Spring in the Florida Keys & Key West brings warm breezes, turquoise waters and that easygoing island rhythm. The season also kicks off a colorful lineup of festivals and events celebrating everything from art, music and fresh seafood to conservation and endurance sports. And in true Keys fashion, things can often take a turn for the delightfully quirky. Whether a music lover, foodie, outdoor adventurer or culture seeker, there’s no shortage of reasons to head south this spring.
ONLY-IN-THE-KEYS CELEBRATIONS
Underwater Easter Egg Hunt April 4
Captain Spencer Slate of Captain Slate’s Scuba Adventures trades his dive gear for a bunny suit every Easter to hide brightly colored hard-boiled eggs on a shallow reef in the Florida Keys National Marine Sanctuary. Divers and snorkelers of all ages hunt for eggs…real ones, painted with nontoxic coloring to protect the marine environment. A specially marked golden egg earns its finder a prize basket of dive trips and gear. The annual fundraiser supports local children in need. Only 26 spots available with departure at 8:30 a.m. Rates: $120 with full gear, $100 tanks and weights only, $65 adult snorkeler, $55 child snorkeler. Booking and information: www.captainslate.com.
Easter Egg Roll at the Truman Little White House April 4
The Harry S. Truman Little White House hosts its 9th Annual Easter Egg Roll on the grounds of Florida’s only presidential museum, 111 Front St., Key West. The free, family-friendly event includes patriotic crafts, photos with the Easter Bunny and a commemorative wooden egg for each child. The event runs 9 a.m.- noon and follows the tradition of the White House Egg Roll, which dates back to 1878. Learn more.
Conch Republic Independence Celebration April 17 – 26
Ever wondered what happens when a city “secedes” for fun? Key West’s legendary Conch Republic Independence Celebration commemorates the island’s playful 1982 declaration of independence with 10 days of quirky festivities. Highlights include the Great Sea Battle, the World’s Longest Parade and the Schooner Wharf Wreckers Cup Race. Expect irreverent humor, lively parades, fresh seafood, local music and plenty of island spirit. Learn more.
Schooner Wharf Minimal Regatta May 22
Boats made of thin plywood and duct tape don’t sound very seaworthy, but they’re the only vessels allowed in the 34th annual Schooner Wharf Minimal Regatta. The wacky Memorial Day Weekend regatta takes place off the Schooner Wharf Bar in the Key West Historic Seaport. Costumes and themed entries are encouraged, and many boats end up being more scenic than seaworthy. 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.
CULTURE & COMMUNITY
30th Annual Key West Songwriters Festival April 29 – May 3
Interested in the stories behind those popular country and pop songs? The five-day Key West Songwriters Festival offers performances and storytelling sessions from the writers who created them. Now marking its 30th year in 2026, the festival brings veteran Nashville songwriters and emerging artists together for performances and songwriter rounds at venues throughout Key West. Headlining artists this year include Ronnie Bowman, The Brummies, Chuck Cannon, Ashley Cooke and many more.Learn more.
Lower Keys Rotary Derby Day Roundup May 2
Experience the best of the Lower Keys at this signature community celebration. Enjoy live music, delicious local cuisine, unique vendors and family-friendly activities in a beautiful island setting. The event showcasesthe welcoming spirit and vibrant culture that define the Florida Keys. Learn more.
Key West Pride June 3 – 7
Every June, Key West Pride transforms the island into a vibrant celebration of diversity, unity and love. The weeklong festival welcomes LGBTQ+ visitors, allies and locals with an exciting schedule of pool parties, drag shows, comedy nights, street fairs and sunset sail cruises. The festivities culminate in a colorful Pride Parade along Duval Street featuring Key West’s iconic 100-foot Sea-to-Sea rainbow flag. 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.
ACTIVE ADVENTURE ON LAND & SEA
Spanish Fly Shark Tournament April 2 – 4
This third annual catch-and-release shark tournament, based out of the Key West Yacht Club, is focused on increasing knowledge of sharks in the Florida Keys and benefits the Jose Wejebe Memorial Foundation. With both inshore and offshore divisions, the challenge is to be televised by Outdoor America. Learn more.
Florida Keys Lionfish Derby April 23 – 26
Divers and snorkelers lend a hand (or a fin?) in conservation efforts during the Florida Keys Lionfish Derby, hosted by the Reef Environmental Education Foundation (REEF). Participants help remove invasive lionfish from local waters while competing for prizes and supporting reef protection. It’s a hands-on way to experience the Keys’ incomparable marine ecosystem while making a positive impact. Learn more.
Tarponian Tournament April 25 – 29
Teams of angler’s fish three nights at the major bridge channels in Marathon in this high-energy tarpon tournament. Organizers plan to present charitable donations at the tournament banquet to Marathon-based animal rescue organizations The Turtle Hospital and Dolphin Research Center. Call 267-210-1952.
I.CARE’s 4th Annual Trash Derby & Festival April 30 – May 3
This eco-minded event invites scuba divers and land lovers to help clean up the Florida Keys. Participants compete to collect the most marine debris, then celebrate their efforts at the festival finale on May 3 at Founders Park in Islamorada. The closing celebration features live music, local food and family-friendly activities. Learn more.
Marathon Bull and Cow Dolphin Tournament May 1– 3
The largest bull and cow dolphin fish (mahi-mahi) combined weight takes first place and a guaranteed prize of $20,000 in this popular annual contest, with cash prizes also awarded for largest bull dolphin, largest cow dolphin plus largest wahoo, blackfin tuna and tripletail. Learn more.
Key West Paddle Classic May 9
Grab a paddle and head for the turquoise waters of Key West for the 29th Annual Key West Paddle Classic. One of the East Coast’s premier paddle races, this beloved event welcomes both seasoned competitors and newcomers for a memorable day on the water. Participants can expect a rewarding course, affordable entry and plenty of camaraderie among fellow paddle enthusiasts. Learn more.
KEYS100 Ultramarathon May 16 – 17
For endurance athletes seeking the ultimate challenge, the KEYS100 Ultramarathon offers a breathtaking route from Key Largo to Key West. Runners can tackle the full 100-mile course or opt for 50-mile and 50K options, finishing just steps from the sand at Higgs Beach in Key West. Learn more.
Skippers Dolphin Tournament May 29 – 31
Headquartered at Skippers Dockside Restaurant in Key Largo, this tournament pays cash prizes of over $60,000, including a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers. Learn more.
Coralpalooza June 4 – 6
Celebrate World Oceans Day in the Florida Keys by joining Coralpalooza, a hands-on coral reef restoration event. Participants head out on boat trips to help outplant corals, monitor reef health and learn about marine conservation, with evening social gatherings bringing the community together. Learn more.
CFK Swim Around Key West & Swim Meets June 12 – 14
During the only sanctioned, insured and US Coast Guard permitted race around Key West, adventure seekers can dive into the 12.5-mile Swim Around Key West, a spectacular open-water challenge. The event also includes additional swim meets and spectator-friendly festivities celebrating the spirit of endurance and ocean adventure. Learn more.
