From Key Largo to Key West: A Summer's Worth of Festivals, Event Traditions and America 250 Celebrations
FLORIDA KEYS & KEY WEST, Fla. (May 22, 2026) — From Memorial Day Weekend through Labor Day Weekend, the Florida Keys & Key West is turning up the heat with a summer calendar running from Key Largo to Key West. Think local traditions, world-class culinary festivals, and landmark America 250 celebrations.
Summer is “Keys Season” in The Florida Keys & Key West offering great value at hotels and resorts, fewer crowds as well as awesome fishing and diving conditions; all set against that classic Keys backdrop of turquoise waters, warm breezes, and relaxed island vibes paired with a packed event calendar. Highlights include:
MEMORIAL DAY WEEKEND
36th Annual Schooner Wharf Minimal Regatta
May 24, 2026
Get ready for a splash-filled afternoon at one of Key West’s most unique and entertaining traditions. Participants build their own boats using a limited set of materials, including plywood, lumber, duct tape, and fasteners, then race them through the Key West Bight in a spirited and often unpredictable competition. Teams of up to six compete across categories such as fastest times, most creative designs, best costumes, and even the most memorable sink. Learn more.
Murph Challenge at Big Pine Key Community Park
May 25, 2026
Honor Memorial Day with the Murph Challenge, a community fitness event open to all levels taking place at Big Pine Community Park in Big Pine Key. This challenging workout includes a one-mile run, pull-ups, push-ups, squats, and another one-mile run, completed with or without a weighted vest, in tribute to Navy SEAL Lt. Michael Murphy. Learn more.
JUNE EVENTS
Key West Pride
June 3 – 7, 2026
June ushers in the kaleidoscopic Key West Pride, one of the most beloved Pride events in the country. With the 2026 theme “Color the Island: A Celebration of Identity Through Color & Creativity,” the island will transform into a vibrant, living work of art filled with music, performances, and community connection, culminating in a joyful parade and unforgettable celebrations. Learn more.
Coralpalooza
June 7, 2026
Divers from across the globe join the Coral Restoration Foundation® for reef restoration dives during this internationally recognized ocean conservation event. Participants work together to outplant coral and help restore vital reef ecosystems, making a meaningful impact beneath the surface while celebrating the beauty of the Florida Keys’ marine environment. Learn more.
Summer Solstice Celebration
June 8 – 21
Celebrate the longest days of the year at the Summer Solstice Celebration in Mallory Square. This nightly festival features live performances, artisan demonstrations and interactive experiences beginning each evening at 7 p.m., creating a festive waterfront atmosphere leading up to the summer solstice. Learn more.
CFK Swim Around Key West & Swim Meets
June 12 – 14, 2026
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 also includes additional swim meets and festivities that celebrate endurance, ocean adventure, and the spirit of competition in a spectacular open water setting. Learn more.
Truman’s Tropical Fruit Festival
June 13
Sample the sweet flavors of the tropics at Truman’s Tropical Fruit Festival at the historic Harry S. Truman Little White House. Taste rare and exotic fruits, learn fascinating fruit lore, purchase tropical trees and enjoy local food, cocktails and family-friendly activities in a lush garden setting. Learn more.
JULY EVENTS
Key Lime Festival
July 1 – 5, 2026
The Key Lime Festival is a vibrant, multi-day celebration held each summer in Key West, Florida, honoring the island’s signature citrus and quirky spirit. Enjoy a zesty lineup of pie tastings, gastronomic events, contests, live music, and creative activities across multiple venues. Culinary events range from cocktail “Sip & Strolls” and pie-hopping tasting tours to intimate dinners and rum tastings infused with the tart flavor of Key lime. Signature competitions include the World Famous Key Lime Pie Eating Championship, Key Lime Pie Drop from the lighthouse, and the fiery 5-Alarm Pie Challenge. Learn more
Key West Mermaid Festival
July 2 – 5, 2026
Make a splash at the annual Key West Mermaid Festival, where the mythical aquatic creatures come to life for several days of whimsical fun. This celebration highlights ocean conservation with an imaginative twist, featuring family friendly events at the Florida Keys Eco-Discovery Center, mermaid-themed pool parties, and more. Learn more.
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, 2026): Celebrate 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, 2026): The Lower Keys Rotary Club hosts an evening of Independence Day festivities at Big Pine Community Park, featuring food, entertainment, family activities, and a fireworks display beginning around 9 p.m.
America 250 5K (July 4, 2026): Celebrate Independence Day with a festive run/walk at Higgs Beach in Key West. Hosted by the Rotary Club of Key West, this annual 5K brings the community together while supporting local scholarships.
Key West (July 4, 2026): Watch the night sky light up over the ocean during Key West’s annual fireworks show, launched from the Edward B. Knight Pier.
Marathon (July 4, 2026): Enjoy a full day of festivities including a patriotic parade followed by fireworks over Sombrero Beach. Guests can take in the show from the shoreline or even from the water.
Islamorada (July 4, 2026): Celebrate at Founders Park with an evening of community fun, live entertainment, and a festive fireworks display in the Upper Keys.
Key Largo (July 4, 2026): The celebration begins with a patriotic parade followed by a community picnic and concludes with fireworks over Blackwater Sound, creating a full day of Independence Day fun.
Lower Keys Underwater Music Festival
July 10 – 11, 2026
Divers and snorkelers can explore part of the continental United States’ only living coral barrier reef while enjoying a one-of-a-kind underwater concert that promotes reef protection. Held at Looe Key Reef within the Florida Keys National Marine Sanctuary, this immersive experience blends music, marine conservation, and unforgettable underwater adventure. Learn more.
Hemingway Days
July 22 – 26, 2026
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work gather annually in Key West for the Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include:
Scores of stocky, bearded men resembling Ernest are to compete in the annual Hemingway® Look-Alike Contest at Sloppy Joe’s Bar, 201 Duval St., a frequent hangout for the legendary writer during his Key West years.
Other festival events include the wacky “Running of the Bulls,” a presentation on 1930s Key West, a commemoration of the 126th anniversary of Ernest’s July 21 birth, a museum exhibit of rare Hemingway memorabilia, a three-day marlin tournament recalling his passion for deep-sea angling, literary readings, a street fair celebrating the island’s lively spirit, and a 5k run and paddleboard race that salutes Hemingway’s sporting interests.
Associated with the festival is the Lorian Hemingway Short Story Competition coordinated by Ernest’s author granddaughter. Learn more.
AUGUST EVENTS
Key West Lobsterfest
August 5 – 9, 2026
Celebrate the much-awaited opening of Florida’s spiny lobster season with an island-wide party packed with flavor and fun. From the savory kickoff Lobster Boil to the lively Duval Street Fair featuring live music, this beloved festival is the ultimate crustacean celebration in the Florida Keys. Learn more.
Tropical Heat
August 12 – 16, 2026
The summer temperatures rise with Tropical Heat, a high-energy, all-male celebration drawing visitors from around the world. Guests enjoy pool parties, dance events, and vibrant nightlife, creating an electrifying atmosphere filled with pulse-pounding music, authentic connection, and island-style fun. Learn more
Key West Rum Fest
August 12 – 16, 2026
Celebrate Caribbean culture and craftsmanship with premium rum tastings, cocktail events, and culinary experiences. Highlights include the Grand Tasting Event, where attendees can sample a wide range of rums, meet master distillers, and enjoy live music and island-inspired cuisine. Learn more.
LABOR DAY WEEKEND
Womenfest Key West
September 2 – 6, 2026
Womenfest brings a soulful and empowering energy to Key West, welcoming women and allies for a celebration of creativity, connection, and community. With the 2026 theme “Lost Women in the Arts,” festival highlights include a poetry reading and art exhibition event, themed and pool parties, live music and DJ sets, bike and trolley tours, a fabulous sunset sail, a clothing-optional snorkel trip, a speed-dating adventure, foodie fun and more. Learn more.
Key West BrewFest
September 5 – 7, 2026
Raise a glass at during this multi-day, island-wide celebration of craft beer featuring tastings, tap takeovers, beer pairings, and themed events. Breweries from across the country join local favorites at venues throughout Key West, culminating in the popular Grand Tasting event at Southernmost Beach Resort. Hosted by the Key West Sunrise Rotary, proceeds support local scholarships and community initiatives, making this one of the Keys’ most spirited events that also gives back. Learn more.
Just a Few Friends Festival
September 3 – 7, 2026
This laid-back celebration is inspired by the music and legacy of the destination’s favorite son — legendary singer-songwriter Jimmy Buffet. From the streets and bars Jimmy sang about to the harbors that sparked his stories, fans can stroll, sip, and sing along in the places that shaped his “changes in latitude, changes in attitude.” The festival is part memorial, part music fest, and all Buffett spirit. Learn more.
Discover more summer events and experiences in the Florida Keys & Key West at https://visitfloridakeys.com/plan-your-trip/plan-book/events.
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Nothing says “Florida Keys summer” quite like swapping sunscreen for scuba gear and helping save the reef. Held in celebration of World Oceans Day, the annual event brings participants together for hands-on efforts including outplanting corals, monitoring reef health and learning about marine conservation. Divers with the Coral Restoration Foundation and many others will take the plunge into Coralpalooza’s feel-good underwater mission on June 7, 2026. The event includes boat trips to restoration sites and community gatherings. (Photo courtesy of the Coral Restoration Foundation)
Buckets, brushes and coral-saving hustle. Check! Coralpalooza turns reef restoration into the coolest group project in the Florida Keys. The annual ocean-loving adventure, held in celebration of World Oceans Day, returns on June 7 and includes guided boat trips, coral planting activities and community gatherings. (Photo courtesy of the Coral Restoration Foundation)
Beard bragging rights are officially earned as Tim Stockwell of Key West, center, celebrates his win in 2025 at the Hemingway Look-Alike Contest at Key West’s legendary Sloppy Joe’s Bar. The contest is held each July at Sloppy Joe's Bar, a favorite Key West haunt of the author, as a centerpiece of the annual Hemingway Days festival. This year’s contest is set for July 22-26, 2026. (Mark Hedden/Florida Keys News Bureau)
Only in Key West, Fla. do “bulls” roll down Duval Street chased by a crowd of Hemingway look-alikes in sneakers and fishing shirts. The famously lighthearted event spoofs the famed bull runs of Pamplona, Spain, which author Ernest Hemingway helped make famous through his fiction. The Running of the Bulls returns during Hemingway Days, set for July 22-26, 2026. (Mark Hedden/Florida Keys News Bureau)
Fueled by faux bulls, island cocktails and impressive white beards, Hemingway fans charge through Key West, Fla. during one of summer’s most gloriously offbeat traditions. Here, Jeff Ownby of Green Cove Springs, Florida, leads hundreds of Hemingway look-alikes and fans in the 44th annual Running of the Bulls on July 26, 2025, in Key West. Ownby has joined the festivities for the past 10 years and reached the semifinals of the 2025 Hemingway Look-Alike Contest. The 45th Running of the Bulls is among the highlights of Hemingway Days and set for July 22-26, 2026. (Mark Hedden/Florida Keys News Bureau)
Thousands of Jimmy Buffett fans, affectionally known by fans as Parrotheads, march down Key West's iconic Duval Street during the festival's parade on Aug. 31, 2025. The event celebrates the life and musical legacy of the late singer-songwriter, who made Key West his home and the setting for much of his music. The Just a Few Friends Key West festival returns Sept. 3-7, 2026. (Mark Hedden/Florida Keys News Bureau)
Parrot hats on, tropical shirts untucked and Jimmy Buffett tunes turned all the way up! That’s how these fans brought their full island energy to Key West’s Just a Few Friends celebration on Aug. 31, 2025. The festival celebrates the life and music of the late singer-songwriter, whose signature island sound was shaped by his years in Key West. The next Just a Few Friends Key West festival is set for Sept. 3-7, 2026. (Mark Hedden/Florida Keys News Bureau)
Sweet victory gets messy fast as Tom Luciano of Venice, Fla., center, raises his arms in victory after winning the Key Lime Pie Eating Championship in Key West on July 4, 2025. Luciano outlasted 24 other competitors in the hands-free contest, among them U.S. Coast Guard Petty Officer Lyndon Engle, left, and Duncan Barks of Key West, right. The battle of whipped cream, pie filling and dignity for the coveted title is a highlight of the annual Key Lime Festival and set for July 1-5, 2026. (Mark Hedden/Florida Keys News Bureau)
Contestants dive face-first into Key West’s wildly messy Key Lime Pie Eating Championship during the annual Key Lime Festival. Here, Jesse Ka, with goggles covered in key lime pie, competes during last year’s July 4, 2025, contest. Ka was one of 25 competitors in the hands-free contest, a highlight of the annual Key Lime Festival, set for July 1-5, 2026. (Mark Hedden/Florida Keys News Bureau)
Mermaids, mischief and a whole lot of shimmer take over Key West, Fla. as colorful sea sirens gather at Lagerheads Beach Bar for the Key West Mermaid Festival, July 2-5, 2026. The annual whimsical island celebration splashes ashore with beach games, ocean-themed fun for all ages and enough sparkling tails to make even the fish jealous.
(Photo courtesy of Key West Mermaid Festival)
Shimmering mermaid tails, seaside whimsy and ocean-inspired fun wash ashore during the Key West Mermaid Festival, transforming the island into a playful undersea escape. From beach parties and mermaid meetups to colorful coastal characters gathered along the shore, the festival invites visitors of all ages to dive into the magic July 2-5, 2026. (Photo courtesy of Key West Mermaid Festival)
Drag royalty QMitch, in a sequined blue gown and towering headdress, waves a rainbow flag along the parade route during Key West Pride. The annual celebration fills the island with parades, performances and events for the LGBTQ+ community and allies. Key West Pride 2026, themed "Color the Island," is set for June 3-7. (Larry Blackburn/Florida Keys News Bureau)
As the sun dips over Key West’s waterfront, street performers, artists and entertainers turn Mallory Square into an open-air playground during the Summer Solstice Celebration. Crowd-favorite performer “Reidiculous Reid” Conklin keeps audiences laughing; and occasionally holding their breath; during the festivities. The nightly waterfront festival features live entertainment, artisan demonstrations and interactive performances each evening beginning at 7 p.m. The 2026 celebration runs June 8-21. (Carol Tedesco/Florida Keys News Bureau)
Some music festivals happen on stage. In the Lower Keys, they happen underwater…complete with mermaids, scuba gear and live tunes drifting through the reef. Donna Whitney of Miami, dressed as a mermaid, performs with a harp during the Lower Keys Underwater Music Festival on Looe Key Reef on July 12, 2025. The festival pipes music through the water as costumed divers and snorkelers explore the reef, in an event staged to promote coral reef protection. The 2026 Lower Keys Underwater Music Festival is set for July 10-11. (Frazier Nivens/Florida Keys News Bureau)
Costumed divers strike a pose beneath the waves during the Lower Keys Underwater Music Festival, where reef-loving revelers celebrate marine life in true Florida Keys fashion. Last year’s underwater performance on July 12, 2025, on Looe Key Reef featured a talented cast of musicians and divers. Front row from left are Donna Whitney and Kristen Livengood; back row from left, Jason Samuse, Ricky Allen and Monroe County Commissioner Holly Merrill Raschein. The 2026 Lower Keys Underwater Music Festival is set for July 10-11. (Frazier Nivens/Florida Keys News Bureau)
ABOUT THE FLORIDA KEYS & KEY WEST
The Florida Keys & Key West is a premier getaway destination located at the southernmost tip of Florida and the continental United States. The Keys stretch over 125 miles connected by 42 bridges and bordered by the Atlantic Ocean and the Gulf. Discover the spectacular array of diverse activities offered in the Florida Keys like fishing, diving, natural wonders, fine dining and cultural heritage. From large resorts, secluded waterfront hideaways and courtyard guest houses, visitors can uncover the perfect place for their vacation. Restoration, renovation and preservation have become a way of life in the Florida Keys. Whether you’re driving or flying into the Keys, one thing is for sure: there’s simply no place quite like it. Want more reasons to visit The Florida Keys & Key West? Get inspired at visitfloridakeys.com and follow us @thefloridakeys on social media.
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