Events in the Florida Keys

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

Events in Florida Keys for 2022

  • February 05 - January 07 Key West
  • Market on the Green
  • Website
  • Held the first Saturday of every month from 10 a.m.- 2 p.m., visitors and residents are invited to browse and shop amazing local artisans. The monthly market is located at the Sunset Green Event Lawn, at Key West’s 24 North Hotel.

  • March 31 - December 11 Key West
  • Key West Bicentennial Exhibit at The Custom House Museum
  • Website
  • Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. 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 25 - December 31 Islamorada
  • History of Diving Museum: Sponge Hunters
  • Website
  • Sponge Hunters: Key West Hookers, Bahamian Free Divers, and the Hard Hat Divers of Tarpon Springs will be on display May 19 through December 31, 2022. Learn about the sea sponge and its uses, from the long history of fishers to modern fisheries, current restoration efforts and the various dive methods used in seeking out this treasured aquatic animal. Mile marker 83 bayside, Islamorada. 10 a.m. - 5 p.m. daily except Thanksgiving, Christmas Day, and New Year’s Day.

  • November 23 - December 31 Key West
  • 2022 Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.


  • December 01 - January 22 Islamorada
  • Florida Keys Gold Cup Sailfish Championship
  • 305-852-2102 Email Website
  • Anglers are to pursue sailfish, the most plentiful billfish in the waters off the Keys, in a series of three competitions - the Islamorada Sailfish Tournament, Dec. 1-4, 2022; the Islamorada Fishing Club Captain's Cup Sailfish Tournament, Jan.17-18, 2023; and the Cheeca Lodge Presidential Sailfish Tournament Jan. 20-22, 2023 - after which the Gold Cup is awarded.

  • December 01 - January 01 Key West
  • Key West Holiday Fest
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

  • December 01 - December 04 Key West
  • COAST is CLEAR Music and Arts Festival
  • Website
  • Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main events are concerts at the festival grounds Saturday and Sunday. Two-day General Admission, VIP tickets and detailed information is available online. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.

  • December 01 - December 04 Islamorada
  • Islamorada Sailfish Tournament
  • Website
  • The Florida Keys Gold Cup Sailfish Championship triple-crown series is to open with the Islamorada Sailfish Tournament, a primary fundraiser for the Islamorada Charter Boat Association Thursday, Dec. 1 through Sunday, Dec. 4. Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83.

  • December 01 - December 03 Key West
  • Tropic Cinema: Neil Young
  • Website
  • "Neil Young: Harvest Time" is a fan piece that has never before been seen. Performance and rehearsal content is intertwined into creative storytelling and includes most of the tracks from the iconic 1972 album Harvest. Created in 1971, this docu-film takes us on a journey to Neil Young’s farm in Northern California for the ‘Harvest Barn’ sessions, to London for an iconic performance with the London Symphony Orchestra and to Nashville where Young worked on various tracks of this signature album. Screenings at 7:30 p.m. on Dec. 1 and Dec. 3. 416 Eaton Street.

  • December 02 - December 03 Key West
  • Revival Roadshow at Sunset Pier
  • Website
  • The Revival is a gathering of Nashville’s biggest hit writers sharing their songs, considered some of the best music in Nashville. In 2022 the Revival took the pew on the road with some of Nashville's greatest songwriters. The tour ends in Key West with two days of live music at Ocean Key Resort's Sunset Pier, Dec 2-3, with performances of 31 Number 1 hit songs by the songwriters that created them. Tickets available online. Single day pass $40; weekend pass $66.50.

  • December 03 - December 03 Islamorada
  • Florida Keys History & Discovery Special Event: Redbone Gallery Show
  • Website
  • The museum opens for a special event Saturday, Dec. 3 to support the Redbone Gallery's mission to "Catch the Cure" for cystic fibrosis. Redbone is selling the remainder of its gallery originals and giclee artwork from some of the foremost saltwater angling artists including Millard Wells, Kathleen Denis, Pasta Pantaleo, Tim Borski, Don Ray, and many more. 82100 Overseas Highway, from 6 to 8 p.m. on the grounds of the Islander Resort. In addition to the special event, all artwork, Redbone holiday ornaments, books and more are for sale at the museum through January 8. Consider your holiday shopping here at the museum and help "Catch the Cure" for cystic fibrosis.

  • December 03 - December 03 Key West
  • Surfrider Florida Keys Key West Beach Cleanup at Smathers Beach
  • Website
  • Join members of Surfrider's Florida Keys Chapter and others for a cleanup of Smathers Beach from 9 to 11 a.m. Free, limited edition t-shirts will be given to the first 25 attendees. Gloves, buckets, grabbers, cold water and good times provided. Please wear close-toed shoes and bring a reusable water bottle to fill. Kids are welcome.

  • December 03 - December 03 Marathon
  • Faro Blanco Resort Lighting of the Lighthouse
  • Website
  • Celebrate the holiday season at Faro Blanco Resort in Marathon for their annual Lighting of the Lighthouse event from 4 until 9 p.m. Enjoy food, drinks, music by Abstract Radio and Santa and Mrs. Claus arriving by train. Mile marker 48.5.

  • December 03 - December 03 Key West
  • Friends of the Key West Library Book Sale
  • Website
  • The Friends of the Key West Library will hold the December Book Sale outside in the library's Palm Garden on Saturday, Dec. 3, from 10am-1pm. Most books are priced at $1, although for this sale, there is a nice selection of art books suitable for holiday gifts priced in the $10-20 range. 700 Fleming Street.

  • December 03 - December 03 Key West
  • Everglades National Park 75th Anniversary Celebration
  • Website
  • Everglades National Park was dedicated Dec. 6, 1947. On Saturday, Dec. 3, as part of a year of celebration of the park's 75th anniversary, the public is invited to attend a re-dedication ceremony between 1:30 and 5 p.m. at the Flamingo portion of the park, which is located inside the park's main entrance. There will be live music, historical reenactors, the re-dedication of Flamingo's Guy Bradley Visitor Center including a reception with refreshments and cash bar, and guided tours of the new Flamingo Lodge facilities, which are under construction. The Flamingo portion of the national park is located in Monroe County at the top of the Upper Keys.

  • December 03 - December 04 Marathon
  • Bethlehem in the Keys
  • Bethlehem in the Keys, a Christmas-themed dinner theater performance, will be performed at Marathon Community Church on Friday, Dec. 3rd. Doors open at 6 p.m., show starts at 7. There will be a matinee on Saturday, Dec. 4 with doors open at 2 p.m. and performance at 3. Tickets are $50 for dinner and $30 for the matinee. Call 305-481-7233 to reserve tickets.

  • December 03 - December 03 Key West
  • Pet Pictures with the Grinch
  • Website
  • Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street from 11 a.m. to 2 p.m. for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary.

  • December 03 - December 03 Big Pine Key
  • Grand Opening: Plant a Million Corals
  • Website
  • Plant a Million Corals invites you to a Grand Opening and Coral Cutting celebration Sat. Dec. 3 from 3 to 5 p.m. Take a tour of the new Restoration Park, see demonstrations of the coral restoration operation and meet the team. Founder Dave Vaughn will be signing copies of his new book, “The Secret Life of Corals: Sex, War, and Rocks that Don’t Roll.” The event is free to attend at 23801 Overseas Hwy, Summerland Key.

  • December 03 - December 03 Key West
  • City of Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park. Seeing Santa is a highlight for kids.

  • December 04 - December 04 Key West
  • Eaton Street Christmas Stroll
  • Website
  • Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts and the Key West United Methodist Church unite for the annual Eaton Street Christmas Stroll. Each venue hosts a short Christmas-themed performance with caroling as you walk from presentation to presentation. At The Studios of Key West, sip Christmas cocktails with a view and get an extra chance to catch the Members Show for some holiday shopping. The Stroll begins at 4 p.m. at St. Paul's.

  • December 04 - December 04 Key West
  • Key West Artisan Market: 10th Anniversary Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and breathtaking ocean views as we celebrate 10 years of the Key West Artisan Market with old and new friends. Also supporting Friends of the Aids Memorial which is located across the street at White & Atlantic at the entrance to the Edward B. Knight Pier. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

  • December 04 - December 04 Key Largo
  • Key Largo Shop, Jingle & Mingle
  • Shop for gifts from local vendors and enjoy some holiday cheer from 11 a.m. to 4 p.m. at this annual event at the Cirque Salon Studios at Tradewinds Plaza, mile marker 101 oceanside in Key Largo.

  • December 04 - December 04 Key West
  • Key West Woman's Club Holiday Open House
  • Website
  • Members have decked the halls of the historic mansion at 319 Duval Street for all to enjoy at Sunday's open house from 4 to 6 p.m. Enjoy appetizers, desserts and Amsterdam eggnog, and an appearance by Santa. Music from the Bahama Village Children's Choir and the Key West Community Orchestra. Official tree lighting by Mayor Teri Johnston. Donations of new, unwrapped clothes for students ages K-12 are appreciated.

  • December 04 - December 04 Key West
  • Pet Pictures with Santa
  • Website
  • Pack up Fifi and Fido and delight in Pet Pictures with Santa Sunday, Dec. 4 from 6 to 8 p.m. at the Christmas tree at the foot of William Street at the Key West Bight Marina. Proceeds benefit the Boys & Girls Club of the Keys.

  • December 07 - December 07 Key West
  • Friends of the Key West Library 50th Anniversary Celebration
  • Website
  • The Friends of the Key West Library kick off their 50th Anniversary celebration with an event at the library, located at 700 Fleming Street, from 4 to 6 p.m. There will be a short program, tours and refreshments in the library lounge.

  • December 07 - December 07 Islamorada
  • Full Moon Yoga
  • Website
  • Meditate and relax under the glow of the full moon and the twinkling stars at Postcard Inn, Islamorada from 6 to 7:30 p.m. Zenfully Aware Yoga, the Islamorada Resort Collection, and Coral Restoration Foundation™ are bringing you on an adventure – a yoga practice centered around how the full moon affects the coral reefs and the spawning and growth of the reefs as the lungs of the earth. 50% of all proceeds will be donated to Coral Restoration Foundation™. Non-guests may register online for $25; free for resort guests.

  • December 07 - December 07 Islamorada
  • Smuggling in the Florida Keys: Part IV
  • Website
  • The Florida Keys History & Discovery Center lecture series "Smuggling in the Florida Keys" Part IV, the final panel in the series, consists of State Prosecutor Allison DeFoor speaking on what it took to convict those who were involved in Smuggling in the Florida Keys, along with Richard "Dickie" Lynn, who served over 30 years in federal custody and was granted compassionate release by a federal judge in 2021. Doors open at 5 p.m. to explore the museum with light appetizers and cash bar available. Presentation 6-7:30 p.m. Advance registration required, $10. Located on the Islander Resort property, mile marker 82.

  • December 07 - December 11 Key West
  • Nutcracker Key West
  • Website
  • A unique subtropical version of the classic holiday ballet "The Nutcracker" awaits Keys visitors, flavored with characters and settings that depict Key West's colorful history, vibrant coral reef environment and even free-roaming local roosters. Blending professional dancers and local talents, the production features exquisite costumes and sets inspired by island lore. Performances take place at the Tennessee Williams Theatre at 5901 College Road.

  • December 09 - December 09 Marathon
  • Tropical Holiday Fun Fest
  • Website
  • Come out to Marathon Community Park for a night of Holiday fun. Enjoy live holiday music, entertainment by the Marathon Community Theater dancers and the Prodigy Dancers, face painting, bounce houses, cotton candy and other treats, and see Santa! Mile marker 49 oceanside.

  • December 09 - December 09 Islamorada
  • "Ocean to Everglades: Stories of the Sea" Film & Discussion
  • Website
  • Join Surfrider Florida Keys and Sereia Films on Friday, December 9th for "Ocean to Everglades: Stories of the Sea" - a night of film screenings and discussion on sustainable seafood in Florida and the ocean livelihoods that depend on it. Happy hour will be from 6:30 to 7 p.m., film screening from 7 to 8:15, followed by a panel discussion on sustainable seafood in Florida and the Keys. Mile marker 80.5 bayside. Online advance registration required.

  • December 09 - December 09 Key West
  • Holiday Historic Inn Tour
  • Website
  • During this enchanted Friday evening, visit and tour four beautifully decorated island locales: Key West Butterfly & Nature Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation between 6 and 8 p.m. Explore the unique architecture and history at each stop while enjoying sweet and savory holiday treats and libation samplings. Limited trolley transportation will be provided between properties, but participants are encouraged to bike, walk or use their own transportation. Purchase tickets online, then pick up tickets after 5 p.m. on Dec. 9 at Butterfly & Nature Conservatory.

  • December 09 - December 09 Key West
  • Holiday Lighted Boat Parade of Stock Island
  • The Rotary Club of Key West and the Perry Hotel & Marina invite you to enjoy a boatload of maritime merriment as a colorful fleet decked in holiday lights parades by the Perry Hotel lawn. This will be a family-fun evening to that also includes entertainment, photos with Santa and more. 7001 Shrimp Road.

  • December 10 - December 10 Marathon
  • Boot Key Harbor Christmas Boat Parade
  • Website
  • The parade will start in from the west side of the harbor (7 mile bridge side) at 6 p.m. and slowly meander east past Lazy Days, Marathon Marina, Pancho's and Burdines, then down to Dockside past the condo's and turn around in the basin at Yacht Haven Marina. Parade awards and party will be at Dockside café following the parade.,

  • December 10 - December 10 Islamorada
  • Pops in the Park: Keys Community Concert Band Holiday Concert
  • Website
  • “Joy to the World” with a free, outdoor concert from Keys Community Concert Band at Founders Park (mm 87, bayside), 4 to 5 p.m. in Islamorada. Bring a blanket or lawn chair and pack a picnic basket for a family-friendly concert of holiday music, sing-along and a visit from Santa. Special guests: Burton Handbell Ringers.

  • December 10 - December 10 Key West
  • Ninth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park in Key West from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2022 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.

  • December 10 - December 11 Islamorada
  • Eighth Annual Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile
  • Website
  • Whether bucket-list runners or newbies, participants of all ages and skill levels are invited to register for this annual subtropical footrace. In the Beach N’ Beer Mile, runners must consume four beers over a 1-mile course in Islamorada. Organizers said the best time to beat for the event is seven minutes. Participants in the Rumrunner 5k receive a finisher medal and a free Rumrunner from the World Famous Tiki Bar. Cash prizes are to be awarded the top three male and female half-marathon finishers, as well as awards for the top three finishers of the 10k. Events start and end at Postcard Inn, mile marker 84.

  • December 10 - December 10 Key Largo
  • Key Largo Boat Parade - A Cartoon Christmas
  • Key Largo's annual holiday boat parade on Blackwater Sound lights up the night beginning at 7:30 p.m. Saturday, Dec. 10 with boats decked out for the holidays. Watch from waterfront locations including various restaurants and nightspots such as Caribbean Club and Jimmy Johnson's Big Chill - both at MM 104 bayside - as well as the public Rowell's Waterfront Park.

  • December 10 - December 10 Key West
  • Schooner Wharf Annual Key West Lighted Boat Parade
  • Website
  • A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Music begins at 6 p.m., parade starts at 8.


  • December 11 - December 11 Key West
  • Key West Triathlon
  • Website
  • The Key West Triathlon challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike and sprint duathlon competitions are featured. Higgs Memorial Beach Park, 1000 Atlantic Boulevard, Key West.

  • December 15 - December 15 Islamorada
  • Morada Way Third Thursday Art Walk in Islamorada
  • Website
  • Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music, 6-9 p.m. Admission is free to this outdoor pre-holiday celebration. Art Walk is held the third Thursday of each month.

  • December 16 - December 17 Key West
  • The 12 Days of Christmas: Burlesque Show Spectacular
  • Website
  • This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members. Doors open at 7 p.m., show at 8. Tickets $45 to $100, available online. Key West Theater, 512 Eaton Street.

  • December 16 - December 16 Key West
  • Holiday Historic Inn Tour
  • Website
  • Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8 p.m. Purchase tickets online, then pick them up after 5 p.m. on the night of the tour at the first property, Hemingway’s Library at Papa's Pilar Distillery. Participants will need to walk, bike or use their own transportation between locations.

  • December 16 - December 18 Islamorada
  • Islamorada Junior Sailfish Tournament
  • Tammy Gurgiolo 305-240-9337 Email
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964. Hosted at the Coconut Palm Inn, mile marker 92 bayside.

  • December 17 - December 17 Key West
  • 14th Annual 5K Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join! Starts and ends at Southernmost Beach Café, 1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 16 from 5-7 p.m. at the Café. Runners and walkers of all ages and abilities are welcome to participate. Registrants receive a free t-shirt; prizes for most festive and unusual PJ’s. Presented by nonprofit group, A Positive Step for Monroe County.

  • December 17 - December 17 Marathon
  • Marathon Latin Festival
  • Website
  • Hosted by Baby Lores, one of the pioneers in the Cuban music scene, this all-day music fest is from 10 a.m. to 10 p.m. at Marathon Community Park at mile marker 49. Enjoy family-free entertainment and activities during the day and a grand fiesta of music from 5 to 10 p.m. by several dozen top Latin musical entertainers. Partial proceeds from this event are to support the Somos Esperanza foundation, that helps provide for sick children, providing necessary medical attention and equipment. Advance purchase tickets are online for $50 per adult, $25 for ages 13-21, with kids 12 and under free. VIP tickets also available. Tickets are also to be on sale the day of the event.

  • December 17 - December 17 Marathon
  • Winter Wonderland at Crane Point
  • Website
  • There's a forecast for snow in the tropical forest at Crane Point Hammock Museum & Nature Trail during Winter Wonderland from 4:30 to 7:30 p.m. Bring the entire family to encounter reindeer ponies, holiday decorations, Santa and snow! Enjoy Santa stew, the chocolate fountain, roasted chestnuts and adult beverages for purchase. 5550 Overseas Highway, Marathon.

  • December 17 - December 17 Key West
  • Key West Botanical Garden Native Plant Sale
  • Website
  • The plant nursery offers native Florida trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month. Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

  • December 18 - December 18 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and splendid ocean views as we offer everything you need to cross off your holiday shopping list. Supporting the Key West Shop Mom & Pop and #shoplocalkey west movement to keep our resources right here in our community. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

  • December 18 - December 18 Key West
  • Key West Lighting of the Menorah
  • Website
  • The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.18 from 5 to 6 p.m. 1320 Truman Avenue.

  • December 18 - December 18 Key West
  • Snowy Sunday Children's Concert at Key West Botanical Garden
  • Website
  • Snowy Sunday, the Key West Tropical Forest & Botanical Garden's annual winter concert, features local classical guitarist, Mateo Jampol performing songs especially for children. The event opens at 1 p.m. and Jampol's concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday activities. Tickets $5 per child at the door with a maximum cost of $10 per family.

  • December 28 - December 29 Key West
  • Old Island Restoration Foundation's Home Tours "Holiday Style"
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 63rd series of tours features self-guided tours of homes festively dressed for the holidays on Dec. 28 and 29. After the holidays, home tour dates are Jan. 13-14, Feb. 17-18, and March 17-18. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • December 31 - December 31 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2023 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

  • December 31 - December 31 Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

  • December 31 - December 31 Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • 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.

  • December 31 - December 31 Islamorada
  • New Year's Eve Party at Postcard Inn
  • Ring in the new year island-style at Postcard Inn's New Year's Eve party at Raw Bar on the water with tropical cocktails, the Touch of the Keys seafood buffet, a live band from 7 to 10 p.m., a DJ from 10 p.m. until the ball drops, and a complimentary midnight champagne toast. $85 per person, $35 for children 12 and under.


  • January 01 - January 01 Islamorada
  • New Year's Day Manatee Plunge at Postcard Inn's Beach
  • Website
  • For a refreshing start to 2023 on New Year's Day, put on a crazy outfit and jump in the ocean for the second annual Manatee Plunge at the Tiki Bar at Holiday Isle. The bar opens at 11 a.m. and the Manatee Plunge starts at 1 p.m. Registration is $10 per person and includes a free beer. Proceeds will be donated to Give Kids the World, an 89-acre, nonprofit resort in Central Florida that provides weeklong, cost-free vacations to children with life-threatening illnesses and their families.

  • January 01 - January 01 Islamorada
  • Key West Artisan Market: The Hangover Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and outstanding ocean views as you work off that New Year's eve celebration with craft made bloody mary's and on the spot treatments from IV Hydration Stations Key West. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

  • January 03 - January 05 Islamorada
  • Islamorada Sail Fly Tournament
  • Randy Towe Email Website
  • Fourteen teams gather for two days of fly fishing for Atlantic sailfish. Considered one of the most challenging, exciting, competitive sailfish tournaments, captains slow-troll with live baits with no hooks to raise and tease the sailfish, so that fly anglers can cast to the fish.

  • January 03 - January 03 Key Largo
  • Orange Bowl Swim Classic
  • Website
  • Hundreds of college swimmers from around the country meet and compete in a popular monthlong winter training session in Key Largo that culminates in the open-to-spectators Orange Bowl Swim Classic event. Competition takes place 10 a.m. until noon and is free for spectators to watch at Jacobs Aquatic Center, mile marker 99.6 oceanside. The sprint-style meet features several fast-paced swimming events.

  • January 05 - January 08 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters from ages 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach, with the main event Saturday. Prize monies for male and female challengers are up for grabs, including additional prize money for any man or woman who breaks the island record. Pancake Breakfast from 8 am – 10 am. Admission Free. Pancake Breakfast tickets are sold onsite.

  • January 06 - January 07 Islamorada
  • Fish for Holly Sailfish Tournament
  • Annie Hagen Email Website
  • Created to raise money for Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at Postcard Inn to compete for top male, female and junior angler awards as well top team and fun fish categories.

  • January 06 - January 08 Marathon
  • Florida Keys Celtic Festival
  • Website
  • Celtic history, culture, food and music are to be celebrated by attendees at the 10th annual Florida Keys Celtic Festival, a favorite family event in the Middle Keys. The event opens Friday, Jan. 6 from 5 to 7 p.m for the free "Kilts in the Keys" celebration at Dockside Boot Key Harbor. During the weekend festival at Marathon Community Park at mile marker 49, enjoy Celtic rock and traditional musicians including Scottish band Albannach and the Screaming Orphans from Ireland. Enjoy Celtic merchandise, food, traditional sheep herding demonstrations and the Florida Police Pipe & Drum Corps. Tickets available online in advance for $10 per day or $15 for a two-day pass; or at the gate, $12 per day or $17 for a two-day pass.

  • January 07 - January 07 Key West
  • Pancake Breakfast - Higgs Beach
  • Website
  • 8 am – 10 am in support of the Key West High School Track Team and the Mays Sands Montessori School. Pancake Booth is located near the African Cemetery and at the Pole Vault in Paradise competition. Unlimited pancakes and one mimosa (adults only) are included. $20 Adults, $10 Children Tickets at the website and on the day of the event.


  • January 12 - January 15 Key West
  • Key West Literary Seminar
  • Website
  • Each year, the Key West Literary Seminar features a particular theme. "Singing America," the 40th seminar, will center on Black American experiences through poetry, fiction, biography, and history. From slavery and Reconstruction to the Harlem Renaissance, the civil rights movement, today, and into the future. All presentations take place at Coffee Butler Amphitheater, 21 Quay Road, within Truman Waterfront Park. Selected portions of the seminar are free-of-charge and open to the public. Find information and registration online.

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

  • January 13 - January 15 Key West
  • 25th Annual Key West Half Marathon & 5k Run
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2023 25th anniversary race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Ranked among 13 must-do U.S. half-marathons by Competitor.com.

  • January 13 - January 14 Key West
  • Old Island Restoration Foundation's 63rd Annual Key West Home Tours
  • Website
  • Enjoy tours of beautiful and historic Key West homes and gardens. Your ticket purchase supports the ongoing mission of preserving and promoting Key West's unique architecture, culture and history. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • January 13 - January 15 Islamorada
  • Baygrass Bluegrass in the Beer Garden
  • Website
  • Florida Keys Brewing Co. and Island Community Entertainment (ICE) are keeping the spirit of Baygrass Bluegrass Festival alive! Enjoy three days of music blending the best of traditional bluegrass with the next generation of bluegrass and some interesting variations of the genre. This year's festival is free to attend (no tickets required) in the beer garden, courtesy of ICE. Music kicks off Friday night with Grandpas Cough Medicine, then continues through the weekend, ending Sunday night with headliner The Grass is Dead. Find the full entertainment lineup and schedule on the website.

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

  • January 14 - January 15 Big Pine Key
  • 19th Annual Nautical Expo
  • 305-872-2411 Email Website
  • Admission and parking at this event are free, held at the Lower Keys Chamber of Commerce grounds, mile marker 31, Saturday from 8 a.m. to 4 p.m. and Sunday 8 a.m. to 2 p.m. Find steals and deals on everything imaginable for boating, fishing, diving and more, from over 100 vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.

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

  • January 17 - January 21 Key West
  • RokIsland Fest 2023
  • Website
  • Staged at the Truman Waterfront Park Amphitheater, the world’s greatest rock bands descend upon the island of Key West for this 4-day music festival in paradise. Single- and multi-day passes available. Performers include Styx, Tesla, Loverboy, Vince Neil, 38 Special, Queensryche, Stryper, Quiet Riot and more.

  • January 17 - January 18 Islamorada
  • IFC Captain's Cup Sailfish Tournament
  • Website
  • Second in the three-pronged 2023 Gold Cup Sailfish Championship series currently underway in the Florida Keys is the Islamorada Fishing Club’s Captain's Cup Sailfish Tournament. Participants vie for an attractive cash payout and the chance to tally points to earn the coveted Gold Cup Series Champion status.

  • January 20 - January 22 Islamorada
  • Cheeca Lodge Presidential Sailfish Tournament
  • Website
  • The final leg of the three-event Florida Keys Gold Cup Championship Series, the Cheeca Lodge Presidential Sailfish Tournament, is scheduled Friday through Sunday, Jan. 20-22. The tournament kick-off and awards events take place at the resort at mile marker 82 oceanside in Islamorada. A limited number of evening event tickets are available for purchase for the Sunday night awards banquet where the Gold Cup trophy as well as other angler awards will be presented. Call 305-587-0574.

  • January 20 - January 22 Marathon
  • Island Boat Show & Festival
  • Bob Phelps 239-691-3290 Website
  • Come enjoy a great show with loads of the top boat brands , silent auction items, food, vendors featuring a variety of merchandise, and fishing seminars. Admission is $10. The show is to take place at Island Community Church, north campus, mile marker 83.4.

  • January 21 - January 21 Key Largo
  • Pops in the Park: Sailing Away to Key Largo
  • Website
  • “Sailing Away to Key Largo” with a free, outdoor concert from Keys Community Concert Band at Murray Nelson Center Peace Park (mm 102, bayside), 4 to 5 p.m. in Key Largo. Bring a blanket or lawn chair and pack a picnic basket for a family-friendly concert of pirate sea shanties and Florida-themed music. Conch blowing contest! Special Guests: Mangrove Swamp Band, Pirates in Paradise and REEF (sea conservation and touch tank).

  • January 24 - January 30 Key West
  • Kelly McGillis Classic
  • Website
  • Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to represent the most international countries, and organizers have hosted teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador, and Sweden.

  • January 24 - January 20 Key West
  • Mile 0 Fest Key West
  • Website
  • Mile 0 Fest Key West is a "must see" boutique destination 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.

  • January 25 - January 29 Key West
  • Key West Food and Wine Festival
  • Email Website
  • Adventurous aficionados of fine food and vintages can explore creative cuisine, premium wines and unique events in a subtropical island setting during the annual celebration. Whet your appetite for island-style excellence, showcasing local chefs’ culinary flair and favorite indigenous ingredients, intriguing libations and distinctive Florida Keys atmosphere. Ticket sales available online.

  • January 28 - January 29 Key West
  • 38th Annual Key West Craft Show
  • 305-294-1243 Email Website
  • The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.

  • January 29 - January 29 Big Pine Key
  • Spanish Fly Music Festival
  • Website
  • Presented by the Jose Wejebe Memorial Foundation, enjoy a family-friendly day of music and activities, auctions and raffles, from 1-6 p.m. at Boondock's Grille and Draft House, mile marker 27.5 on Ramrod Key. Live musical lineup includes Brian Roberts and Gunner and the Grizzly Boys.

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