DECEMBER 2024 – JANUARY 2025
Dec 1, 2024 – Jan 5, 2025 Islamorada
THE PROTECT CENTER: SEA OF TREES
Over 100 uniquely decorated and sponsored trees light your way nightly from 10 a.m. to 6 p.m. daily from Nov. 29 through Jan. 5. In addition to the beautiful lights and trees, you’ll find photo opportunities and shopping. On these select nights – Nov. 29, 30; Dec. 1, 6, 7, 13, 14, 20, 21, 22 from 6 to 9 p.m. – enjoy Santa’s Village with holiday-themed cocktails and snacks, workshops for kids and visits with Santa. Admission of $10 adults; $5 kids supports the Dolphin ICU at The Protect Center. MM 82 bayside.
JANUARY
Jan 2 – 4, 2025 Key West
WATERFRONT PLAYHOUSE: VAGINA MONOLOGUES
Featuring talented local voices, Waterfront Playhouse presents Eve Ensler’s groundbreaking show, “The Vagina Monologues.” The show is part of the theater’s Spotlight series. Shows at 8 p.m. 407 Wall St. at Mallory Square.
Jan 2 – 30 Key West
STUDIOS OF KEY WEST: JEFFREY CARDENAS – ON THE REEF
Key West resident Jeffrey Cardenas has traveled from Polynesia to the Mediterranean and Caribbean Sea, photographing vibrant coral reef ecosystems. His work reveals the beauty and essential role of coral reefs in supporting diverse marine life, prompting reflection on their significance and the urgent need for their conservation. 533 Eaton St.
Jan 4 Key West
POLE VAULT IN PARADISE
Pole Vault in Paradise is an all-comers pole vault competition taking place from 9 a.m. to 6 p.m. on Jan. 4 at Higgs Beach, 1000 Atlantic Ave. Participants compete in youth, masters and elite categories, with prize money for the elites. All pole vaulters are welcome and should register online. If you’re not a pole vaulter, bring a chair or beach towel and watch the competition. Admission is free and food and beverage sales support the Key West High School track team. The event is sanctioned by the USATF and is on the World Athletic Calendar.
Jan 5 – 9 Key West
KEY WEST LITERARY SEMINAR: WRITERS’ WORKSHOP PROGRAM
Writers at all stages of development have opportunities to explore the craft of writing at eight distinct workshops available through Key West Literary Seminar before the main seminar begins. Workshops available on the January 2025 program are: Small Miracles: An Exploration of the Short Story; Key West and the Queer Home; Paths Through the Labyrinth: Plot and Structure, Structure and Plot; The Poet as Chronicler of Our Times; Writing Into the Unknown; Developing the Young Adult Voice; Writing Poetry Alongside The Iliad; and The Intersection of Home, Memory and Imagery in Memoir.
Jan 7 – 8 Key West
STUDIOS OF KEY WEST: SUSAN WERNER & JONATHA BROOKE IN CONCERT
Join acclaimed folk rock artists Susan Werner and Jonatha Brooke for a night of innovative songwriting, captivating harmonies, and masterful musicianship. Jan. 7 at 7 p.m. in the Studio’s Helmerich Theater and Jan. 8 at 6 p.m. on the rooftop at Hugh’s View. 533 Eaton St.
Jan 9 – 12 Key West
KEY WEST LITERARY SEMINAR: FAMILY
The Key West Literary Seminar is a four-day literary celebration that explores a different theme each year. The 2025 seminar theme is “Family” — the one we’re born into, those we’ve later built or chosen, and the ones we’ve lost or found or run as far away from as possible. For “Family,” the seminar brings together writers who can help us understand how the ties that bind shape the stories we tell, the worlds we move through, and all the imagination’s possibilities for human connection. Featured writers include John Irving, Brando Skyhorse, Paul Harding, Nathan Hill, Dani Shapiro and many more. Programs take place at the historic San Carlos Institute, 516 Duval St.
Jan 9 Key West
KEY WEST THEATER: PAUL POUNDSTONE
Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She performs at Key West Theater for one night. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
Jan 10 Key West
KEY WEST ART & HISTORICAL SOCIETY HISTORIC SEAPORT SAIL: HARRY S. TRUMAN IN KEY WEST
Enjoy a 2-hour Historic Harbor Tour with Truman Little White House docent Rick Warmbold on the S/V Argo Navis, talking about “Harry S. Truman’s Eleven Key West Visits.” The trips departs from the Historic Seaport docks at 0 Margaret St. at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with lite breakfast fare as Warmbold dives into Truman’s eleven working vacations, and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Book reservations online in advance.
Jan 10 -11 The Florida Keys
WOUNDED WORRIER PROJECT SOLDIER RIDE
The Wounded Warrior Project Solider Ride takes place in the Upper, Middle and Lower Keys Jan. 5 and 6. U.S. 1 will be open, but motorists are asked to be patient, use caution and be prepared for possible rolling lane shifts. The ride starts Friday at 8:30 a.m. departing Key Largo VFW, ending around 10:30 a.m. at Three Waters Resort. Riders will then be transported to Marathon, where they will depart from Marathon fire station and cross the 7 Mile Bridge between 1:30 and 2:30 p.m. Saturday, riders depart from NAS Key West at Boca Chica at 10:30 a.m., headed for Bayview Park in Key West. The public is invited to join the riders for a community ride from Bayview Park at 12:45 p.m. to historic military sites in Key West. Patriotic bike decorations are encouraged, along with a suggested donation of $20.
Jan 12 Key West
KEY WEST ARTISAN MARKET: DON’T BE TRASHY!
Key West Artisan Market invites you to help keep our island clean and learn more about the efforts of Plogging the Keys and the Keep Key West Beautiful initiative. Find out how you can help and ways to be a part of the solution. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians, meet local authors and support our featured charity. 10 a.m. to 2 p.m. 1801 White St.
Jan 14 Key West
KEY WEST THEATER: BITCH TROUBLE
Writer performer Alice Johnson Boher takes you on a coming-of-age roller coaster ride of the giddy highs and codependent lows of best friendship. Told in three chronological tales, Bitch Trouble charts Alice from friendless youngster in a lame southern subdivision all the way to one-half of an iconic friend duo in the shadows of Hollywood. Performance takes place in the theater’s Back Stage Listening Room. Doors open 6 p.m.; show 7 p.m. 512 Eaton St.
Jan 14 – 25 Key West
FRINGE THEATER: I LOVE YOU, YOU’RE PERFECT, NOW CHANGE
A hilarious and insightful musical exploration of the epic truths and challenges of modern love and romance. Nightly showtimes 7 p.m. at Key West Armory, 600 White Street.
Jan 15 – 19 Key West
KEY WEST KINGFISH MAYHEM
Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $75,000 first prize with $35,000 and $20,000 going to the second and third place teams, respectively. The tournament is headquartered at The Perry Hotel & Marina.
Jan 16 – 19 Key West
27TH ANNUAL KEY WEST HALF MARATHON & RUNFEST WEEKEND
Enjoy a weekend filled with running and camaraderie including 5k, 8k, 10k and half marathon races. Participants can also sign up for the Papa’s Pilar Rum Stroll and the Bech N’ Beer Mile, and celebrate with recovery and farewell parties.
Jan 21 – 25 Key West
MILE 0 FEST
Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.
Jan 21 – 27 Key West
KELLY MCGILLIS CLASSIC INTERNATIONAL FLAG FOOTBALL CHAMPIONSHIP
Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico, Honduras and El Salvador. Kelly McGillis will serve as grand Marshall for the players’ parade from the historic seaport down Duval Street on Thursday, Jan. 25. Game activities throughout the weekend Jan. 26-28 are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive off Flagler Ave.
Jan 22 Key West
KEY WEST THEATER: MELISSA ETHERIDGE
Don’t miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.
Jan 23 – 16 Key West
WALK ON WHITE THIRD THURSDAY ART WALK
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
Jan 24 Islamorada
COCONUT COVE RESORT % MARINE: ROARING FOR RESCUES
Enjoy an elegant, 1920s-style event from 6 to 10 p.m. at the 6th annual Roaring for Rescues benefit for the Upper Keys Humane Society. Enjoy dancing to live music by Retro Rebel, dinner, entertainment, raffles, a silent auction and more. Mile marker 84.8 oceanside.
Jan 25 Key West
TROPIC CINEMA: MOVIES UNDER THE STARS – WAR GAMES
Don’t miss the monthly free Movies Under the Stars screening – this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins at approximately 6:30 p.m. 416 Eaton St.
Jan 27 – Feb 2 The Lower Keys
WINTER STAR PARTY
Astronomers and astrophotographers from around the globe gather in the Lower Florida Keys to enjoy 180-degree viewing of the Southern Cross and other constellations, comets and stars during the Winter Star Party.
Jan 31 Key West
COFFEE BUTLER AMPHITHEATER: CHICAGO
Hailed as one of the most important bands in music since the dawn of the rock and roll era, the legendary rock and roll band with horns, Chicago, came in as the highest charting American band in Billboard Magazine’s Top 125 Artists Of All Time. And, Chicago is the first American rock band to chart Top 40 albums in six consecutive decades. Doors open at 6:30 p.m.; show at 8 p.m. 21 Quay Rd
FEBRUARY
February 4 Key West
STUDIOS OF KEY WEST: WILL KIMBROUGH IN CONCERT
William Adams Kimbrough is an American singer-songwriter, multi-instrumentalist and producer based in Nashville, Tenn. Kimbrough’s songs have been recorded by Jimmy Buffett, Little Feat, and Jack Ingram, among others. Most recently, their co-written song “Bubbles Up” became Buffett’s first posthumous single and a viral hit. He performs in concert Feb. 4 at 7 p.m. at the Studio’s Helmerich Theater and Feb. 5 at 6 p.m. on the Hugh’s View rooftop. 533 Eaton St.
February 6 – 8 The Lower Keys
CUDA BOWL
Lower Keys shallow water, all release spin and fly flats tournament for barracuda. The event is held the Friday and Saturday before Super Bowl Sunday annually. Tournament events held at South of the Seven, 17075 Overseas Hwy., Sugarloaf Key.
February 7 – 8 Islamorada
KEYS KIDS SAILFISH TOURNAMENT
The 2nd annual Keys Kids Sailfish Tournament for anglers age 16 and younger begins with a kickoff meeting on Friday, Feb. 7 and fishing on Saturday, Feb. 8. More details to come closer to the tournament date. Sponsored by Tackle Center of Islamorada.
February 8 Key West
COFFEE BUTLER AMPHITHEATER: THE GIPSY KINGS FEATURING NICHOLAS REYES
Nicolas Reyes has been the leader and co-founder of the Gipsy Kings for well over 30 years. In the past three decades, the group has dominated the World Music charts and sold more than 14 million albums worldwide. Doors open at 6:30 p.m.; show at 8 p.m. 21 E. Quay Rd.
February 13 – 17 Key West
PRESIDENTIAL FAMILIES WEEKEND
A series of special events takes place over Presidents’ Day Weekend at the Harry S. Truman Little White House. On Thursday, Feb. 13, there is a kickoff “Happy Hour at Harry’s” cocktail and trivia event. Sat. Feb. 15, there is a discussion panel with presidential descendants. There will also be a traditional President’s Day cookout on Monday, Feb. 17 from 11:30 a.m. to 1:30 p.m. with picnic-style food available for purchase. Find more event information and ticket sales online. 111 Front Street, Key West.
February 15 Key West
KEY WEST TROPICAL FOREST & BOTANICAL GARDEN: RUM INFUSED ADULT SCAVENGER HUNT
Don your best pirate or mermaid costume for a night of rum-infused fun during the 2nd annual scavenger hunt throughout Key West Tropical Forest and Botanical Garden. Teams will be created to follow the scavenger hunt rules, with points given for the most items found within one hour. Enjoy food and beverages, including special rum cocktails, and music by John Bartus. Prizes will be awarded for the best pirate and mermaid costume. Proceeds benefit funding bus transportation for Monroe County school children’s educational trips to the garden in the coming year.
February 16 Key West
KEY WEST THEATER: DEBBIE GIBSON
Legendary singer, songwriter and theatrical performer Debbie Gibson is a celebration of passion, innovation, and community. Embrace the opportunity to explore the world of music with her. Doors open at 7 p.m.; show at 8 p.m. 512 Eaton St.
February 17 Key West
COFFEE BUTLER AMPHITHEATER: WILLIE NELSON & FAMILY
With a seven-decade career, Willie Nelson has earned every conceivable award as a musician and amassed reputable credentials as an author, actor, and activist. He continues to thrive as a relevant and progressive musical and cultural force. The iconic entertainer returns for a show Feb. 17 at 7 p.m. with family members and featured artist Randall King at Coffee Butler Amphitheater, 21. E. Quay Rd.
February 17 Key West
KEY WEST THEATER: GARRISON KEILLOR TONIGHT
Garrison Keillor Tonight is an evening of stand-up, storytelling, audience song, and poetry. One man, one microphone. There are sung sonnets, limericks and musical jokes, and the thread that runs through it is the beauty of growing old.
February 21 Key West
KEY WEST ART & HISTORICAL SOCIETY: LET’S DISCO, A NIGHT OF GLITTER, GLAM & GROOVE!
This fundraiser for the Key West Art & Historical Society is the ultimate night to dance, sip and feast in true 70s style! Get ready for a vibrant and high-energy event where the beats are hot, the drinks are flowing at our open bar, and the food is just as fabulous as the fashion. It’s a throwback celebration packed with nonstop fun and retro glamour as well as a fantastic silent auction. 6 to 9 p.m. at Fort East Martello Museum, 3501 S. Roosevelt Blvd.
February 21 – 23 Marathon
SOMBRERO BEACH RUN WEEKEND
Stocked with food, drinks, music and entertainment, the running event is to be staged Saturday, Feb. 22 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. Those completing the event’s 15k challenge receive special gifts. Celebrations and beach activities Friday through Sunday fill the weekend.
February 22 – 23 Islamorada
GIGANTIC NATUTICAL MARKET
You’ll find bargains on everything nautical including clothing, fishing and diving gear, boats, motors, furniture for your boat and home, original artwork and much more. There’s fun for the entire family. Gates open at Founders Park at mile marker 87 bayside at 8 a.m. Saturday and 9 a.m. Sunday. There will be 18 food trucks spread around the park. Parking is available at Coral Shores High School with free shuttle service to the park.
February 22 – 23 Key West
KEY WEST ART & CRAFT FESTIVAL
The Key West Craft Show and Old Island Days Art Festival are now combined to create the Key West Art & Craft Festival. The event includes artist demonstrations, a patron comfort station with valet package check, upscale food trucks, plenty of seating, and fun events and activities for children. The location for the combined show is along the Quay at Truman Waterfront Park, 100 Southard Street.
February 28 Key West
COFFEE BUTLER AMPHITHEATER: BEACH BOYS
See the band whose songs forever changed the musical landscape, The Beach Boys, on the Endless Summer Gold Tour at Key West’s Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Rd. Doors open at 6 p.m.; show at 7:30 p.m.
MARCH
March 2 Key West
KEY WEST THEATER: KEVIN NEALON
Kevin Nealon has set himself apart from other comedic performers with his unique sense of humor, dry wit, and likeable demeanor. Nealon is best known for his nine-year stint as a cast member of NBC’s “Saturday Night Live.” More recently, Nealon has received critical acclaim for his role in the Showtime series “Weeds” and appearances in a string of Adam Sandler movies. He performs two shows on March 2, at 6 p.m. and 9 p.m. Doors open an hour before each showtime. 512 Eaton St.
March 4 – 29 Key West
RED BARN THEATRE: BROOKLYN LAUNDRY
This remarkable comic drama about three sisters and a guy who runs a Brooklyn laundry will remind you of what is important in life. Shows at 7:30 p.m. 319 Duval St.
March 5 – 6 Key West
STUDIOS OF KEY WEST: OVER THE RHINE IN CONCERT
Supremely-talented husband and wife duo Over the Rhine brings their masterful, road-tested music to Key West March 5 at 7 p.m. in the Studio’s Helmerich Theater and March 6 at 6 p.m. on the Hugh’s View rooftop.
March 6 Key West
KEY WEST LITERARY SEMINAR: ELIZABETH BISHOP HOUSE & GARDEN OPENING
Celebrate Key West Literary Seminar’s completed restoration of this national treasure, where the celebrated poet lived and worked in the 1930s and 1940s. Open to the community. 4 to 6 p.m. 624 White St.
Mar 8 – 9 Marathon
MARATHON SEAFOOD FESTIVAL
The Marathon Seafood Festival is the premier event for delicious fresh seafood and entertainment in the Florida Keys. There is to be live music throughout the festival weekend, games for children and adults, raffle giveaways, and over 200 vendors selling jewelry, clothing, art, boats and more. On Sunday, both active and retired military and law enforcement personnel enter for free. The festival takes place at Marathon Community Park, 200 36th Street oceanside. Parking is available directly across U.S. 1 at Stanley Switlick Elementary.
March 8 Key West
An island tradition, 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. The contest takes place in the garden of the Oldest House, 322 Duval Street. It’s free to participate in, and to attend. All ages are invited to compete. Registration begins at 10 a.m., the contest starts at noon.
March 8 Key West
KEY WEST TROPICAL FOREST & BOTANICAL GARDEN: GARDENFEST
The chance to explore a rare open-air “living museum” and view and purchase unique plants awaits nature lovers Saturday, March 8, during the annual gardening, craft, food and music festival at the Key West Tropical Forest & Botanical Garden. Docent-led tours are to guide visitors through the 15-acre habitat. The free-admission open-air event is set for 10 a.m. to 4 p.m. at the 5210 College Rd. property, acclaimed as the only frost-free subtropical moist forest and garden in the continental United States.
March 8 Key West
COFFEE BUTLER AMPHITHEATER: BRETT YOUNG
From his self-titled debut in 2017, Brett Young has captured the hearts of fans everywhere through his honest lyrics and West Coast-meets-Southern sound, aptly dubbed “Caliville” style. With an impressive string of seven No. 1 hits and multiple hit albums defined by an undeniable romantic spark, he has cemented his status as a master of matters of the heart. Doors open 6 p.m.; show at 7:30 p.m. 21 E. Quay Rd.
March 10 – 13 Key West
MARCH MERKIN INVITATIONAL PERMIT TOURNAMENT
This charity flats-and-fly-only invitational tournament, presented by the Lower Keys Guides Association, challenges anglers to catch and release silvery permit to vie for elite titles. The event is held at Oceans Edge Key West Resort & Marina, 5950 Peninsular Ave.
March 11 – 12 Key West
STUDIOS OF KEY WEST: ELLIS PAUL & RADOSLAV LORKOVIC IN CONCERT
Singer-songwriter Ellis Paul teams with blues and classical keyboardist Radoslav Lorkavic in concert at the Studio’s Helmerich Theater March 11 at 7 p.m. and at 6 p.m. on the Hugh’s View rooftop March 12. 533 Eaton St.
March 14 – 16 Key West
ROBERT THE DOLL PARANORMAL WEEKEND
Experience a weekend in Key West full of supernatural events including exclusive haunted tours, seances and other paranormal experiences with ghost hunters and paranormal experts.
March 18 – 19 Key West
STUDIOS OF KEY WEST: BETH CHAPMAN IN CONCERT
Songwriters Hall of Fame member Beth Chapman performs in concert at the Studio’s Helmerich Theater March 18 at 7 p.m. and at 7 p.m. March 19 on the Hugh’s View rooftop. 533 Eaton St.
March 20 Key West
WALK ON WHITE THIRD THURSDAY ART WALK
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
March 27 – 29 Key West
WATERFRONT PLAYHOUSE: A DISTANT COUNTRY CALLED YOUTH
During the annual Tennessee Williams Festival, this Spotlight Series production stars Thomas Lanier Williams as Tennessee Williams growing up, exploring and finding his artistic voice. 407 Wall St. at Mallory Square.
March 28 Key West
Keith Sykes has written over 100 songs recorded by top artists, including Coast of Marseilles and Volcano, recorded by Jimmy Buffett. The two met in 1972 in Key West. Sykes joined the Coral Reefer Band for its 1979 tours, including the Volcano Tour. Doors open at 6 p.m.; show at 8 p.m.
March 29 – 30 Key West
NAS KEY WEST: SOUTHERNMOST AIR SHOW SPECTACULAR
The U.S. Navy flight demonstration team Blue Angels and other military and civilian aerial performances will fill the skies at this free-admission, family friendly event. In addition to the Blue Angels, aerial demonstrations by military and civilian performers, and static military and vintage aircraft are planned. Gates open at 10 a.m. both days. Air show starts at 11 a.m. with Blue Angels flying at 2:30 p.m. VIP and preferred seating options are available for purchase. Free parking. Northbound traffic, enter the Naval Air Station Key West gate at mile marker 7; southbound traffic, enter the main gate at mile marker 8. VIP pass holders, ride share vehicles and handicapped vehicles, enter the commercial gate at mile marker 9.
APRIL
April 3 – 24 Key West
STUDIOS OF KEY WEST: A FIFTY YEAR RETROSPECTIVE WITH WORKS BY DAVID WEGMAN
Long-time resident and self-described pirate David Wegman epitomizes Key West’s bohemian spirit. His artwork vividly portrays his seafaring life, bringing to life the vibrant places he has explored and the colorful characters he has encountered along the way. 533 Eaton St.
April 3 – 5 Key West
The 2nd annual Spanish Fly Shark Tournament comes to Key West Yacht Club, 2315 N. Roosevelt Blvd. with another exciting event dedicated to gathering data on the bull shark population in the Keys. The tournament action is to be filmed for broadcast by Outdoor America. All captains or boat owners must have an HMS permit with a shark endorsement.
April 4 – 6 Islamorada
The 33rd annual Florida Keys Island Fest features a juried art show, a sand sculpture competition, the “What Floats Your Boat” homemade boat races on Saturday, live music, great food, classic cars, interactive activities for kids, and on Sunday, the annual “Taste of Islamorada” restaurant competition. Free entry; onsite parking $5. 10 a.m. to 5 p.m. both days at Founders Park, mile marker 87 bayside.
April 5 Marathon
7 MILE BRIDGE RUN
The 44th annual Seven Mile Bridge Run takes place Saturday, April 5. Motorists need to be aware that the bridge will close in both directions from 6 a.m. to 9 a..m. Saturday morning. Law enforcement will open the bridge to traffic promptly at 9 a.m. The race is a bucket list adventure for the field of 1,500 runners who participate.
April 6 Key West
KEY WEST THEATER: AWAKEN, THE MUSIC OF YES
Since 2018, Awaken has provided its fans with the most authentic live YES show in the world by performing YES music the way the fans remember it. By combining elements from the original studio recordings along with the inspirational power of past live YES performances, AWAKEN provides a truly authentic and dramatic musical experience. Doors open t 7 p.m.; show at 8 p.m. 512 Eaton St.
April 12 Key West
TRUMAN WATERFRONT PARK: MOTE MARINE’S OCEAN FEST
Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment at Mote’s Ocean Fest: A Community Celebration. Proceeds and donations from the festival support Mote Marine Laboratory’s coral reef restoration and research programs. From 10 a.m.–3 p.m. in Truman Waterfront Park, 0 Southard St., enjoy a fun day of crafts, games, music, food, local brews (for ages 21+) and shopping, and explore conservation and environmental exhibits. Meet Mote scientists along with other conservation and environmental organizations from around Florida, and learn about the work they are doing and how you can help.
April 15 – 16 Key West
STUDIOS OF KEY WEST: JOHN MCCUTCHEON IN CONCERT
Praised as “folk music’s Rustic Renaissance Man,” John McCutcheon bring his multi-instrumentalist, songwriting and performing talents to the Studio’s Helmerich Theater April 15 at 7 p.m. and April 16 at 8 p.m.
April 17 Key West
WALK ON WHITE THIRD THURSDAY ART WALK
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
April 19 Key West
The Key West Southernmost Runners’ 26th annual Earth Day 5k Run/Walk takes place Saturday at Truman Waterfront Park at the end of Southard St. The start and finish line is near the U.S Coast Guard Cutter Ingham Maritime Museum. Proceeds from the race benefit the Conch Republic Marine Army, a local non-profit grassroots organization dedicated to cleaning and restoring the shallow mangrove habitats of the Florida Keys.
Apr 24 – 26 Marathon
MARATHON PREMIER SAILFISH TOURNAMENT
This sailfish challenge benefits Mission Fishin’, a South Florida nonprofit that helps fund marine adventures for foster children, kids with special needs, and their families. Prizes are to be awarded to the top three boat teams and top male, female and junior anglers.
Apr 25- 27 Marathon
7 MILE OFFSHORE GRAND PRIX
This spectacular race event from Race World Offshore offers excitement and heart-pounding action in the Gulf of Mexico, with viewing of the entire race course available from the pedestrian-friendly Old Seven Mile Bridge. The race is the kick-off event in the American Powerboat Racing Association National Series.
April 25 Key West
KEY WEST LITERARY SEMINAR: ELIZABETH BISHOP’S POSTCARDS – A CONVERSATION WITH THE CURATORS
Join Arlo Haskell, Executive Director of Key West Literary Seminar; Ronald Patkus, Head of Special Collections and College Historian at Vassar College; and curators Jonathan Ellis of the University of Sheffield and Susan Rosenbaum of the University of Georgia, for a conversation in the Bishop Garden about the exhibition, composed of 55 postcards drawn from Vassar’s collection of more than 500. 5:30 to 7:30 p.m. 624 White St.
Apr 30 – May 4 Key West
29th ANNUAL KEY WEST SONGWWRITERS FESITVAL
The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West.
MAY
May 1 – 4 The Florida Keys
I.CARE: Trash Derby & Festival
I.CARE’s Trash Derby, sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas, brings teams of environmentally-conscious debris collectors in divisions including dive charters, private boat owners and land lovers. After two days of trash collecting, there is a free festival Sunday at Founders Park, mile marker 87 bayside from noon to 6 p.m. The festival is open to the public. There is to be an awards ceremony to include cash and other special prizes. The festival features live music, food vendors, games and activities, raffles, a silent auction and exhibitors including local organizations helping to restore Keys coral reefs.
May 1 – 29 Key West
STUDIOS OF KEY WEST: ISAAC VALDES – THE WAY IT WAS
Experience the historical charm and vibrant culture of Old Key West through intricate wood carvings. This exhibition captures the essence of Key West’s bygone days, depicting its unique architecture, lush landscapes, and colorful local life. 533 Eaton St.
May 2 – 5 Islamorada
NICK SHEAHAN DOLPHIN RODEO
Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $456,000 to Coral Shores High School students. The event features cash prizes for the top three adult anglers with the heaviest dolphin fish. If an angler breaks the Florida dolphin fish record (81 pounds) they win the grand prize of $25,000. Tournament events held at Tavernier Creek Marina, mile marker 90.8 bayside.
May 9 -10 Marathon
19TH ANNUAL MOTHER’S DAY DOPPHIN TOURNAMENT
Cash and prizes will be awarded for the heaviest fish and to anglers who finish second through fifth place in this popular, annual tournament. There are four categories for prizes: professional, weekend warrior, ladies, and junior angler. There is to be a captain’s meeting Friday night and one day of fishing on Saturday, followed by an awards banquet Saturday night. The event benefits Habitat for Humanity of the Middle Keys.
May 15 Key West
WALK ON WHITE THIRD THURSDAY ART WALK
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.In May, there will be a bike parade down White Street for American Bike Month.
May 15 Key West
KEY WEST THEATER: DUANE BETTS & PALMETTO MOTEL
Duane Betts, son of Dickey Betts of Allman Brothers Band fame, performs guitar-slinging, story-driven American rock and roll along with Palmetto Motel. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
May 16 – 18 Islamorada
LADIES LET’S GO FISHING SCREAMIN REELS TOURNAMENT
Intended for novice anglers and returning participants, this weekend is about learning and a non-intimidating, fun competition with the “Ladies Let’s Go Fishing” university organizers. Participants can join on a professional charter boat or fish on their own boat. This is a casual tournament with prizes for the heaviest offshore fish and longest inshore fish, drawings for prizes for those who caught fish, plus bonus drawings. The Friday kickoff takes place at The Tavernier Elks Club, mile maker 92 bayside; most Saturday and Sunday charters depart from Whale Harbor Marina, mile marker 83 oceanside.
May 18 – 21 Islamorada
GOLDEN FLY INVITATIONAL TARPON TOURNAMENT
The Golden Fly Tournament attracts top fly anglers and world class guides to test their abilities in Islamorada during the famed tarpon migration. The 3-day, invitation only tournament launches from the Lorelei Restaurant & Marina, 96 Madeira Rd.
May 30 – Jun 1 Key Largo
11TH ANNUAL SKIPPERS DOLPHIN TOURNAMENT
This highly competitive, family-friendly tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn at mile marker 100. Cash prizes of over $50,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.
JUNE
Jun 7 – 8 The Lower Keys
LOWER KEYS CHAMBER OF COMMERCE DOLPHIN TOURNAMENT
The Lower Keys Chamber of Commerce presents the 32nd 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 — this prize is available only to the anglers on the first 50 boats registered for the tournament. Additional prizes await winners in open, ladies and youth divisions.
Jun 7- 8 Key Largo
FLORIDA KEYS ELKS LADIES DOLPHIN TOURNAMENT
Female anglers vie for cash and prizes for the heaviest weight of three mahi mahi in the 10th annual Ladies Dolphin Tournament. Tournament events are to be held at the Elks Lodge, mile marker 92.6 bayside in Tavernier.
Jun 8 Key Largo
REEF ENVIRONMENTAL EDUCATION FOUNDATION: GRAND OPENING
The new REEF Ocean Exploration Center for Marine Conservation is to be unveiled June 8, 2025, on World Oceans Day in a grand opening celebration. The center, located in the median of U.S. 1 at mile marker 98, is designed to inspire curiosity and wonder for the oceans, foster scientific research and collaboration, and serve as an immersive experience that helps everyone discover their unique role in protecting our blue planet
Jun 13 – 14 Marathon
FATHER’S DAY DOLPHIN DERBY
This popular dolphin tournament with check-in on Friday and fishing Saturday pays out thousands in cash and prizes to the top four adults with the heaviest fish. Junior anglers age 15 and under vie for rod and reel combos.
June 13 – 15 Key West
KEY WEST GATOR CLUB DOLPHIN DERBY
Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 13 through 15. Tournament location to be announced. The team weighing in the heaviest dolphin fish takes home a grand prize of $5 thousand. Proceeds benefit scholarships for Key West High School graduates attending University of Florida.
June 14 Key West
COLLEGE OF THE FLORIDA KEYS SWIM AROUND KEY WEST
Embark on an adventurous competitive 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. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.
June 20 – 22 Key West
VFW’s annual fishing tournament returns with over $75,000 in cash and prizes. The big change for 2025 will be that all registered boats are able to fish two days, with no separate registration required for each fishing day. Tournament events are held at the VFW post at 2200 N. Roosevelt Blvd.
June 22 – Sep 1 Key West
Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to get lost in the magic of the southernmost city, rediscover Key West and discover how the island has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!
Jun 25 – 26 Islamorada
ISLAMORADA FISHING CLUB CAPTAIN’S CUP DOLPHIN TOURNAMENT
Teams of up to four anglers compete for top prizes with the total combined weight of three fish determining the winning team. If up to 25 boats register, first prize cash winnings can reach $25,000. Tournament activities are to be held at the Islamorada Fishing Club, 80939 Overseas Highway.
Jun 27 – 29 The Lower Keys
FLORIDA KEYS PBA CHARITY DOLPHIN TOURNAMENT
This fishing tournament is hosted by volunteers of the South Florida Police Benevolent Association and headquartered at Oceans Edge Resort and Marina on Stock Island, 5950 Peninsular Ave. Cash prizes for first- through fourth-place anglers are based on the number of entries, and increase as participation increases. Cash prizes are also awarded to top junior, female and PBA member. Over $15 thousand in prizes are to be awarded. The angler with the biggest tuna wins a rod and reel combo. Register online. Proceeds primarily benefit the Autism Society of the Keys and the Love Fund.
Check back as events are updated for later this year.
JULY
Jun 5 – Jul 31 Key West
STUDIOS OF KEY WEST: MANGO MADNESS ANNUAL SUMMER MEMBERS SHOW
Every member of The Studios is invited to participate in the annual members’ exhibit, and the result is a bounty of creativity in every form and style imaginable. Artists are not asked to make work about mangoes exactly, but it is hoped that the work brings them – and you – similar joy. 533 Eaton St.
July 16 – 23 Key West
Coinciding with the 45th 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. Entry is limited to the first 75 boats. Tournament events are based out of Stock Island Marina Village, 7005 Shrimp Rd..
July 22 – 27 Key West
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West 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 on Sat. July 26, literary presentations, a commemoration of the 126th anniversary of Hemingway’s July 21 birth, a museum exhibit, a marlin tournament, a 5k run and paddleboard race, a street fair and more.
July 30-31
SPINY LOBSTER SPORT SEASON
Daily bag limit – 6 per person in Monroe County
Must be larger than 3 inches measured in the water.
AUGUST
August 7-10
28th ANNUAL LOBSTERFEST
August 7 – Original Lobster Boil: A traditional lobster boil kicks off the festivities in the historic Porter Mansion courtyard at Caroline’s Café from 6 pm to 9 pm. Tickets are required due to limited space.
August 8 – Duval Pub Crawl: Beginning at 8 pm, explore Duval Street’s bars, for $25 including an official Lobsterfest T-shirt.
August 9 – Street Fair & Free Concert: The festival’s main event runs from 12 pm to 11 pm, featuring lobster dishes from various vendors along Duval Street, and free concerts.
August 10 – Lobster Brunch: The weekend concludes with an all-you-can-eat-and-drink lobster brunch at First Flight Island Restaurant & Brewery from 10 am to 2:30 pm (tickets required).
Food, music, and entertainment.
Aug 29 – Sept 2
KEY WEST BREW FEST
Brewfest is a multi-day festival hosted by Southernmost Beach Resort! It includes beer pairing dinners, pool parties, tap takeovers, and culminates with a signature tasting event with over 150 beers available for tasting. Events take place at many restaurants, hotels, and bars around town making Brewfest a great way to experience Key West!
Aug 29 – Sep 1 Key West
JUST A FEW FRIENDS KEY WEST
Join us in Key West for Labor Day weekend to celebrate the 2nd Annual Just a Few Friends memorial, honoring our favorite son, the late Jimmy Buffett. Festivities kick off with an official pre-party meetup on Thursday, August 28. On Friday morning the City of Key West will proclaim “State of Florida Jimmy Buffett Day,” followed by activities on and off the water, foodie events, and great times. Saturday features a run/walk, the Margarita Bar Crawl, along with tours, lectures, rum tastings, and music events across town. Sunday’s highlight is the epic Second Line Parade starting at 5 pm culminating in a free music festival at Truman Waterfront Park with local and national entertainment, food trucks and vendors. Come Monday continue the celebration with a variety of activities and entertainment options to suit every interest.
SEPTEMBER
Sep 13 Islamorada
SWIM FOR ALLIGATOR LIGHTHOUSE
Join Islamorada’s annual world-class, 8-mile open-water swim out to the iconic Alligator Reef Lighthouse and back. This unique and challenging experience can be conquered solo or on 2-, 3- or 4-person relay teams. Proceeds from the race go toward the effort to fully restore and re-light the 152-year old lighthouse.
Sep 19- 25 Key West
TRUMAN WATERFRONT FARMERS MARKET – EVERY THURSDAY
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Sep 26 – 28 Key Largo
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
October 17 – 26 Key West
“Bedtime Stories & Magical Monsters” is the official theme for Fantasy Fest 2025, Key West’s annual multi-day costuming extravaganza in paradise. From October 17-26, revelers can explore an array of exciting events, including the the exuberant Goombay Festival in the streets, the Zombie Bike Ride, a Bedtime Stories and Magical Monsters-themed 5K run/walk, the Captain Morgan Masquerade March (aka “Locals Parade”), the Royal Coronation of the 2025 Fantasy Fest King and Queen, plus concerts, theater productions, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and the world-famous Key West Fantasy Fest Parade on Saturday, Oct. 25.
October 19 Key West
ZOMBIE BIKE RIDE
The Rock & Roll costumed Halloween bike ride. More details to come.
NOVEMBER
November 7 Key West
KEY WEST POWERBOAT RACES
Sunset Pier 9AM -4PM
0 Duval Street
General Admission viewing area around the Sunset Pier Bar. Standing Room / Limited Seating / Cash Bar & Food. VIP Tent & Reserved Tables – contact sales@oceankey.com
DECEMBER