Calendar of Events

May 2023: Florida Keys Events

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Image for LIONFISH JEWELRY WORKSHOP Image for LIONFISH JEWELRY WORKSHOP Image for LIONFISH JEWELRY WORKSHOP Image for LIONFISH JEWELRY WORKSHOP
  • Sponsored Event
  • Apr 17, 2024 - Apr 17, 2024 Key Largo
  • LIONFISH JEWELRY WORKSHOP
  • Website REEF Environmental Education
  • 98300 Overseas Hwy Key Largo FL 33037
  • Amy Lee 305-852-0030 E-mail
  • REEF Lionfish Jewelry Workshops encourage a consumer market that promotes lionfish removal. Workshop instructors will provide a step-by-step tutorial on how to make lionfish jewelry, while also giving an informative presentation on the invasive species.
  • Call now!
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Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret Image for Christopher Peterson's Eyecons at Birdcage Cabaret
Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest Image for Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest
Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race
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Image for 42nd Annual Conch Republic Independence Celebration Image for 42nd Annual Conch Republic Independence Celebration Image for 42nd Annual Conch Republic Independence Celebration Image for 42nd Annual Conch Republic Independence Celebration
Image for Key West Art & Historical Society: Bahama Village - Relics of a Fading Community
  • Jan 13, 2023 - May 21, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Bahama Village - Relics of a Fading Community
  • Website
  • Bahama Village, in the westernmost portion of the city, was a neighborhood comprised of Black Bahamians and Black Cubans, Chinese, and other groups of color since the 1800s. In this exhibition, their history and stories are woven together through various events that shaped the Black and Indigenous cultures of Key West. “Bahama Village: Relics of a Fading Community" contains never-before-on-view objects that tell the inspiring history, culture and contributions of the island’s Black residents. Located at the society's Custom House Museum, 281 Front Street.
Image for Connections Project: Mural on Display in Key West
  • Apr 21, 2023 - May 5, 2023 Key West Arts & Culture
  • Connections Project: Mural on Display in Key West
  • Website
  • The Florida Keys Council of the Arts' Connections Project mural road show is underway, and this location is its final stop. This year's mosaic of 300 small paintings by Keys artists celebrates the Keys' unique history and bicentennial with the theme "Pirates to Pineapples in Paradise - 200 Years in Monroe County." The mural will be on display at the Florida Keys Council of the Arts headquarters at the historic Gato Building in Key West through May 5. 1100 Simonton Street.
Image for Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Apr 25, 2023 - Jul 31, 2023 Key West Arts & Culture
  • Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Website
  • Visitors can spot 20 imaginative creations by19 Florida Keys artists surrounded by the 15-acre habitat’s rare and indigenous plants and trees. Continuing through July 31, the Art in the Garden exhibition features large outdoor pieces crafted out of natural and recycled materials, installed among the property’s boardwalks, trails, and hidden glades. Find the garden at 5210 College Rd.
Image for Marathon Community Theatre: Scapino!
  • Apr 27, 2023 - May 13, 2023 Marathon Arts & Culture
  • Marathon Community Theatre: Scapino!
  • Website
  • An Italian menu – think minestrone, macaroni, ravioli - sung to a snappy tune opens SCAPINO!, a fun-filled adaptation of Moliere's ''Les Fourberies de Scapin." Set in contemporary Naples, Italy, the leading character, Scapino, devises a complex plot to help two pairs of lovers against parental opposition that, it turns out, does not even exist. Scapino, a fast-talking, quick-thinking scamp cleverly manipulates and cajoles everyone around him into doing what he intends them to do. Slap-stick, over-the-top hilarity ensues in this uniquely musical farce. Shows at 8 p.m. except for a Sunday matinee on May 7 at 3 p.m. Tickets $28, available online. 5101 Overseas Highway, oceanside.
Image for Key West Art & Historical Society: Out of the Box - The Art of the Cigar Label
  • Apr 28, 2023 - Oct 22, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Out of the Box - The Art of the Cigar Label
  • Website
  • The Key West Art & Historical Society presents “Out of the Box: The Art of the Cigar Label." The exhibition offers a compelling sampling and interpretation of 19th and early 20th century inner and outer cigar labels, showcasing more than 40 lithographs related to the Key West and Cuba cigar manufacturers. Included with museum general admission. Custom House Museum, 281 Front Street, 10 a.m. to 5 p.m. daily.
Image for 36th Annual Faro Blanco Invitational Tarpon Tournament
  • Apr 29, 2023 - May 6, 2023 Marathon Fishing
  • 36th Annual Faro Blanco Invitational Tarpon Tournament
  • Donna Vankirk E-mail Website
  • This unique team tournament in the heart of tarpon season, with two to four anglers per team/boat, allows anglers to fish three of the four nights with three different captains at three different bridges: Bahia Honda, Long Key and the world-famous Seven Mile Bridge. Proceeds from the charity tournament benefit Ronald McDonald House. Tournament activities take place at Faro Blanco Resort, 1996 Overseas Hwy. bayside.
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Image for Keys Concerts By Candlelight: May the 4th Be With You
  • May 4, 2023 Key West
  • Keys Concerts By Candlelight: May the 4th Be With You
  • Website
  • Keys Concerts by Candlelight presents “May the Fourth Be With You.” The unique concert experience features the music of Star Wars composer John Williams played by string quartet, and is led by the Southernmost Chamber Music Society member and violinist, Irie Monte. Hosted by comedian Steve Crane, the evening also features special guest appearances by the Sunshine State Stormtroopers. Doors open at 7, concert at 8 p.m. Tennessee Williams Theatre Cabaret, 5901 College Rd.
Image for Full Moon Yoga with Coral Restoration Foundation
  • May 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 7:30 to 8:30 p.m.on the deck at Postcard Inn, Islamorada, located at mile marker 84. $25 for non-guests of the resort.
Image for Tarponian Tournament
  • May 6, 2023 - May 10, 2023 Marathon Fishing
  • Tarponian Tournament
  • E-mail
  • Rules of this high-energy three-evening tournament mandate that each team fishes with a different captain each outing. Teams also rotate among the three major bridge channels in Marathon, so any potential “hot spots” are shared among all anglers. The tournament's opening and closing events take place at Florida Keys Steak & Lobster House, mile marker 48 bayside. Call 267-210-1952 for information.
Image for Shakedown on the Green -- Key West Island Market
  • May 6, 2023 Key West Arts & Culture
  • Shakedown on the Green -- Key West Island Market
  • Website
  • All are welcome the first Saturday of every month for Shakedown on the Green: Key West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.
Image for Key Largo Triathlon
  • May 7, 2023 Key Largo
  • Key Largo Triathlon
  • Website
  • This event features an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race. The swim takes place in the water off Cannon Beach at John Pennekamp Coral Reef State Park; the bike will be out and back on Overseas Highway and Card Sound Road. The run portions takes participants through a lovely, laid-back Florida Keys neighborhood. Motorists are advised that one northbound lane on U.S.1 from mile marker 102.5 (the entrance to Pennekamp) to mile marker 105 will be coned off for cyclists’ use between 6:30 and 9:30 a.m. Sunday. The other northbound lane will remain open to vehicular traffic. This is the first of two 2023 Key Largo Triathlons; the second one takes place August 20th.
Image for USS HIGBEE Community Concert with Howard Livingston
  • May 10, 2023 Key West Arts & Culture
  • USS HIGBEE Community Concert with Howard Livingston
  • Website
  • Join Navy League Key West Chapter as they host a Community Concert at Coffee Butler Amphitheater to welcome the crew of the USS Lenah Sutcliffe HIGBEE DDG123 to Key West. The concert features a lineup of acclaimed musicians including country artist Cliff Cody, American Idol singer-songwriter Kristen McNamara, and headliner Howard Livingston and the Mile Marker 24 Band. This is your opportunity to meet the HIGBEE crew before the ship is commissioned on May 13. Tickets $10 available online. Active military free, as are children under 12. Food and drinks available for purchase - no outside coolers. Doors open at 4 p.m. 21 Quay Road.
Image for Florida Keys History & Discovery Center Lecture: Dr. Corey Malcolm - Monroe 200, the Bicentennial
Image for I.Care Trash Derby
  • May 11, 2023 - May 13, 2023 Islamorada Environmental
  • I.Care Trash Derby
  • Website
  • To help reduce the amount of debris impacting the Keys, I.CARE is hosting its inaugural Trash Derby, sponsored by National Marine Sanctuary Foundation in support of clean seas. Register to team with a private dive operator or form your own team for either private boat or land-based divisions. The derby starts Thursday evening with a captains meeting at Bud & Mary's Marina, mile market 79.8. at 6:15 p.m. Trash collection takes place on land and sea from Key Largo to Big Pine Key all day Friday and half the day Saturday, followed by a family-friendly public festival at Founders Park (mile marker 87) on Saturday from 1 to 8 p.m. The festival is open to the public and includes food, music, games, an award ceremony, raffles, silent auction, environmentally-minded vendors, and local organizations working to improve our reefs.
Image for Fish I.D. Class with REEF
  • May 11, 2023 Key Largo Environmental
  • Fish I.D. Class with REEF
  • Learn about the fantastic fish that you can see while exploring the underwater portions of John Pennekamp Coral Reef State Park. Experts from REEF Environmental Education Foundation will hold a fish identification class at 11 a.m. inside the Visitor Center and Aquarium. Class is free with regular park entry. Mile marker 102 oceanside.
Image for Kona Kai Resort & Gallery: Artist Taylor Hale Reception
  • May 12, 2023 Key Largo Arts & Culture
  • Kona Kai Resort & Gallery: Artist Taylor Hale Reception
  • Website
  • Kona Kai Resort and Gallery invites you and your guests to attend a reception to shine a light on Key Largo artist Taylor Hale, known for his stunning artistic representations of the interactions between the sky, clouds and water in the Florida Keys. Hale's "A Colorful World" exhibit is currently on display at the resort's gallery. Enjoy hors d'oeuvres, refreshments and giveaways from 5 to 7 p.m., mile marker 97.8 bayside. Free to attend, RSVP requested (click website link).
Image for Wyland Repaints Murals at Crane Point Hammock
  • May 13, 2023 Marathon Arts & Culture
  • Wyland Repaints Murals at Crane Point Hammock
  • Website
  • Join world-renowned muralist and fine artist Wyland, along with local artist and educator Shannon P. Wiley, as they recreate murals at Crane Point Hammock. Special admission price of $10 for adults and children get in free. Free food and drinks will be available. 11 a.m. to 5 p.m. 5550 Overseas Highway.
Image for World Migratory Bird Day Programs at John Pennekamp State Park
Image for Commissioning of USS Lenah Sutcliffe Higbee (DDG 123)
  • May 13, 2023 Key West
  • Commissioning of USS Lenah Sutcliffe Higbee (DDG 123)
  • Website
  • The USS Lenah Sutcliff Higbee (DDG-123) is to be commissioned in Key West Harbor during a ceremony from 10 a.m. to noon on Saturday, May 13. Tickets to the commissioning event are no longer available, but the event will be live-streamed at the website link in this event listing. The ship is the Navy’s 36th Arleigh Burke class Guided-Missile Destroyer.
Image for Sunset Green: Na Ma Sit & Stay Yoga with Your Dog
  • May 14, 2023 Key West
  • Sunset Green: Na Ma Sit & Stay Yoga with Your Dog
  • The Keys Collection offers Na Ma Sit & Stay Yoga with Your Dog the second Sunday of each month at 9:30 am. at the Sunset Green event lawn in Key West. Admission is free but a $10 donation is suggested, with all proceeds donated to Florida Keys SPCA. Bring your dog and your own mat. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.
Image for Schooner Wharf Bar: Celebrating 26 Years of Magic!
  • May 15, 2023 Key West Arts & Culture
  • Schooner Wharf Bar: Celebrating 26 Years of Magic!
  • Schooner Wharf celebrates 26 years of their very own Comedy Magic Bar featuring magician Frank Everhart. Frank will be on hand with a collection of special guests with magic, stories, and songs up their sleeves to commemorate another wonderful year of legendary Magical entertainment. The magical fun and live music from The Newton's Toko Irie starts at 7 p.m. 202 William Street.
Image for History of Diving Museum: Immerse Yourself - Aquanauts to Astronauts
  • May 17, 2023 Islamorada Arts & Culture
  • History of Diving Museum: Immerse Yourself - Aquanauts to Astronauts
  • Website
  • With nearly 30 years at NASA supporting human space flight and over 43 days spent in space, Dr. Michael Gernhardt is a seasoned astronaut and expert engineer. He led the installation of the International Space Station's airlock and helped to pioneer breathing techniques to combat decompression sickness risk in space. In addition to his NASA career, Gernhardt was a professional deepsea oilfield diver and founder of Oceaneering Space Systems. The Museum will also be unveiling our new exhibit all about the fascinating connection between spaceflight and diving; Aquanauts to Astronauts! Exhibit Preview the new exhibit from 5:30-6:45 p.m.; Immerse Yourself presentation begins at 7 p.m. The museum is located at 82990 Overseas Highway bayside. Register online for either in-person or Zoom.
Image for Monroe County Bicentennial Celebration on Old Seven Mile Bridge
  • May 19, 2023 Marathon Arts & Culture
  • Monroe County Bicentennial Celebration on Old Seven Mile Bridge
  • A commemorative celebration of the bicentennial of the founding of Monroe County commences at 6 p.m. on the Old Seven Mile Bridge. Attractions are to include live music and dancing, local artists painting on-site, catered tidbits by the Marathon High School culinary class and a sunset toast with vodka distilled from breadfruit grown at the Lower Keys’ Grimal Grove. Past and present commissioners who helped guide Monroe County are to be honored during the evening. Attendees can park at Marathon’s 7 Mile Marina property, 1090 Overseas Highway, with trolley service to the bridge provided by the Pigeon Key Foundation.
Image for  Afro Roots Fest - Islamorada
  • May 19, 2023 - May 21, 2023 Islamorada Arts & Culture
  • Afro Roots Fest - Islamorada
  • Website
  • Three days of music and fun with an all-star lineup of Afro Roots artists takes place on the stage at Florida Keys Brewing Company, 81611 Old Highway. On Friday at 6 p.m., the Miami-based power quartet Electric Kif opens the three-day event. Saturday at 6 p.m., enjoy the Cuban stylings of Cortadito and the Afro-Brazilian rhythms of Miamibloco. On Sunday, jam to the Nag Champions, Johnny Dread and Group Barrio Abajo beginning at 2 p.m. All three shows take place in the beer garden and admission is free.
Image for History of Diving Museum: Aquanauts to Astronauts Exhibit
  • May 20, 2023 - Dec 31, 2023 Islamorada Arts & Culture
  • History of Diving Museum: Aquanauts to Astronauts Exhibit
  • Website
  • The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.
Image for Key West Business Guild: Pride Follies
  • May 20, 2023 Key West LGBTQ
  • Key West Business Guild: Pride Follies
  • Website
  • The Key West Business Guild presents Pride Follies, a fun evening of the best and worst of local Key West entertainment, hosted by the former Queen of Fantasy Fest, Destiny Montgomery. Doors open at 7 p.m. and show starts at 8 p.m. at Key West Theater, 512 Eaton Street. Tickets $15 to $35.
Image for Key West Art & Historical Society: Remember the USS Maine 125th Anniversary
  • May 20, 2023 Key West
  • Key West Art & Historical Society: Remember the USS Maine 125th Anniversary
  • Website
  • In this Distinguished Speaker Series program, KWAHS's Dr. Cori Convertito presents a commemorative program on the 125th anniversary of the sinking of the USS Maine in Havana Harbor. The cause of the massive explosion that killed most of her crew in 1828 has never been definitively resolved, but it was a precipitating cause of the Spanish-American War that began shortly thereafter. Her talk will reveal surprising results of her own research into the destruction of the USS Maine. The presentation takes place from 6 to 7 p.m. at Tropic Cinema, 416 Eaton St. Tickets $15.
Image for End of the Road 5k to Benefit Reef Relief
  • May 20, 2023 Key West Environmental
  • End of the Road 5k to Benefit Reef Relief
  • Website
  • Start & finish your 5k run or walk Saturday morning at 8 a.m. at Key West's most iconic landmark, Mile Marker 0, and follow a route through Truman Waterfront Park, past the Southernmost Point Buoy Marker, Key West Lighthouse, the Hemingway Home & other favorite visitor destinations. Each participant receives a Mile Marker 0 bottle opener medal and sticker, along with a free beer or Bloody Mary while enjoying live music at the post race party at Mary Ellen's Bar, 420 Appelrouth Lane. Proceeds benefit Reef Relief. Register online at RunSignUp. $39 for runners and walkers.
Image for Keys 100 Ultramarathon Races
  • May 20, 2023 - May 21, 2023 The Florida Keys
  • Keys 100 Ultramarathon Races
  • Website
  • The Keys 100 Ultramarathon is a point-to-point running race that takes place Saturday through Sunday from Key Largo to Key West. The 100 Mile Individual Ultra and Team Relay races begin at Divers Direct at mile marker 100 in Key Largo at 5:30 a.m. Saturday, and continue through Sunday to Key West. Other options include the 50 Mile Individual Ultra and Team Relay races from the Marathon Garden Club to Key West. A 50k Individual Ultra goes from the Lower Keys Chamber of Commerce in Big Pine Key to Key West. Each racer and team must provide their own support. All racers along the Florida Keys Overseas Heritage Trail and U.S. 1 during the overnight hours between Saturday and Sunday must wear reflective material and L-E-D lights. All races finish at Higgs Beach on the Atlantic Ocean in Key West. KEYS 100 promotes charitable fundraising for The Cancer Foundation of the Florida Keys.
Image for Key West Tropical Forest & Botanical Garden: Speaker Series
  • May 20, 2023 Key West Arts & Culture
  • Key West Tropical Forest & Botanical Garden: Speaker Series
  • Website
  • Speaker John Bratton, professor of anthropology at University of West Florida, presents a program titled "Hope and Resolve" about the garden's Cuban Chug exhibit, a collection of homemade migrant boats telling a visual story of desperate migrants seeking freedom. He will also discuss artifact conservation and maritime archaeology tracking the decades of relations between the Florida Keys and Cuba, and the Cubans who helped build Key West over the past 200 years. The talk begins at 1 p.m. at the garden, 5210 College Rd. $10 per person; free for garden members.
Image for History of Diving Museum: Opening of Aquanauts to Astronauts Exhibit with Special Guest
  • May 20, 2023 Islamorada Arts & Culture
  • History of Diving Museum: Opening of Aquanauts to Astronauts Exhibit with Special Guest
  • Website
  • Meet Sydney Hamilton, aerospace engineer, commercial astronaut, and mathematician. She will speak on her aquanaut experience during Marine Resources Development Foundation's Project Neptune 100 undersea meeting with Dr. Joe Dituri and how it relates to her astronaut training. Hamilton promotes future careers in the fields of Science, Technology, Engineering, and Math (STEM) for young women and underrepresented youth. 3:30 to 4:30 p.m., 82990 Overseas Highway. Adults $15; kids 6-11 $7; kids under 5 free. Active military and their families free as part of Blue Star Museums.
Image for Waterfront Playhouse: Arsenic & Old Lace
Image for 10th Annual Running of the Chihuahuas
  • May 21, 2023 Key West
  • 10th Annual Running of the Chihuahuas
  • Website
  • The smallest dogs with the biggest personalities are invited to enter the Chihuahua Races and win prizes along with bragging rights. Come to Rick’s Bar, 202 Duval Street on Sunday to see all the fun. Doors open at 1 p.m.; races start at 2 p.m. There are three categories of races -- Chihuahua pure and mixed breeds; senior pups; and all other small dogs. Preregister or show up on Sunday, $25 per dog. Spectators are free. Proceeds benefit Florida Keys SPCA.
Image for The Studios of Key West: Tangos to Tarantellas
  • May 21, 2023 Key West Arts & Culture
  • The Studios of Key West: Tangos to Tarantellas
  • Website
  • The Music Room presents Tangos to Tarantellas, an annual children’s welfare fundraiser showcasing the best classical musicians in the Keys. The twist? They’re all under 18 years old. Join musical director Robin Kaplan and her students for “a happy hour soiree” of classical dance music while enjoying refreshments and delectable bites. Helmerich Theater, tickets free at the door. Show starts at 5 p.m. 533 Eaton St., Key West.
Image for NAS Key West 27th Annual Dolphin Derby Fishing Tournament
  • May 26, 2023 - May 27, 2023 Key West Fishing
  • NAS Key West 27th Annual Dolphin Derby Fishing Tournament
  • Website
  • The tournament kicks off Friday evening with a captains meeting and final registration at 6 p.m. at Sunset Lounge at Sigsbee Park, 911 Sigsbee Rd. (open to military patrons). Fishing takes place Saturday beginning at sunrise. Open to anglers with a valid military issued ID card and their guests. Only one military ID card holder is required per boat. Cash prizes for 1st through 3rd place.
Image for Reggae Rehab Sunday Pool Party
  • May 28, 2023 Key West
  • Reggae Rehab Sunday Pool Party
  • Website
  • The Reggae Rehab pool party is open to the public from 1 to 4 p.m. Sunday at The Marker Key West Harbor Resort. Music from Reggae Lou, drink specials, delicious barbecue and more.
Image for Schooner Wharf Minimal Regatta
  • May 28, 2023 Key West
  • Schooner Wharf Minimal Regatta
  • Website
  • To compete in the wacky challenge, each six-member team must construct a craft out of the most minimal supplies: a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners and a trusty roll of duct tape. Regatta rules even forbid the use of caulking or adhesives, though epoxy paint is permitted. The "sink or swim" challenge is a Memorial Day Weekend tradition in the Florida Keys, with Sunday's fun scheduled to begin at 11 a.m. when teams can register at the Schooner Wharf Bar, 202 William St.
Image for Sunset Green: Live at Sunset Concert
  • May 30, 2023 Key West Arts & Culture
  • Sunset Green: Live at Sunset Concert
  • Website
  • The Keys Collection presents the "Live at Sunset" free monthly concert series on the last Tuesday of every month on the Sunset Green. The lawn opens at 6 p.m., with local talent performing from 7-10 p.m. Free entry and parking, food & drinks for purchase. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.
Image for Key West Art & Historical Society: Sushi in the Shoe
  • May 31, 2023 - Jun 30, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Sushi in the Shoe
  • Website
  • After 25 years of ‘dropping’ in a giant red glitter high-heeled shoe on New Year’s Eve, Key West’s legendary drag queen Sushi has hung up the heel. Since its inception, the Red Shoe Drop has become so famous that it’s often featured on national and international New Year’s Eve television programs including CNN. The commemorative exhibit includes the Gary Marion - also known as Sushi - collection of original gowns. Included with general admission. 281 Front Street.
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