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May 24th
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2020 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.


April 2020

CANCELLED-2020 PAPIO KINETIC SCULPTURE AND ART BIKE PARADE: APRIL 3-5

Apr 3 to Apr 5

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.

CANCELLED-SONGWRITER SPEAKEASY SERIES-LOCAL SPOTLIGHT

Apr 5

The annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The speakeasy series is part of Rams Head Productions lineup of Key West shows.

POSTPONED-38TH ANNUAL CONCH REPUBLIC INDEPENDENCE CELEBRATION

Apr 17 to Apr 26

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.

CANCELLED- 25th Annual Taste of Key West

Apr 20

For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions at Mallory Square – each taste costing between $3 – $8. Always well attended, this lively event will have you bouncing from cuisine to cuisine, all the while enjoying the generous selection of fine wines available in a collectible wine glass. 6pm – 9pm, Mallory Square (400 Wall Street, Key West). Admission to the event is FREE. Food tickets sold in $1 increments.


May 2020

KEY WEST PADDLE CLASSIC 2020

May 1 to May 3

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.

ONE NIGHT OF QUEEN PERFORMED BY GARY MULLEN & THE WORKS

May 5

We will, we will rock you! Get all the Queen hits you can handle with this electric rendition of a rock classic. The show will take place at Tennessee Williams Theatre.

KEY WEST SONGWRITERS FESTIVAL 2020

May 6 to May 10

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.

MICHAEL FRANTI & SPEARHEAD RETURN TO SUNSET GREEN EVENT LAWN

May 10

Don't miss this show, he is a local favorite and drawls a crowd from near and far. Michael Franti is a musician, humanitarian, filmmaker, and activist who is recognized as a pioneering force in the music industry. He believes that there is a great battle taking place in the world today between cynicism and optimism, so he made his most recent album, Stay Human Vol. II, his highest charting album to date, to remind himself - and anyone who's listening - that there is still good in the world and that it is worth fighting for.


June 2020

KEY WEST PRIDE 2020

Jun 3 to Jun 7

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.

44TH ANNUAL SWIM AROUND KEY WEST

Jun 6

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 the Gulf of Mexico, ending where they began at Higgs Beach.

MANGO FEST 2020

Jun 24 to Jun 28

This locally created festival celebrates the Mango! The most delicious fruit you can find growing all over Key West. Mango Fest of Key West features all things mango including mango tasting, mango trees and mango daiquiris. The culinary competitions between local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. The Vendor Village gives art collectors and foodies the experience of a festival atmosphere. Music is provided along with live radio broadcasts. From 10AM to 3PM, Bayview Park, 1400 Truman Ave.

MYSTERY FEST KEY WEST 2020

Jun 26 to Jun 28

Open to authors, aspiring authors and non-writing mystery-buffs alike—2017 headliners are John Hemingway, grandson of Ernest and author of 'Strange Tribe,' Keynote Speaker Clifford Irving, and Mystery Writers of America Florida Chapter past-President Randy Rawls. Lisa Black, James O. Born, Nancy J. Cohen and Heather Graham are the featured presenters among a criminally stellar hit-list of some two dozen high-profile and award winning mystery and crime fiction authors and true-crime experts.


July 2020

THE 2ND ANNUAL KEY WEST MERMAID FESTIVAL

Jul 1 to Jul 5

The Key West Mermaid Festival is founded by a Key West native mermaid, and local mermaid boutique owner. She, along with her drew and pod, invite you to step back in time to an island called Cayo Hueso (Bone Cay), where the Gulf meets the Atlantic, and the captains, seafarers, and fishermen would tell their stories of the sweet sirens' songs.

8TH ANNUAL KEY LIME FEST

Jul 2 to Jul 6

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.

4TH OF JULY FIREWORKS 2020

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.

DEL BROWN PERMIT TOURNAMENT 2020

Jul 20

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.


August 2020

SLIGHTLY STOOPID WITH PEPPER, COMMON KINGS AND DON CARLOS RETURN TO KEY WEST AMPHITHEATER

Aug 1

Rams Head Key West is thrilled to welcome Slightly Stoopid back to Key West Amphitheater! Enjoy local food vendors, stocked bars, take home items from local artisans and a one in a million view of The Gulf of Mexico while residents of Key West and beyond come together for a summer night under the stars filled with all of those good vibes served up by four excellent bands.

24TH ANNUAL LOBSTER FEST 2020

Aug 6 to Aug 9

All the staff at Vacation Homes of Key West - VHKW, look forward to this festival all year. Indulge in lobster prepared every which way you can imagine by some of the most creative local lobster lovers. This annual event celebrates the beginning of Lobster Season with a 4 day long summer party where thousands enjoy eating lobster and drinking favorite beverages.

STOCK ISLAND MARINA VILLAGE KEY WEST MARLIN TOURNAMENT

Aug 12 to Aug 16

Anglers ply the waters once fished by writer 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.


September 2020

WOMENFEST 2020

Sep 3 to Sep 7

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 2020

FANTASY FEST 2020

Oct 16 to Oct 25

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.

KEY WEST BREWFEST 2020

Oct 16 to Oct 25

During a festival “crafted” for Labor Day weekend, attendees can sample nearly 200 beers and ales while also discovering the flavors of the continental United States’ southernmost city. The annual Key West BrewFest is highlighted by a lavish oceanside tasting festival, beer-focused brunches, pool parties featuring specialty beers, daytime tap takeovers and dinners pairing each course with brews that complement the cuisine.


November 2020

WORLD CHAMPIONSHIP POWERBOAT RACES 2020

Nov 8 to Nov 15

Race World Offshore Championships 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 2020

HOLIDAY PARADE 2020

Dec 5

Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. The holiday parade runs down Duval street at 7 PM and features floats made by local businesses. Other holiday events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.


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