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October 6th
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2022 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 2022

Matilda The Musical

Jan 12 to Jan 29

The award winning musical Matilda will preview at the Waterfront Playhouse on Wednesday January 12, with a grand opening on Thursday January 13 and playing Wednesday through Saturdays at 8pm through January 29.

Roks Island Fest 2022

Jan 14 to Jan 17

RokIsland Fest is a 4-Day Rock Music Festival located on the island paradise of Key West, Florida

24th Annual Key West Half Marathon & 5k

Jan 15 to Jan 16

The 2022 Key West Half Marathon will take place during the week-end of January 15-16, 2022

The Southernmost Regatta

Jan 17 to Jan 21

The Southernmost Regatta is 5 consecutive days of ORC Racing / Cruising Keelboats.

Key West 200

Jan 21 to Dec 11

On display in the Bryan and Bumpus Galleries at the Custom House Museum, 281 Front Street.The Key West Art & Historical Society announces the opening of Key West 200 commemorating the 200th anniversary of the first permanent settlement of Key West in 1822.

Florida Keys SPCA Artisan Market

Jan 23

Pet friendly event across from the White Street Pier.

Mile 0 Fest

Jan 25 to Jan 29

Mile 0 Fest is a boutique destination festival bringing the best of Red Dirt & Americana Music to Paradise every year.

Key West Master Chefs Classic Hosted by The Marc House

Jan 30

From 4-7 p.m. at Opal Key Resort & Marina, 245 Front St, a Cocktail Competition and tasting.


February 2022

Augst Wilson's "How I Learned What I Learned"

Feb 8 to Feb 12

August Wilson takes us through a heartfelt theatrical memoir describing his journey through life's trials and tribulations.

Rams Head Presents Tom Papa

Feb 11

Live at the Key West Theater located just a blocks from Duval.

The Chooi Brothers

Feb 13

The Chooi brothers are skilled violinists performing at St. Paul's Episcopal Church at 4pm.

Clue (Live On Stage)

Feb 16 to Mar 5

Based on the iconic 1985 Paramount movie which was inspired by the classic Hasbro board game, Clue is a hilarious farce-meets-murder mystery.

25th Anniversary Gala

Feb 17

The Silver Anniversary Gala hosted by "The Community Foundation"


April 2022

Florida Keys Seafood Festival

Apr 2 to Apr 3

A festival commemorating locally caught seafood from local fisherman.

Conch Republic - The Musical

Apr 21 to Apr 24

Details the history of how Conch Republic came to be. Follow the link to find tickets and reserve a spot to the show!

Reef Relief's 2nd Annual Luau Fundraiser

Apr 22

Partnered with Lagerheads Beach Bar & Grill to celebrate Earth Day featuring live music, games and a silent auction from 6-8pm

Mote Marine Labartory's Ocean Fest

Apr 23

A Saturday of activities hosted by Mote Marine Laboratory to showcase the local marine environment while raising money to benefit our oceans. Donations from the festival support Mote’s coral reef restoration and research programs.

Adam Lambert at Key West Ampitheater

Apr 28

Solo performance by Adam Lambert, who rose to fame in 2009 after finishing as runner-up on the eighth season of American Idol. He has performed alongside Queen as their lead vocalist over the years. Tickets available online.


May 2022

Key West Songwriters Festival

May 4 to May 8

The festival is 5 days and 5 nights of live music throughout downtown Key West


June 2022

Key West Pride

Jun 1 to Jun 6

Hosted by The Key West Business Guild with a timeline of events all week!

I Love Stock Island Festival

Jun 15 to Jun 19

A 5-day festival through Fathers Day Weekend, that embodies the local community of Stock Island.

9th Annual VFW Fishing Tournament

Jun 18 to Jun 20

A family fun tournament with cash prizes!


July 2022

Key West Marlin Tournament

Jul 20 to Jul 23

Hosted by the Stock Island Marina & Village with nightly festivities leading up to an awards banquet.

Key West Half Marathon & 5k

Jul 23

33rd Anniversary Hemingway Key West 5k sunset run & paddleboard race. Registration open now!


August 2022

26th Annual Key West Lobsterfest

Aug 11 to Aug 14

The annual Lobsterfest is enjoyed by all, and features a schedule of events in downtown Key West


September 2022

Key West BrewFest

Sep 1 to Sep 5

Key West BrewFest has grown to be the largest event put on by Key West Sunrise Rotary. The multi-day festival hosted by Southernmost Beach Resort includes beer pairing dinners, pool parties along with other activities around town culminating with the signature tasting event. Each day offers things to do with events taking place at many restaurants, hotels, and bars all over Key West.

Mel Fisher Days

Sep 2 to Sep 6

Celebrate 400 Years of Nuestra Senora De Atocha. There will be five days of exciting events and special ceremonies.

Key West Womenfest

Sep 7 to Sep 11

Womenfest has a simple goal: to celebrate ALL women! Key West Womenfest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away.


October 2022

25th Annual Key West Paddle Classic

Oct 1

A race around the continental United States' Southernmost island, presented by Lazy Dog Adventures. This 12-mile challenge includes paddleboards and other self propelled watercraft.

Legends of Music Row Music Festival

Oct 13 to Oct 15

Legends of Music Row is coming to the Key West Coffee Butler Amphitheater. This year's special guest is the "King of Country" George Strait. Book your tickets today!

Fantasy Fest 2022

Oct 21 to Oct 30

Fantasy Fest is back! Fantasy Fest is an annual 10-day party in paradise, for grown-ups only. This year's theme is Cult Classics and Cartoon Chaos.


November 2022

Annual Meeting of the Minds

Nov 2 to Nov 6

Parrot Heads in Paradise gather to celebrate another year in paradise. Join this fun loving event for a week of dancing on the beach and other island celebrations. This is a nonprofit event inspired by Jimmy Buffet. The festival raises millions of dollars each year towards various charities.

Race World Offshore World Championship

Nov 6 to Nov 13

The World's best offshore power boat teams compete for the championship in Key West Harbor.


December 2022

Key West Holiday Fest

Dec 1 to Jan 1

Key West's busy holiday season includes the Harbor Walk of Lights, The Lighted Boat Parade, The Hometown Holiday Parade, trolley tours and other fun events for the whole family.

New Years Eve 2023

Dec 31 to Jan 1

Ring in the New Year in Key West style!


January 2023

Key West Food & Wine Festival

Jan 25 to Jan 29

The Key West Food and Wine Festival is a series of themed culinary events showcasing diverse wines and creative cuisines. Join us for this 14th annual festival with over 20 unique venues.


February 2023

Old Island Days Art Festival

Feb 25 to Feb 26

Fine Art lovers will enjoy creative offerings from over 100 artists. This open-air show takes place at Key West Truman Waterfront Park, from 10 am to 5 pm.


March 2023

Anne Mckee Artist Fund Fine Art Auction

Mar 12

The Anne McKee Artists Fund (AMAF) was established in 1992 after its founder, Anne McKee, saw a pressing need to assist individual artists from Key West. Now, after more than 30 years, this non-profit organization supports an array of visual, literary & performance artists whose creative contribution adds to the quality of life throughout the Florida Keys


April 2023

Conch Republic Independence Celebration

Apr 14 to Apr 23

Celebrate 41 years of the Conch Republic. This is an annual event honoring Key West's quirkiness with silly events. Declare your Fun-dependence with humor and become part of Key West's One Human Family.


May 2023

Key West Song Writer's Festival 2023

May 3 to May 7

The largest singer-songwriter festival of it's kind in the World. Join us for 5 days of live music from up and coming performers and well known artist. This event takes place at some of the island's most popular Beaches, Boats, Bars, Resorts and Historic Theatres.


June 2023

Key West Pride 2023

Jun 7 to Jun 11

Celebrate PRIDE in Paradise. Key West is known for it's open and accepting atmosphere which makes the island so special. Join the party and experience the island's One Human Family philosophy.


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