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.
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.
Jan 15 to Jan 22
Enjoy a true island paradise, paddling beside sea turtles and railroad visionary Henry Flagler's 'Eighth Wonder of the World' in the azure waters of the Florida Keys. You'll journey 77 miles beside white sand beaches and mangrove islands, from Long Key State Park to Key West. Register by: January 1, 2016
Jan 16 to Jan 17
The 11th Annual Florida Keys Seafood Festival is tentatively set for Saturday, January 16 and Sunday, January 17, 2016, at Bayview Park, at the corner of Truman Avenue
Jan 18 to Jan 22
This exciting challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts compete for class championships in this international regatta. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West's Atlantic-front restaurants, resorts and beaches.
Jan 27 to Jan 31
From Last Year's Event - "Welcome to the 2015 Key West Food and Wine Festival showcasing our tropical paradise’s distinctive restaurants, fresh seafood, funky atmosphere, stunning sunsets and gorgeous weather. Our world-class restaurant, arts and lodging community is an
integral part of our island and the well-being of our economy. We are proud to pay
tribute to our culinary community while promoting their vast talent, unique island
fusion food style and fine wines"
Feb 12 to Feb 13
Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements their architecture and adds a unique Key West flavor. Transportation between homes on the famous Conch Train is provided by Historic Tours of America. Tickets