Dec 1, 2022 – Jan 1, 2023 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.”
JANUARY
Jan 1 – The Florida Keys
Key West Artisan Market: The Hangover Edition
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.
Jan 3 – Key Largo
Orange Bowl Swim Classic
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 5 – 8 – Key West
Pole Vault in Paradise Competition
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.
Jan 7 – Key West
Pancake Breakfast – Higgs Beach
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.
Jan 12 – 15 – Key West
Key West Literary Seminar
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.
Jan 13 – 15 – Key West
25Th Annual Key West Half Marathon & 5K Run
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.
Jan 14 – 15 – The Lower Keys
19th Annual Nautical Expo
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.
Jan 14 – 15, 2023 Key West
17Th Annual Florida Keys Seafood Festival
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.
Jan 16 – 20, 2023 Key West
The Southernmost Regatta
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.
Jan 17 – 21 – Key West
Rokisland Fest 2023
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.
Jan 20 – 22 – Marathon
Sombrero Beach Run Weekend
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.
Jan 20 – 22 – Marathon
Island Boat Show & Festival
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.
Jan 21 – Key Largo
Pops in the Park: Sailing Away to Key Largo
“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).
Jan 24 – 30, 2023 Key West
Kelly Mcgillis Classic
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.
Jan 24 – 28 – Key West
Mile 0 Fest Key West
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 Amphitheater, 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.
Jan 25 – 29 – Key West
Key West Food And Wine Festival
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.
Jan 28 – 29 – Key West
38Th Annual Key West Craft Show
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.
Jan 29 – The Lower Keys
Spanish Fly Music Festival
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.
Jan 31 – Feb 4 – Key West
Key Western Fest
More than 20 of the very best classic country bands bring their massive hits to the Southernmost City in the U.S. for a week of unforgettable songs, sun & sand. Take in the warm sunshine and tunes during the day at the island’s iconic bars, snag a bite from one of the renowned restaurants, leave your troubles on land during a live-music sail on a comfy catamaran, and then sing your heart out under the stars at night at the Truman Waterfront Amphitheater, 21 Quay Rd, Key West. Passes and packages available online.
FEBRUARY
Feb 2 – 5 – Key Largo
Buccaneer Blast Regatta 2023
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. 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, 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 18 – Key Largo
Upper Keys Garden Club Annual Garden Walk
Visitors can stroll among and view native plants and lush landscaping among private, resort and public gardens while getting ideas for tropical gardening. Event tickets with a map of featured garden locations are to be available, hours traditionally are open from 10 a.m. to 4 p.m.
Feb 18 – Islamorada
Pops in the Park: “Who Let the Dogs Out?
Uh-Oh…“Who Let the Dogs Out?!” 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 animal-themed music. Bring your pooch for a Puppy Parade. Special Guest: Humane Animal Care Coalition with adoptable pets.
Feb 18 – 20 – Key West
Presidential Families Weekend Celebrates History And Bipartisanship
The Key West Harry S. Truman Foundation, in partnership with The Society of Presidential Descendants, presents a series of special events Presidents’ Day Weekend at the Harry S. Truman Little White House. On Sat. Feb. 18, a panel of presidential descendants discusses American Bipartisanship, and on Sun. and Mon., Clifton Truman Daniel, the grandson of Harry S.Truman, performs the acclaimed stage production, “Give ‘Em Hell, Harry!” Find more event information and ticket sales online. 111 Front Street, Key West.
Feb 25 – 26 – Key West
Old Island Days Art Festival
Aficionados of fine art can discover creative offerings by approximately 100 artists, chosen from several hundred applicants from around the United States and Canada. The nationally recognized open-air show takes place from 10 a.m. to 5 p.m. each day at Key West’s Truman Waterfront Park, located at the end of Southard Street past the Truman Annex neighborhood. The two-day event typically features a blend of Florida Keys talents and fine artists from other locations, all gathered to showcase their work to connoisseurs, collectors and other attendees during the free-admission show.
MARCH
Nov 8 2022 – Mar 7 2023 – Key West
Tuesday Evening GLOW Hours at Hugh’s View Rooftop
Just in time for sunset, The Studios of Key West’s Hugh’s Rooftop remains open on Tuesday evenings to panoramic vistas and a cash bar. Doors open at 5 and close at 5:30 p.m., or when capacity of 50 guests is reached. The bar is open until 7 p.m., admission is free, and everyone looks great in the golden twilight. 533 Eaton St., Key West.
Mar 5 – Key West
60Th Annual Conch Shell Blowing Contest
An island tradition for 60 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.
Mar 11 – 12 – 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 – Key West
Anne Mckee Artists Fund Fine Art Auction
Aficionados can expect to find fabulous works from some of the Keys’ established local favorites as well as discover the talent of some exciting new emerging artists. The auction is a great opportunity to add some unique new treasures to your art collection. Collectors can choose from the works of celebrated and renowned local masters to fresh new talents. To be held at Studios of Key West, doors open 6:15 p.m., starts 7 p.m.
Mar 18 – Islamorada
Pops in the Park: Keys Community Concert Band
“Festival of Music” 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 movie, Broadway, and patriotic music, including a special sensory presentation of Vivladi’s Four Seasons. Special Guest: Ukelule Joy and the Sweet Teas!
APRIL
Apr 1 – 2 – Islamorada
31st Annual Florida Keys Island Fest
Island Fest returns to Islamorada with a juried art show, live music, vendors, food and drinks, sand castle building contest, 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 7 – 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, and the third in the Redbone Trilogy Series. Anglers are to fish twice, at sunrise and sunset. There are prizes for guided and unguided categories, as well as a silent auction for great merchandise and fishing trips.
Apr 15 – 16 – Key West
Nas Key West 2023 Southernmost Air Spectacular
The U.S. Navy Flight Demonstration Squadron the Blue Angels are to be taking to the skies at Boca Chica Field, at Naval Air Station Key West. This year’s theme is ‘200 Years of the Navy in Key West.’ The NAS Key West Southernmost Air Spectacular is the largest family-oriented event in the Florida Keys, attracting over 50,000 spectators in a single weekend. It is an unmatched source of FREE family entertainment.
Apr 21 – 30 – Key West
41st Annual Conch Republic Independence Celebration
Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent “nation’s” 41st birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, and more. The annual Conch Republic Independence Celebration commemorates the Keys’ symbolic 1982 secession from the United States and reinvention as the eccentric republic.
Apr 22 – The Florida Keys
Pops in the Park: Keys Community Concert Band
“What a Wonderful World” 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 international music, story slams, poetry and narrative music. Special Guest: Upper Keys Drum Circle (bring your drum or use one of ours!)
Apr 28 – 30 – Marathon
7-Mile Offshore Grand Prix
Race World Offshore is excited to bring offshore racing back to Marathon and showcase the world’s best and fastest boats, in this kick-off to the 2023 APBA National Race Series. Race boats will navigate a new course in the Gulf of Mexico, close to shore, alongside the recently renovated Old 7 Mile Bridge, that allows fans to be up close. Further course details, lodging and event details are to be announced,
MAY
May 3 – 7 – Key West
27Th 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 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 7 – Key Largo
Key Largo Triathlon
This event will feature an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race. Swim, bike and run in paradise! Come for the weekend or make it an escape. The swim takes place in the beautiful clear waters at John Pennekamp Coral Reef State Park (MM 102.5); the bike will be out and back on Overseas Highway/Card Sound Road. The 10K/5K run takes you through a lovely, laid back Florida Keys neighborhood.
JUNE
Jun 7 – 11 – Key West
Key West Pride
Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make 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, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively “Rainbow Roast.”
Jun 9 – 11 – Key Largo
Miami Boat Rally
Designed as a recreational, nautical, and sporting activity for the whole family to kick off summer vacation, up to 100 boats of various sizes and models are expected to meet up and safely navigate roundtrip from/to Miami, through staged stops and sandbars offshore of Key Largo and Islamorada. Each boat earns points for timing and activity participation based on the rally schedule. An awards ceremony with prizes and raffle drawings is to cap off the day’s fun.
Jun 17 – Key West
CFK Swim Around Key West
Embark on an adventurous swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 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 22 – 25 – Key West
Sixth Annual Mango 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 2023 event.
JULY
Dec 1, 2022 – Jul 31, 2023 – Key West
Key West Fishing Tournament
More than 40 species of fish are targeted during the multimonth 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.
Key West / July 1
Shakedown on the Green — Key West Island Market
All are welcome the first Saturday of every month for Shakedown on the Green: Key West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.
Marathon / July 1 – 4
Isla Bella Resort: Country in the Keys
A four-day concert series featuring a variety of artists direct from the world of country music and talent from Sony Music Publishing Nashville. The event concludes the night of July 4th with a grand finale fireworks show. The concert and fireworks are exclusive to Isla Bella resort guests. The resort is located at 1 Knights Key Boulevard oceanside.
Key West / July 1
Meet the Mermaids at Florida Keys Eco-Discovery Center
“Meet the Mermaids” under the sea at the newly renovated Eco-Discovery Center at 35 E. Quay Rd. Enjoy two hours of an educational, “fintastic” time from 10 a.m. to noon while you meet and take plenty of “shell-fies” with the 2023 Key West Mermaid Pod. There will be special appearances by King Neptune, and everyone’s favorite under-the-sea couple, Ariel and Prince Eric. A $10 cash donation is suggested to the Florida Keys National Marine Sanctuary. The event is part of this year’s Key West Mermaid Festival taking place through July 4th.
Key West / July 1 – 4
Key West Mermaid Festival
The family-friendly festival features interactive mermaid adventures while raising awareness of oceans and salty shores. Events include mermaid meet-ups, swim encounters with the festival’s mermaid pod, ocean-themed parties and more. A portion of festival proceeds is to benefit Reef Relief’s efforts to protect the coral reef ecosystem.
Key West / July 2
Key Lime Pie Drop
An part of the Key Lime Festival, come out to see the most creative minds in Key West attempt to outsmart gravity by finding a way to drop a Key lime pie from the top of the lighthouse to the ground… without damaging the pie. Try dropping your own pie, or just enjoy the spectacle from the ground. It’s free to watch and to enter the competition, but participants must register in advance on the festival website. The winner takes home a cash prize. 11 a.m. to 2 p.m. at the lighthouse, 938 Whitehead Street.
Big Pine & the Lower Keys / July 3
Monroe County Bicentennial Fireworks & World’s Largest Key Lime Pie
The public is invited to celebrate Monroe County’s bicentennial July 3 — 200 years to the day after Monroe County’s 1823 establishment — with a 5 to 10 p.m. family-friendly gathering at Big Pine Community Park at 31009 Atlantis Road. Highlights are to include the creation and serving of the world’s largest Key lime pie, live music by Brian Roberts and the Prime Movers and others, a bounce house and games for kids, food trucks, beverages for sale, and a glittering fireworks and laser show from a barge in the Gulf. Fireworks begin at 9 p.m.
Key West / July 4
Fourth of July Firecracker 5k Run/Walk
Start the holiday on Tuesday, July 4th with a bang at the annual Firecracker 5k, which begins and ends at the Edward B. Knight Pier, 1800 White Street. The race starts at 7:30 a.m. Cost is $30 for both runners and walkers. Advance registration available online.
Key West / July 4
World Famous Key Lime Pie Eating Contest
Watch contestants compete for the title of Key Lime Pie Eating Champion in this annual competition, the highlight o the Key Lime Festival. Eaters must clock the fastest time to consume an entire 9-inch Key lime pie topped with whipped cream, without using their hands. $25 for contestants to enter; free for spectators. Enjoy the Key Lime Vendor Village beginning at 11 a.m., with the contest starting at 1:30 p.m., all at the Southernmost Beach Cafe, 1405 Duval Street.
Key West / July 4
Dinner Under the Fireworks, Key West
The Rotary Club Key West holds its annual Patriotic Dinner Under the Fireworks next to the Edward B. Knight Pier at Indigenous Park, 1801 White Street, with dinner and a cash bar by Catered Affairs, music and front row seats to the spectacular fireworks. The event begins at 7 p.m. Tickets are $100 per person.
Key West / July 4
Key West Fireworks
The Rotary Club of Key West presents the annual fireworks show starting at 9 p.m. from the Edward B. Knight Pier, 1800 White Street. View for free from Higgs Beach, Smathers Beach or by boat. Rotary also offers a ticketed VIP dinner event at Indigenous Park next to the pier.
Marathon / July 4
Marathon Fourth of July Parade & Sombrero Beach Park Celebration
The annual Marathon Fourth of July Parade begins at 11 a.m. at Marathon High School, 350 Sombrero Beach Rd., proceeding to Sombrero Beach Park, 2130 Sombrero Beach Rd. An all-day holiday celebration at the park begins after the parade with burgers, hot dogs, beer and other food and drink sales by the Rotary Club of Marathon to fund scholarships for local students. What is known as the biggest and the best fireworks display in the Keys is to begin just after sunset.
Big Pine & the Lower Keys / July 8
39th 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 local radio station, U.S. 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs. Photographers, videographers and filmmakers come from around the world to film the colorful festival, with costumed divers pretending to play faux musical instruments in the undersea environment to music piped underwater. The festival’s primary purpose is to promote reef protection and eco-conscious diving, but also offers a bucket-list underwater experience.
Key West / July 11
24 North Hotel: Paint & Sip Night with Artist Lance Berry
Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West character, artist, and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you’ll need to create your own masterpiece. The class takes place at Republic Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.
Marathon / July 14 – 15
Florida Keys Brew-BQ
The third annual BrewBQ takes place Friday and Saturday at Marathon Community Park, mile maker 49, featuring mouth watering barbecue and and plenty of craft beer to wash it down. Highlights include the amateur BBQ cooking competition along with vendors, live music, kids’ games and more. Friday from 5 to 9 p.m.; Saturday 11 a.m. to 8 p.m. Sponsored by the Marathon Chamber of Commerce. $5 per person, per day.
Key West / July 15
Mel Fisher Days
This annual tribute celebrates Mel Fisher, the Key West treasure hunter who lead the 16-year search for the Spanish galleon Atocha, and whose motto “Today’s the Day” inspired people world-wide to follow their dreams. The Dock Party celebration takes place Saturday at Schooner Wharf Bar, 202 William St. beginning at 4 p.m., with Mel Fisher trivia games, a 50/50 raffle, silent and live auctions, live entertainment and the presentation of the Mel Fisher Lifetime Achievement Award. An online auction opens in advance of the event on June 15. Net proceeds benefit Wesley House Family Services and the Michael J. Abt Have a Heart Foundation.
Big Pine & the Lower Keys / July 16 – 19
Del Brown Permit Tournament
Anglers fly fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well. All tournament events are based at South of Seven at Sugarloaf Lodge, mile marker 17 bayside.
Key West / July 18 – 23
Hemingway Days
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Tuesday through Sunday, July 18-23, 2023, for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky “Running of the Bulls,” presentations, prose and poetry readings, a commemoration of the 124th anniversary of his July 21 birth, a museum exhibit, a 3-day marlin tournament, a street fair, a 5k run and paddleboard race, a walking tour and the announcement of the Lorian Hemingway Short Story Competition. Find details online.
Key West / July 19 – 22
Key West Marlin Tournament
Coinciding with the 43rd annual Hemingway Days celebration, anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. The event awards $25,000 to the first-place team with the most points for blue marlin, white marlin and spearfish. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day for additional points. Tournament events are based out of the Perry Hotel & Marina, 7005 Shrimp Road.
Key West / July 20 – 22
2023 Hemingway® Look-Alike Contest
Dozens of stocky, bearded men resembling Ernest Hemingway are to return to Key West for the 2023 Hemingway® Look-Alike Contest. Staged at Sloppy Joe’s Bar, where it began some 40 years ago, the contest’s preliminary rounds are slated for 6:30 p.m. July 20 and 21. The winner is to be chosen July 22, in a final round starting at 6:30 p.m., from a field of about 24 Hemingway hopefuls.
Key West / July 22
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 Street. Celebrate your accomplishment while easing sore muscles from the race with an all-levels yoga recovery session Sunday, free to all participants. The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.
AUGUST
Key Largo / August 4 – 6
Miami Boat Rally
Designed as a recreational, nautical and sporting activity for the whole family, up to 100 boats of various sizes and models are expected to meet up and safely navigate roundtrip from/to Miami, through staged stops and sandbars offshore of Key Largo and Islamorada. Each boat earns points for timing and activity participation based on the rally schedule. An awards ceremony with prizes and raffle drawings is to cap off the fun.
Key West / August 5
Shakedown on the Green — Key West Island Market
All are welcome the first Saturday of every month for Shakedown on the Green: Key West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.
Marathon / August 5
Family Color Run
The Family Color Run is a fun, 5k run event where participants are showered with brightly colored, non-toxic powder or paint at various points along the route in vibrant hues of red, blue, green, yellow and pink. Be a part of this fun and festive event. $25 per person includes race shirt, goodie bag, medal, plus food and drink. Race starts at 11 a.m. at Marathon Community Park, 200 36th Street Ocean.
Key Largo / August 8
REEF Fish & Friends: Introduction to Fish Portraits
Stacey Henderson, Program Services Coordinator at REEF, will share tips and tricks for taking your best underwater photos. No matter what camera you are using, or whether you consider yourself a beginner or expert photographer, there is something for everyone. As a well-versed underwater photographer, Stacey will discuss composition, lighting, and most importantly, how to get your keeper shot. The free evening kicks off with a social from 6:15 to 7 p.m., followed by the presentation from 7 to 8 p. m. at the REEF campus, 98300 Overseas Highway (median).
Key West / August 9 – 13
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 events range from all-male theme parties, pool parties and entertainment showcase at the island’s LGBTQ venues. Attendees can also enjoy activities ranging from eco-tours to museum explorations.
Key West / August 10 – 13
26th Annual Key West Lobsterfest
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” with a savory and packed schedule of events ranging from a traditional lobster boil to special dinners, and a lively street fair. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. The free street fair takes place Saturday, Aug. 12th on Duval Street from noon until 11 p.m. with live music and over 80 vendors selling fresh Florida lobster, plus other food and drink options.
Islamorada / August 14
Bartenders Dolphin Tournament
This new one-day “funday” dolphin tournament is open to bartenders and restaurant employees. Kick-off and weigh-in events are to be held at the Florida Boy restaurant at mile marker 68 in Layton.
Key Largo / August 20
Key Largo Triathlon
This event features an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race through flat calm, crystal clear water at the main beach at John Pennekamp Coral Reef State Park. The beautiful clear salt water with no current will be warm and relatively shallow. Your bike will be out and back on Overseas Highway/Card Sound Road. The 10k/5k run takes you through a lovely, laid-back Florida Keys neighborhood. Finish back at Pennekamp and bask in the glory as you receive your coral reef finisher medal.
Key West / August 31 – September 4
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, Sept. 2nd on Key West’s South Beach and other enticements.
SEPTEMBER
Key West / August 31 – September 4
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, Sept. 2nd on Key West’s South Beach and other enticements.
Marathon / September 1 – 3
Florida Keys Heroes Salute 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 5k Run/Walk, live entertainment by local musicians, a fireworks show, food, games and contests.
Marathon / September 3
Hawks Cay Resort: Keys to Country
Hawk’s Cay Resort on Duck Key presents the next “Keys to Country” concert and resort package starring Craig Morgan & Friends appearing live on Sept. 3rd. Headliner Morgan’s signature hits include “Redneck Yacht Club,” “Bonfire,” Almost Home,” “Wake Up Loving You,” and more. Other artists in the lineup include Marla Cannon and Shane Minor. The concert is limited to resort guests who book the Keys to Country package. Hawk’s Cay Resort is located at 61 Hawks Cay Blvd.
Key West / September 6 – 10
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.
Key Largo / September 7 – 10
Florida Keys Lionfish Derby and Festival
Hosted by Reef Environmental Education Foundation, the event includes two full days of lionfish fishing by teams of up to four divers. Prizes are to be awarded for the most lionfish, smallest and largest lionfish and the most lionfish prize in each of two divisions. The tournament is followed by an open-to-the-public lionfish festival on Sunday at Postcard Inn Beach Resort & Marina to include lionfish fillet, dissection and cooking demonstrations, lionfish tastings, raffle prizes and more. The lionfish derby awards ceremony takes place at 3:30 p.m. at the festival.
the Florida Keys / September 13 – 18
Big Gay Key West
Come to the island paradise of Key West for the Big Gay Key West for this gay men’s social event for chubs, bears, chasers and friends with exclusive access to Key West’s four beautiful and luxurious all-male resorts: Island House, New Orleans House, Alexander’s Guesthouse and Equator Resort. Enjoy reciprocal access to all of the guesthouses, which are a short walking distance from each other. Nightly happy hours, rotating pool parties at multiple resorts and bars with complimentary cocktails, hors d’oeuvers, 24/7 access to health club amenities at Island House and many surprises. Book event packages and lodging online.
Islamorada / September 15 – 17
Herman Lucerne Memorial Backcountry Fishing Championship
Named after the man known affectionately as “Mr. Everglades,” the event is headquartered at the Islander Resort. Anglers target fish in multiple species only in the boundaries of Everglades National Park, fishing areas that Lucerne favored. Anglers are challenged to catch at least one tarpon, redfish, snook, seatrout, snapper, bonefish, and black drum. Awards are given in 22 individual categories.
Key Largo / September 22 – 24
Take Stock in Children Backcountry Challenge
This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. Fishing is allowed around the clock from Friday night through Sunday afternoon. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.
OCTOBER
Islamorada / October 9 – 11
Islamorada All-Tackle Bonefish and Permit Championship
Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants.
Islamorada / October 13 – 15
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 skills-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.
Key Largo / October 19 – 22
Reef Fest 2023: 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.
Key West / October 20 – 29
Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. In recognition of the 200-year anniversary of Monroe County and Key West’s first Naval base, the 2023 theme is ‘“Uniforms & Unicorns — 200 Years of Sailing into Fantasy.” Check the website for the full schedule and more details.
Key West / October 23
Heroes and Villains 5k Run/Walk
Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at Southernmost Beach Café, 1405 Duval Street. The post-race party is the Official Fantasy Fest Monday Night Party. You can register online for both the race and the post-race Hog Roast and Party, or register separately for either event.
NOVEMBER
Key West / November 5 – 12
Race World Offshore – Key West 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. Fan zone and entertainment at Truman Waterfront Park. Both general admission and VIP viewing options available.
Islamorada / November 9 – 11
11th Annual All-American Backcountry Fishing Tournament
Each year anglers compete for honors in the fly, general tackle, and artificial divisions for snook, redfish, bonefish, tarpon and permit with tournament activities at the Cheeca Lodge & Spa. Each year several war heroes are invited to compete in honor of Veterans Day. Proceeds from the tournament benefit the Bonefish & Tarpon Trust, a nonprofit organization whose mission is to conserve and restore bonefish, tarpon and permit fisheries and habitats through research, stewardship, education and advocacy.
Key West / November 15 – 19
Key West Film Festival
The Key West Film Festival is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. It strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. Named one of the “25 Coolest Film Festivals in the World” by Moviemaker Magazine. Films for the 2023 festival are still being submitted and evaluated. Stay tuned to find the full program of films, presentations and events online.
Big Pine & the Lower Keys / November 17 – 19
Sugarloaf Showdown
Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. Participants must use either spin or fly tackle to pursue the catch-and-release tournament’s target species of bonefish, permit and barracuda. A maximum of three fish of each species can be scored per team per day.
DECEMBER
Islamorada / May 20 – December 31
History of Diving Museum: Aquanauts to Astronauts Exhibit
The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.
Key West / December 3
Mote’s Ocean Fest: A Community Celebration
Underwater and outdoor enthusiasts, ecotravelers 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.
Key West / December 8
Key West Art & Historical Society: 7th Annual Holiday Concert & Bazaar
This popular annual celebration features some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. The bazaar offers shoppers a treasure trove of unique gift items to choose from, and there will be plenty of food and festive libations at this event that is free and open to the public. Located on the front porch and the street in front of the museum at 281 Front Street.
Key West / Dec 31
New Year’s Celebration at Schooner Wharf
The Unique Schooner Wharf Bar’s Seaport Tradition – Lowering of the Pirate Wench at Midnight. Party starts early in the day with 3 Local and National Acts – Party Favors – Champagne & Fun