Key West Events
Vacation Homes of Key West brings you an updated calendar of Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.
Apr 17 to Apr 26
Celebration of Key West’s brief secession from the United States. Event highlights include drag (queen) races on Duval Street (April 18, 1-11pm), and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale Cuban bread at Coast Guard vessels and each other in a mock secession (April 24, 6pm). Kick-off party at the Schooner Wharf bar on April 17th, 7pm.
Apr 30 to May 3
4-Mile Open Race and a 12-Mile Distance Race. Choose the one you want that suits you best. Paddle over crystal blue waters, circling Key West through scenic mangroves, passing by the Historic Seaport district and more. The race around Key West is open to paddlers on stand-up paddleboards, prone boards, outrigger canoes, dory boats, surf skis and kayaks.
Key West Higgs Memorial Beach, located at 1000 Atlantic Boulevard (about 1 mile from Smather’s Beach, is the staging grounds. Here you find clean changing rooms and bathrooms, a full service restaurant, and parking!
May 1 to May 8
A 'moveable feast' road show of small art canvases comprising a 24-foot mosaic mural of six-by-six-inch fine art works. Almost all medial represented. Final stop of the road art show will be at the Gato Building, 1100 Simonton Streets in Old Town Key West. This is a fundraiser to support Key West artists and cultural organizations sponsored by the Florida Keys Council of the Arts, located at the Gato Building.
Meet up - 6:30 pm at Thai Island Restaurant, 711 Palm Avenue, Key West. Learn about the running club whose purpose is to promote and encourage long distance running through the education of the community on the benefits of physical fitness and sport. Learn about all the running events coming up. Join the club. Volunteers always needed. Great way to be healthy in paradise!
Popular annual dolphin fishing tournament headquartered at Key West's Historic Seaport. Anglers compete for more than $13,000. Participants are scored on the highest total combined weight of three dolphin catches. Other prizes include four-night tropical fishing vacation for four. This tournament is open to all anglers. There is no limit on the number of boats that can register. Entry fee is $750.
Here's your chance to fulfill that fantasy of swimming around an island! This long distance race invites solo swimmers and relay teams of up to 6 people to take the plunge, with or without fins. When you're done you can say you swam through the waters of the Atlantic Ocean and the Gulf of Mexico! All ages welcome. For more info, contact Lori Bosco
Jun 10 to Jun 14
A celebration of the LGBTA community in Key West. This event includes a parade and street fair. The parade features the largest pride flag in the world, stretching from one end of Duval street to the other. A complete list of events and information on participating can be found on the event website.
Jun 20 to Jun 22
Charity tournament for college scholarships sponsored by the Key West Gator Club. Anglers compete to catch dolphin fish which are plentiful in the summertime off-shore Key West. Grand prize is $5000. to the boat with the largest aggregate weight in dolphin fish over a 2 day period. Divisions for men, women, and juniors to participate. Total prizes of $15,000. Cocktail parties and dinner. Speaker from UF Alumni Association.
Super Powerboat Interntional Races - 4th of July Weekend
Jul 3 to Jul 5
Off-Shore Powerboat Racing Association (CROPRA) brings the big boats back to the Keys this year, where they'll meet up in Marathon, FL to race along the world famous 7-Mile Bridge. It's breathtaking to see these powerful machines. For more information contact John Carbonell
Jul 9 to Jul 12
Who doesn't love the mystique of underwater treasure Mel Fisher discovered off shore Key West? Gather with one of the most interesting and historic meet-ups on the island, to celebrate the anniversary of his discovery of the shipwreck 'Atocha.' Call for more information.
Jul 23 to Jul 25
Sloppy Joe's Bar hosts the world famous annual Hemingway look-alike contest in 2015. If you think you look like Papa, why not register and see if you can be 'Papa' for the year? YOu can download the forms on-line. Preliminary rounds will be held at 6:30 pm, Thurs. and Fri., July 23rd and 24th; final round on July 25th. Otherwise, come and join in on the fun when the Key West celebrates the years Ernest Hemingway live in Key West and wrote some of his most important works.
Aug 6 to Aug 9
Indulge in lobster prepared every which way you can imagine by some of the most creative local lobster lovers. This annual event celebrates the beginning of Lobster Season with a 4 day long summer party of eating lobster, and drinking your favorite beverages. Vendors can download an application here: http://www.keywestlobsterfest.com/Vendor_Information.html
Aug 13 to Aug 16
All-male 4 - day gathering with pool and dance parties, adventures on the water, and a fund raising fashion show. Proceeds go to a local non-profit. Contact the Key West Business Guild for more information.
Key West Brewfest - 6th Annual
Sep 3 to Sep 7
A 5 day Key West party where you get to taste more than 150 micro-brews and beers, all collected proceeds are for charity. This is the 6th annual event which benefits the Key West Sunrise Rotary Club's commitment to programs in the Conch Republic. Come and eat and drink like a conch (local) with happy hours, beer dinners, late night parties, beer brunches the next day, and pool parties.
Sep 14 to Sep 20
For 43 years, a call has been made to all motorcycle riders around the USA to ride down the fabulous Florida Keys scenic highway to Key West. Play poker on the way down to raise money for charity. Winner takes all, AND can win a new Harley Davidson Motorcycle! This outrageous event culminates on Duval St., where thousands of bikes line the street. Motorcycle enthusiasts are all invited to Key West to take in the scene. Contact Drew Peterson:
Oct 23 to Oct 24
2015 marks the 37th Annual Goombay Festival in Key West's Bahama Village. A favorite local's party, this is a kind of 'kick-off' for Fantasy Fest. Food, music, live entertainment, people hanging out in the streets creates an authentic Caribbean vibe that will have you feeling like you are in The Bahamas.
Oct 23 to Nov 1
2015 marks the 37th year of Key West Fantasy Fest! This annual adult-themed extravaganza goes for 10 days, with every night featuring some kind of contest or event. All week long fun loving revelers 'let down their guard.' The island really rocks with the culmination of the famous Fantasy Fest Parade that works its way up Duval St. See the official Fantasy Fest website for detailed information and announcements for the annual theme.
Get dressed up as a ZOMBIE, get on your bicycle, and meet-up with 100's of other ZOMBIES at the Fort East Martello Towers, on South Roosevelt Blv, Key West. Ride along the Blvd. in concert with the other ZOMBIES. All ages join in the fun. An ever popular and growing fun-loving October event. Presented by 'We Cycle Bike Shop' who says, 'Ride a bike and change the world!'
Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40 ) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at The Reach, A Waldorf Astoria Resort and ends with a luau.
Nov 4 to Nov 8
In the wake of Key West Fantasy Fest, the Parrot Heads descend on Key West for fun and philanthropy at their annual 'Meeting of the Minds.' This year their meeting theme is 'A Salty Piece of Land.' Their giving includes one of the largest blood drives in the Florida Keys. Contact Andrew Talbert, Director of Parrot Head conventions. (305)292-1435
Nov 6 to Nov 8
Redbone @ Large Sunrise / Sunset Celebrity Tarpon Tournament. Proceeds benefit the Cystic Fibrosis Foundation. Kick-off welcome cocktail reception with silent auction and daily continental breakfast and lunch dockside for each angler.
Nov 8 to Nov 15
Adrenaline flows strong when international super power boat teams descend on Key West in November. After serious racing competitions April through October, the biggest and the fastest gather in Key West to race off-shore for the World Championships.
Nov 11 to Nov 15
Key West is building a reputation for this film festival that has become an annual event. Beautiful Old Town venues, including the Tropic Cinema and the historic San Carlos Building, stage the 5 day event showcasing excellent films in storytelling from multiple genres, plus social events with film makers and actors. Come and be part of the film lovers who rave about this growing event.
Nov 27 to Nov 29
Three days of art in Old Town Key West. Show rotates around multiple neighborhood districts. Live mural painting, gallery openings, performing art, theater, and musical performances.
Schooner Wharf Bar and Galley Lighted Boat Parade - 24th Annual. Schooner Wharf Bar, 202 William St., Key West, FL 8:00 pm - 10:30 pm Over $20,500 in Prizes awarded to Top 12 Vessels with Free Raffle for all Participating Parade Entries.
Dec 31 to Jan 1
New Years Eve tradition at the Schooner Wharf Bar, 202 William St., Key, West, FL "Chief Pirate Wench and co-owner of the bar, Evalena Worthington, is lowered onto the deck of the schooner yacht America 2.0 at midnight, to the fanfare of cannon fire and the release of white doves.
Dec 31 to Jan 1
World famous drag queen, Sushi, is lowered in a giant red high heel shoe from the top of The Bourbon St. Pub, 724 Duval St., Key West. Huge crowd cheers below as this major Key West event is broadcast live on CNN. Live entertainment all night.