Key West Events Calendar

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.
Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

There is never a shortage of activity on Key West. A new year is here and the events keep on coming. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven!  There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.

2022

Due to coronavirus, some Key West events may be canceled. We are trying to update this page as information comes in, but please check the individual event’s website or call its organizer for more details.

January 2022

January 21 – 31, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

February 2022

February 1 – 28, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

February 8, 2022

  • Celebration of Elizabeth Bishop’s 111th Birthday – Everyone is welcome at the Elizabeth Bishop Key West Committee’s celebration of the 111th birthday of internationally renowned poet, Elizabeth Bishop (1911-1979), a U.S. Poet Laureate who lived and was a homeowner in Key West. The event, a poetry reading with a birthday cake in Bishop’s honor, will be held from 5:30 to 7:30 p.m. at The Gardens Hotel, 526 Angela St.

February 8 – 12, 2022

  • Fringe Theater presents: How I Learned what I Learned – August Wilson’s journey from school dropout to Pulitzer Prize winning playwright is the focus of this one-man play. Presented in celebration of Black History month. Tickets, show times and dates online. Performances start 7 p.m., Fringe Theater, 600 White St.

February 12 – 13, 2022

  • Studios of Key West presents: Mary Gauthier & Jamie Harris – Mary Gauthier, an Artist in Residence at the Studios, is to be joined by Jaimee Harris, a Texas-raised folk n’ roll singer, songwriter and criminal justice reform activist. The duo is to perform both musical shows at the rooftop Hugh’s View, starting at 8 p.m. Saturday and 7 p.m. Sunday. Tickets are limited and available online.

February 13, 2022

  • Impromptu Classical Concert – Gifted violinists Timothy Chooi and his brother Nikki are back in Key West for a repeat Impromptu Classical Concert. Both violinists are united by a profound understanding and genuine passion for the violin, which renders their musical union extraordinarily rich. All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free. 

February 14, 2022

  • Friends of the Key West Library present: Meg Cabot – New York Times bestselling author Meg Cabot will speak at the Tropic Cinema from 6-7PM. This event is to be followed by a showing of the movie made from her book, The Princess Diaries. As in past years the speaker series are free and open to all, but you must register online. The friends will follow the Tropic Cinema Covid guidelines, including 50% seating capacity and masks recommended. 

February 15, 2022

  • The World of Peter Max Retrospective – The exhibition opens with an evening preview event on February 15  from 5-8 p.m.  The Exhibition extends through February 20, with three gallery receptions complimentary to the public. All events are complimentary, however RSVP’s are requested.

February 16 – March 5, 2022

  • The Waterfront Playhouse presents: Clue – Performances at 8 p.m., Waterfront Playhouse, 407 Wall St.; visit website for show dates and details.

February 18, 2022

  • Honky Tonk Heartbreak – Key West Burlesque pays tribute to the classic country-and-western songbook in a down-home and dirty burlesque extravaganza. Featuring a live band of local C&W musicians, Honky Tonk Heartbreak: a Country-and-Western Revue is an anthology of stories, songs, and striptease. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

February 19, 2022

  • Give ‘Em Hell, Harry! – The Key West debut of the stage production “Give ‘Em Hell, Harry!”, starring President Harry S. Truman’s grandson Clifton Truman Daniel, the first direct descendant to portray a presidential ancestor in a one-man show of this kind. Truman Little White House.
  • 3rd Annual Pup Crawl – Bring your four-legged companion and join the Florida Keys SPCA to help the homeless animals of the Florida Keys! This is a doggone fun-filled day you won’t want to miss. The fun kicks off at noon at Hank’s Hair of the Dog Saloon, then you and your furry friend ‘crawl’ from bar to bar and engage in various activities at each location. Gather up toys, treats, prizes from contests and even a mini pool party as you mingle with local pups up for adoption.
  • Key West Tropical Forest Speaker – The Key West Botanical Garden Society presents Dr. Cori Convertito, Curator for the Key West Art & Historical Society as the featured speaker, at 1 p.m. in the Toppino Nature Chapel at the Key West Tropical Forest & Botanical Garden, located at 5210 College Road on Stock Island. Dr. Convertito’s subject is to be “Key West at the 200 Year Mark.” The program is free and will also be recorded and available after this date on the Garden’s website.    
  • Key West Cemetery Stroll – Interpreters tell the fascinating stories of the deceased in brief monologues. Among the gravesites to be visited are those of Frank Adams, Willard Gomez, the Figueredo plot, the Cobo plot, and the Castillo plot. The 90-minute tours for small groups depart at 9:30, 9:50, and 10:10 a.m. Reservations are necessary; a donation of $20/pp to the Historic Florida Keys Foundation is recommended. Proceeds are devoted to cemetery restoration.  Participants may enter the cemetery by either the Windsor Street or Frances Street gate and go to the registration table on Second Ave.

February 21, 2022

  • Key West Theater presents: Livingston Taylor – Livingston maintains a performance schedule of more than a hundred shows a year, delighting audiences with his charm and vast repertoire of his 22 albums and popular classics. Doors open 7 p.m., show starts 8 p.m.

February 25 – 26, 2022

  • Key West Garden Club Tour – Take a stroll through the iconic Meadows area of Key West. Join us for an exclusive tour of seven, diverse gardens which provide attendees a rare chance to see spectacular designs and displays of landscaping in a tropical paradise.

February 26, 2022

  • 38th Annual Key West Headress Ball – Kick off Mardi Gras season at the Coffee Butler Amphitheater, Truman Waterfront Park for the outdoor gala, rescheduled from October due to coronavirus concerns. Doors open 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online. Ticket holders from 2021 event can carry over.

February 27, 2022

  • Impromptu Classical Concert – The Soul of the Americas features unique combinations of piano, cello and percussion, and will take the listener on a sizzling journey through both hemispheres. All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free. 

March 2022

March 1 – 31, 2022

  • Tennessee Williams Birthday Celebration – Internationally renowned playwright Tennessee Williams, who lived in Key West for more than 30 years, once said of his chosen home, “I work everywhere, but I work best here.” Fans of Williams’ classic plays can explore his writing and life in the island city through screenings of films adapted from his work, prose and poetry contests, theater presentations, curator-led tours of Key West’s Tennessee Williams Museum, located at 513 Truman Ave., and a commemoration of the 111th anniversary of his birth.
  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

March 2, 2022

  • Key West NOW Women’s Film Fest – Five fabulous films are on the docket for the five Wedesdays in March. Opens Wednesday, March 2 at the Tropic Cinema. Ana DuVernay’s 2012 award-winning film, “Middle of Nowhere” begins the festival with an intimate glimpse into the life of a Black nurse whose husband is incarcerated. All films will be shown at 6:30 p.m. Tickets are available online or at the door. For everyone’s safety, covid protection policy requires attendees show a negative PCR done within the past 72 hours or a completed vaccination document and to wear masks.

March 6, 2022

  • The Beach Boys – The Beach Boys transcended their music and have come to represent Californian culture. Doors open 5:30 p.m., show stats 7 p.m. at Coffee Butler Amphitheater. Tickets online.

March 7 – 10, 2022

  • March Merkin Invitational Permit Tournament – This charity flats-and-fly-only tournament challenges anglers to catch, tag and release silvery permit to vie for elite titles. The event is traditionally held at the Key West Harbour Yacht Club on Stock Island, and features a silent online auction.

March 12, 2022

  • Florida Keys SPCA 14th Annual Spring Social – Enjoy a day to benefit the homeless animals of the Lower Keys at the Coffee Butler Amphitheater!  Their biggest celebration of the year will include dinner, a live & silent auction, entertainment, complimentary wine & beer with cash liquor bar and is a night not to be missed!  VIP tickets include a Champagne Reception starting at 5:30 p.m. before the main event, passed appetizers, a sneak peek at one of the largest silent auctions on the island, reserved seating and VIP food stations. The VIP Reception begins at 5:30 p.m. and General Admission entry is at 6:30 p.m. Tickets are available for purchase online.

March 12 – 13, 2022

  • Key West Orchid Society Fair – From 10 a.m. to 4 p.m. each day, at W. Martello Gardens, White St. Free admission and parking. Favorite orchid vendors along with KWOS member plants for sale. Food truck ‘One Love,’ a local treasure , is on hand with a wonderful menu and beverages. Orchid raffles and judging of local orchids are to show what wonderful growers the Keys have!

March 13, 2022

  • Impromptu Classical Concert Series – The first American in four decades, and youngest musician ever, to win First Prize at the International Tchaikovsky Competition Cello Division, Zlatomir Fung is poised to become one of the preeminent cellists of his time, astounding audiences with his boundless virtuosity and exquisite sensitivity. This 21-year-old has already proven himself to be a star among the next generation of world-class musicians. Fung’s impeccable technique demonstrates a mastery of the canon and exceptional insight into the depths of contemporary repertoire. All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free. 

March 15-26, 2022

  • Fringe Theater presents: Looped – Inspired by the true story of an eight-hour recording session with an intoxicated Tallulah Bankhead in 1965. It’s a battle of the wills between star and film editor. Tickets, show times and dates online. Performances start 7 p.m., Fringe Theater, 600 White St.

March 19 – 30, 2022

  • Key West 200th Anniversary Celebration – Join the multi-day 200th anniversary of Key West’s first permanent settlement, commemorating the date of March 25, 1822, when U.S. Navy Lt. Matthew Perry planted the American flag on island soil, thereby solidified Key West’s special place in history. Celebrate the island’s history, architecture, food, culture, art, industries, residents and more. Planned activities include historical events, talks and shared history, a parade, heritage festival, fireworks, even a time capsule intended to be reopened at the 250th celebration in 2072. Events Friday, March 25 are set to begin at 2 p.m., including a re-enactment of Perry’s planting of the American flag. Staged at Mallory Square beside Key West Harbor, activities feature the dedication of a granite time capsule to be opened in 50 years and the designation of four Key West children to be ambassadors at the island’s 250th anniversary celebration. A parade along historic Duval Street is to follow, with an evening Key West Bicentennial Celebratory Gala at the Oldest House Museum and Gardens, 322 Duval St. On Saturday, March 26, an all-day Bicentennial Heritage Festival at Truman Waterfront Park is planned. The Key West 200th Heritage Festival is to be held at the Truman Waterfront Park from 10 a.m. to 9 p.m., for locals and visitors alike to celebrate the bicentennial with exhibits, stage performances, history reenactments and a variety of vendors. The evening caps off with a 15-minute silent drone fireworks show set to music.

March 22 – 30, 2022

  • Waterfront Playhouse presents: Something Rotten – When a local soothsayer foretells that the future of theatre involves singing, dancing and acting at the same time, Nick and Nigel Bottom set out to write the world’s very first musical. But amidst the scandalous excitement of opening night, the Bottom Brothers realize that reaching the top means being true to thine own self, and all that jazz. A funny musical comedy. Performances at 8 p.m., at Waterfront Playhouse, 407 Wall St.; visit website for show dates.

March 27, 2022

  • Impromptu Classical Concert – With an international reputation as one of the most popular brass ensembles today, the Canadian Brass has truly earned the distinction of ‘the world’s most famous brass group.’ All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free. 

April 2022

April 1 – 30, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

April 1 – 16, 2022

  • Waterfront Playhouse presents: Something Rotten – When a local soothsayer foretells that the future of theatre involves singing, dancing and acting at the same time, Nick and Nigel Bottom set out to write the world’s very first musical. But amidst the scandalous excitement of opening night, the Bottom Brothers realize that reaching the top means being true to thine own self, and all that jazz. A funny musical comedy. Performances at 8 p.m., at Waterfront Playhouse, 407 Wall St.; visit website for show dates.

April 2 – 3, 2022

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

April 8 – 9, 2022

  • The Magic of Spring – Key West Burlesque favorites and internationally known performers shimmy and shake their way through the most magical months of the year. Set to a score of classical music, these superstar performers will dazzle and delight in this flight of fancy. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

April 14 – 24, 2022

  • Conch Republic Independence Celebration – Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration, a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol checkpoint that stopped traffic at the top of the Florida Keys Overseas Highway, the only road in and out of the Keys.

April 21 – 24, 2022

  • Fringe Theater presents: Conch Relic the Musical – It’s the (mostly) true story of how the Conch Republic was born! Presented in celebration of the 40th Anniversary of the Conch Republic harrowing (and hilarious) tale. Performances start 7 p.m., Fringe Theater, 600 White St. Tickets, show times and dates online.

April 22, 2022

  • Luau Fundraiser for Reef Relief to Celebrate Earth Day – Enjoy a family friendly evening from 5-8 p.m., at Lagerheads Beach Bar, 0 Simonton St. The luau-themed event is to be filled with live music, games, a silent auction and raffle drawings, food and drink specials. Proceeds benefit Reef Relief, a nonprofit membership organization dedicated to improving and protecting the Keys’ coral reef ecosystem.

April 23, 2022

  • MOTE Oceanfest – Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment! From 10 a.m. to 4 p.m., enjoy an outdoor community celebration of the oceans at Truman Waterfront Park. A day of family activities, raffles, live music, shopping and environmental exhibits are to be featured. 

April 30, 2022

  • Papio Kinetic Sculpture Parade – A people-powered parade of colorful mobile structures rolls through Key West’s historic downtown intended to intrigue and inspire fans of creative recycling and ‘outsider’ art. The event is an artistic, creative way to raise awareness about the legacy and the importance of artists in the Florida Keys while using recycling as a key component.

May 2022

May 1 – 31, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

May 4 – 8, 2022

  • 26th 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.

May 13 – 14, 2022

  • Key West Harry Truman Foundation presents the 19th Annual Truman Legacy – The event will be officiated by Clifton Truman Daniel, grandson of 33rd U.S. President Harry S. Truman, in the company of fellow presidential descendants and other dignitaries. Friday, the entourage is to travel south along the Harry S. Truman Overseas Highway to Key West, where a welcome sunset cocktail reception is to take place aboard the celebrated U.S. Coast Guard Cutter Ingham at the Truman Waterfront, followed by a VIP gathering at the nearby Harry S. Truman Little White House. Saturday, May 14, the Key West Harry S. Truman Foundation’s signature event— the Truman Legacy Symposium — takes place, with presidential descendants and distinguished experts engaged in moderated topical discussions throughout the day, followed by a cocktail reception, elegant dinner and closing presentation.

June 2022

June 1 – 30, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

June 1-5, 2022

  • Fringe Theater presents: Lillian Baxter – Hollywood’s favorite Has-Been returns to Key West. Show tunes? You bet! Gay anthems? Why not! Fabulous costumes? As long as they’re within budget. Buckle in, glitter up, and spend A Fabulous Evening with Lillian Baxter. Performances start 7 p.m. at Fringe Theater, 600 White St. Tickets, show times and dates online.
  • Key West Pride Fest – 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, a street fair on famed Duval Street, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively “Rainbow Roast.”

June 15 – 19, 2022

  • I LOVE Stock Island Festival – This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experience in local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West.

June 17, 2022

  • Swim Around Key West – Embark on an adventurous swim – a 12.5 loop around the island with fantastic landscape views of Key West and swimming in the pristine waters. Compete in different categories of either a solo swimmer, a solo swimmers with fins, a solo swimmers using a mermaid tail or a monofin or gather your friends and compete in the relay category of a 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.

June 17 – 19, 2022

  • VFW Fishing Tournament – A family fun tournament, this event is to award over $50,000 in total cash and prizes, including $5,000 for the heaviest dolphin among other awards for individual anglers and other species. A Super Prize of either a new Toyota Corolla or $20k in cash (winner’s choice) has also been added for 2022. Captains and anglers can choose to fish either day of the two-day tournament. The 10th annual event is to celebrate the history of the tournament. All proceeds benefit disabled and needy veterans of Monroe County.

June 23 – 26, 2022

  • 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 2022 event.

June 30, 2022

  • Key Lime Festival – Enjoy fun-filled days and evenings of culinary and libation adventures, saluting the tiny fruit that inspired Key lime pie, the Florida Keys’ signature dessert. A festival highlight is the mouthwatering World Key Lime Pie Eating Championship. Participants with their hands behind their backs must dive in face-first to devour an entire 9-inch Key lime pie faster than their rivals. The event is free for spectators.

July 2022

July 1 – 31, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

July 1 – 4, 2022

  • Key Lime Festival – Enjoy fun-filled days and evenings of culinary and libation adventures, saluting the tiny fruit that inspired Key lime pie, the Florida Keys’ signature dessert. A festival highlight is the mouthwatering World Key Lime Pie Eating Championship. Participants with their hands behind their backs must dive in face-first to devour an entire 9-inch Key lime pie faster than their rivals. The event is free for spectators.

July 20 – 23, 2022

  • Stock Island Village Marina Key West Marlin Fishing Tournament – Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

July 23 -24, 2022

  • Hemingway 5K – 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.

August 2022

August 1 – 31, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

August 10 – 14, 2022

  • Key West Tropical Heat – Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s intriguing events range from pool parties to a sunset cruise to late-night gatherings at the island’s LGBTQ bars and nightclubs.

August 11 – 14, 2022

  • 26th Annual Key West Lobsterfest – Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.

September 2022

September 1 – 30, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

September 1 – 5, 2022

  • Key West Brewfest – Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, the lavish BrewFest Tasting Festival held Saturday on Key West’s South Beach and other enticements.

September 7 – 11, 2022

  • Key West WomenFest – The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination.

October 2022

October 1 – 31, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

October 21 – 30, 2022

  • Fantasy Fest – This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2022 theme is ‘Cult Classics and Cartoon Chaos.’

November 2022

November 1 – 30, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

December 2022

December 1 – 11, 2022

  • Key West Bicentennial Exhibit at the Customs House – Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. This major exhibition commemorates the 200th anniversary of the first permanent settlement of Key West in 1822 and will be on display in the Bryan and Bumpus Galleries through December 11, 2022. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

More About Key West

For more information about the fun side of Key West, things to do and see in our island city, go to our Key West Web Site. And, remember to check out our restaurant reviews as you surely must eat while down here! 

Island Genn – Key West Concierge