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Calendar of Events

Current Florida Keys Events

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
Image for Garden Club Midtown West Meander Image for Garden Club Midtown West Meander Image for Garden Club Midtown West Meander Image for Garden Club Midtown West Meander
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 NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
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 Art Guild of the Purple Isles Annual Members' Judged Art Show
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 Marathon Community Theatre: "Celebrating Keys Talent" Silent Auction & Variety Show
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.
  • Feb 3, 2023 - Feb 5, 2023 Islamorada Fishing
  • Islamorada Women's Sailfish Tournament
  • Tammy Gurgiolo Email
  • In this light-tackle challenge, awards await the grand champion team (boat), first runner-up and second runner-up team, captain and mate. Other awards are presented for the high-point angler, outstanding catch and largest tuna, dolphin fish and kingfish. Proceeds benefit Florida Keys charities. Contact Tammy Gurgiolo at 305-240-9337 .
Image for Friends of the Key West Library Book Sale
Image for Market on the Green
  • 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 Buccaneer Blast Regatta
  • Feb 4, 2023 - Feb 5, 2023 Key Largo
  • Buccaneer Blast Regatta
  • Website
  • The Buccaneer Blast Regatta welcomes youth sailors ages 8 through 18 from around the country and the Caribbean to Key Largo for a weekend of competitive racing. Sailors in the Optimist, Laser/ILCA and Junior Windsurfing classes are to participate. Buccaneer Blast has become the largest sailing event held in the Florida Keys each year. Activities are staged at Rowell’s Waterfront Park at mile marker 104.5 bayside. The public is invited to watch the near-shore racing Saturday from noon to 4:30 p.m., then buy tickets for a live raffle event for the chance to win notable prizes. Racing continues from 10 a.m. to 3 p.m. on Sunday. On both days, spectators can watch from shore or board a pontoon boat for a small donation to see the racing up close on Blackwater Sound.
Image for St. Columba Tea Party & Fashion Show
Image for Full Moon Kayak Excursion
  • Feb 4, 2023 The Lower Keys Environmental
  • Full Moon Kayak Excursion
  • Website
  • The Florida Keys Wildlife Society, supporting the National Wildlife Refuges in the Keys, has its next full moon kayak excursion on Saturday, Feb. 4 from 4:30 to 6:30 p.m., departing from Old Wooden Bridge Marina on Big Pine Key. Kayak across the water to No Name Key and then north from there with Captain Bill Keogh of Big Pine Kayak Adventures. Call 305-872-7474 for details and to reserve your spot. $30 per person, which supports Florida Keys Wildlife Society.
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 Grimal Grove Launch Party for Mutiny Island Vodka
  • Feb 5, 2023 The Lower Keys
  • Grimal Grove Launch Party for Mutiny Island Vodka
  • Website
  • Grimal Grove is having a public launch party for Mutiny Island Vodka - Grimal Grove Reserve, the first and only spirit made from Florida Keys agriculture. The limited reserve vodka is distilled with organic breadfruit from Grimal Grove on Big Pine Key. Stop by the grove from 2 to 5 p.m. for the event. There is a $10 entry fee. Live music with the Jericho Rockabilly Quartet along with raffles and prizes. 258 Cunningham Lane, Big Pine Key.
Image for Full Moon Yoga with Coral Restoration Foundation
  • Feb 5, 2023 Islamorada Environmental
  • Full Moon Yoga with Coral Restoration Foundation
  • Website
  • Relax and meditate during a yoga practice centered around how the moon affects our coral reefs, triggering coral spawning and the start of a new life for one of our planet's most precious ecosystems. Class takes place 6 to 7 p.m.on the deck at Postcard Inn, Islamorada, located at mile marker 84. $25 for non-guests of the resort.
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 Celebrate the Wild: Reverse the Red Day with Coral Restoration Foundation
  • Feb 7, 2023 Key Largo Environmental
  • Celebrate the Wild: Reverse the Red Day with Coral Restoration Foundation
  • Website
  • The International Union for Conservation of Nature has a "red list" of living species at risk for extinction, and several coral species are on that list. The Coral Restoration Foundation is holding a Reverse the Red Day at John Pennekamp Visitor Center and Aquarium from 10 a.m. to 2 p.m. that is to include a virtual reality coral restoration experience, along with coral chemistry experiments to demonstrate how changing ocean chemistry affects endangered corals. Meet some rare corals and their fishy friends in the visitor center's aquarium exhibits. The program is included with paid park admission or Florida State Park Annual Pass.
Image for The Connections Project: Grand Opening Reception
  • Feb 7, 2023 Key Largo Arts & Culture
  • The Connections Project: Grand Opening Reception
  • Website
  • Join the Florida Keys Council of the Arts for the grand opening reception and unveiling of this year's traveling mural of vibrant and unique canvases. This year's Connections Project mural is themed celebrates the Keys bicentennial with the theme "Pirates to Pineapples in Paradise - 200 Years in Monroe County." Tuesday, Feb. 7 from 5 to 7 p.m. in the 1st floor lobby at Baker's Cay Resort, mile marker 97 bayside in Key Largo.
Image for Poor Girls Sailfish Tournament
  • Feb 7, 2023 - Feb 8, 2023 Islamorada Fishing
  • Poor Girls Sailfish Tournament
  • Website
  • This regional charity competition raises money to spay and neuter feral cats in the Upper Keys. Trophies are awarded to the first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others. Events take place at the Islander Resort, mile marker 82.
Image for Florida Keys History & Discovery Center Lecture: Growing Up in the Keys
  • Feb 8, 2023 Islamorada Arts & Culture
  • Florida Keys History & Discovery Center Lecture: Growing Up in the Keys
  • Website
  • Enjoy first-hand accounts from residents who grew up in the Keys. Len Rhodus, who grew up on Plantation Key, Ron Watson from Key Largo and Eddie Whiteman, raised on Islamorada’s Matecumbe islands are to reminisce. Doors open at 5, lecture from 6 to 7:30 p.m. at the center, located at the Islander Resort, mile marker 82. Tickets $10, advance registration required. Doors open at 5 p.m. with the lecture from 6 to 7:30 p.m. at the center, located at the Islander Resort, mile marker 82.
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 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 Cuda Bowl
  • Feb 9, 2023 - Feb 11, 2023 The Lower Keys Fishing
  • Cuda Bowl
  • Email Website
  • The toothy barracuda are prey for competitors in this annual challenge. The all-release flats tournament got its name because it’s scheduled each year just before the Super Bowl NFL football championship. The event is headquartered at South of Seven Restaurant on Sugarloaf Key, mile marker 17. Prizes are awarded to the top angler guide in spin and fly divisions. Top scoring female and junior anglers are also recognized.
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 Sheriff's Animal Farm Open House
  • Feb 12, 2023 The Florida Keys
  • 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.
Image for Wine Pairing for Pets & Humans at Crane Point Hammock
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 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 The Studios of Key West: Chicago Farmer in Concert
Image for Fringe Theater: El Isleno 1921 - The Untold Key West Story
Image for Morada Way Third Thursday Art Walk in Islamorada
  • Feb 16, 2023 Islamorada Arts & Culture
  • Morada Way Third Thursday Art Walk in Islamorada
  • Website
  • The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
Image for Old Island Restoration Foundation's 63rd Annual Key West Home Tours
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 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 Run with Deer 5k
  • Feb 18, 2023 The Lower Keys Environmental
  • Run with Deer 5k
  • Website
  • Run or walk this fun 5k through Key deer habitat on Big Pine Key and support the Florida Keys Wildlife Society. They raise funds for our Florida Keys National Wildlife Refuges. Start and end at Big Pine Community Park. Awards will be give to the 5k top overall male and female winners; top masters male and female; the first and second in each age group; and to the top three overall male and female walkers. Find the registration form at southernmostrunners.com or stop by the Florida Keys National wildlife Refuge Nature Center to sign up. $20 to run or walk for age 14 and over; $10 for 13 and under
Image for Garden Club of the Upper Keys Annual Garden Walk
  • Feb 18, 2023 Key Largo Environmental
  • Garden Club of the Upper Keys Annual Garden Walk
  • Website
  • Visitors can stroll among and view native plants and lush landscaping at private gardens while getting ideas for tropical gardening. There will also be activities including plant sales, vendors and an art show at the Francis Tracy Garden Center, mile marker 94 bayside. Event tickets with a map of featured garden locations are to be available online and at various locations for pickup. Tours available from 10 a.m. to 4 p.m.
Image for Pops in the Park:
  • Feb 18, 2023 Islamorada Arts & Culture
  • Pops in the Park:
  • Website
  • “Who Let the Dogs Out?" is the theme for this month's free, outdoor concert from Keys Community Concert Band at Founders Park, mile marker 87, bayside, from 4 to 5 p.m. Saturday afternoon. Bring a blanket or lawn chair and pack a picnic basket for a family-friendly concert of animal-themed music. Bring your pooch to prance in the Puppy Parade. The Humane Animal Care Coalition will be there with adoptable pets.
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 Brewing Company 8th Anniversary Festival
  • Feb 19, 2023 Islamorada
  • Florida Keys Brewing Company 8th Anniversary Festival
  • Website
  • The Florida Keys Brewing tasting room and beer garden welcomes everyone for a family- and pet-friendly fun day with live music, food trucks, face painting, art vendors and special release local beers from noon to 10 p.m. The music lineup include Cortadito with traditional Cuban music from 1 to 3:30 p.m. and rock and roll with the Carousers from 5 to 9 p.m. 81611 Old Highway, Islamorada, in the Morada Way Arts and Cultural District between mile markers 81 and 82, oceanside.
Image for Backcountry Fly Championship Series
  • Feb 24, 2023 - Feb 25, 2023 Islamorada Fishing
  • Backcountry Fly Championship Series
  • Website
  • Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish.
Image for Sombrero Beach Run Weekend
  • Feb 24, 2023 - Feb 26, 2023 Marathon Environmental
  • Sombrero Beach Run Weekend
  • 305-743-4582 Email Website
  • Each year, several hundred racing circuit runners are attracted by a weekend filled with sunshine and athletic fun. Stocked with food, drinks, music and entertainment, the running event is to be staged Saturday, Feb. 25 at Sombrero Beach at the end of Sombrero Beach Road, mile marker 50. Awards are given to overall finishers in the 10k run, 5k run and 5k walk.
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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