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.
Mar 2 to Mar 31
Celebrate the 104th birthday of Tennessee Williams and his life in Key West during the month of March. Events planned include a series of classic movies adapted from Tennessee Williams' award winning plays, a poetry contest, artist challenge and more.
Mar 13 to Mar 14
The annual Key West house tours are sponsored by the Old Island Restoration Foundation and funded in part about the Monroe County Tourist Development Council. Each tour features lovely homes and gardens reflecting the varied tastes and originality of their owners.
You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more.
Mar 16 to Mar 19
All proceeds from the tournament after the deduction of direct tournament costs will be donated to the Tarpon
Apr 12 to Apr 13
Presented by the Key West Garden Club, this event visits private gardens with local experts identifying plants. 10am – 3pm at Ft. West Martello, 1100 Atlantic Blvd.
19th Annual Taste of Key West – For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions along the Truman waterfront.
Apr 18 to Apr 27
Celebration of Key West’s brief secession from the United States. Event highlights include drag (queen) races on Duval Street (April 19, 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 25, 6pm). Kick-off party at the Schooner Wharf bar on April 18th, 7pm.
One of the most unique running races in the world attracts 1500 runners from around the world. The race spans the 7 mile Bridge spanning out over the Florida Keys on the spectacular Overseas Highway from Marathon, Florida. Apply early as it fills up fast o...
Apr 23 to Apr 27
2nd Annual Key West Sailfish Championship - Three days of catch-an-release fishing by professional and amateur anglers with big cash prizes, including $50,000 for first place in the pro division.
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.
Key West Island Swim: Swim Around the Island
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
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!'
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 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.