Events & Festivals

Jan 12, 2023 – Jan 15, 2023
Key West Kingfish Mayhem
This the first tournament of the five-leg Kingfish Mayhem Pro Series. In the winter, Key West is the staging ground for King Mackerel before they start their annual migration in the Gulf. Big fish from the 50-70 lb. range are common in these areas, which creates an exciting and competitive environment at the weigh-in. This event has been enhanced by adding tuna, mahi and wahoo, for a four-species tournament. Teams from all around travel to join this world-class event for their shot at claiming King of Key West!

Jan 12, 2023
Badfish: A Tribute to Sublime Concert on Sunset Pier
Badfish: A Tribute to Sublime plays in concert on Sunset Pier, Thursday from 6 to 9 p.m. along with special guests Kash’d Out. General admission is free; $40 for front stage VIP area.

Jan 13, 2023 – Jan 15, 2023
25th Annual Key West Half Marathon & 5k Run
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2023 25th anniversary race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Ranked among 13 “must-do” U.S. half-marathons by competitor.com.

Jan 13, 2023 – Jan 14, 2023
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.

Jan 14, 2023 – Jan 15, 2023
17th Annual Florida Keys Seafood Festival
Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. This event is a fundraiser for the Florida Keys Commercial Fishermen’s Association FKCFA and goes to support sustainable fishing programs, marine restoration projects and college scholarships. A $10 admission is good for BOTH Saturday and Sunday and the festival is to be held at Bayview Park. 1320 Truman Avenue, Key West.

Jan 16, 2023 – Jan 20, 2023
The Southernmost Regatta
Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort’s marina, 617 Front Street, after each day’s races.

Jan 17, 2023 – Jan 21, 2023 Key West Arts & Culture
RokIsland Fest 2023
More than 20 of the best and most iconic rock bands bring their massive hits to the Southernmost City in the U.S. for five days of unforgettable songs, sun & sand at RokIsland Fest. The lineup includes Styx, Loverboy, Vince Neil, Tesla, Quiet Riot and many more. Single day and four day passes are available with performances at Truman Waterfront Park.

Jan 24, 2023 – Jan 28, 2023
Mile 0 Fest
More than 60 artists are to perform at the annual Mile 0 Fest, all representing the Red Dirt and Americana musical styles that incorporate elements of rock, country and the American roots tradition. The event’s “Mile 0” moniker refers to Key West’s location at “mile 0” of U.S. Highway 1. Headliners include American Aquarium, Ian Munsick Pat Green and Shane Smith & the Saints. Performances are scheduled for Truman Waterfront Park as well as “pop-up” performance locations at popular bars, resorts and theaters around Key West.

Jan 24, 2023 – Jan 30, 2023
Kelly McGillis Classic
Women from countries far and wide will be descending upon Key West for the 31st annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador and Sweden. Kelly McGillis will serve as grand Marshall for the players’ parade from the historic seaport down Duval Street on Thursday, Jan. 26. Game activities throughout the weekend are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive.

Jan 25, 2023 – Jan 29, 2023
Key West Food and Wine Festival
The 2023 Key West Food & Wine Festival celebrates the flavors, vintages and culture of Argentina at multiple events across the southernmost island city. Events include the Carnival de Buenos Aires gaucho parade and vintner dinner, a Last Tango in Cayo Hueso Brunch and the festival highlight SLaM grand tasting where guests can sample vintages from every wine region in Argentina. Tickets to individual events are going fast – purchase online at KeyWestFoodandWineFestival.com

Jan 28, 2023 – Jan 29, 2023
38th Annual Key West Craft Show
The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.

Jan 31, 2023 – Feb 4, 2023
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. Take in the warm sunshine and tunes during the day at the island’s iconic bars, snag a bite from one of the renowned restaurants, leave your troubles on land during a live-music sail on a comfy catamaran, and then sing your heart out under the stars at night at the Truman Waterfront Amphitheater, 21 Quay Rd, Key West. Passes and packages available online.

Feb 25, 2023 – Feb 26, 2023
Old Island Days Art Festival
Aficionados of fine art can discover creative offerings by approximately 100 artists, chosen from several hundred applicants from around the United States and Canada. The nationally recognized open-air show takes place from 10 a.m. to 5 p.m. each day at Key West’s Truman Waterfront Park, located at the end of Southard Street past the Truman Annex neighborhood. The two-day event typically features a blend of Florida Keys talents and fine artists from other locations, all gathered to showcase their work to connoisseurs, collectors and other attendees during the free-admission show.

Feb 25, 2023
Master Chef’s Classic
One of Key West’s most spectacular food events, this culinary competition and tasting benefits the Monroe Association for ReMARCable Citizens, which provides life services for adults with developmental and intellectual disabilities in the Florida Keys. Restaurants compete in appetizer, entree and dessert categories, providing an array of incredible food for attendees. Awards are given in each category by judges and people’s choice ballots. Held on the Opal Key Resort & Marina pier from 4 to 7 p.m., 245 Front St.

Mar 5, 2023
60th Annual Conch Shell Blowing Contest
An island tradition for 60 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.

Mar 13, 2023 – Mar 16, 2023
March Merkin Invitational Permit Tournament
This charity flats-and-fly-only invitational tournament challenges anglers to catch and release silvery permit to vie for elite titles. The event is held at Oceans Edge Resort & Marina in Key West.

Mar 31, 2023
Keys to the Keys: A Tropical Gala
The annual fundraiser gala benefiting Habitat for Humanity of Key West and the Lower Florida Keys is a tropical-themed event that will be a fun night filled with music, drinks, dining, dancing, games, auctions and more. All money raised helps build and repair affordable homes for Keys residents. The event takes place from 6 to 10 p.m. at the Truman Little White House, 111 Front Street, Key West. Call 305-294-9006 for more information and to RSVP.

Apr 4, 2023 – Apr 9, 2023
Red Barn Theatre: Short Attention Span Theatre
One of Red Barn Theatre’s favorites each year, “Short Attention Span Theatre” is a funny and fast-paced evening filled with pertinent and hilarious short plays, helmed by a group of directors guiding a big handful of favorite Key West actors. You never know what you’ll see next at “Short Attention Span Theatre!” Order tickets online or at the box office. Showtime 8 p.m. 319 Duval Street.

Apr 15, 2023 – Apr 16, 2023
NAS Key West Southernmost Air Show Spectacular
The U.S. Navy flight demonstration team Blue Angels and other military and civilian aerial performances will fill the skies at this free-admission, family friendly event celebrating the 200th anniversary of the Navy’s presence in Key West. In addition to the Blue Angels, aerial demonstrations by military and civilian performers, and static military and vintage aircraft are planned. Gates open at 10 a.m. both days. Air show starts at 11 a.m. with Blue Angels flying at 2:30 p.m. VIP and preferred seating options are available for purchase. Free parking.

Apr 21, 2023 – Apr 30, 2023
41st Annual Conch Republic Independence Celebration
Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent “nation’s” 41st birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, and more. The annual Conch Republic Independence Celebration commemorates the Keys’ symbolic 1982 secession from the United States and reinvention as the eccentric republic.

Apr 28, 2023 – Apr 29, 2023
Key West Association of Realtors Sailfish Tournament
As well as releasing sailfish in the fun yet competitive challenge, anglers can target dolphin fish, blackfin tuna and kingfish for points. Awards await the top three boat teams, top overall angler and woman angler, and those who catch the biggest dolphin fish, tuna and kingfish. The tournament benefits Fair Insurance Rates in Monroe.

May 3, 2023 – May 7, 2023
27th Annual Key West Songwriters Festival
Since 1997, BMI has been a presenting sponsor of the festival, one of the largest festivals of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.

Jun 7, 2023 – Jun 11, 2023
Key West Pride
Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively “Rainbow Roast.”

Jun 17, 2023
CFK Swim Around Key West
Embark on an adventurous swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim.

Jun 22, 2023 – Jun 25, 2023
Sixth Annual Mango Fest Key West
Experience all things Mango through shopping, education and demonstrations. Stroll virtually through a vendor village, enter a poetry contest, photo contest, see virtual culinary and cocktail demos, and more. Details to come for the 2023 event.

Jul 22, 2023
Hemingway 5k Sunset Run & Paddleboard Race
The Hemingway 5k Sunset Run & Paddleboard Race is to challenge competitors Saturday, July 23. Race begins 5 p.m., from Southernmost Beach, 1405 Duval St. Celebrate your accomplishment while easing sore muscles from the race with an all-levels yoga recovery session Sunday, free to all participants. The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.

Oct 20, 2023 – Oct 29, 2023
Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. In recognition of the 200-year anniversary of Monroe County and Key West’s first Naval base, the 2022 theme is ‘“Uniforms & Unicorns — 200 Years of Sailing into Fantasy.” Check the website for the full schedule and more details.

Dec 31, 2023
New Year’s Celebration at Schooner Wharf
The Unique Schooner Wharf Bar’s Seaport Tradition – Lowering of the Pirate Wench at Midnight. Party starts early in the day with 3 Local and National Acts – Party Favors – Champagne & Fun