Events & Festivals


Dec 31, 2019 – Jan 1, 2020
New Year’s Eve Shoe Drop Celebration
The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

Dec 31, 2019
Schooner Wharf “Rigging” in the New Year
The popular waterfront watering hole once again will present its nautical New Year’s Eve tradition with “The Lowering of the Pirate Wench” from the towering mast of the tall ship America 2.0 docked in front of the bar in the Key West Bight. Everyone’s favorite pirate wench and co-owner of Schooner Wharf Bar, Evalena Worthington, will descend dramatically against large, illuminated countdown numbers. The stroke of midnight will signal the start of 2020 with cannon fire and the jubilant sound of horns and noisemakers from the crowd against a backdrop of the ship’s crew dressed as pirates.

Jan 1, 2020
Polar Paddle Plunge
Plunge into a new decade! Blue Moon Kayak is honoring the tradition of cleansing the past year away and getting a refreshing start to 2020. What a better way than cleaning with purifying natural sea salt in the Gulf of Mexico. Start the year off right! $50 per person, departs from Sunset Marina, 5555 College Rd.

Jan 3, 2020 – Apr 3, 2020
First Fridays on Fleming
Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First Fridays on Fleming showcase boutiques, galleries and eateries in the 500 block of Fleming Street with events such as jewelry trunk shows, art openings, book signings, tastings and libations. Participants include The Roost Bar and Liquor Store, La Rubia Authentic Panama Hats, Key West Island Books, Key West Local Luxe Jewelry, Amanda Johnson Fine Art, Sea Store Antiques, Assortments Menswear, Island Antiques, Duck & Dolphin Antiques, Clemente’s Trolley Pizzaria, La Petite Grignote French Bakery, Thirsty Mermaid Seafood and Jean Pierre Klifa Resort Wear. First Fridays are scheduled Jan. 3, Feb. 7, March 6 and April 3.

Jan 9, 2020 – Jan 12, 2020
Pole Vault in Paradise
Presented by Key West Track and Field Club, Pole Vault in Paradise is an all-comers pole vault competition with events spread across four days. Youth, College, Elite and Masters divisions. Pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Saturday’s activities are free admission. Enjoy food and drink vendors, and world class competition beginning at 9 a.m. at the beautiful Truman Waterfront Park. Bring your lawn chairs.

Jan 12, 2020
Rams Head Promotions presents: Grace Potter
An acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. Sunset Green Event Lawn is a multipurpose event space located between 24 North Hotel and The Gates Hotel. Tickets can be purchased online or visiting the Key West Theater box office at 512 Eaton St.

Jan 15, 2020 – Jan 20, 2020
22nd 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 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. Named as one of the United States’ leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by

Jan 16, 2020 – Jan 19, 2020
Key West Kingfish Mayhem
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.

Jan 18, 2020 – Jan 19, 2020
15th Annual Florida Keys Seafood Festival
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.

Jan 21, 2020 – Jan 27, 2020
29th Annual Kelly McGillis Classic International Flag Football Championship
Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.

Jan 23, 2020
Rat Pack Together Again at Key West Theater
A toast to the original Rat Pack, ‘Rat Pack Together Again,’ takes you on a musical journey featuring the greatest hits from the legendary Frank Sinatra, Dean Martin, and Sammy Davis Jr. This production will treat you to Sinatra classics including, ‘Come Fly With Me,’ ‘My Way,’ and ‘New York…’ Dino with great songs like, ‘Everybody Loves Somebody,’ and ‘That’s Amore!’ …and from the dynamic Sammy Davis Jr., ‘Mr. Bojangles’ and Candy Man.’ After watching these performers, you will leave the show feeling as though The Rat Pack is still going strong after all these years. Show Starts 8 p.m., Key West Theater, 512 Eaton St. Tickets available online.

Jan 26, 2020
26th Annual Key West Master Chefs Classic
Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.

Jan 26, 2020 – Feb 2, 2020
Key West Food & Wine Festival
Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.

Jan 28, 2020 – Feb 1, 2020
Third Annual Mile 0 Fest Key West
Mile 0 Fest Key West is a “must see” music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

Jan 30, 2020 – Feb 1, 2020
Cuda Bowl
Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

Feb 14, 2020
Tennessee Williams Theater presents: Mandy Patinkin
Mandy Patinkin in Concert: DIARIES, presents the acclaimed actor / singer / storyteller in his most electrifying role: concert performer. “Mandy Patinkin is in the business of showstopping,” raves The New Yorker, and that’s exactly what he does in this powerful, passionate evening of song. DIARIES is a marriage of many of Mandy’s favorite Broadway and classic American tunes, along with selections from his newest recordings on Nonesuch Records, Mandy Patinkin Diary January 2018 and Mandy Patinkin Diary April/May 2018. From Randy Newman to Stephen Sondheim, from Harry Chapin to Rufus Wainwright, Mandy Patinkin takes you on a dazzling musical journey you’ll never forget. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd

Feb 17, 2020
Willie Nelson At Key West Amphitheater
With a six-decade career and 200 plus albums, this iconic Texan is the creative genius behind the historic recordings of Crazy, Red Headed Stranger, and Stardust. Willie Nelson has earned every conceivable award as a musician and amassed reputable credentials as an author, actor, and activist. He continues to thrive as a relevant and progressive musical and cultural force. Doors open 5:30 p.m., show starts 7 p.m. Tickets available online starting Friday, Nov. 22.

Feb 21, 2020
Rams Head Production presents: Kool & the Gang, with The Village People
From Nairobi to Newark, Kool & the Gang has performed continuously longer than any R&B group in history and their bulletproof funk and jazzy arrangements have also made them the most sampled R&B band of all time. Village People is considered the greatest disco group in the world, their music part of the international songbook. Victor Willis who was Village People before Village People even existed returned with a fresh re-boot of the group. Doors open 5:30 p.m. at Key West Amphitheater, 21 Quay Rd. showtime 7 p.m. Tickets on sale Aug. 23, available online.

Mar 5, 2020 – Mar 28, 2020
Waterfront Playhouse presents: Priscilla Queen of the Desert, the Musical
Based on the smash-hit movie; a heartwarming, uplifting adventure of three friends, Tick, Bernadette and Adam, played by Christopher Peterson, Dave Bootle and Connor Cook, searching for love and friendship and end up finding more than they ever could have ever dreamed of. With a hit parade of dance floor favorites including “It’s Raining Men,” “I Will Survive,” “Hot Stuff,” “Boogie Wonderland,” “Go West,” “Girls Just Wanna Have Fun,” and “I Love The Nightlife,” this wildly fresh and funny musical is a journey to the heart of FABULOUS! Showtimes 8 p.m.

Mar 7, 2020
58th Annual Conch Shell Blowing Contest
An island tradition for over 50 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 8, 2020
George Thorogood & the Destroyers
Make your way to Sunset Green Event Lawn for what is sure to be an epic night of live music with a rock legend! Enjoy a good old-fashioned lunch-bucket rock & roll show that includes signature hits like “Get A Haircut”, “I Drink Alone”, “One Bourbon, One Scotch, One Beer”, “Move It On Over”, “Who Do You Love” and the definitive badass anthem “Bad To The Bone,” among others. Sunset Green is situated between 24 North Hotel and The Gates Hotel. Gates open 5:30 p.m., show starts 7 p.m.

Mar 9, 2020 – Mar 12, 2020
March Merkin Invitational Permit Tournament
A charity flats-and-fly-only tournament with a twist – in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Yacht Harbor Marina on Stock Island.

Mar 28, 2020
Mote Marine Laboratory’s Annual Ocean Fest: A Community Celebration
From 10 a.m. – 6 p.m. at NOAA’s Florida Keys Eco-Discovery Center and Truman Waterfront. Underwater and outdoor enthusiasts, eco-travelers and families are encouraged to celebrate the marine environment as we explore conservation exhibits, view and purchase wares from local artists and vendors, experience touch tanks, and listen to live music all while raising funds for coral reef research and restoration.