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Calendar of Events

Current Key West Events

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Image for 63rd Annual Key West Home Tours Image for 63rd Annual Key West Home Tours Image for 63rd Annual Key West Home Tours Image for 63rd Annual Key West Home Tours
  • Sponsored Event
  • Dec 28, 2022 - Mar 18, 2023 Key West
  • 63rd Annual Key West Home Tours
  • Website
  • 305-294-9501 E-mail
  • Facebook Instagram
  • The 63rd Annual Home Tours hosted by the Old Island Restoration Foundation offers a chance to peek into into some of the most beautiful 19th and 20th century residences on the island, learn fascinating history, and enjoy fine art collections and antiques.
Image for 16th Annual Sombrero Beach Run Image for 16th Annual Sombrero Beach Run Image for 16th Annual Sombrero Beach Run Image for 16th Annual Sombrero Beach Run
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Image for Monday and Tuesday Evening GLOW Hours at Hugh's View Rooftop
Image for Key West Fishing Tournament
  • Dec 1, 2022 - Jul 31, 2023 Key West Fishing
  • Key West Fishing Tournament
  • Website
  • More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
Image for Key Western Fest
  • Jan 31, 2023 - Feb 4, 2023 Key West Arts & Culture
  • Key Western Fest
  • Website
  • More than 20 of the very best classic country bands bring their massive hits to the Southernmost City in the U.S. for a week of unforgettable songs, sun & sand. Artists include The Oak Ridge Boys, Sawyer Brown, The Marshall Tucker Band and many more. Take in the warm sunshine and tunes during the day at the island’s iconic bars, or leave your troubles on land during a live-music sail on a comfy catamaran, then sing your heart out under the stars at night at the Coffee Butler Amphitheater, 21 Quay Road at the Truman Waterfront. Passes and packages available online.
Image for Red Barn Theatre: Flaming Guns of the Purple Sage
  • Jan 31, 2023 - Feb 25, 2023 Key West Arts & Culture
  • Red Barn Theatre: Flaming Guns of the Purple Sage
  • Website
  • Be ready to take a wild and crazy ride into the classic mash-up spoof of a Western-Horror “B” movie with Jane Martin’s hilarious “Flaming Guns of the Purple Sage." Big 8, a rodeo competitor, is facing foreclosure on the Wyoming ranch where she rehabilitates injured rodeo cowboys. The arrival of a shocking woman named Shedevil and a one-eyed Ukrainian biker named Black Dog leads to violence and horror in this satire of pulp western writers like Zane Grey. Order tickets online or at the box office. Showtime 8 p.m. 319 Duval Street.
Image for Key West Gallery: Meet & Greet British Artist Mackenzie Thorpe
  • Feb 3, 2023 - Feb 4, 2023 Key West Arts & Culture
  • Key West Gallery: Meet & Greet British Artist Mackenzie Thorpe
  • Website
  • All are invited to several public meet & greet sessions with beloved British artist Mackenzie Thorpe at Key West Gallery. He will introduce his brand new collection "Warm In Love" featuring artwork ranging from bronze and stainless steel sculpture, originals, and limited editions all brimming with love. Receptions are Friday from 7 to 10 p.m. and Saturday 11 a.m. to 3 p.m. and 7 to 10 p.m. Attendance is free but RSVPs are recommended. Call 305-292-9339.
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  • Feb 4, 2023 Key West Arts & Culture
  • Market on the Green
  • Website
  • Held the first Saturday of every month from 10 a.m.- 2 p.m., visitors and residents are invited to browse and shop amazing local artisans. The monthly market is located at the Sunset Green Event Lawn, at Key West’s 24 North Hotel, 3820 N. Roosevelt Boulevard.
Image for Roaring '20's Gala to Benefit May Sands Montessori
  • Feb 4, 2023 Key West
  • Roaring '20's Gala to Benefit May Sands Montessori
  • Website
  • Don your pinstripe suit or flapper dress for a Roaring '20's Gala to benefit May Sands Montessori, Key West's only tuition-free Montessori School. Doors open at 6 p.m. for the event to be held at Key West Woman's Club, 319 Duval St. Prohibition ends at the door for this extravaganza, complete with food, libations, entertainment and live and silent auctions. Roaring 20's attire is encouraged but not required.
Image for Friends of the Key West Library Book Sale
Image for The Studios of Key West: Jazz on the Roof with Libby York
  • Feb 6, 2023 Key West Arts & Culture
  • The Studios of Key West: Jazz on the Roof with Libby York
  • Website
  • Critically acclaimed vocalist Libby York is known for her swinging renditions of Great American Songbook classics, bossa nova gems and obscure treasures. She’s appeared at top venues in New York, Chicago, LA and Paris. Her recordings are featured on jazz radio worldwide. This "First Monday" Jazz on the Roof concert will feature her trio in the beautiful Hugh’s View rooftop setting. Show starts at 5:30 p.m. Tickets $40. 533 Eaton St., Key West.
Image for The Studios of Key West: Miss Tess in Concert
  • Feb 7, 2023 Key West Arts & Culture
  • The Studios of Key West: Miss Tess in Concert
  • Website
  • Miss Tess -- according to Rolling Stone Magazine -- "Swings and swaggers, rooted in a retro groove that's equal parts blues, mid-century rock & roll and Booker T-worthy R&B." Performing at The Studios of Key West Helmerich Theater. Tickets $40 to $50. Show starts at 7 p.m. 533 Eaton St., Key West.
Image for Florida Keys Council of the Arts:
  • Feb 9, 2023 Key West Arts & Culture
  • Florida Keys Council of the Arts:
  • Website
  • Join the free opening reception for "Seeing," the new exhibition of contemporary and abstract works by Ruth Gilmore Langs and Scott Jeffries on Thursday, Feb. 9th from 5 to 7 p.m. at the historic Gato Building, 1100 Simonton St, Key West. Enjoy an artist’s meet-and-greet and refreshments. The show will be on display through April 30.
Image for Party in the Park: "Just a Few Friends" Before the Jimmy Buffett Feb. 9 Concert
  • Feb 9, 2023 Key West Arts & Culture
  • Party in the Park: "Just a Few Friends" Before the Jimmy Buffett Feb. 9 Concert
  • Website
  • The Thursday, Feb. 9 market at Truman Waterfront Park expands into a Jimmy Buffett-themed gathering from 2 to 7 p.m. on the afternoon before his concert at the adjacent Coffee Butler Amphitheater. Come out with your picnic best and enjoy the afternoon. The Famers Market will be in full swing with food stalls and trucks, a full bar from Great Events catering, arts and crafts and more. TropRock acoustic jam session from 4 to 6 p.m. hosted by singer-songwriter Dani Hoy. Note: You will not be able to clearly hear the concert from the park, and the market space will close at 7 p.m.
Image for Coffee Butler Amphitheater: Jimmy Buffett & The Coral Reefer Band
Image for Coffee Butler Amphitheater: Jimmy Buffett & The Coral Reefer Band
Image for Get Your Heart On 5k to Benefit Reef Relief
  • Feb 11, 2023 Key West Environmental
  • Get Your Heart On 5k to Benefit Reef Relief
  • Website
  • Grab your favorite partner and get your heart thumping at this year's Get Your Heart On 5k presented by Southernmost Point Bar, Feb. 11 at 8 a.m. Costumes are encouraged in this run to support Reef Relief. Grab your medal and finish strong at the post race after party. All participants 21+ will receive one free mimosa or bloody Mary. The race starts at 8 a.m. at 1327 Duval Street. $34.99 to sign up, and there is a virtual option as well.
Image for Friends of the Key West Library Presents Carl Hiaasen
  • Feb 13, 2023 Key West Arts & Culture
  • Friends of the Key West Library Presents Carl Hiaasen
  • Website
  • The Friends of the Key West Library's speaker series presents Carl Hiaasen, the author of 24 bestselling novels for adults, six books for young readers, and several works of non-fiction on Monday, Feb. 13 at 6 p.m. Hiaasen's talk will be outdoors in the Palm Garden at the Library at 700 Fleming Street. The lecture is free, but you must register for a ticket, which are close to being sold out. If you don't receive a ticket, you can join the standby line at the Fleming Street gate. A gala fundraising reception after the talk is sold out, but you can join a waitlist.
Image for The Studios of Key West: Chicago Farmer in Concert
Image for Wesley House Family Services Valentine's Day Gala
  • Feb 14, 2023 Key West Arts & Culture
  • Wesley House Family Services Valentine's Day Gala
  • Website
  • This Valentine's Day, take your special someone to the beautiful Customs House Museum. Included with your ticket price, from 6 to 9:30 p.m., is the island's largest silent auction, open bar, dancing to the sounds of The Prime Movers, and an elegant dinner designed and prepared by Catered Affairs. VIP and General Admission tickets available.
Image for Back in Time Fundraiser at the A1A Speakeasy
  • Feb 17, 2023 Key West Arts & Culture
  • Back in Time Fundraiser at the A1A Speakeasy
  • Website
  • Step back in time with Key West Art & Historical Society’s Annual Fundraiser Dinner for a Prohibition Party like you’ve never seen. Fort East Martello will transform into the A1A Speakeasy. Swing to jazz music and enjoy free-flowing cocktails, a surf and turf dinner, hand-rolled cigars and sips of delicious rum.
Image for Old Island Restoration Foundation's 63rd Annual Key West Home Tours
Image for Presidential Families Weekend Celebrates History and Bipartisanship
  • Feb 18, 2023 - Feb 20, 2023 Key West Arts & Culture
  • Presidential Families Weekend Celebrates History and Bipartisanship
  • Website
  • The Key West Harry S. Truman Foundation, in partnership with The Society of Presidential Descendants, presents a series of special events Presidents' Day Weekend at the Harry S. Truman Little White House. On Sat. Feb. 18, a panel of presidential descendants discusses American Bipartisanship, and on Sun. and Mon., Clifton Truman Daniel, the grandson of Harry S.Truman, performs the acclaimed stage production, "Give 'Em Hell, Harry!" Find more event information and ticket sales online. 111 Front Street, Key West.
Image for Florida Keys SPCA Annual Pup Crawl
  • Feb 18, 2023 Key West
  • Florida Keys SPCA Annual Pup Crawl
  • Tiffany Email Website
  • You and your pup are in for a waggin' good time at the 4th annual SPCA Pup Crawl. Start at noon at either Hank’s Hair of the Dog Saloon or Tattoos & Scars. Then crawl from 1 to 5 p.m. from bar-to-bar engaging in various activities at each location. Gather up toys, treats and prizes from contests and even a mini pool party as you mingle with local pups up for adoption. $25 for humans; dogs are free.
Image for South Florida Symphony at Tennessee Williams Theatre
  • Feb 18, 2023 Key West Arts & Culture
  • South Florida Symphony at Tennessee Williams Theatre
  • Website
  • South Florida Symphony Orchestra's 25th Anniversary Season continues with Brahms’ final symphonic work, Double Concerto, featuring Geneva Lewis (violin) and Gabriel Martins (cello); along with the Fifth Symphony by famed Finnish composer Sibelius; and the spirited overture to Berlioz’s Béatrice et Bénédict.
Image for Old Island Days Art Festival
  • Feb 25, 2023 - Feb 26, 2023 Key West Arts & Culture
  • Old Island Days Art Festival
  • Website
  • This nationally-recognized, juried art show takes place along Whitehead and Caroline Streets within the Truman Annex residential enclave with as many as 100 fine artists from across the country displaying their wares. Explore the show from 10 a.m. to 5 p.m. both Saturday and Sunday.
Image for Sheriff's Animal Farm Open House
  • Feb 26, 2023 Key West
  • Sheriff's Animal Farm Open House
  • Website
  • Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Come visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a lemur, an alpaca, a skunk, a prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road on Stock Island, at the Sheriff's Office Headquarters complex. Open the second and fourth Sundays of the month.
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