The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by www.fla-keys.com.

Events in the Florida Keys for February, 2023
Year: Month:  
January 31 to February 04,  in Key West
Key Western Fest
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.


January 31 to February 25,  in Key West
Red Barn Theatre: Flaming Guns of the Purple Sage
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.


February 02,  in Marathon
Aquarium Encounters "GroundConch" Day
Come one, come all to celebrate Groundhog, or "GroundConch" Day, from 8 to 9 a.m. at Aquarium Encounters, mile marker 53 bayside. Will the Marathon Meteorologist Mollusk see its shadow? Will we have six more weeks of winter? Free admission during the event to celebrate this new Keys tradition.


February 02 to February 04,  in Marathon
Marathon Community Theatre: "Celebrating Keys Talent" Silent Auction & Variety Show
Don't miss the annual silent auction fundraiser and variety show taking place three straight nights. Bid on items at the silent auction followed by a variety show performed by the talented local Keys community. $45 tickets include dinner buffet and champagne toast. Doors open at 7 p.m., 5101 Overseas Hwy.


February 03 to February 05,  in Islamorada
Islamorada Women's Sailfish Tournament
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 .
Contact: Tammy Gurgiolo
Email: [email protected]

February 03 to February 04,  in Key West
Key West Gallery: Meet & Greet British Artist Mackenzie Thorpe
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.


February 04,  in Marathon
St. Columba Tea Party & Fashion Show
Enjoy a delightful fashion show and tea party complete with fine china, tea sandwiches, scones and mimosas. Raffles featuring beautiful gift baskets, a 50/50 raffle and door prizes. Tickets $20. 2 p.m. at 451 W. 52nd St., Marathon


February 04,  in Key West
Friends of the Key West Library Book Sale
Monthly used book sale from 10 a.m. to 1 p.m. in the garden at the library, located at 700 Fleming Street. Most books are priced at $1.


February 04,  in Key West
Market on the Green
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.


February 04 to February 05,  in Key Largo
Buccaneer Blast Regatta
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.


February 04,  in Big Pine
Full Moon Kayak Excursion
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.


February 04,  in Key West
Roaring '20's Gala to Benefit May Sands Montessori
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.


February 05,  in Big Pine
Grimal Grove Launch Party for Mutiny Island Vodka
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.


February 05,  in Islamorada
Full Moon Yoga with Coral Restoration Foundation
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.


February 06,  in Key West
The Studios of Key West: Jazz on the Roof with Libby York
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.


February 07,  in Key West
The Studios of Key West: Miss Tess in Concert
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.


February 07 to February 08,  in Islamorada
Poor Girls Sailfish Tournament
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.


February 07,  in Key Largo
Celebrate the Wild: Reverse the Red Day with Coral Restoration Foundation
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.


February 07,  in Key Largo
The Connections Project: Grand Opening Reception
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.


February 08,  in Islamorada
Florida Keys History & Discovery Center Lecture: Growing Up in the Keys
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.


February 09,  in Key West
Party in the Park: "Just a Few Friends" Before the Jimmy Buffett Feb. 9 Concert
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.


February 09,  in Key West
Coffee Butler Amphitheater: Jimmy Buffett & The Coral Reefer Band
Jimmy Buffett launches his 2023 Second Wind tour with this first of two sold out shows in Key West. Gates open for ticket holders at 5:30; show starts at 7 p.m.


February 09 to February 11,  in Big Pine
Cuda Bowl
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.
Email: [email protected]

February 09,  in Key West
Florida Keys Council of the Arts:
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.


February 11,  in Key West
Get Your Heart On 5k to Benefit Reef Relief
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.


February 11,  in Key West
Coffee Butler Amphitheater: Jimmy Buffett & The Coral Reefer Band
Jimmy Buffett launches his 2023 Second Wind tour with this second of two sold out shows in Key West. Gates open for ticket holders at 5:30; show starts at 7 p.m.


February 12,  in Marathon
Wine Pairing for Pets & Humans at Crane Point Hammock
Crane Point Hammock hosts a pet-friendly wine and food pairing event in the beautiful tree-lined hammock. Humans $40; pets are admitted with either an SPCA pet food donation or $10. Call 305-393-9501 for ticket information.


February 13,  in Key West
Friends of the Key West Library Presents Carl Hiaasen
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.


February 14,  in Key West
The Studios of Key West: Chicago Farmer in Concert
Chicago Farmer - otherwise known as Cody Diekhoff - is a working-class folk musician with small town, farming community roots and a city streets mentality who is profoundly inspired by fellow midwesterner John Prime. Tickets $40 to $50 for his Helmerich Theater show, 7 p.m. 533 Eaton St., Key West.


February 14,  in Key West
Wesley House Family Services Valentine's Day Gala
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.


February 16,  in Islamorada
Morada Way Third Thursday Art Walk in Islamorada
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.


February 17 to February 18,  in Key West
Old Island Restoration Foundation's 63rd Annual Key West Home Tours
Enjoy tours of beautiful and historic Key West homes and gardens. Your ticket purchase supports the ongoing mission of preserving and promoting Key West's unique architecture, culture and history. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.


February 17,  in Key West
Back in Time Fundraiser at the A1A Speakeasy
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.


February 18,  in Key West
Florida Keys SPCA Annual Pup Crawl
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.
Contact: Tiffany
Email: [email protected]

February 18,  in Islamorada
Pops in the Park:
“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.


February 18 to February 20,  in Key West
Presidential Families Weekend Celebrates History and Bipartisanship
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.


February 18,  in Key Largo
Garden Club of the Upper Keys Annual Garden Walk
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.


February 18,  in Big Pine
Run with Deer 5k
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


February 18,  in Key West
South Florida Symphony at Tennessee Williams Theatre
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.


February 19,  in Islamorada
Florida Keys Brewing Company 8th Anniversary Festival
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.


February 24 to February 26,  in Marathon
Sombrero Beach Run Weekend
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.
Contact: 305-743-4582
Email: [email protected]

February 24 to February 25,  in Islamorada
Backcountry Fly Championship Series
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.


February 25 to February 26,  in Key West
Old Island Days Art Festival
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.


February 26,  in Key West
Sheriff's Animal Farm Open House
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.




The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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