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Events in the Florida Keys

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

Events in Florida Keys for 2021

  • March 06 - February 05 Key West
  • Market on the Green
  • Website
  • Presented by The Keys Collection of resorts, the versatile Sunset Green Event Lawn, located between sister hotels the Gates Key West and 24 North, transforms into a local artisan market the first Saturday of each month, from 10AM to 2PM.

  • April 21 - December 31 Islamorada
  • History of Diving Museum Exhibit: Diving in Pop Culture
  • Website
  • Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.

  • November 04 - January 31 Key West
  • Arts Council presents 2021 Members Show ‘Dazzling Horizons’
  • 305-295-4369 Website
  • The Opening Reception will be held Nov. 4, from 5:30 – 7:30 pm at the historic Gato Building, 1100 Simonton St. The exhibition will remain on display through January 2022. Dazzling Horizons - a look forward and a look around - the creativity is inspirational! Our magnificent sunsets, colorful skies, shiny moon, and endless glistening waters encourage us to preserve and enjoy nature.

  • November 24 - January 01 Key West
  • Key West 'Bight' Before Christmas
  • Website
  • Enjoy a free Keys holiday event to celebrate the spirit of the season. ‘Harbor Walk of Lights’ comes alive each evening at dusk, through New Year’s Eve, and runs along water past Greene St., William St., Margaret St., to the Key West Ferry Terminal. Traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree. Colorful lights and nautical holiday displays include ship’s anchors, tropical birds, tropical fish, pink flamingos, pelicans, manatees, animated sea turtles and dolphins, and even a festive moray eel, along with thousands of lights all around and in lighted palm trees.

  • 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 02 - December 30 Key West
  • The Studios of Key West presents: Winter Members' Show
  • Website
  • The winter members’ exhibition ‘Piece by Piece’ is to be on display in all four galleries: Sanger, XOJ, Zabar Lobby and Zabar Project Galleries. The annual winter members’ show is a celebration and serves as a kick off for TSKW’s season of events. Galleries are open Tue-Sat, 10 a.m.- 4 p.m., and are free to visit, at 533 Eaton St.

  • December 10 - December 10 Key West
  • Fifth Annual Holiday Concert and & Bazaar
  • Website
  • Join the Key West Art & Historical Society, from 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum.  The immensely popular celebration is to feature some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show of magical vector projections on the face of the Custom House Museum. Browse hundreds of unique gift options while enjoying the music, food and libations, on and around the island’s architectural crown jewel.  

  • December 10 - December 11 Marathon
  • Home for the Holidays
  • Website
  • Enjoy a family friendly evening filled with cheer, joy and music at Marathon Community Theatre's Annual Holiday Show & Sing-Along concert. Doors open 7 p.m., show starts at 8 p.m.; tickets $10 per person, available online. The annual family-friendly show is to run one hour with no intermission and include musical selections from the Island Harmony Singers, the MCT Children’s Chorus as well as local church groups and singers. Be entertained by dancers from Prodigy Dance Center and the MCT Dance Department as they dance to classic Holiday Tunes!

  • December 10 - December 10 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During this enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. each night, revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. Participating destinations are the Key West Butterfly and Nature Conservatory, The Gardens Hotel, Island City House Hotel, and Amsterdam’s Curry Mansion Inn.

  • December 10 - December 12 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.

  • December 11 - December 11 Key West
  • Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
  • 305-292-3302 Website
  • Decorated dinghies, fishing craft and classic tall ships are to light up the Key West Historic Seaport and harbor areas during the 30th annual Schooner Wharf Bar Lighted Boat Parade. Spectators can view the dozens of creatively bedecked vessels from the Schooner Wharf, the parade’s headquarters where the judges stand is located, and from other bars, restaurants and resorts on and around the seaport’s harborwalk and docks. Festivities including steel band performances begin at 6 p.m.

  • December 11 - December 11 Key Largo
  • Key Largo Holiday Lighted Boat Parade
  • Website
  • Boats of all sizes are to show off festive decorations in a lively procession of vessels on Key Largo’s Blackwater Sound. Presented by the Key Largo Sunset Rotary Club, the parade is to be themed “Nauty-cal & Nice!” in salute to the community’s lighthearted holiday spirit. Spectators can enjoy the fun from viewing spots at Sundowners, Cactus Jack’s, Señor Frijoles, the Key Largo Bay Marriott Beach Resort and Caribbean Club, all around mile markers 103-104.

  • December 11 - December 11 Big Pine Key
  • Kiki's Annual Lighted Boat Parade
  • All boats are welcome to enter the Pine Channel Causeway parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. The best recommended viewing is from Kiki's Sandbar, 183 Barry Ave. on Little Torch Key. Parade begins at 7 p.m.

  • December 11 - December 11 Key West
  • Eighth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park 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 2021 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 11 - December 11 Islamorada
  • Seventh 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 the 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. 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.

  • December 11 - December 11 Key West
  • Rams Head presents: The Temptations at Coffee Butler Amphitheater
  • Website
  • The Temptations, often referred to as “American Music Royalty,” are world-renowned superstars of entertainment, revered for their phenomenal catalog of music, and prolific career. Otis Williams, the sole surviving original Temptation, Ron Tyson, a lead vocalist with the group for 37 years, Terry Weeks, a lead vocalist for 23 years, and Willie Greene, Jr., base vocalist with the group for four years, are still serenading fans with their soulful voices, lighting up stages with their famous Temptations’ Walk, and bringing joy to audiences of all ages. Doors open 5:30 p.m., show starts 7 p.m.

  • December 11 - December 11 Islamorada
  • Pops in the Park with Keys Community Concert Band
  • Some of the best things in life are free, at least in the Florida Keys. Through the dedication and talent of Florida Keys Community Concert Band members and supporters, music enthusiasts can enjoy an entire Pops in the Park season of themed outdoor concerts free, Saturdays at 4 p.m., at Founder’s Park, mile marker 87 bayside in Islamorada. This month’s theme is “(Not So) White Christmas.”

  • December 12 - December 12 Key West
  • The Kingston Trio at Key West Theater
  • Website
  • All three current members, Mike Marvin, Tim Gorelangton and Don Marovich, have intrinsic links to and experience with the original group: Mike is the adopted son of founding member Nick Reynolds, who was also his musical mentor; Tim, a close friend since boyhood, is one of the few musicians outside the Trio who has recorded with Nick Reynolds; and Don Marovich, who has performed with the Trio and who plays the guitar, banjo and mandolin. Many of their personal memories recall the iconic trio’s performances and journey as folk music made its extraordinary ascent to the pinnacle of popular culture – and the top of the music charts. Doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.

  • December 12 - December 12 Marathon
  • Key Colony Beach Lighted Boat Parade
  • (305) 743-7214 Website
  • Christmas lights on outriggers and displays on boat decks are part of the beautiful festivities at the Key Colony Beach Boat Parade, set to begin at the 7th Street canal at 6 p.m. Great viewing spots include Sadowski Causeway at mile marker 53.5. Sponsored by the Key Colony Beach Fishing and Boating Club, participants vie for awards in Best Boat Overall, Best Boat under 30 ft, Best Boat over 30 ft.

  • December 15 - December 17 Key West
  • Sugar Rum Cherry: A Burlesque Nutcracker
  • Website
  • Slip into your stockings and pull out your sugarplums for the outrageously cheeky production of Sugar Rum Cherry: A Burlesque Nutcracker. This naughty but nice two-act holiday reverie showcases a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

  • December 16 - December 16 Key West
  • Walk on White
  • Website
  • From 5-8 p.m. enjoy a monthly art walk through the White Street Arts District, from Southard St to United St. Walk on White is to continue on the Third Thursday of each month. Participants include galleries (such as Stone Soup, Harrison Gallery, Shade Ceramics and Shutter Photography, and Bone Island Graphics), studios such as Artists at the Armory and Coffee Mill Dance Studios, eateries such as Mayanjali Cafe, and other fine businesses.

  • December 17 - December 17 Key West
  • Holiday Historic Inn Tours 2021
  • Website
  • During an enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with tasty holiday treats and libation samplings. From 6-8 p.m. revelers can avail themselves of free trolley transportation or use their own bikes, trikes, or vehicles to travel to the various properties, enjoy self-guided tours, and delight in the island’s warm tropical holiday ambience. December 17 destinations are The Mermaid & The Alligator, Winslow’s Bungalows, Wicker Guesthouse, and the Weatherstation Inn.

  • December 18 - December 18 Key West
  • 13th Annual Rudolph Red Nose 5K Run/Walk
  • Website
  • Don your festive holiday jammies and join in the fun! Race starts and ends at the 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. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt. Register online.

  • December 19 - December 19 Key West
  • Children’s Concert at Key West Botanical Garden
  • Website
  • The Key West Tropical Forest & Botanical Garden hosts this family friendly children’s concert featuring local classical guitarist, Mateo Jampol, who is to perform songs especially for children. Performance is to start at 1 p.m. until 1:30 pm in the Garden’s Courtyard.   Following the concert a craft project will be available for to create their own holiday ornament.    This “Snowy Sunday” event is to have snow cones, beverages and treats for sale. Cost is $5 per child with a maximum cost of $10 per family. The Garden is located at 5210 College Road on Stock Island. 

  • December 19 - December 19 Key West
  • Key West Artisan Market Market, 'Holiday/Shop Local' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This week's Market benefits Keys-crafted local, artists and creators.

  • December 29 - January 15 Key West
  • Fringe Theater presents: Diva! Live From Hell
  • Website
  • The high school drama club president literally kills for a role and finds himself starring in a "flaming hot" cabaret presented nightly -- live from hell. Wickedly fun. Tickets, show dates and times online. Performances begin at 7 p.m., Fringe Theater, 600 White St.

  • December 31 - December 31 Marathon
  • New Years Eve Party at Faro Blanco Resort
  • Website
  • Toast to the New Year with complimentary champagne and the resort’s famous anchor drop from the iconic Faro Blanco lighthouse at midnight! Dinner at Lighthouse Grill is to be served 5-9 PM. Reservations are highly encouraged. Enjoy DJ music, dancing, photo booth & more, from 9 p.m. to midnight.

  • 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 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2022 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.

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

  • January 04 - January 06 Islamorada
  • Islamorada SailFly Tournament
  • Randy Towe at 305-394-2667 Email
  • This time of year, the weather is typically ideal for a hot Atlantic sailfish bite. Entrants can compete in one of the toughest and most exciting angling events of the year.

  • January 05 - January 05 Key West
  • ZEN by Karen Moore Malas & Mantras at Sacred Space Key West
  • Website
  • Get meditative and creative in the New Year and walk away with a personally designed 108-piece mala bead necklace handcrafted by YOU! Class participants learn about the history, uses and energetic meaning of the natural elements and gemstones through the creation of your very own mala necklace in this fun jewelry-making workshop. Class is from 5:30-7:30 p.m.; price is $138 per person and includes all supplies and a glass of New Year's bubbles! Reserve a spot online.

  • January 06 - January 09 Key West
  • Key West Literary Seminar
  • Website
  • Each year, the Key West Literary Seminar explores a particular literary theme. For “A Seminar Named Desire” we’re interested in literary explorations of the profane and the profound, the inventive, the graphic, and the deeply felt. This will be a unique gathering of some of today’s most acclaimed writers in conversation about the elemental urge at the center of human activity: desire.

  • January 06 - January 27 Key West
  • South of Southernmost by Mark Hedden
  • Website
  • Ballast Key is a backcountry island seven miles west of Key West, south of the Southernmost point, once listed for sale for $15.8 million. It was owned and used as a getaway for the influential and the creative by David Wolkowsky, a friend of Tennessee Williams and Truman Capote, and a member of a family with deep and storied Florida roots. Wolkowsky died recently at 99. Under the guidance of the Nature Conservancy, the island was donated to the National Wildlife Refuge system, with the intention of it becoming a backcountry research station. So this amazing, coveted, living fantasy of an island is going back to nature, or at least to being primarily managed for the benefit of the natural world. South of Southernmost is a photography project that documents the shift in Ballast Key’s gravity, as the arc of its story switches from the human to the wild. View the exhibition in The Studios of Key West’s Sanger Gallery, open Tue-Sat., 12-4 .m., free of charge.

  • January 06 - January 08 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters from age 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. 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.

  • January 07 - January 08 Islamorada
  • Fish for Holly Sailfish Tournament
  • 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 08 - January 09 Marathon
  • The Florida Keys Celtic Festival
  • Website
  • Some of America's most celebrated Celtic musical masters are to be featured at the Marathon Community Park, MM 49. The festival also features Irish and Scottish dancing, Highland athletics, Celtic merchandise, food and beverage booths and children's activities. Hours and events schedules TBD.

  • January 09 - January 09 Key West
  • Key West Artisan Market Market, 'Preserve Island Life' Edition
  • Website
  • From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote community causes. All artists who show at the event are carefully selected and live and create in the Keys. This week's Market spotlights the City of Key West's efforts to preserve local culture.

  • January 13 - January 16 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 14 - January 16 Islamorada
  • 10th Annual Baygrass Bluegrass Festival Weekend
  • Website
  • A series of three, single-band concerts are planned for the weekend, in a redesigned festival format for 2022. Performances include Hare of the Dawg, from 6-9 p.m. Jan. 14 at Florida Keys Brewing Co.'s beer garden; Belle and the Band Duo play from 2-6 p.m. at the Blue Marlin stage; and Jan. 16, Grass is Dead performs from 6-9 p.m. at Florida Keys Brewing Co. Venues are located in the Morada Way Arts & Cultural District, 81599 Old Hwy. Admission is free, sponsored by Islamorada Community Entertainment.

  • January 15 - January 16 Key West
  • 16th Annual Florida Keys Seafood Festival
  • Website
  • Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. A $10 admission is good for BOTH Saturday and Sunday. New location this year is to be at Truman Waterfront Park at the end of Southard Street. This event is a fundraiser for the Florida Keys Commercial Fishermen's Association FKCFA and goes to support sustainable fishing programs, marine restoration projects & college scholarships.

  • January 15 - January 16 Big Pine Key
  • 18th 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, MM31, Saturday from 8AM to 4PM and Sunday 8AM to 2PM. Find steals and deals on everything imaginable for boating, fishing, diving and more, from dozens of vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.

  • January 15 - January 16 Key West
  • 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 race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by Competitor.com.

  • January 17 - January 21 Key West
  • The Southernmost Regatta
  • Website
  • This event offers five consecutive days of racing on the picturesque blue waters off Key West, and is open to One Design and ORC Racing / Cruising Keelboats. Enjoy a fun, sustainable event that features high-quality racing and social activities! Event organizers expect to provide two races per day on two courses — a One Design Course and an ORC Course. Also to be offered is one distance race each day for ORC cruisers.

  • January 21 - January 23 Marathon
  • Sombrero Beach Run Weekend
  • 305-743-4582 Email Website
  • Each year, several hundred racing circuit runners are attracted by a weekend filled with sunshine and athletic fun. Stocked with food, drinks, music and entertainment, the running event is to be staged Saturday at Sombrero Beach at the end of Sombrero Beach Road, mile marker 50. Awards are given to overall finishers in the 10k run, 5k run and 5k walk.

  • January 21 - January 23 Islamorada
  • Cheeca Lodge Presidential Sailfish Tournament
  • Liz Hill 305-451-5094 Website
  • The Presidential is one of the most prestigious offshore tournaments in the Florida Keys, and serves as the third and final leg of the three-pronged Florida Keys Gold Cup Championship. The FKGC is both an angler tournament as well as a team tournament. Each team must fish aboard the same boat in all three events. At least one angler of each team entered must fish all three events. This format stems from a long history of sailfish tri-fectas. Teams compete to win the coveted Florida Keys Gold Cup Sailfish Tournament trophy.

  • January 21 - January 23 Marathon
  • Island Boat Show & Festival
  • Bob Phelps 239-691-3290 Website
  • Come enjoy a great show with loads of the top boat brands , auction items, food, vendors featuring a variety of merchandise, great fishing seminars presented by local captains... all at a very reasonable $10 admission. The show is to take place 1-5:30 p.m. Friday, 10 a.m. to 5:30 p.m. Saturday and 10 a.m. to 3 p.m. Sunday. Venue at Hawks Cay Resort. Free parking and shuttle service.

  • January 22 - January 22 Key Largo
  • Pops in the Park with Keys Community Concert Band
  • Some of the best things in life are free, at least in the Florida Keys. Through the dedication and talent of Florida Keys Community Concert Band members and supporters, music enthusiasts can enjoy an entire Pops in the Park season of themed outdoor concerts free, starting at 4 p.m., at Murray E. Nelson Center, mile marker 102 bayside in Key Largo. This month’s theme is “Instant Concert.”

  • January 24 - January 31 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 have the most international countries represented, and organizers are expecting teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador, and Sweden.

  • January 26 - January 27 Islamorada
  • IFC Sailfish Tournament
  • Website
  • Presented by the Islamorada Fishing Club, the event this year is the third and final leg of the three-pronged Florida Keys Gold Cup Championship series, attracting teams of elite sport fishermen. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.

  • January 30 - January 31 Islamorada
  • Islamorada Bartenders Sailfish Open
  • Dianne Harbaugh at 305-522-4868 Email
  • Headquartered at the Lorelei Restaurant & Cabana Bar, this fun fishing event is only for actively employed bartenders and restaurant employees. Trophies are awarded to individual anglers as well as the bar a team represents, with the huge perpetual trophy going to the winners along with bragging rights for a year.

  • January 30 - January 30 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, Ty Thurman, Adrienne Z, John Bartus, and Gunner and the Grizzly Boys.

  • February 01 - February 02 Islamorada
  • Poor Girls Sailfish Tournament
  • Website
  • This regional charity competition raises monies to spay and neuter feral cats in the Upper Keys. Trophies are awarded to the first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others.

  • February 04 - February 06 Islamorada
  • Islamorada Women’s Sailfish Tournament
  • 305-240-9337 Email
  • In this light-tackle challenge, awards await the grand champion team (boat), first runner-up and second runner-up team, captain and mate. Other awards are presented for the high-point angler; outstanding catch; largest tuna, dolphin fish and kingfish; and hard luck. Proceeds benefit Florida Keys charities.

  • February 04 - February 06 Key Largo
  • Buccaneer Blast Regatta 2022
  • Website
  • The Buccaneer Blast Regatta invites youth sailors ages 8 through 18 from all around the country and the Caribbean to Key Largo for a weekend of competitive racing. Sailors in the Optimist, Laser/ILCA and Junior Windsurfing classes are welcome to participate. With well over 200 participants attending the 2021 regatta, the Buccaneer Blast has become the largest sailing event held in the Florida Keys each year. Activities are to be staged at Rowell’s Waterfront Park at 104550 Overseas Hwy. Catch near-shore racing Saturday and Sunday and take part in an 'Auctions & Concoctions' event Saturday afternoon from 2-6 p.m. Enjoy live music, beer and wine, and a live raffle event where the whole community along with regatta families can buy tickets for the chance to win fantastic prizes.

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