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April 25th
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2018 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.


February 2018

GardenFest: The Green Market Place

Feb 17 to Feb 18

A giant plant sale offers visitors the opportunity to peruse a wide array of native and exotic tropical plants, earth-based art and healthy living vendors. Enjoy a perfect day in the Garden where organic and healthy food vendors as well as a beer and wine bar will be available in the Courtyard along with the talents of local musicians. Open from 10 a.m. to 4 p.m. each day. Key West Tropical Forest and Botanical Garden is located at 5210 College Road.

Key West Garden Club Gardens Tour

Feb 23 to Feb 24

Between 10 a.m. and 3 p.m., both days, attendees can explore the oceanfront site at 1100 Atlantic Blvd. that has been the garden club’s headquarters for more than a half-century. The bricks and archways of the Civil War--era fort are the backdrop for spectacular orchids and bromeliads, stands of black bamboo, indigenous plants, a peace garden and a dramatic new pool and fountain in addition to many other attractions.

53rd Annual Old Island Days Art Festival

Feb 24 to Feb 25

The 53rd annual juried outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town.

Tennessee Williams Birthday Celebration

Feb 28 to Apr 9

A kickoff party is to be staged at the home of the Tennessee Williams Key West Exhibit founders Dennis Beaver and Bert Whitt Feb. 28, and the festival, a 6-week commemoration of the literary icon who lived on the island for thirty-four years, is to continue into April and boasts a full roster of writing and painting contests, film and poetry forums, curator tours of the Tennessee Williams Museum at 513 Truman Avenue, a March 26th birthday party for the playwright, and 2 one-act theatre productions of the Pulitzer-Prize-winner’s work. Presented by the newly-merged Tennessee Williams Key West Exhibit and the Key West Art & Historical Society.


March 2018

Conch Shell Blowing Contest

Mar 3

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with 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 a.m., contest starts at noon.

March Merkin Invitational Permit Tournament

Mar 12 to Mar 15

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 Yacht Harbor Marina on Stock Island.

58th Annual Key West House & Garden Tours

Mar 16 to Mar 17

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.


April 2018

23rd Annual Taste of Key West

Apr 16

Scores of area restaurants present mouthwatering samples of their cuisine to benefit AIDS Help Inc. The culinary celebration takes place at Mallory Square. The open-air gala traditionally spotlights indulgent edibles such as tropical and Caribbean-influenced cuisine, fresh-off-the-boat local seafood, vegetarian dishes and European specialties — all accompanied by a selection of wines from around the world.

36th Annual Conch Republic Independence Celebration

Apr 20 to Apr 29

With activities ranging from wacky bed race to a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys.

Key West Paddle Classic

Apr 28

Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.


May 2018

Third Annual Papio Kinetic Sculpture Parade

May 4 to May 6

If one man’s junk is another man’s treasure, then the late Key Largo folk artist Stanley Papio was a treasure hunter extraordinaire. Fans of “outsider art” can celebrate the renegade metal sculptor’s legacy with a people-powered parade of mobile sculptures crafted in the spirit of his extraordinary creations. The Papio Kinetic Sculpture Parade features colorful sculptural floats, tricycles with exotically costumed riders, fantastically decorated bicycles and other moving works of art — all powered by human effort alone — and are to follow a route along the length of Key West’s Duval Street.

Key West Songwriters’ Festival

May 9 to May 13

The annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The largest festival of its kind in the world celebrates its 23 years as both a tourist attraction and favorite of island locals. The festival revolves around five days and nights of big stars in intimate settings, introducing audiences to the faces, voices and stories behind the songs.


June 2018

Key West Pride

Jun 6 to Jun 10

Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.

Sixth Annual Key Lime Festival

Jun 30 to Jul 4

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

Key West Island Swim: FKCC Swim Around Key West

Jun 30

The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.


July 2018

Annual 4th of July Fireworks

Jul 4

Fireworks blast from the end of White Street Pier at Higg’s Beach as the island takes on Independence Day Key West style. Bring your family to congregate with the locals at the end of White Street to get the best view from land of the southernmost fireworks show or book a cruise on one of many Key West charter vessels to watch from the water. This must see event is the perfect way to conclude the island celebration.


August 2018

Ninth Annual Key West Brewfest

Aug 30 to Sep 3

More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities.


September 2018

46th Annual Phil Peterson’s Key West Poker Run

Sep 14 to Sep 16

Motorcyclists from throughout the United States are to travel one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (U.S. Highway 1), the 113-mile roadway from mainland Florida to Key West that features 42 bridges and long vistas of breathtaking open water.


October 2018

39th Annual Key West Fantasy Fest

Oct 19 to Oct 28

This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.


November 2018

37th Annual Key West World Championship Races

Nov 4 to Nov 11

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.


December 2018

New Years Eve at Sloppy Joe's Bar - 24th Annual Dropping of the Giant Conch Shell

Dec 31 to Jan 1

World Famous Dropping of 'The Conch Shell' at Sloppy Joe's Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night with confetti, streamers, and lights filling the sky. Crowds start the party in the street at about 10:00 pm and wait til count down to midnight. No Reservations. No Tickets Sold.

New Year's Eve Giant Shoe Drop of Drag Queen Sushi at the Bourbon St. Pub

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.


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