Events & Festivals

Jun. 1, 2019
43rd Annual Swim Around Key West
The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. There are three categories: solo swimmer, two-person relay team and three-person relay team. Presented by Key West Athletics Association.

Jun. 5, 2019 – Jun. 9, 2019
Key West Pride
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.

Jun. 9, 2019
Key West Concerts presents: Slightly Stoopid
The Ocean Beach, California-based band formed by multi-instrumentalists Kyle McDonald and Miles Doughty has matured into a versatile musical ensemble consisting of drummer Ryan “Rymo” Moran; percussionist Oguer “OG” Ocon; saxophonist Daniel “Dela” Delacruz; keyboardist Paul Wolstencroft; trumpet and trombone player Andy Geib, and an arsenal of guests that frequent the stage, most notably Karl Denson (Rolling Stones/Greyboy Allstars), Don Carlos, Chali 2na (Jurassic 5) and Rashawn Ross (Dave Matthews Band). Special guests include Matisyahu, Tribal Seeds and Hirie. Gates open 3:30 p.m., show states 4:30 p.m., Key West Amphitheater.

Jun. 15, 2019
FKCC Swim Around Key West
The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.

Jun. 15, 2019
Seventh Annual VFW Fishing Tournament
Sponsored by the Southernmost VFW Post 3911, this family oriented inshore and offshore tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee, senior angler and active service member. The heaviest Dolphin: 1st-$3000.00; 2nd-$1000.00; and 3rd $500.00. Weigh-in at Murray Marine. All proceeds benefit VFW Relief Fund for Monroe County veterans, and local charities.

Jun. 21, 2019 – Jun. 23, 2019
Key West International Guitar Festival: Bridges to Paradise
The festival features a fusion of master guitarists performing classical, jazz, Latin, blues, folk & contemporary music in historic venues throughout the island, in a series of world-class concerts. Food and wine events are to be paired with music throughout the island offering a culinary and cultural experience highlighted by a special event, “Virtuoso Chefs of Key West.” Featured artists include Mateo, Belle, Rolando Rojas and Larry Baeder. Tickets on sale April 6, online.

Jun. 21, 2019 – Jun. 23, 2019
Mystery Fest Key West
Renowned mystery writers, aspiring authors, true crime experts and fans meet in America’s southernmost city. The Fest features a who’s-who of award-winning and bestselling mystery/suspense authors and true crime experts, Mystery Fest Key West is a fun and fascinating meet-and-greet where writers can catch up with old friends and readers can meet leading authors, collect signed books and participate in workshops, panels, and presentations where the most devious of minds explain why—and how—they do it.

Jun. 29, 2019
Key West Mango Fest 2019
Mango Fest of Key West features all things mango including mango tasting, mango trees and mango daiquiris. The culinary competitions between local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. The Vendor Village gives art collectors and foodies the experience of a festival atmosphere. Music is provided along with live radio broadcasts. From 10AM to 3PM, Bayview Park, 1400 Truman Ave.

Jul 4, 2019 – Jul 7, 2019
Seventh Annual Key Lime Festival
A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

Jul 5, 2019 – Jul 7, 2019
Inaugural Key West Mermaid Festival
Our crew and mermaid pod are over the waves excited to bring you this three-day weekend event, packed with so many fun and mervelous events. From “Mermaid Meet & Greets” and our “Sunday Funday with Mermaids”, to mermaid vendors with a splash of entertainment and heaps of ocean awareness, dancing under the sea, and much, much more! With activities for the little mermaids and adult mermaids at heart, the Key West Mermaid Festival is an entire island family friendly event welcoming Florida Keys locals and visitors from across all of our oceans!

Jul 11, 2019 – Jul 13, 2019
Mel Fisher Days
Each year a celebration is held to commemorate Mel Fisher’s famous 16-year search for the Spanish galleon Atocha, which led to a $450 million dollar treasure discovery in the waters off Key West. Celebration highlights typically include the chance to explore the Fisher family’s 90-foot working salvage boat J.B. Magruder, behind-the-scenes tours of the family’s private artifact conservation lab, and social events where attendees can mingle with members of the “golden crew” that found the Atocha’s riches.

Jul 13, 2019 – Jul 16, 2019
Del Brown Permit Tournament
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released 513 permit on fly tackle off the Florida Keys in his lifetime. Begun in 2001, the tournament is based out of Hurricane Hole Marina. Each year the event makes a contribution to the Bonefish Tarpon Trust and the Jon Ain Memorial Fund to continue permit research.

Jul 16, 2019 – Jul 21, 2019
Hemingway Days
The 39th annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

Jul 17, 2019 – Jul 20, 2019
Stock Island Marina Village Key West Marlin Tournament
Anglers ply the waters once fished by writer Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Jul 20, 2019
27th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race
This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.

Aug 14, 2019 – Aug 18, 2019
Tropical Heat
The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

Aug 29, 2019 – Sep 2, 2019
10th Annual Key West Brewfest
Nearly 200 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event (Aug. 31) are some of the offered activities.