Annual Events
Annual Events in the Florida Keys
The Florida Keys host various annual events throughout the year, offering a diverse range of activities and celebrations. Below we will list some of our favorites that we feel are MUST-DO's throughout the islands!
Fantasy Fest
Fantasy Fest is an annual 10 day adult festival that takes place at the end of October. It is one of the most anticipated events in the Florida Keys and draws thousands of visitors from around the world. It's known for it's extravagant costumes, creative body paint and lively parties, from nightly themed events at local bars and clubs to off-the-wall street parties.
One of the highlights of Fantasy Fest is the street parade, which takes place on the last Saturday of the festival. The parade features elaborately decorated floats, marching bands and participants in flamboyant costumes, many of which align with that years theme of the festival. Spectators line the streets to watch the parade and join in the festivities. Throughout the 10 day celebration, there are numerous parties, concerts, live performers and events happening across Duval Street. You will find live music, DJs, costume contests and a wide array of other entertainment.
It's worth noting that Fantasy Fest is an adult-oriented event, and some of the parties and costumes will be risqué or provocative. There are a few day events like the pet masquerade and street fair that are family friendly but this is 99% an adults only event, so probably best to keep the kids at home!
Mile 0 Fest Key West
Mile 0 fest is an annual music festival that celebrates Americana music, bringing together a diverse lineup of renowned artists and emerging talent in the genre. It offers several days of live performances across multiple stages and bars, showcasing a mix of Americana, country, rock and folk music. The festival attracts both locals fans and visitors from all over the country who come to enjoy the beautiful island setting and incredible music. In addition to the main stage performances, Mile 0 Fest also includes intimate songwriter showcases where artists share the stories behind their songs and perform in a more intimate setting.
In addition, the organizers behind Mile 0 Fest also hold the Key Western Fest and the RokIsland Fest, which are held in conjunction with Mile 0 Fest. KeyWestern Fest has included a variety of 90's country stars from Clint Black to Pam Tillis to Deanna Carter, while RokIsland has featured performers from Stone Temple Pilots, to Dee Snyder to Bret Michaels. We highly recommend booking all concerts, as they are held consecutively and you can get a combined package for a smokin' deal!
Key West Songwriters Festival
The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris.
In its over 27 years, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers. The festival takes place every May.
Key West Powerboat Races
The Race World Offshore Key West Championships take place annually every November. This is an exhilarating annual event that brings the world's top offshore boat racers to Key West. Every fall, the beautiful water off of the coast of Key West is a proving ground where professional boat racers push the limits.
Key West Lobsterfest
Key West Lobsterfest is an annual celebration of all things lobster in the beautiful city of Key West. It typically takes place in August and attracts both locals and tourists who share a love for lobster. Plan to indulge in an array of lobster-centric dishes, from classic lobster rolls and lobster bisque to more adventurous creations like lobster ceviche or grilled lobster tails.
The festival also features live music, parties, a street fair and various entertainment activities. Whether you're a seafood lover or just looking for a fun and lively event to enjoy with friends and family, the Lobsterfest is a unique experience that combines great food, entertainment, and the vibrant spirit of Key West.
Onesie Pub Crawl
Onesie Pub Crawl in Key West is a whimsical and fun event held by locals favorite bar Tattoos & Scars Saloon that takes pace in the vibrant streets of the tropical paradise of Key West. The pub crawl takes place the first week of February every year when the days are cooler and it's not too hot to pub crawl in a onesie. Imagine a group of people, all dressed in colorful and creative onesies, hopping from one pub to another enjoying drinks and reveling in the eccentric atmosphere.
The crawl has designated bars, allowing participants to visit a variety of establishments each with it's own distinct vibe and offerings. Along the way you will encounter fellow onesie-clad revelers, forming new friendships and sharing laughter as you navigate through the bustling streets. Be prepared to take photos and field questions from tourists who aren't in onesies but really want to join the fun! Check out the Tattoos & Scars Facebook page for more information.
Island Fest & Taste of Islamorada
7 Mile Bridge Run
The first race was in 1982 when a group of Marathon runners ran over the newly built 7 mile bridge before it was opened by the DOT for vehicle traffic. The 7 Mile Bridge Run is the only major race in the U.S. which has water on both sides throughout the entire race. The distance of the race is 6.8 miles, and is closed off to only 1,500 runners each year.
Anyone wishing to enter the race has less than 15 minutes to register as soon as registration opens each year because of the high demand of runners wanting to be part of history. It's one of the most stunning and scenic runs that you will ever do!
Hemingway Days
Ernest Hemingway look-alikes, writers and fans of the late author’s work gather annually in Key West in mid July, for the annual 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.
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 prose and poetry readings, the “Running of the Bulls,” a commemoration of the 124th anniversary of his July 21 birth, a museum exhibit of rare Hemingway memorabilia, a three-day marlin tournament, a street fair celebrating Key West’s lively spirit, a 5k run and paddleboard race that honor Hemingway’s sporting interests, and the announcement of the winner of the Hemingway Short Story Competition coordinated by Ernest’s author granddaughter.
Key West Brewfest
Brewfest is a multi-day festival hosted by Southernmost Beach Resort! It includes beer pairing dinners, pool parties, tap takeovers, and culminates with a signature tasting event with over 150 beers available for tasting.
Brewfest is a beer lover's paradise, attracting both locals and visitors to the southernmost city in the continental US. This annual event showcases the finest craft beers from around the country, offering a unique opportunity to indulge in a wide variety of brews while enjoying the tropical atmosphere of Key West.
Events take place at many restaurants, hotels, and bars around town making Brewfest a great way to experience Key West!At its heart Brewfest is a fundraising event put on by the Rotary Club of Key West Sunrise in the Conch Republic, a non-profit organization dedicated to serving the community and worldwide needs. Proceeds from the event benefit local scholarships and the Take Stock in Children program.