Key West Events
Vacation Homes of Key West brings you an updated calendar 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.
World Famous Dropping of 'The Conch Shell' at Sloppy Joes Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night to giant six foot tall bottles of champagne.
The Southernmost City also celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.
Jan 9 to Jan 19
"The Dark Side" 32nd Annual Key West Literary Seminar Each year the Key West Literary Seminar explores a unique literary theme. Readers from all over the world join the best writers of our time for the readings, discussions, lectures, and parties that make up today’s smartest and most high-spirited literary gathering. The 32nd annual Seminar will explore the mystery, crime, and thriller genres, led by celebrated authors. Two independent sessions are offered: Chapter One, January 9-12; and the Final Chapter, January 16-19. Additionally, our Writers’ Workshop Program is held January 12-16. Advance registration is required to attend. Chapter One is already sold out; all workshops and the Final Chapter are expected to fill up well before January.
Jan 18 to Jan 19
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. Free admission; hours open from 11 a.m. - 8 p.m on Saturday 1/18, 11a.m. to 5 p.m. on Sunday 1/19. Bayview Park at Truman Avenue and Jose Marti Drive.
Jan 19 to Jan 24
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.
16th Annual Half Marathon
Stock Island Village Marina King Mackerel Tournament
Jan 24 to Jan 26
Big king mackerel migrate to the waters around Key West each winter, and a fittingly large prize awaits the winner of this challenge. The angler who weighs in the heaviest mackerel, also known as kingfish, is to go home with $10,000.
Jan 25 to Jan 26
The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Exhibitors will set up along Whitehead Street from Greene Street to Eaton, and on Caroline Street through the famous Presidential Gates into the beautiful Truman Annex. Set among historical attractions such as Audubon House, the Little White House and Mel Fisher Museum, the City of Key West closes two blocks of Whitehead Street and another block of Caroline Street to vehicle traffic for the show. Visitors can leisurely browse the beautiful displays of pottery, fabric, glass, wood, jewelry and other colorful handmade works by the selected artists.
A full and half iron distance triathlon in the southernmost city. Individuals and relay teams can participate in this USA Triathlon-sanctioned event. The minimum age allowed for participation in the Bone Island Full is 18 years of age. The minimum age allowed for participation in the Bone Island Half is 15 years of age. Visit website for complete course and registration details.
Local restaurants vie for top honors in three categories; appetizers, entrees and desserts. Participants get to taste all the food made at this event while judges pick the winners. Benefits the Monroe Association for ReMARCable Citizens (MARC provides life services for developmentally disabled adults in the Florida Keys).
Jan 30 to Feb 1
4th Annual Cuda Bowl 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 7 to Feb 8
The 2014 Season Opener of the Ragnar Relay Series begins in Miami, and takes runners South toward the Southernmost Point in the USA. Runners will be able to kick off their running season by tackling miles and miles of sunshine, scenic ocean views and sandy beaches. This race traverses the Seven Mile Bridge and hops from Key to Key until you reach the amazing finish line party in Key West. Make it a Runcation and spend the weekend dipping your tired toes in the surf and sipping a fruity drink. Experience the Ragnar with the best Sunrise in the series and register your team today.
Feb 14 to Feb 15
A popular event that was featured in February returns again in March where you can tour inside and the outside gardens of another selection of unique homes of Key West. Even if you attended in February, come back to tour new amazing addresses. Presented by the Old Island Restoration Foundation as a fundraiser for its efforts.
322 Duval St., Key West, FL 33040.
Admission is $25. per person.
Feb 15 to Feb 16
South Florida's top nurseries are to show bromeliads, orchids, fruit trees, palms, tropical flowers and natives at the Key West Tropical Forest
Feb 22 to Feb 23
In it's 49th year, The Old Island Days Art Festival is a two day juried outdoor fine art festival. This nationally recognized show brings over 100 fine artists to this beautiful historic area of Key West. Exhibitors will set up along Whitehead Street from Greene Street to Eaton, and on Caroline Street through the famous Presidential Gates into the beautiful Truman Annex.
52nd Annual Conch Shell Blowing Contest
n Old Island Days tradition, this unique contest features novel sounds produced by contestants in several age categories as they attempt to make "music" on fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10:30 a.m. and contest begins at noon.
The Rotary Club of Key West is extremely pleased to announce the Fourth Annual “ConchFest- A Celebration Of Conch Heritage”. There will be vendors selling arts and crafts of every imaginable kind, and other treasures. There will be a Queen Conch cook-off, lots of great food for sale including conch fritters, conch salad, pork, and other more traditional fare. There will be children’s activities; a co-ed softball tournament live music and much more.
54th Annual House Tours
Mar 14 to Mar 15
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. Details about each house tour will be posted when available. No smoking, food, drinks, pets, or photography will be permitted in the tour homes.
Mar 17 to Mar 20
This charity flats-and-fly-only tournament has a twist. In addition to catch and release, anglers earn extra points for tagging their fish. The event is held at the Key West Harbour Yacht Club on Stock Island.
Enjoy the excitement aboard Schooner America 2.0 under the sunny sky of Key West as you race for victory! The boat that gets there first, \"wins\"! Then relax and sail back to the dock where there is an award ceremony at the Schooner Wharf Bar for the first, second, and third place winners. Highlights along the way: Complimentary Beer, Wine, Champagne and Soft Drinks The famed Sand Key Reef, Mallory Square, and Sunset Pier. Keep your eyes peeled for wildlife: dolphins, sea turtles, and waterbirds. A waterside view of Fort Zachary Taylor. A gourmet box lunch from a local Key West Cafe! Not to brag, but America 2.0 won all 4 races in 2013! Bring your family and/or friends and join our courteous and professional crew for this adventurous race that will complete the Key West experience in comfort, excitement, and style! Special Note: The boat will depart at 12:30 pm but the race officially begins at 1 pm and we typically return at 3:30.
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 on a 'first apply, first serve basis.' Contact The Marathon Runners Club, P.O. Box 500110, Marathon, FL 33050.
Apr 8 to Apr 12
The 12th annual World Sailfish Championship is one of South Florida's most prestigeious sailfish tournaments. Elite anglers compete for $125,000 in cash that includes a $75,000 guaranteed 1st place, $25,000 2nd place, and $10,000 3rd prize Check their website for registration details and get the kick-off party on your calendar.
Apr 12 to Apr 13
Private gardens with plant id's and docents Kim Gordon
A major annual benefit for AIDS Help, Inc is a Key West tradition staged on the Truman Waterfont. Join us in this amazing culinary celebration that includes booths of over 50 of Key West's restaurants presenting delectable samples of their best cuisine and wines representing a100 vineyards.
Apr 18 to Apr 27
32nd Anniversary of the birth of a micro-nation, 'The Conch Republic.' Celebrate the spirit of the Conch Republic with a commemoration of its founding in response to a U.S. Border Patrol roadblock that stopped traffic in and out of the Florida Keys on April 23, 1982. Celebrations begin with 'The Raising of the Colors' at Fort Zachary Taylor complete with the firing of cannons, crescendos with the world's only 'Great Battle for the Conch Republic' in the Key West Harbor, and ends with a 'Miniature Golf Challenge' in Ramrod Key. Check the schedule for all the unique events, both on the water and off, with something for everyone.
May 7 to May 11
19th Annual Key West Songwriters' Festival showcase features some of America's foremost performing and upcoming songwriters. Concerts in intimate casual settings including beautiful resort settings, popular bars, and historic meeting venues throughout the island of Key West. A fantastic opportunity to hear awesome new and famous talent and take in beautiful and unique island settings. An exclusive presentation by The Key West Song Writers Festival. Plan a vacation around this event.
May 17 to May 18
A 100 or 50 mile marathon race down the Florida Keys. A point-to-point event that begins at the top of the Florida Keys in Key Largo (for the 100 mile race) or Marathon (for the 50 mile race), and ends in Key West, the Southernmost point in the USA. Support stations with water and ice will be located at 5 mile intervals along the route. Funds benefit prostate cancer education, screenings, and research in the Florida Keys and South Florida.
13th Annual Yamaha Dolphin Masters Invitational
In this challenge headquartered at Key West's Historic Seaport, more than $13,000 awaits the angler scoring the highest total combined weight of three dolphin catches. Many additional prizes await other top anglers, and there is no limit on the number of participating boats.
Jun 11 to Jun 15
A festival honoring the Key West concept of "One Human Family" that embraces and honors diversity, openness and freedom in the little island city that is recognized as one of the world's top gay and lesbian vacation destinations. The celebration hosts a variety of entertainment, forums, parties, dances, contests, water activities, and an amazing Pride Parade down Duval Street.
38th Annual Swim Around Key West
12.5 Mile Endurance Swim Competition. The historic, round-the-island event is the longest-running sporting event in the Florida Keys, founded in 1977. The 38th Annual Swim Around Key West will be held on June 28, 2014, beginning at Smathers Beach.
Jul 10 to Jul 13
Key West celebrates legendary treasure hunter Mel Fisher, whose undying tenacity and commitment led to the discovery of the Spanish galleon
Jul 13 to Jul 16
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.
Jul 15 to Jul 20
The 34th annual celebration of the legendary author's work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest (July 17-19) and a pre-birthday "party" commemorating Ernest's July 21st birthday. Street Fair on July 19th.
Jul 16 to Jul 19
Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.
Oct 17 to Oct 18
A local's favorite. This is an authentic Caribbean island street fair situated in the heart of Key West's unique Bahama Village. Some streets are closed to traffic, and locals and visitors alike stroll and enjoy local flavors, entertainment, and shop for c...
A Key West famous tradition that is broadcast on National Television on CNN at midnight - right from "Bourbon Street Pub" at 801 Duval Street. A saucy drag queen named "Sushi," is "dropped" in a red shoe to bring in the New Year. You've never seen anything like this before, and you'll never know what she'll say.
The Schooner Wharf Bar at the foot of William Street on the Key West Historic Seaport, rings in the New Year in real Pirate fashion with the "Dropping of the Wench" from a tall wooden mast. Just before midnight the wenchy begins her descent from the top of the mast amidst a festival of live music and dancing in proper revelry style.