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 2 to May 20
Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events.
The parade feature troops of dancers and motorized and non-motorized floats. The parade will travel down Truman to Duval, then on to Eaton street. Come out and get into the holiday spirit!
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 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 4 to Feb 6
Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.
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
Featured performer is Robert Randolph and the Family Band, his accompanists, with Caffeine Carl. Randolph calls his "thing" really upbeat, uptempo, with great guitar riffs. Key West Theater located at 512 Eaton Street. Tickets available online.
Mar 14 to Mar 17
A charity flats-and-fly-only tournament with a twist - in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Harbour Yacht Club on Stock Island.
Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? Join zany-dressed participants for the world's only Zero K across one of the shortest bridges in the Keys. The event is free to watch.
The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer
VFW Fishing Tournament
This family oriented 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 and active service member. Heaviest Dolphin is worth $2,500. All proceeds benefit disabled and/or needy veterans in Monroe County.
Jul 2 to Jul 4
A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime Martini and Margarita Sip and Stroll will kickoff the weekend-long event.
Jul 9 to Jul 12
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.