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December 17th
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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.

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.


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.

Mel Fisher Days

Jul 12 to Jul 14

Come commemorate the anniversary of Mel Fisher’s famous 16-year search for the Spanish galleon Atocha and the discovery of the Atocha Mother Load . Annual Dock Party at Schooner Wharf Bar, with tours of salvaging vessels, raffle, silent and live auctions and live entertainment. Proceeds from these events are to benefit Wesley House Family Services, Inc.

Hemingway Days

Jul 17 to Jul 22

The 38th annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

Sloppy Joe’s 38th annual “Papa” Hemingway Look-Alike Contest

Jul 19 to Jul 21

The look-alike challenge takes place at Sloppy Joe’s Bar, 201 Duval St., frequented by Hemingway when he lived and wrote on the subtropical island throughout the 1930s. The contest’s preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 19 and 20, and the newest “Papa” is to be chosen during a final round beginning at 6:30 p.m. Saturday, July 21.


August 2018

Tropical Heat

Aug 15 to Aug 19

The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

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

Womenfest 2018

Sep 5 to Sep 9

Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.


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.

Key West Film Festival

Nov 14 to Nov 18

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.


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.


January 2019

59th Annual Key West House & Garden Tours

Jan 18 to Jan 19

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.


February 2019

Cuda Bowl

Feb 1 to Feb 2

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.

59th Annual Key West House & Garden Tour

Feb 15 to Feb 16

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.


March 2019

57th Annual Conch Shell Blowing Contest

Mar 2

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.

NAS Key West 2019 Southernmost Air Spectacular

Mar 30 to Mar 31

The U.S. Navy Flight Demonstration Squadron the Blue Angels will be taking to the skies at Naval Air Station Key West. The 2019 theme is "Women in Aviation" with a focus on the "Future of Flight." Organizers expect highlights to include civilian performers like an all-female parachute jump team, the Misty Blues, Patty Wagstaff flying an Extra 330SC, Ashley Shelton, Wing Walker and the world famous Shockwave Jet Truck.


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