independence Cookout (July 3) — The event celebrates America’s 250th anniversary at a free, family-friendly cookout on the lawn of the Truman Little White House in Key West.
Lower Keys (July 3) — The Lower Keys Rotary Club hosts an evening of Independence Day festivities at Big Pine Community Park with food, entertainment, family activities, and a fireworks display.
America 250 5K (July 4) — A festive run/walk at Higgs Beach in Key West hosted by the Rotary Club of Key West, supporting local scholarships.
Key West (July 4) —The night sky lights up over the ocean during Key West’s annual fireworks show, launched from the Edward B. Knight Pier.
Marathon (July 4) — a full day of festivities including a patriotic parade followed by fireworks over Sombrero Beach
Islamorada (July 4) — a celebration at Founders Park with an evening of community fun, live entertainment, and a festive fireworks display.
Key Largo (July 4) — The celebration begins with a patriotic parade followed by a community picnic, concluding with fireworks over Blackwater Sound.
Lower Keys Underwater Music Festival (July 10 – 11) — A music festival where divers and snorkelers explore part of the continental U.S.’s only living coral barrier reef with a one-of-a-kind underwater concert that promotes reef protection.
Hemingway Days (July 22 – 26) — Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work gather annually in Key West for this celebration honoring the legacy of the American literary giant who lived and wrote on the island for most of the 1930s.

August Events

Key West Lobsterfest (August 5 – 9) — Lobsterfest celebrates Florida’s spiny lobster season opening with an island-wide party. From the savory kickoff Lobster Boil to the lively Duval Street Fair featuring live music, this festival is the ultimate crustacean celebration in the Florida Keys.
Tropical Heat (August 12 – 16) — Tropical Heat is a high-energy, all-male celebration drawing visitors from around the world with pool parties, dance events and vibrant nightlife.
Key West Rum Fest (August 12 – 16) — The Key West Rum Fest celebrates Caribbean culture and craftsmanship with premium rum tastings, cocktail events and culinary experiences.

Labor Day Weekend

Womenfest Key West (September 2 – 6) — Womenfest is Tropical Heat's opposite. The event brings a soulful and empowering energy to Key West for a celebration of creativity, connection, and community. The 2026 theme “Lost Women in the Arts” festival highlights poetry reading, an art exhibition event, themed pool parties, live music, DJs, bike and trolley tours, a sunset sail, clothing-optional snorkel trip, speed-dating, foodie fun and more.
Key West BrewFest (September 5 – 7) — Brewfest is an island-wide celebration of craft beer featuring tastings, tap takeovers, beer pairings, and themed events. Breweries from across the U.S. join local favorites culminating in the popular Grand Tasting event at Southernmost Beach Resort.
Just a Few Friends Festival (September 3 – 7) — a laid-back celebration inspired by the music and legacy of the destination’s favorite son — legendary singer-songwriter Jimmy Buffet.