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Key West Time
October 27th
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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.


January 2020

NEW YEARS EVE AT SLOPPY JOE'S BAR - ANNUAL DROPPING OF THE GIANT CONCH SHELL

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 AT THE 801 BOURBON BAR - WATCH DRAG QUEEN SUSHI RIDE THE GIANT RED SHOE DOWN FORM THE BALCONY

Jan 1

Big crowds gather in the 800 block of Duval St. in front of the 801 Bourbon Bar to watch the famous performing Key West drag queen Sushi ride a giant red ruby hi-heel shoe down from a balcony as the clock strikes midnight.

THE LOWERING OF THE 'WENCH' FROM THE TOWERING MAST OF THE TALL SHIP AMERICA AT THE SCHOONER WHARF BAR

Jan 1

Delightful New Year's Eve tradition at the popular waterfront 'Schooner Wharf Bar - "The last little piece of paradise." Everyone's favorite 'pirate wench' dons her most beautiful pirate gear, and is slowly lowered from the masthead of the wooden tall ship 'America.' The ship is docked in front of the bar at the Key West Historic Seaport at the foot of William St. Eat, Drink, Dance on the boardwalk of the seaport.

38th ANNUAL KEY WEST LITERARY SEMINAR

Jan 9 to Aug 12

Renowned Annual literary seminar that features many world famous writers. Workshops and seminars fill up way in advance. Readers and writers are welcomed to this four day event. Other events include a young writers studio and a literary walking tour in Old Town Key West.

15TH ANNUAL FLORIDA KEYS SEAFOOD FESTIVAL

Jan 18 to Aug 19

Held at Bayview Park (Truman Ave. and Jose Marti Drive) , on of Key West's largest green spaces, families and friends gather to enjoy local fresh Florida Keys Seafood and drinks. Live music, activities for the kids, marine related crafts. 11 am - 8 pm on Saturday and 11 am to 5 pm on Sunday.


March 2020

OPEN AIR AND MUSIC AFFAIR ON THE KEY WEST WATERFRONT

Mar 6

Held on the colorful waterfront setting near the Schooner Wharf Bar, at 202 William St., Key West, skilled Florida Keys artists display and sell their creations. Local musicians provide entertainment. Always held the first Saturday in March.

58TH ANNUAL KEY WEST CONCH SHELL BLOWING CONTEST

Mar 7 to Aug 7

This event is held in the spacious back yard garden of the Oldest House and Gardens in Key West at 322 Duval St. Gather round and watch or join in as enthusiastic participants pucker up and blow a conch shell - Sometimes called the 'conch honk.' You can buy a conch shell at the garden. Everyone is invited to participate and celebrate the history of the conch shell in Key West and the Florida Keys.

KEY WEST ARTISAN MARKET: SPRING FORWARD

Mar 8

Don't forget to set your clocks and don't miss this fabulous artisian market may the Atlantic Ocean across the street from Higgs' Beach. Curated outdoor market offering fine crafts, jewelry, and art from talented local Florida Keys artists. Also a food market with fresh produce, artisan cheeses, local seafood, honey, and more. 10 - 2 pm Repeats again on March 15.

60th ANNUAL HOME TOURS

Mar 13 to Mar 14

The annual Key West Home Toursâ„¢ is one of the oldest and longest-running home tours in America, with the first tour in 1960. Each tour is unique, featuring five lovely homes and gardens that reflect the unique and varied tastes of their owners. This one is from 10


April 2020

CANCELLED FOR 2020 - PAPIO KINETIC SCULPTURE AND ART BIKE PARADE: APRIL 3-5 - DATES FOR 2021 TBD

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' celebrate the legacy of the renegade metal sculptor with a people-powered parade of mobile sculptures that are crafted in the spirit of his extraordinary creations. The Papio Kinetic Sculpture Parade features colorful sculptural floats, tricycles with exotically costumed riders on fantastically decorated bicycles and other moving works of art. All sculpture floats are powered by human effort alone. The parade is a route that goes the length of Key West's famous Duval Street.

CANCELLED FOR 2020 - SONGWRITER SPEAKEASY SERIES-LOCAL SPOTLIGHT - DATES FOR 2021 TBD

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.

CANCELLED FOR 2020 - 25th ANNUAL TASTE OF KEY WEST - DATE FOR 2021 TBD

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 $3.00 and $5.00. This lively well attended event presents an opportunity to sample much of the best cuisine that Key West has to offer. Along with the food, enjoy a fabulous selection of fine wines available in a collectible wine glass. From 6 pm to 9 pm at Mallory Square (400 Wall Street, Key West). Admission to the event is FREE. Food tickets are sold in $1 increments.


May 2020

CANCELED FOR 2020 - KEY WEST PADDLE CLASSIC - DATES FOR 2021 TBD

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.

CANCELLED FOR 2020 - ONE NIGHT OF QUEEN PERFORMED BY GARY MULLEN & THE WORKS - RESCHEDULED FOR MAY 10, 2021

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.

CANCELLED FOR 2020 - KEY WEST SONGWRITERS FESTIVAL 2020 - DATES FOR 2021 TBD

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 Key West locals. The Key West Songwriters festival revolves around five days and nights of big stars in intimate settings, where audiences are introduced to the faces, voices, and stories behind the songs.

CANCELLED FOR 2020 - 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

CANCELLED FOR 2020 - KEY WEST PRIDE - RESCHEDULED FOR JUNE 2 - 6, 2021

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.

CANCELLED FOR 2020 - 44TH ANNUAL SWIM AROUND KEY WEST - DATE FOR 2021 TBD

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 - THIS YEAR IT IS ON-LINE

Jun 24 to Jun 28

THIS YEAR IS IT VIRTUAL - ON-LINE. 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.

CANCELLED FOR 2020 - MYSTERY FEST KEY WEST 2020 - DATE FOR 2021 TBD

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

CANCELLED FOR 2020 - THE 2ND ANNUAL KEY WEST MERMAID FESTIVAL - RESCHEDULED FOR JULY 4 - 5, 2021

Jul 1 to Jul 5

The Key West Mermaid Festival was 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.

CANCELLED FOR 2020 - 8TH ANNUAL KEY LIME FEST - DATE FOR 2021 TBD

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.

CANCELLED 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.

CANCELLED FOR 2020 - DEL BROWN PERMIT TOURNAMENT - RESCHEDULED FOR JULY 18 - 21, 2021

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

CANCELLED FOR 2020 - SLIGHTLY STOOPID WITH PEPPER, COMMON KINGS AND DON CARLOS RETURN TO KEY WEST AMPHITHEATER - RESCHEDULED FOR AUGUST 6, 2021

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.

CANCELLED FOR 2020 - 24TH ANNUAL LOBSTER FEST 2020 - RESCHEDULED FOR AUGUST 12 - 15, 2021

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

CANCELLED FOR 2020 - KEY WEST WOMENFEST 2020 - RESCHEDULED FOR SEPTEMBER 1 - 5, 2021

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

CANCELLED FOR 2020 - FANTASY FEST 2020 - RESCHEDULED FOR OCTOBER 22 - 31, 2021

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. This is an adult event. Book early for this event.

CANCELLED FOR 2020 - NINTH ANNUAL KEY WEST BREWFEST - RESCHEDULED FOR SEPTEMBER 2 - 6, 2021

Oct 16 to Oct 25

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

CANCELLED FOR 2020 - PARROT HEADS IN PARADISE MEETING OF THE MINDS - RESCHEDULED FOR NOVEMBER 4 - 6, 2021

Oct 29 to Oct 31

Parrot Heads in Paradise (PHIP) Clubs are inspired by Jimmy Buffet music and the carefree tropical island lifestyle that grew out of the music. The group gathers to have fun as a humanitarian group and engage in charitable and educational activities the contribute to the betterment of the community. During th past 17 years, they have raised over $53 million. The Parrotheads in Paradise Meeting of the Minds in Key West usually includes a visit from Jimmy Buffet for a spontaneous concert that is greatly anticipated by everyone, but kept secret until Jimmy shows up.


November 2020

CANCELLED FOR 2020 - WORLD CHAMPIONSHIP POWERBOAT RACES - RESCHEDULED FOR NOVEMBER 7 - 14, 2021

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.

CANCELLED FOR 2020 - KEY WEST PRIDE WEEK - RESCHEDULED FOR JUNE 2 - 6, 2021

Nov 18 to Nov 22

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.

CANCELLED FOR 2020 - 38TH ANNUAL CONCH REPUBLIC INDEPENDENCE CELEBRATION - DATES FOR 2021 TBD

Nov 27 to Dec 6

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.


December 2020

HOLIDAY - CHRISTMAS PARADE 2020 - DATE AND ROUTE TBD

Dec 5

Still on for 2020 Parade route TBA for 2020. Local's favorite. The route may be moved to allow for more participant social distancing. Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Usually 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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