Events in the Florida Keys

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Florida Keys for 2023

  • March 13 - October 31 Key West
  • Tuesday Evening GLOW Hours at Hugh's Rooftop
  • Website
  • The Studios of Key West's Hugh's Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Tuesday evenings from 6 to 8 p.m. through Oct. 31. Stay tuned for new hours beginning Nov. 7th after the time change when sunset will be earlier. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.

  • April 28 - October 22 Key West
  • 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.

  • July 14 - November 05 Key West
  • Key West Museum of Art & History: Don Pinder - Eyes on the Island
  • Website
  • The Key West Museum of Art & History's Custom House Museum's latest exhibition—Don Pinder: Eyes on the Island—is the first exhibition devoted exclusively to the work created by Key West Citizen photographer Don Pinder (1925-2003) during his long career in Key West—including many works never before published or shown. The show, on display through Nov. 5, includes more than 50 black-and-white and color photographs made during his 35-year career of documenting Key West history and culture. 10 a.m. to 5 p.m. daily, 281 Front St.

  • September 05 - October 15 Key West
  • Kids Keys Deals
  • Website
  • The Kids Keys Deals program is in effect through Oct. 15, offering free admission for one child age 12 and under with each paying adult at multiple Keys attractions and excursions in Key West, Marathon and Islamorada. Find the full list of attractions and links to coupons at KidsKeysDeals.com. The program is spearheaded by the Key West Attractions Association.

  • September 28 - September 28 Key Largo
  • John Pennekamp Coral Reef State Park: REEF Fish ID Talk
  • Website
  • Representatives from REEF Environmental Education Foundation present a Fish ID talk at 11 a.m. in the Visitor Center auditorium. Learn how to identify the many species of fish you can spot while snorkeling the reefs within John Pennekamp Coral Reef State Park. Free with regular park admission. Mile marker 102.5 oceanside.

  • September 29 - September 30 Islamorada
  • Conch Scramble Charity Golf Tournament
  • Website
  • Floating greens, golf boats and biodegradable fish food balls highlight the annual “par-tee” on the water. Fans of golf and boating can expect to have a “hole” lot of fun honing their swings and raising money for charity one shot at a time. Teams of four and a designated boat driver “caddy” make stops at nine Islamorada waterfront venues and come ashore to tee off. Each player has two shots at the floating holes using biodegradable golf balls that dissolve into fish food after 90 hours in the water. Both the Friday night kick-off party and Saturday tournament start take place at SD. Marine, 85500 Overseas Hwy. bayside.

  • September 29 - September 30 Marathon
  • Sword Fest
  • Website
  • Warriors on the Water and Two Conch Charters present the first annual Sword Fest tournament -- the ultimate swordfish battle. Cash payouts increase with the number of entry fees. With 30 boats, first place for heaviest swordfish pays $10,000. The tournament benefits Warriors on the Water, providing a positive outlet for veterans to enjoy nature and one-of-a-kind charter fishing experiences.

  • September 30 - September 30 Key West
  • Key West Paddle Classic
  • Website
  • The 26th annual Key West Paddle Classic is a 12-mile open-water distance race around Key West that is open to paddlers on stand-up and prone paddleboards, outrigger canoes, surf skis, kayaks, pedal-craft kayaks, row and dory boats. Events are headquartered at Higgs Beach, 1000 Atlantic Blvd. Start time for the race is 9 a.m. Paddlers have up to five hours to complete the race, with a lunch and awards celebration starting at 1 p.m.

  • September 30 - September 30 Key Largo
  • ReMARCable Tour de Keys
  • Website
  • The ReMARCable Tour de Keys is a 100-mile, one-day bicycle ride from Key Largo to Key West. Each rider is asked to raise $100 for the Monroe Association for ReMARCable Citizens, providing services for developmentally disabled adults. This event is not a race, but rather a charity "century" ride. The supported ride departs from the Holiday Inn at MM 100 in Key Largo at 7:00 a.m. with expected arrival at the Opal Key Resort in Key West at MM 0 at 3 p.m., with a party at the resort from 3 to 5 p.m. Pre- and post-ride hotel rooms and bicycle rentals are available to book for ride participants at special rates. Find more info and registration at marchouse.org

  • October 01 - October 01 Key West
  • Fort East Martello: Family Museum Day with Paper Kite-Making
  • Website
  • Families of all ages are invited to explore Fort East Martello for free from 11 am. to 2 p.m. There will be a guided art program in making paper kites inspired by the late Cuban American folk artist Mario Sanchez. The program is free and registration is not required. The Fort is located at 3501 S. Roosevelt Blvd.

  • October 01 - October 01 Marathon
  • Fall Harvest at Crane Point
  • Website
  • Celebrate Fall at Crane Point Hammock and Nature Trail Sunday afternoon from 4 to 7:30 p.m. with games, hayrides, a puppet show and fall treats. Adult beverages are to be available for purchase. $10 adults, $5 kids, age 3 and under free. 5550 Overseas Highway bayside.

  • October 05 - October 21 Marathon
  • Marathon Community Theatre: Richard O'Brien's Rocky Horror Show
  • Website
  • Let's do the Time Warp again! The cult classic interactive stage musical plays Thursday, Friday and Saturday nights through Oct. 21 with showtimes at 8 p.m.; along with one Sunday matinee on Oct. 15 at 3 p.m. This is an 18+ only show -- IDs will be required at the door. Audience participation scripts, props, feather boas and other costumes are to be available for attendees. Tickets $33. 5501 Overseas Highway oceanside.

  • October 08 - October 08 Big Pine Key
  • Sheriff's Animal Farm Open House
  • Website
  • Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, 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 at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex. The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month.

  • October 08 - October 11 Islamorada
  • Islamorada All-Tackle Bonefish and Permit Championship
  • Email Website
  • Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants.

  • October 10 - October 10 Key West
  • 24 North Hotel: Paint & Sip Night with Artist Lance Berry
  • Website
  • Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you'll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.


  • October 14 - October 14 Big Pine Key
  • Stock Island Cleanup & Community Day
  • Website
  • Everyone is welcome to enjoy music, food, crafts, a silent auction and booths showcasing environmentally-minded organizations in the Coastlove Education Village at Bernstein Park, 6751 5th St., Stock Island from 10 a.m. to 2 p.m. Group cleanup teams are invited to register in advance to spend the morning cleaning up locations around Stock Island, but everyone can enjoy the celebration in the park.

  • October 14 - October 14 Islamorada
  • Hispanic Heritage Month Celebration
  • Community Arts & Culture presents Cortadito, Miami's version of the famed Buena Vista Social Club, along with DJ Le Spam, for an evening of live and selected music in the Beer Garden at Florida Keys Brewing Co., located in the Morada Way Arts & Cultural District, mile marker 81.6 oceanside. All ages are welcome. No cover. The music begins at 6 p.m.

  • October 18 - October 27 Key West
  • Waterfront Playhouse: The Rocky Horror Show
  • Website
  • Opening October 18 and Playing for 10 performances only will be a revival of Richard O’Brien’s The Rocky Horror Show. This wacky, tacky musical comedy traditionally plays to standing room only houses at the Waterfront Playhouse. Doors at 7 p.m., show at 8 p.m. 407 Wall St. at Mallory Square

  • October 19 - October 19 Islamorada
  • Morada Way Third Thursday Art Walk
  • Website
  • 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.

  • October 19 - October 22 Key Largo
  • Reef Fest 2023: An Annual Celebration of Marine Conservation
  • Email Website
  • Ocean lovers attend REEF Fest each fall to celebrate their love of marine life and learn about the latest in conservation. Hosted by the REEF Environmental Education Foundation, the schedule is to include dive, snorkel and kayak trips, seminars with renowned ocean experts, social gatherings and more.

  • October 19 - October 19 Key West
  • Key West Theater: The Wailers
  • Website
  • The Wailers perform one night only on Thursday, Oct. 19. Doors open at 7; show at 8 p.m. Tickets $53 to $73. 512 Eaton St.

  • October 20 - October 21 Key West
  • Fantasy Fest: Goombay Festival
  • Website
  • This exuberant street party is the official kick-off for the annual Fantasy Fest costuming extravaganza with the action taking place noon to midnight both days. Find the main entertainment stage Key West's Bahama Village neighborhood at the corner of Petronia and Fort streets. Popular musicians offer nonstop tunes in genres ranging from gospel to calypso and vendors offer multicultural taste treats. Other festival highlights include Friday night's opening ceremonies and Saturday night’s Junkanoo Gawds Parade of costumed marchers and dancers, beginning at 6 p.m. and traveling through Key West’s historic downtown.  

  • October 20 - October 29 Key West
  • Key West Fantasy Fest
  • Website
  • “Uniforms & Unicorns—200 Years of Sailing into Fantasy” is the official theme for this year's Fantasy Fest, Key West’s annual multi-day costuming extravaganza. The theme reflects the Florida Keys' 2023 bicentennial. Revelers can explore an array of exciting events, including the world-famous Bud Light Fantasy Fest parade, the all-hands-on-deck Captain Morgan Masquerade March (aka “Locals Parade”), the exuberant Goombay Festival in the streets, Royal Coronation of the 2023 Fantasy Fest King, Queen, and royal court, plus concerts, theater productions, a “Heroes and Villains” 5K run/walk, the enchanting Key West Pet Masquerade, the 40th annual Headdress Ball pageant, and more.

  • October 20 - October 20 Key West
  • Fantasy Fest: Fun & Furryous Coronation
  • Website
  • Kick off Fantasy Fest at the Fun & "Furryous" Royal Coronation event to see who becomes the King and Queen of Fantasy Fest 2023! The King and Queen are each selected based on the most money raised to benefit the furry friends-in-need at Florida Keys SPCA. This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves. Each $100-per person ticket includes reserved seating, a 3-course plated dinner and two votes for the candidates of your choice. Reserved ticket sales close Oct. 15. General admission entry is FREE with open lawn space for self-seating. Cash bar for all. 6 p.m. doors, 7 p.m. show at Coffee Butler Amphitheater, 21 Quay Rd.

  • October 22 - October 22 Big Pine Key
  • Sheriff's Animal Farm Open House
  • Website
  • Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, 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 at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex. The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month.

  • October 22 - October 22 Key West
  • Fantasy Fest: Zombie Bike Ride
  • Website
  • The Rock & Roll costumed Halloween bike ride returns for another wild run on Sunday, Oct. 22. The Zombieland pre-ride party takes place at Fort East Martello from 2 to 6 p.m. with face and body painters, food vendors and a full bar. The ride, with thousands of costumed zombies, rolls out at 6 p.m. going down A-1-A then through downtown. The ride ends with a dance party at the Coffee Butler Amphitheater presented by Rams Head. Register online in advance for $10.

  • October 23 - October 23 Key West
  • Fantasy Fest: Heroes and Villains 5k Run/Walk & Hog Roast
  • Beth Moyes 305-747-8563 Email Website
  • Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at Southernmost Beach Café, 1405 Duval Street. The post-race party is the Official Fantasy Fest Monday Night Party. You can register online for both the race and the post-race Hog Roast and Party, or register separately for either event.


  • October 26 - October 26 Islamorada
  • History of Diving Museum: Treasure Treat Night
  • Website
  • Bring the entire family between 5:30 and 7:30 p.m. for a night of haunted exhibits, trick-or-treating through the museum, kids activities and a costume contest with prizes. The costume contest will be at 6:15 p.m. MM 82.9 bayside.

  • October 27 - October 27 Key Largo
  • Laura Quinn Wild Bird Sanctuary: Owl-O-Ween Trick or Screech
  • Website
  • Come for some spooky fall festival fun from 4 to 8 p.m. at the annual Owl-O-Ween celebration, including trick or treating, a dunk tank, face painting, a spooky photo-op area, cookie decorating, arts and crafts, a silent auction, a food truck and more. New this year -- the Conservation Village featuring local environmental organizations, each with spooky booths and interactive displays. MM 93.6 bayside.

  • October 28 - October 28 Islamorada
  • I.Care's Annual Underwater Critter Costume Party
  • Join the I.Care team at Florida Keys Brewing Co. at 6 p..m. for the Underwater Critter Costume Party. Come dressed as your best jellyfish, shark, sea turtle, brain coral or other underwater critter to win some fabulous prizes. There's also a raffle with more prizes. Proceeds go to help I.Care's work to replenish and maintain Islamorada-area reefs.

  • October 28 - October 28 Big Pine Key
  • Key West Tropical Forest & Botanical Garden: Screaming Green Halloween
  • Website
  • Kids should come in costume to hunt for tricks and treats along the garden pathways and other secret locations from 10 a.m. to 2 p.m. There's a costume contest for ages 5 and under at 12:15 p.m. and ages 6 to 12 at 1:15 p.m. There'll be arts, crafts, games and candy stations throughout the garden. Enjoy this fun and safe Halloween event and learn about how to use recycled items for costumes, decorations, crafts and more. The garden is located at 5210 College Rd.

  • October 28 - October 28 Key Largo
  • Amoray Dive Center: Underwater Pumpkin Carving Contest
  • 800-426-6729 Website
  • Divers become underwater artists as they turn pumpkins into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. This year's carving theme is Mermaids & Sailors. Prizes such as dive trips are awarded to the creator of the most creative jack-o-lantern. Entry fee is $115 per certified diver for the 12:30 p.m. dive trip. Space is limited, contact Amoray Dive Center at 800-426-6729 for reservations and information.

  • October 31 - October 31 Key West
  • Green Parrot 49th Annual Halloween Costume Party
  • Website
  • Party at the Parrot on Halloween night with a costume contest and music by the Empire Strikes Brass band, bringing jam, rock and R&B to the Parrot stage. Shows at 9 and 11 p.m. with the party carrying on until 12:30 a.m.

  • November 03 - November 03 Islamorada
  • Dia de los Muertos
  • Website
  • Remember loved ones who have passed during Islamorada's annual Dia de los Muertos celebration. Dress in bright colors, incorporate flowers into your costume and paint your face in the style of a traditional sugar skull. Begin at 5 p.m. with a kid-friendly sugar skull-making workshop at Florida Keys Brewing Company - mile marker 81.6 bayside. The workshop is free for youth under 21 and $5 for adults. It is followed by a Day of the Dead procession and traditional Afro-Mexican Fandango with special guest choreographers and music by the Ameyal Folkloric Ensemble.

  • November 05 - November 05 Big Pine Key
  • Sheriff's Animal Farm Open House
  • Website
  • Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, 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 at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex. The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month.

  • November 05 - November 05 Islamorada
  • BaconFest & Vendor Show
  • Website
  • Take a Sunday stroll on the Old Highway while enjoying the creative offerings of local and regional artists and vendors accompanied by lots of tasty bacon. Try a wide range of bacon-based treats and other dishes. Islamorada Moose Lodge, at MM 81 oceanside.

  • November 05 - November 12 Key West
  • Race World Offshore - Key West Offshore World Championship
  • Website
  • Racing teams and fans are to gather in Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event. Fan zone and entertainment at Truman Waterfront Park. Both general admission and VIP viewing options available.

  • November 09 - November 11 Islamorada
  • 11th Annual All-American Backcountry Fishing Tournament
  • Website
  • Each year anglers compete for honors in the fly, general tackle, and artificial divisions for snook, redfish, bonefish, tarpon and permit with tournament activities at the Cheeca Lodge & Spa. Each year several war heroes are invited to compete in honor of Veterans Day. Proceeds from the tournament benefit the Bonefish & Tarpon Trust, a nonprofit organization whose mission is to conserve and restore bonefish, tarpon and permit fisheries and habitats through research, stewardship, education and advocacy.

  • November 11 - November 11 Key West
  • Coffee Butler Amphitheater: Boats & Boots Concert
  • Website
  • Celebrate the biggest night of powerboat race week with Boats and Boots, a show with some of the hottest musicians in Key West, including Cliff Cody, the Key West Kings, the Wolf Love Band and Sam Carlson. General admission $25; VIP including dinner and private full-service bar $225. Showtime 5 to 11 p.m. 21 Quay Rd. at Truman Waterfront Park.

  • November 14 - November 14 Key West
  • 24 North Hotel: Paint & Sip Night with Artist Lance Berry
  • Website
  • Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you'll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.

  • November 15 - November 19 Key West
  • Key West Film Festival
  • Website
  • The Key West Film Festival is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. It strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. Named one of the “25 Coolest Film Festivals in the World” by Moviemaker Magazine. Films for the 2023 festival are still being submitted and evaluated. Stay tuned to find the full program of films, presentations and events online.

  • November 16 - November 18 Big Pine Key
  • Sugarloaf Showdown
  • Email Website
  • Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. Participants must use either spin or fly tackle to pursue the catch-and-release tournament’s target species of bonefish, permit and barracuda. A maximum of three fish of each species can be scored per team per day.

  • November 18 - November 18 Key Largo
  • Light Up Key Largo
  • Get in the holiday spirit Nov. 18 from 4 to 8 p.m. during Light Up Key Largo. This annual free event kicks off the holiday season with holiday shopping from local vendors, seasonal music, great food, photos with Santa, a wreath decorating contest and the lighting of the Key Largo holiday tree. Murray Nelson Government and Cultural Center, MM 102 bayside.

  • November 19 - November 19 Big Pine Key
  • Sheriff's Animal Farm Open House
  • Website
  • Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, 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 at 5525 College Rd. on Stock Island at the Sheriff's Office Headquarters complex. The family-friendly Sheriff's Animal Farm is open 1 - 3 p.m the second and fourth Sundays of the month.

  • November 22 - November 22 Key West
  • Lighting of the Bight: Key West Harbor Walk of Lights
  • Website
  • Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2023 Key West “Harbor Walk of Lights” with lights and creative displays reflecting the “Maritime History of Key West.” The Key West “Harbor Walk of Lights” stays lit nightly through New Year's Eve, stretching along the Key West Historic Seaport and Key West Bight Marina.

  • November 24 - November 24 Key West
  • Black Friday Shopping Extravaganza
  • Website
  • Find one of a kind gifts, unique handmade items, exquisite art and awesome people along with delicious culinary delights, yummy beverages and the views you won't find at any mall make this a can't-miss shopping event. Find this holiday shopping extravaganza featuring local vendors from the Key West Artisan and Waterfront Markets from 10 a.m. to 6 p.m. along Weech Way at Truman Waterfront Park.

  • November 25 - November 25 Big Pine Key
  • Island Art Festival
  • Website
  • Get your holiday shopping off to a musical start at the Lower Keys Chamber of Commerce's Island Art Festival. Find beautiful, one-of-a-kind, hand-crafted art items by many talented artisans from both near and far at reasonable price points, Enjoy great music and food throughout the event from 9 a.m. to 3 p.m. Located at the Chamber of Commerce grounds, MM 31 oceanside.

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