2022 Calendar of Events – We got end of year updates! | Key West / Florida Keys Money Saving Discount Coupons

JANUARY

Dec 1, 2021 – Jan 1, 2022 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.”

Jan 3 – Orange Bowl Swim Classic in Key Largo

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.

Jan 6 – Jan 8 – Key West Pole Vault in Paradise Competition

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.

Jan 6 – Jan 27 – Key West South of Southernmost by Mark Hedden

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.

Jan 8 – Key Largo Brew on the Bay

Presented by the Key Largo Rotary Club, this Craft Beer & Home Brewers tasting event is to feature more than 30 microbrews. Event is set to be located at Rowell’s Marina grounds, at mile marker 106.8 bayside. Proceeds benefit the Rotary Scholarship Foundation. Hours and ticket information TBD.

Jan 13 – Jan 16 – Key West Kingfish Mayhem

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!

Jan 15 – Jan 16 – Key West 16th Annual Florida Keys Seafood Festival

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.

Jan 21 – Jan 23 – Islamorada Cheeca Lodge Presidential Sailfish Tournament

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.

FEBRUARY 2022

Mar 6, 2021 – Feb 5 – Key West Market on the Green

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.

Feb 4 – 6 – Islamorada Women’s Sailfish Tournament

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.

Feb 4 – 6 Key Largo – Buccaneer Blast Regatta 2022

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.

Feb 8 – Key West – The Studios of Key West Presents: Susan Werner in Concert

Called “one of the most innovative songwriters working today,” (Chicago Tribune), Susan Werner crafts lyrics that are as sharp as thistles, and every bit as funny as they are on point. A giant on the acoustic scene, Werner is by turns wry and passionate on stage and famous for her live shows. As she says, “If you can’t laugh about it, you might be in the wrong line of work.” Tickets online; performance starts 6 pm, on the rooftop Hugh’s View, at Studios of Key West, 533 Eaton St.

Feb 10 – Feb 12 – Key West Fishing Cuda Bowl

The toothy barracuda are prey for competitors in this annual challenge. The all-release flats tournament got its name because it’s scheduled each year just before the Super Bowl NFL football championship. Fishing is scheduled Friday and Saturday and must not exceed eight hours per day. Anglers and guides can leave from and return to the marina of their choice, but rules mandate that by 5:30 p.m. each day they must bring their catch forms and photos of fish caught to the Hurricane Hole Marina.

Feb 12 – Big Pine Key – Stock Island Art Stroll

Experience Stock Island’s unique art scene and creative culture, tour Stock Island’s best art studios from 11 am – 5 pm. Start at The Perry Hotel look for a positive energy-filled Valentine’s Day gift with featured artist ZEN by Karen Moore Jewelry Pop-Up event. Make a day of it and treat yourself to several local artisan offerings. Each location offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art.

Feb 13 – Key West – Impromptu Classical Concert Series Celebrates 50 years: Chooi Brothers

Gifted violinists Timothy Chooi and his brother Nikki are back in Key West for a repeat Impromptu Classical Concert. Both violinists are united by a profound understanding and genuine passion for the violin, which renders their musical union extraordinarily rich. Together the Chooi Brothers have an intrinsic musical partnership that makes their duo artistry unique and interesting. The Edmonton Journal describes their performance as a ‘beauty of color and tone.’ All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free.

Feb 14 – Marathon – Florida Keys Concerts Association Presents: Rastrelli Cello Quartet

Kira Kraftzoff, Sergio Drabkin, Mischa Degtjareff and Kirill Timofeev – the four gentlemen of the Rastrelli Cello Quartet began working together in 2002 and have devoted themselves ever since to exploring and experiencing the cello’s world of sound. They are committed to tradition, but completely uncoupled from the conventional approach, which only serves as a solid foundation. Tickets $30. Performance begins at 7:30 p.m., Marathon High School Performing Arts Center.

Feb 16 – Mar 5 – Key West – Waterfront Playhouse Presents: Clue (Live on Stage)

Clue is a hilarious farce-meets-murder mystery. The tale begins at a remote mansion, where six mysterious guests assemble for an unusual dinner party where murder and blackmail are on the menu. When their host turns up dead, they all become suspects. Led by the Wadsworth , Miss Scarlett, Professor Plum, Mrs. White, Mr. Green, Mrs. Peacock and Colonel Mustard race to find the killer as the body count stacks up. Performances at 8 p.m., Waterfront Playhouse, 407 Wall St.; visit website for show dates and details.

Feb 17 – Key West 25th Anniversary Gala of the Community Foundation of the Florida Keys

Join your Community Foundation in celebrating 25 years of serving the Keys by connecting people, resources, and needs through philanthropy. Dance the night away with the Prime Movers. Ticket and other information online.

Feb 18 – Key West Honky Tonk Heartbreak: A Classic Country and Western Burlesque Revue

Key West Burlesque pays tribute to the classic country-and-western songbook in a down-home and dirty burlesque extravaganza. Featuring a live band of local C&W musicians, Honky Tonk Heartbreak: a Country-and-Western Revue is an anthology of stories, songs, and striptease. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

Feb 18 – 21 – Key West – Presidential Families Weekend and Forum

Presented outdoors on the elegant tropical grounds of the Harry S. Truman Little White House, the “Presidential Families Weekend and Forum,” launches on Friday afternoon with the Key West debut of the highly acclaimed and long-running stage production, “Give ‘Em Hell, Harry!” starring Clifton Truman Daniel, the first direct descendant to portray a presidential ancestor in a stage production of this kind. Monday, the spacious lawn of the Harry S. Truman Little White House is to be the setting for a traditional President’s Day lunchtime picnic.

Feb 19 – 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 “Jungle Jamboree.”

Feb 19 – Key Largo Garden Walk 2022

Presented by the Garden Club of the Upper Keys. From 10 a.m. to 4 .m, tour five neighborhood gardens. Event is rain or shine. Art show, vendors, and plant sale at Francis Tracy Garden Center, mile marker 94 bayside.

Feb 25 – 26 – Islamorada – Backcountry Fly Championship Series

Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish. The field is limited to 30 boats.

Feb 26 – Key West – 38th Annual Key West Headdress Ball

Kick off Mardi Gras season at the Coffee Butler Amphitheater, Truman Waterfront Park for the outdoor gala, rescheduled from October due to coronavirus concerns. Doors open 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online. Ticket holders from 2021 event can carry over.

Feb 27 – Big Pine Key – Habitat for Humanity of Key West and the Lower Keys Music Festival

Featuring Keys favorite performers Terry Cassidy, John Bartus, and a line-up of local musicians, the festival is held from 1-6 p.m. at Boondocks Grille and Draft House, mile marker 27.5. Highlights include a silent auction, raffles, vendors, and more at the annual family-friendly event.

Feb 28 – Marathon – Florida Keys Concerts Association Presents: Voyage Through The Americas

Voyage Through the Americas features unique combinations of piano, cello and percussion, and will take the listener on a sizzling journey through both hemispheres. Tickets $30. Performance begins at 7:30 p.m., Marathon High School Performing Arts Center.

MARCH

Mar 1 – Islamorada – Florida Keys Concerts Association Presents: Voyage Through The Americas

Mar 1 – 5 – Key Largo – Jimmy Johnson’s National Billfish Championship

Hosted by Jimmy Johnson, two-time Super Bowl-winning coach and former head coach at the University of Miami, the prestigious event benefits the Sylvester Comprehensive Cancer Center and other charities. Anglers on the winning boat receive custom-designed Jimmy Johnson’s NBC Championship rings. Participants fish in 100 miles of waters from Key Largo to Palm Beach.

Mar 6 – Key West – Rams Head presents: The Beach Boys

For almost six decades, The Beach Boys’ music has been an indelible part of American history. Their brilliant harmonies conveyed simple truths through sophisticated, pioneering musical arrangements. The Beach Boys transcended their music and have come to represent Californian culture. Doors open 5:30 p.m., show starts 7 p.m. at Coffee Butler Amphitheater. Tickets online.

Mar 7 – 10 – Key West Fishing March Merkin Invitational Permit Tournament

This charity flats-and-fly-only tournament challenges anglers to catch, tag and release silvery permit to vie for elite titles. The event is traditionally held at the Key West Harbour Yacht Club on Stock Island, and features a silent online auction.

Mar 12 – 13 – Marathon – Original Marathon Seafood Festival

One of the middle Keys’ signature family events, delicacies from the waters of the Florida Keys highlight this annual munch-fest at Marathon Community Park, mile marker 49 oceanside. Sponsored by Organized Fishermen of Florida and Marathon Chamber of Commerce. Live music, vendor booths, sweets, treats and beverages make for a delectable weekend. An open-air boat show is to be staged at entrance to the festival.

Mar 12 – Islamorada – Pops in the Park with Keys Community Concert Band

Mar 12 – Key West – Florida Keys SPCA 14th Annual Spring Social

Enjoy a day to benefit the homeless animals of the Lower Keys at the Coffee Butler Amphitheater! Their biggest celebration of the year will include dinner, a live & silent auction, entertainment, complimentary wine & beer with cash liquor bar and is a night not to be missed! VIP tickets include a Champagne Reception starting at 5:30 p.m. before the main event, passed appetizers, a sneak peek at one of the largest silent auctions on the island, reserved seating and VIP food stations. The VIP Reception begins at 5:30 p.m. and General Admission entry is at 6:30 p.m. Tickets are to be available for purchase online.

Mar 12 – Big Pine Key – Stock Island Art Stroll

Experience Stock Island’s unique art scene and creative culture, tour Stock Island’s best art studios from 11 a.m. – 5 p.m. Each location offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art.

Mar 13 – Key West – Impromptu Classical Concert Series Celebrates 50 Years: Cellist Zlatomir Fung

The first American in four decades, and youngest musician ever, to win First Prize at the International Tchaikovsky Competition Cello Division, Zlatomir Fung is poised to become one of the preeminent cellists of his time, astounding audiences with his boundless virtuosity and exquisite sensitivity. This 21-year-old has already proven himself to be a star among the next generation of world-class musicians. Fung’s impeccable technique demonstrates a mastery of the canon and exceptional insight into the depths of contemporary repertoire. All concerts are to take place at 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St. Admission is $20 at the door. All students will be admitted free. Due to the ongoing pandemic, facial masks are required and special anniversary face masks will be provided free. Attendees are requested to be Covid-vaccinated and symptom-free.

Mar 27 – Islamorada BayJam Music Festival

Backed by Florida Bay’s turquoise waters, an innovative lineup of musicians play from midday into the evening during the annual BayJam music festival that takes place at the ICE Amphitheater at Founders Park, mile marker 87 bayside on Plantation Key. Performers representing a wide array of genres come from around the country. The daylong music festival is presented by the not-for-profit Islamorada Community Entertainment, and event donations and proceeds directly help fund in-school programs as well as art, music and dance scholarships to Upper Keys high school students.

APRIL

Apr 2 – Marathon 41st Annual Seven Mile Bridge Run

An estimated field of 1,500 runners are to participate in the annual foot race across the longest segmental bridge in the world. The April contest has become one of the most popular running events in the southeastern United States. Registration is online only.

Apr 2 – 3 – Key West – NEW DATES: 16TH Anual Florida Keys Seafood Festival

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 and the festival is to be held at Bayview Park. 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.

Apr 2 – 3 – Islamorada – 30TH Annual Island Fest

Island Fest returns to Islamorada with a juried art show, live music, great for, classic cars and more. Hours are 10 a.m. to 7 p.m. Saturday, and Sunday, 10 a.m. to 5 p.m., featuring the Taste of Islamorada competition. Event is outdoors at Founders Park, mile marker 87 bayside. Parking is available for a $5 donation.

Apr 8 – 9 – Key West The Magic of Spring: A Burlesque Awakening

As flowers bloom and birds begin to sing, an all-star cast takes to the stage to celebrate The Magic of Spring! Key West Burlesque favorites and internationally known performers shimmy and shake their way through the most magical months of the year. Set to a score of classical music, these superstar performers will dazzle and delight in this flight of fancy. Doors open 7PM, show starts 8PM at Key West Theater, 512 Eaton St.

Apr 8 – 10 – Islamorada Robert James Sales Redbone @ Large Sunrise/Sunset Tarpon Tournament

The Upper Keys competition is one of dozens of fishing events held each year whose proceeds benefit the Cystic Fibrosis Foundation.

Apr 14 – 24 – Key West – Conch Republic Independence Celebration

Every year visitors join Florida Keys residents for the Conch Republic Independence Celebration, a quirky event honoring the birth of the republic and its place in Keys history. The republic was founded in April 1982 to protest the installation of a U.S. Border Patrol checkpoint that stopped traffic at the top of the Florida Keys Overseas Highway, the only road in and out of the Keys.

Apr 21 – 23 – Marathon – Inaugural Marathon Sailfish Tournament

Anglers can not only showcase their fishing talents but help make a difference in people’s lives. This fun sailfish competition is to raise funds for a Keys charity, Mission Fishin’ that helps foster children, children with special needs, and their families. Thursday kickoff event is at the Fairfield Inn & Suites Tiki from 3-6 p.m. Lines-in fishing is Friday and Saturday, 8 a.m. – 4 p.m. and 8 a.m.- 3 p.m., with awards banquet to follow at Florida Keys Aquarium Encounters. Register online.

Apr 21 – 24 – Key West – Fringe Theater Presents: Conch Republic The Musical!

It’s the (mostly) true story of how the Conch Republic was born! Presented in celebration of the 40th Anniversary of the Conch Republic harrowing (and hilarious) tale. Performances start 7 p.m., Fringe Theater, 600 White St. Tickets, showtimes and dates online.

Apr 23 – Key West – MOTE Ocean Fest

Underwater and outdoor enthusiasts, eco travelers and families are encouraged to celebrate the marine environment! From 10 a.m. to 4 p.m., enjoy an outdoor community celebration of the oceans at Truman Waterfront Park. A day of family activities, raffles, live music, shopping, and environmental exhibits are to be featured.

Apr 23 – Islamorada – Pops in the Park with Keys Community Concert Band

Apr 24 – Apr 28 – Islamorada Herman Lucerne Memorial Tarpon Cup

This is an old school, ‘downtown Islamorada’ kind of tournament, to be headquartered at the Islander Resort. True to the Herman Lucerne spirit of inclusiveness, the Tarpon Cup includes both a Guided and Unguided division. Teams are limited to 20.

Apr 30 – Key West – Papio Kenetic Sculpture Parade

A people-powered parade of colorful mobile structures rolls through Key West’s historic downtown intended to intrigue and inspire fans of creative recycling and ‘outsider’ art. The event is an artistic, creative way to raise awareness about the legacy and the importance of artists in the Florida Keys while using recycling as a key component.

MAY

May 1 – 4 – Marathon – Tarponian Tournament

Rules of this high-energy three-evening tournament mandate that each team fishes with a different captain each outing. Teams also rotate among the three major bridge channels in Marathon, so any potential “hot spots” are shared among all anglers.

May 4 – 8 – Key West – 26TH Annual Key West Songwriters Festival

Since 1997, BMI has been a presenting sponsor of the festival, one of the largest festivals of its kind in the world, and has helped it grow into both a tourist attraction and a favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices, and stories behind the songs.

May 5 – 7 – Marathon Offshore Bull and Cow Dolphin Tournament

A grand prize of up to $10,000 cash is to go to the team that catches the largest bull and cow dolphin fish combined. Cash prizes for second-and third-place as well. Other prizes are awarded to anglers catching the largest dolphin, wahoo, tuna and tripletail.

May 6 – 8 – Islamorada Nick Sheahan Dolphin Rodeo

Fishing for a cause! Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $170,000 to date. Hosted at Tavernier Creek Marina, the event features cash prizes and $25,000 to the angler with a dolphin fish that beats the state record.

May 13 – 14 – Key West – Key West Harry S Truman Foundation Presents: 19TH Annual Truman Legacy

The event will be officiated by Clifton Truman Daniel, grandson of 33rd U.S. President Harry S. Truman, in the company of fellow presidential descendants and other dignitaries. Friday, the entourage is to travel south along the Harry S. Truman Overseas Highway to Key West, where a welcome sunset cocktail reception is to take place aboard the celebrated U.S. Coast Guard Cutter Ingham at the Truman Waterfront, followed by a VIP gathering at the nearby Harry S. Truman Little White House. Saturday, May 14, the Key West Harry S. Truman Foundation’s signature event— the Truman Legacy Symposium — takes place, with presidential descendants and distinguished experts engaged in moderated topical discussions throughout the day, followed by a cocktail reception, elegant dinner and closing presentation.

May 14 – Big Pine Key – Stock Island Art Stroll

Experience Stock Island’s unique art scene and creative culture, tour Stock Island’s best art studios from 11a.m. – 5 p.m. Each location offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art.

May 16 – 19 – Marathon – 35TH Annual Faro Blanco Invitational Tarpon Tournament

This unique team tournament in the heart of tarpon season, with two to four anglers per team/boat, allows anglers to fish three of the four nights with three different captains at three different bridges: Bahia Honda, Long Key and the world-famous Seven Mile. Proceeds from the charity tournament benefit Ronald McDonald House.

JUNE

Jun 1 – 5 – Key West – Key West Pride

Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that makes the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, a street fair on famed Duval Street, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively “Rainbow Roast.”

Jun 1 – 5 Key West – Fringe Theater Presents: A Fabulous Evening with Lillian Baxter!

Hollywood’s favorite Has-Been returns to Key West. Show tunes? You bet! Gay anthems? Why not! Fabulous costumes? As long as they’re within budget. Buckle in, glitter up, and spend A Fabulous Evening with Lillian Baxter. Performances start 7 p.m. at Fringe Theater, 600 White St. Tickets, show times and dates online.

Jun 3 – 5 – Lower Keys 29th Annual Original Big Pine & Lower Keys Dolphin Tournament

The Lower Keys Chamber of Commerce presents this annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in open, ladies and youth divisions.

Jun 3 – 5 – Key Largo With Annual Skippers Dolphin Tournament

This tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn. Cash prizes of over $60,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.

Jun 10 – 12 – Islamorada Ladies Let’s Go Fishing Screamin’ Reels Tournament

Intended for novice anglers, this weekend is about learning and a non-intimidating, fun competition with the Ladies Let’s Go Fishing university organizers. Species include legal inshore and offshore fish. Charter a professional boat or fish on your own boat. This is a casual tournament with prizes for heaviest offshore fish, longest inshore fish and drawings for prizes of those who caught fish, plus bonus drawings. Dates and schedule subject to change.

Jun 10 – 11 – Islamorada Eighth Annual Ladies Dolphin Tournament

Hosted by the Florida Keys Elks Lodge, this sixth annual event welcomes female angler teams to compete for the highest aggregate weight of three dolphin fish, as well as junior anglers under 16 years of age. Cash and prizes are awarded to first- through third-place finishers, and for the largest dolphin caught. Registration form online.

Jun 15 – 19 – Key West – I love Stock Island Festival

This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experience in local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West.

Jun 17 – Key West – CFK Swim Around Key West

Embark on an adventurous swim – a 12.5 loop around the island with fantastic landscape views of Key West and swimming in the pristine waters. Compete in different categories of either a solo swimmer, a solo swimmers with fins, a solo swimmers using a mermaid tail, or a monofin or gather your friends and compete in the relay category of a 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim.

Jun 17 – 19 – Key West VFW Fishing Tournament

A family fun tournament, this event awards over $15,000 in total cash and prizes, including $5,000 for the heaviest dolphin. All proceeds benefit disabled and needy veterans of Monroe County.

Jun 20 – 24 – Islamorada – 59th Annual Gold Cup Tarpon Tournament

This annual challenge appeals to “tarpon addicts,” and both experienced and novice anglers apply to compete in what is referred to locally as the “Wimbledon of tarpon fishing.” Headquartered at the Lorelei Restaurant and Marina, the all-release event is limited to 25 anglers by invitation only. Partial proceeds benefit the Guides Trust Foundation of the Florida Keys.

Jun 23 – 26 – Key West – 5th Annual Manog Fest Key West

Experience all things Mango through shopping, education and demonstrations. Stroll virtually through a vendor village, enter a poetry contest, photo contest, see virtual culinary and cocktail demos, and more. Details to come for the 2022 event.

Jun 24 – 26 – Islamorada – Ladies Let’s go Fishing Screamin’ Reels Tournament

Jun 29 – Islamorada IFC Captains Cup Dolphin Tournament

Teams of up to four anglers compete for top prizes, and the total combined weight of three fish determines the winning team. If up to 25 boats register, first-prize cash winnings can reach $25,000.

JULY

Jul 9 – Big Pine Key – 38TH Annual Underwater Music Festival

This annual event for both divers and snorkelers is staged at Looe Key Reef, an area of the Florida Keys National Marine Sanctuary about 6 miles south of Big Pine Key. Hosted by the Lower Keys Chamber of Commerce and a local radio station, US1 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs. The festival’s primary purpose is to promote reef protection and eco-conscious diving, but also offers a bucket-list underwater experience.

Jul 16 – 17 – Marathon – 2nd Annual Florida Key’s BrewBQ

Located at Marathon Community Park, the smoked barbecue and craft beer festival-style event is to feature mouth watering BBQ, and tons of delicious craft beers to wash it down. Highlights also are to include an amateur BBQ cooking competition with prizes, vendors, boats, live music, kids’ games and more. Daily hours Saturday 11 a.m. to 9 p.m., Sunday noon to 5 p.m. Sponsored by the Marathon Chamber of Commerce.

Dec 1, 2021 – Jul 31, 2022 Key West Fishing Tournament

More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

Jul 20 – 23 – Key West Stock Island Marina Village Key West Marlin Tournament

Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Jul 23 – 24 – Key West – Hemingway 5K Sunset Run & Paddleboard Race

The Hemingway 5k Sunset Run & Paddleboard Race is to challenge competitors Saturday, July 23. Race begins 5 p.m., from Southernmost Beach, 1405 Duval St. Celebrate your accomplishment while easing sore muscles from the race with an all-level yoga recovery session Sunday, free to all participants.

AUGUST

Aug 10 – 14 – Key West – Key West Tropical Heat

Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s intriguing events range from pool parties to a sunset cruise to late-night gatherings at the island’s LGBTQ bars and nightclubs.

Aug 11 – 14 – Key West – 26th Annual Key West Lobsterfest

Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.

SEPTEMBER

UPDATES FOR THE REMAINDER OF 2022. IT’S TIME TO LIVE LIFE!

Sept 1 – 5 – Key West – Key West Brewfest

Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, the lavish BrewFest Tasting Festival held Saturday on Key West’s South Beach and other enticements.

Sept 2 – 4 – Marathon – Florida Keys Hero’s Tribute Weekend

Military, fire rescue, police and medical personnel are to be honored with specially priced rooms at Hawks Cay Resort and recreational programs as part of an annual Heroes Salute Labor Day weekend. Highlights of the patriotic, “heroes in action” weekend include a family fun night, a virtual 5k Run/Walk, live entertainment by local musicians, food, games and contests.

Sept 6 – Oct 16 – Key West – Kids Free Florida Keys

Through Oct. 16, families can explore Florida Keys attractions, tours, watersports and other offerings with a value-added program that provides free admission or opportunities for children ages 12 and under. Download coupons for visits to nature-themed and historic attractions, restaurants and activities ranging from snorkel tours to aquarium explorations. The site features links to participating businesses and information about their offerings. Each child must be accompanied by at least one paying adult. Presented by the Key West Attractions Association.

Sept 10 – Islamorada – Swim for Alligator Lighthouse

Individuals, two- and four-person relay teams have up to seven hours to complete the eight-mile roundtrip course. The course features an in-water start and a beach finish, ending shoreside during this tropical open-water swimming event.

Sept 7 – 11 – Key West – Womenfest Key West

The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination.

Sept 7 – 11 – Key Largo – Florida Keys Lionfish Derby and Festival

REEF’s 13th annual event will include two full days of lionfish fishing culminating in a family-friendly festival, open to the public and to include Lionfish scoring, fillet and dissection demonstrations, Lionfish tastings, Lionfish games and crafts, raffle prizes, live music and other activities and products from dozens of environmentally-minded vendors. Chefs will be providing lionfish cooking demonstrations and special dishes and drink special will be available. Early-bird registration discounts are available.

OCTOBER

October 1 – Key West – 25th Annual Key West Paddle Classic

Water sports enthusiasts on paddle boards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.

Oct 7 – 9 – Islamorada – Ladies Let’s Go Fishing! Keys Saltwater Weekend Seminar & Fishing Fever Inshore/Offshore Tournament

Female fishing fans can learn or polish angling skills during the award-winning weekend seminar. More than 8,000 female graduates have immersed themselves in the annual lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.

Oct 13 – 15 – Key West – Legends of Music Row Music Festival

Book your tickets for this extraordinary three-night event, including an option for a VIP experience with an exclusive, up-close-and-personal concert setting featuring songwriting legends in country music. A musical experience like no other, Legends of Music Row is to be hosted by Country Music Hall of Fame songwriter Dean Dillon.

Oct 13 – 16 – Key Largo – Reef Fest 2022: An Annual Celebration of Marine Conservation

REEF Fest includes diving, snorkeling, kayak eco-tours, ocean-themed seminars, and social events. Since 2015, REEF has hosted REEF Fest each fall in the Florida Keys. Divers, snorkelers, and ocean lovers attend REEF Fest to celebrate their love of marine life and learn about the latest in conservation. Weekend schedule is to include REEF Marine Conservation Programs, dive, snorkel and kayak trips, seminars with renowned ocean experts and more.

Oct 21 – 30 – Key West – Key West Fantasy Fest

This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2022 theme is ‘Cult Classics and Cartoon Chaos.’ Check the website for the full schedule and more details.

Oct 21 – 22 – Key West – Bahama Village Goombay Festival

Held in Key West’s historic Bahama Village neighborhood, the lively, family-friendly Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage. FREE event, noon to midnight both days.

Oct 22 – Key West – Smallest Parade in the Universe

Everyone’s favorite miniature parade returns! Artists compete for cash prizes and bragging rights with pint-sized floats to suit this year’s Fantasy Fest theme: Cult Classics and Cartoon Chaos! The fantastical entries are on view all month before being auctioned Oct 22 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House

Oct 23 – Key West – Zombie Bike Ride

A pre-Halloween tradition for visiting and local families and groups, the ride typically draws several thousand men, women and children — and even a few pets. Garbed in ragged costumes and frightening face and body makeup, they pedal along the island city’s Atlantic Ocean shore in a deliciously scary spectacle. The wacky event begins at 2 p.m. when Zombie Land opens, at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd. Live music, entertainment and face painting.

Oct 26 – Key West – Pet Masquerade

This year’s carousel of frisky pets and playful owners perform for fame, fortune and prizes onstage at Key West Amphitheater, at Truman Waterfront Park. Starts 6:30 p.m. Proceeds benefit the Lower Keys Friends of Animals; free to watch.

Oct 27 – Key West – 39th Annual Key West Headdress Ball

Talented headdress makers compete for first- through third-place prizes. The popular event returns to the Coffee Butler Amphitheater, Truman Waterfront Park. Doors open to the outdoor gala around 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online.

Oct 28 – Key West – Masquerade March

Costumed merrymakers parade through Old Town. Begins at Old Town Wine & Spirits, Truman Avenue at 5:30 pm; free to join the crowd as they parade through Old Town with music and noisemakers

Oct 29 – Key West – Bud Light Fantasy Fest Parade

Lavishly decorated floats, costumed characters, bands and elaborately garbed marching groups are to make a splash on Key West’s Duval Street. The glittering parade is the traditional highlight of the annual Fantasy Fest masking and costuming celebration. Parade steps off at 7 p.m. Floats, bands and other parade participants traditionally travel down Whitehead toward the Gulf of Mexico, turn onto Front Street and then proceed the mile down Duval to the Atlantic Ocean

NOVEMBER

Nov 5 – Marathon – Stone Crab Claw Eating Contest

In this unique contest, amateur eaters age 18 and over compete to crack and consume 25 stone crab claws, picking them clean, in the fastest time. If a tie occurs, a 10-claw tiebreaker will be held to determine the winner. The much-anticipated event is to begin at 1p.m., staged at Keys Fisheries Market and Marina, located off U.S. Highway 1 on Marathon’s 35th Street gulfside. Contestants must register by noon. Stone crab season runs from Oct. 15 to May 1.

Nov 6 – 13 – Key West – Race World Offshore World Championship

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.

Nov 10 – 13 – Key West – Green Fairy Fest

An official Raceworld Offshore event, enjoy grand tastings, silent auction, concerts, sunset sails, performers, cocktail competitions, tastings and much more. Events are to be headquartered at Stock Island’s Absinthe House.

Nov 12 – Islamorada – MOTE’S Ocean Fest

Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment! From 10 a.m. to 4 p.m., enjoy a day of fun, crafts, games, music, food and shopping during the outdoor community celebration of the oceans at Founders Park’s green lawn and amphitheater. Attendees can explore conservation and environmental exhibits, meet live animals and experience touch tanks, view and purchase wares from local marine artists and vendors, enjoy music and try their skill at active amusements. Meet Mote scientists along with other conservation and environmental organizations.

Nov 13 – Key Largo – First State Bank Key Largo Bridge Run

Runners from around the U.S. and other countries can challenge their best times amid spectacular scenery during this Half Marathon &5k Run/Walk weekend event over the beautiful Jewfish Creek Bridge at the top of the Florida Keys Overseas Highway, overlooking the Key Largo Bay. Sunday’s race starts and finishes at Gilbert’s Resort. The course is USATF certified.

Nov 26 – Big Pine & the Lower Keys – Big Pine & The Lower Keys Island Art Festival

Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts and handcrafted holiday items. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside, from 9AM to 3PM. Admission is free.

DECEMBER

Dec 1 – Jan 1 – Key West – Key West Holiday Fest

Dec 17 – Key West – 14th Annual 5K Rudolph Red Nose Run

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.

Dec 31 – Key West – New Year’s Eve: Conch Shell Drop at Sloppy Joe’s

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.

Dec 31 – Key West – New Year’s Eve Shoe Drop Celebration

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