Calendar of Events

Current Florida Keys Events

Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest Image for Key West Half Marathon & Runfest
Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo
Image for Truman Waterfront Farmers Market - Every Thursday
  • Sep 19, 2024 - Sep 25, 2025 Key West
  • Truman Waterfront Farmers Market - Every Thursday
  • Website
  • 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.
Image for The Protect Center: Sea of Trees
  • Dec 1, 2024 - Jan 5, 2025 Islamorada Arts & Culture
  • The Protect Center: Sea of Trees
  • Website
  • 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.
Image for Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Dec 6, 2024 - May 18, 2025 Key West Arts & Culture
  • Key West Art & Historical Society: Collecting Key West - The Works of Mario Sanchez
  • Website
  • Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
Image for Red Barn Theatre: The Foreigner
  • Dec 18, 2024 - Jan 11, 2025 Key West Arts & Culture
  • Red Barn Theatre: The Foreigner
  • Website
  • This very funny comedy is an American classic, winning the Best New American Play for 1985 by the Outer Critics Circle. Set at a rural Georgia fishing lodge, a pathologically shy man adopts a persona as a non-English speaking foreigner in an attempt to avoid conversation. Hilarity ensues as an outrageous group of characters reveal secrets and scandals. Shows at 7:30 p.m. 319 Duval St.
Image for Waterfront Playhouse: Vagina Monologues
Image for Studios of Key West: Jeffrey Cardenas - On the Reef
  • Jan 2, 2025 - Jan 30, 2025 Key West Arts & Culture
  • Studios of Key West: Jeffrey Cardenas - On the Reef
  • Website
  • 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.
Image for Studios of Key West: First Thursday Open House
  • Jan 2, 2025 Key West Arts & Culture
  • Studios of Key West: First Thursday Open House
  • Website
  • Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh's Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!
Image for Key Largo Library: First Friday Concert - Li'l Rev
  • Jan 3, 2025 Key Largo Arts & Culture
  • Key Largo Library: First Friday Concert - Li'l Rev
  • Website
  • First Friday Concerts are free and begin at 6 p.m. at the library in Tradewinds Shopping Plaza, MM 101.5. Lil’ Rev is a world-class entertainer and steward of vintage song and lore. Performing with ukulele, harmonica, mandolin, guitar and banjor, Rev has an unmatched reporteire of both traditional and original song, poetry, storytelling and humor.
Image for Orange Bowl Swim Classic
  • Jan 3, 2025 Key Largo
  • Orange Bowl Swim Classic
  • Website
  • College swimmers from around the country meet and compete in a popular monthlong winter training session in Key Largo that culminates in the open-to-spectators Orange Bowl Swim Classic event. Competition takes place 10 a.m. until noon and is free for spectators to watch at Jacobs Aquatic Center, mile marker 99.6 oceanside. The sprint-style meet features several fast-paced swimming events.
Image for Fish for Holly Sailfish Tournament
  • Jan 3, 2025 - Jan 5, 2025 Islamorada Fishing
  • Fish for Holly Sailfish Tournament
  • Annie Hagen 305-304-1762 Website
  • Created to raise money for Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at the Islander Resort, mile marker 82, to compete for top male, female and junior angler awards as well top boat and fun fish categories.
Image for Pole Vault in Paradise
  • Jan 4, 2025 Key West
  • Pole Vault in Paradise
  • Website
  • 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.
Image for Key Largo Library: Special Saturday Concert Featuring Hungrytown
Image for Caribbean Club - Church on the Beach & Blessing of the Pets
  • Jan 5, 2025 Key Largo
  • Caribbean Club - Church on the Beach & Blessing of the Pets
  • Website
  • The Caribbean Club hosts a church service on the beach by St. James Episcopal Church from 10 a.m. to 12 p.m. From noon to 2 p.m., bring your pet for a personal Pet Blessing, with a cost of $10 per family to go to Upper Keys Humane Society. There is also to be a pet contest with categories like: Best Trick, Best Dressed, Best Kiss, Best Owner and Dog Costumes.
Image for Key West Literary Seminar: Writers' Workshop Program
  • Jan 5, 2025 - Jan 9, 2025 Key West Arts & Culture
  • Key West Literary Seminar: Writers' Workshop Program
  • Website
  • 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.
Image for Studios of Key West: Susan Werner & Jonatha Brooke in Concert
Image for Connections Project: A Mosaic of the Keys Grand Opening
  • Jan 8, 2025 Marathon Arts & Culture
  • Connections Project: A Mosaic of the Keys Grand Opening
  • Website
  • This year's Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. Each venue will feature a mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians. The opening event takes place at the Marathon Chamber After Hours members event at Berkshire Hathaway Keys Real Estate, 9141 Overseas Hwy., from 5:30 to 7:30 p.m.
Image for Key West Theater: Paul Poundstone
Image for Key West Literary Seminar: Family
  • Jan 9, 2025 - Jan 12, 2025 Key West Arts & Culture
  • Key West Literary Seminar: Family
  • Website
  • 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.
Image for Wounded Warrior Project Soldier Ride
  • Jan 10, 2025 - Jan 11, 2025 The Florida Keys
  • Wounded Warrior Project Soldier Ride
  • Website
  • 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.
Image for Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
  • Jan 10, 2025 Key West Arts & Culture
  • Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
  • Website
  • 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.
Image for Key West Outdoor Movies
  • Jan 10, 2025 Key West Arts & Culture
  • Key West Outdoor Movies
  • Website
  • Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.
Image for Classical Keys in the Keys
  • Jan 11, 2025 Islamorada Arts & Culture
  • Classical Keys in the Keys
  • Website
  • Enjoy an evening of classical piano music featuring piano virtuoso Frederic Chiu as he presents "Heart & Soul," one of his signature Classical Smackdowns, where the audience votes for one of two legendary composers, round by round. The program has been performed around the world with the voting results captured for each venue. Doors open at 6 p.m. at Matecumbe Methodist Church, 81831 Overseas Hwy. VIP experience options available including cocktails and light bites at Kaiyo Grill & Sushi.
Image for Florida Keys Celtic Festival
  • Jan 11, 2025 - Jan 12, 2025 Marathon Arts & Culture
  • Florida Keys Celtic Festival
  • Website
  • Experience the unique sights and sounds of the Scottish Highlands and the Emerald Isle in the heart of the Florida Keys. The resounding rhythms and "Bareknuckle Pipes and Drums" of Scottish band Albannach and the harmonies of Irish sisters, "The Screaming Orphans" headline the entertainment. Other highlights include bagpipers, Irish step dancers, a variety of highland athletic games, authentic Celtic food and vendors offering Tartan kilts along with jewelry, gifts, clothing and more. 10 a.m. to 7 p.m. Saturday; 11 a.m. to 5 p.m. Sunday. Kids age 12 and under get in free with paying adult. Marathon Community Park, MM 49 oceanside.
Image for Lower Keys Guides Association: Get Trashed Cleanup
Image for Key West Artisan Market: Don't Be Trashy!
  • Jan 12, 2025 Key West Arts & Culture
  • Key West Artisan Market: Don't Be Trashy!
  • Website
  • 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.
Image for Impromptu Classical Concerts: Thomas Mesa & Greg Zelek
  • Jan 12, 2025 Key West Arts & Culture
  • Impromptu Classical Concerts: Thomas Mesa & Greg Zelek
  • Website
  • Cellist Thomas Mesa and organist Greg Zelek will present a special duo concert showcasing the historic pipe organ at St. Paul’s Episcopal church. Mr. Mesa has established himself as one of the most charismatic, innovative, and engaging performers of his generation, and is the recipient of the Sphinx Organization’s 2023 Medal of Excellence, its highest honor. Mr. Zelek is the Principal Organist of the Madison Symphony Orchestra and Curator of the Overture Concert Organ, where he regularly performs and oversees all the MSO's organ programming. 4 p.m. at St. Paul's, 401 Duval St.
Image for Florida Keys Concert Association: Boilermaker Jazz Band
  • Jan 13, 2025 - Jan 14, 2025 The Florida Keys Arts & Culture
  • Florida Keys Concert Association: Boilermaker Jazz Band
  • Website
  • The 55th season for Florida Keys Concert Association includes six concerts, each taking place in two locations. The first concert features the Boilermaker Jazz Band from Pittsburgh, that has been performing swing and hot jazz worldwide for over 30 years. Shows begin at 7:30 p.m. On Monday, Jan. 13, the band plays at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 14 the show is at Coral Shores High School, 89901 Old Hwy.
Image for Key West Library Speaker Series: Mondays at 6 p.m.
  • Jan 13, 2025 - Jan 27, 2025 Key West Arts & Culture
  • Key West Library Speaker Series: Mondays at 6 p.m.
  • Website
  • Authors in the Key West Library Speakers series appear on Mondays, January through March. January's featured speakers are: January 13: Ayana Mathis, author of The Unsettled (Knopf, 2023), named a New York Times and Washington Post Notable Book of 2023. January 20: Jimin Han, author of The Apology, named best book of the summer by the Los Angeles Times, Vanity Fair and others. January 27: Cathy Salustri in conversation with David Sloan - Salute is author of Florida Spectacular: Extraordinary Places and Exceptional Lives. Free to attend and no registration required. Talks take place in the library's Palm Garden, 700 Fleming St. at 6 p.m.
Image for Key Largo Library: Eco Voices & Art
  • Jan 13, 2025 Key Largo Environmental
  • Key Largo Library: Eco Voices & Art
  • Website
  • Join a representative from the Florida Keys Wild Bird Rehabilitation Center at 11 a.m. to learn all about the unique birds of the Florida Keys, the center's role in rescuing them and how you can help local bird populations. From 1 to 4:30 p.m., artist Gloria Avner leads a batik workshop to create amazing images of birds. The library is located at Tradewinds Plaza, mile marker 101.5.
Image for Key West Theater: Bitch Trouble
  • Jan 14, 2025 Key West Arts & Culture
  • Key West Theater: Bitch Trouble
  • Website
  • 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.
Image for Studios of Key West: Dom Flemons, the American Songster in Concert
Image for Islamorada Fishing Club Captain's Cup Sailfish Tournament
  • Jan 14, 2025 - Jan 15, 2025 Islamorada Fishing
  • Islamorada Fishing Club Captain's Cup Sailfish Tournament
  • Dianne Harbaugh 305-522-4868 E-mail Website
  • Presented by the Islamorada Fishing Club, this is the second leg of the Florida Keys Gold Cup Series, with a field of up to 25 boat teams of elite sport fishermen. A total cash payout for a full field at the IFC Captain's Cup Sailfish Tournament could reach $25,000. Kick off is Jan. 14 with one day of fishing on Jan. 15, with the awards ceremony immediately after at the Islamorada Fishing Club.
Image for Fringe Theater: I Love You, You're Perfect, Now Change
Image for History of Diving Museum: Dive Into Art
  • Jan 15, 2025 - Apr 16, 2025 Islamorada Arts & Culture
  • History of Diving Museum: Dive Into Art
  • Website
  • The History of Diving Museum's latest featured exhibit, "Dive Into Art: Fintastic Fish of Florida" is on display through April 16. The exhibit features artistic creations from students across the Keys, as well as from the Art Guild of the Purple Isles. These works focus on the diverse fish of the Florida coast, along with sustainable fishing, aquaculture, and conservation.
Image for Key West Tropical Forest & Botanical Garden: Rum Infused Adult Scavenger Hunt
  • Jan 15, 2025 Key West Arts & Culture
  • Key West Tropical Forest & Botanical Garden: Rum Infused Adult Scavenger Hunt
  • Website
  • 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.
Image for Key West Kingfish Mayhem
  • Jan 15, 2025 - Jan 19, 2025 Key West Fishing
  • Key West Kingfish Mayhem
  • Website
  • 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.
Image for 27th Annual Key West Half Marathon & Runfest Weekend
Image for Marathon Community Theater: Always a Bridesmaid
  • Jan 16, 2025 - Feb 8, 2025 Marathon Arts & Culture
  • Marathon Community Theater: Always a Bridesmaid
  • Website
  • This comedy follows four Southern high school friends who vow serve as bridesmaids in each other's weddings, no matter what. Fast forward to 30 years later, they are still determined to honor their vow and navigate the challenges of love and marriage as bridesmaids through multiple weddings. Showtimes at 8 p.m. 5101 Overseas Hwy.
Image for Morada Way Third Thursday Art Walk
  • Jan 16, 2025 Islamorada Arts & Culture
  • Morada Way Third Thursday Art Walk
  • Website
  • The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.
Image for Baygrass Bluegrass Festival
  • Jan 17, 2025 - Jan 20, 2025 Islamorada Arts & Culture
  • Baygrass Bluegrass Festival
  • Website
  • This year's festival includes three days of music in the Morada Way Arts and Cultural District from Friday, Jan. 19 through Sunday, Jan. 19; then concluding with an evening concert on Monday, Jan. 20 at the amphitheater at Founders Park. Details on the music lineup coming soon.
Image for Art Under the Oaks
  • Jan 18, 2025 Key Largo
  • Art Under the Oaks
  • Website
  • Explore original arts and crafts at booths spread under the towering oak trees in the San Pedro Church Gardens, MM 89.5 from 9 a.m. to 4 p.m. There will be live music, specialty and international food booths and trucks, and homemade goodies in the bake sale. Parking available at Plantation Key School.
Image for Connections Project: A Mosaic of the Keys Pop-Up at Art Under the Oaks
Image for Weinerpalooza
  • Jan 18, 2025 Key West Arts & Culture
  • Weinerpalooza
  • Website
  • Key West's annual Dachshund Parade takes place Saturday, Jan. 18. All parade revelers are to gather at 11:30 a.m. in front of Customs House, 281 Front St., for a group portrait followed by the parade at 12 noon. Tails wag all along the parade route that ends at Hank's Hair of the Dog Saloon. All doggies are welcome and pet costumes are encouraged. Enjoy drink specials, raffles to benefit the Friends of Luci Fund and live entertainment.
Image for Paddle for Paws
  • Jan 18, 2025 The Lower Keys Arts & Culture
  • Paddle for Paws
  • Glennis Walter 305-743-4800 E-mail Website
  • Take your pup for a leisurely paddle around Cudjoe Key, departing from Cudjoe Gardens Marina, 477 Drost Dr. Check-in at 9 a.m.; paddle at 10 a.m. Don't miss the post-paddle party and libations at Bent Prop, 457 Drost Dr., along with a silent and live auction to benefit the Florida Keys SPCA Clinic Fund. Bring your own paddle board or kayak.
Image for Florida Keys Concert Association: Famous Opera Highlights
  • Jan 20, 2025 - Jan 21, 2025 The Florida Keys Arts & Culture
  • Florida Keys Concert Association: Famous Opera Highlights
  • Website
  • The 55th season for Florida Keys Concert Association includes six concerts, each taking place in two locations. The second concert features Chelea Duo, Soprano and Joe Luis Maldonado, Barton with pianist Benedicte Jourdois, offering an evening of spine-tingling music including arias and duets from Carmen, La Traviata, The Barber of Seville and Carousel. Shows begin at 7:30 p.m. On Monday, Jan. 20, they perform at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 21, the show is at Coral Shores High School, 89901 Old Hwy.
Image for The Southernmost Regatta
  • Jan 20, 2025 - Jan 25, 2025 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.
Image for Kelly McGillis Classic International Flag Football Championship
  • Jan 21, 2025 - Jan 27, 2025 Key West LGBTQ
  • Kelly McGillis Classic International Flag Football Championship
  • Website
  • 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.
Image for Mile 0 Fest
  • Jan 21, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Mile 0 Fest
  • Website
  • 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.
Image for Key West Theater: Ben Harrison
  • Jan 21, 2025 Key West Arts & Culture
  • Key West Theater: Ben Harrison
  • Website
  • Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater's Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Image for Connections Project: A Mosaic of the Keys Pop-Up at Cheeca Lodge
  • Jan 21, 2025 Islamorada Arts & Culture
  • Connections Project: A Mosaic of the Keys Pop-Up at Cheeca Lodge
  • Website
  • The Florida Keys Council of the Arts Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. View this year's artful mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at the Islamorada Chamber of Commerce's Members After Hours event at Cheeca Lodge, 81800 Overseas Highway oceanside beginning at 5:30 p.m.
Image for Key West Theater: Melissa Etheridge
  • Jan 22, 2025 Key West Arts & Culture
  • Key West Theater: Melissa Etheridge
  • Website
  • 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.
Image for Waterfront Playhouse: The Angel Next Door
  • Jan 22, 2025 - Feb 8, 2025 Key West Arts & Culture
  • Waterfront Playhouse: The Angel Next Door
  • Website
  • The wonderfully funny script by Paul Slade Smith captures the joy and wit of 1940s screwball comedies. Brace yourself for what a critic called "a perfect storm of comedic chaos, irresistible charm and rapid-fire banter." Showtimes 8 p.m. plus a 2 p.m. matinee on Feb. 1. 407 Wall St. at Mallory Square.
Image for Walk on White Third Thursday Art Walk
  • Jan 23, 2025 - Jan 16, 2025 Key West Arts & Culture
  • Walk on White Third Thursday Art Walk
  • Website
  • 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.
Image for Everglades National Park Flamingo Campground: Two Nights Under the Stars
  • Jan 24, 2025 - Jan 26, 2025 Key Largo Environmental
  • Everglades National Park Flamingo Campground: Two Nights Under the Stars
  • Website
  • Join the Alliance for Florida's National Parks for an unforgettable weekend adventure. Activities include a tour of the historic Nike missile base inside the park, stargazing, kayaking, yoga, hikes, campfires, storytelling and more. Each campsite includes a picnic table and a fire ring. Bring your own tent, sleeping gear and personal supplies. Rooms may also be available at Flamingo Lodge. Tickets required to participate in the weekend programming.
Image for Coconut Cove Resort & Marina: Roaring for Rescues
Image for Islamorada Junior Sailfish Tournament
  • Jan 24, 2025 - Jan 26, 2025 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • Randi Rowland-Knowles E-mail
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under celebrates its 60th year. Due to heavy winds on the previously-scheduled December dates, the tournament is rescheduled for Jan. 24-26.
Image for Island Boat Show
  • Jan 24, 2025 - Jan 26, 2025 Islamorada Fishing
  • Island Boat Show
  • Website
  • Billed as the Florida Keys’ premier boat show, Island Boat Show is held on the grounds of Island Community Church in Islamorada. Planned attractions include top boat brands and dealers, large silent auction, food and drink vendors, and nautical merchandise for the entire family. The show is open Friday from 1 to 5 p.m.; Saturday from 10 a.m. to 5 p.m.; and Sunday from 10 a.m. to 3 p.m., mile marker 83.4 bayside.
Image for Old Island Restoration Foundation: January Home Tours
  • Jan 24, 2025 - Jan 25, 2025 Key West Arts & Culture
  • Old Island Restoration Foundation: January Home Tours
  • Website
  • Key West is home to what is considered the largest predominantly wooden historic district in the United States. One weekend a month, from January through March, five distinctive homes and their gardens open, revealing a range of architectural gems, eclectic art, transformed cigar-makers cottages, shipbuilders’ craft, re-imagined Victorian mansions, and the stories behind the facades. Home tour tickets provide entry to 5 homes at your self-guided pace during the Friday-Saturday tour dates. All tickets for sale online. Your receipt will be your ticket to enter the home. If you prefer to have a physical ticket, you can pick one up at the Oldest House Museum gift shop, 322 Duval St., the week before the tour date.
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • 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 a half hour after sunset. 416 Eaton St.
Image for 21st annual Big Pine & the Lower Keys Nautical Expo
  • Jan 25, 2025 - Jan 26, 2025 The Lower Keys Fishing
  • 21st annual Big Pine & the Lower Keys Nautical Expo
  • 305-872-2411 E-mail Website
  • Find steals and deals on everything imaginable for boating, fishing, diving and more, from over 100 vendors. You'll also find clothing, jewelry, arts and crafts, food and beverages, and live music during the two-day event. Admission and parking are free at the Lower Keys Chamber of Commerce grounds, mile marker 31 on Big Pine Key, Saturday from 8 a.m. to 4 p.m. and Sunday 8 a.m. to 2 p.m.
Image for Tropic Cinema: Movies Under the Stars - War Games
  • Jan 25, 2025 Key West Arts & Culture
  • Tropic Cinema: Movies Under the Stars - War Games
  • Website
  • 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.
Image for Connections Project: A Mosaic of the Keys Pop-Up at Lower Keys Nautical Expo
Image for Key West Cemetery Tour
  • Jan 26, 2025 Key West Arts & Culture
  • Key West Cemetery Tour
  • Historic Florida Keys Foundation 305-304-1453 E-mail Website
  • Historic Florida Keys Foundation holds its first Key West Cemetery tours of the season on Sunday, Jan. 26 at 9:30, 9:50 and 10:10 a.m. Groups of visitors will be escorted to the grave sites of Juana Borrero Pierra, William Curry, George Adderly, May Douglas, Hilda Russel and the USS Maine Monument. The 90-minute tour will cover about one mile - wear comfortable shoes. A donation of $20 to the foundation is appreciated. Reservations are required. Email hfkf@bellsouth.net or call 305-304-1453.
Image for Impromptu Classical Concerts: Simone Porter
  • Jan 26, 2025 Key West Arts & Culture
  • Impromptu Classical Concerts: Simone Porter
  • Website
  • Violinist Simone Porter has been recognized as an emerging artist of impassioned energy, interpretive integrity, and vibrant communication. In the past few years, she has debuted with the New York Philharmonic, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Born in 1996, Simone made her professional solo debut at age 10 with the Seattle Symphony and her international debut with the Royal Philharmonic Orchestra in London at age 13. 4 p.m. at St. Paul's, 401 Duval St.
Image for Florida Keys Concert Association: Fred Moyer, Pianist
  • Jan 27, 2025 - Jan 28, 2025 The Florida Keys Arts & Culture
  • Florida Keys Concert Association: Fred Moyer, Pianist
  • Website
  • The 55th season for Florida Keys Concert Association includes a selection of concerts, each taking place in two locations. The third concert in the series features Frederick Moyer. During more than thirty years as a full-time concert virtuoso, Moyer has appeared as piano soloist with numerous world-renowned orchestras in all parts of the globe. A consummate communicator and educator, he is one of the concert association's favorite artists and is returning with his magnificent performances of classical music. Shows begin at 7:30 p.m. On Monday, Jan. 27, he plays at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 28, the show is at Coral Shores High School, 89901 Old Hwy.
Image for Connections Project: A Mosaic of the Keys Pop-Up at The Hale Gallery
Image for Winter Star Party
  • Jan 27, 2025 - Feb 2, 2025 The Lower Keys Environmental
  • Winter Star Party
  • Website
  • 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.
Image for Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
Image for Registration Opens for 7 Mile Bridge Run
  • Jan 28, 2025 Marathon
  • Registration Opens for 7 Mile Bridge Run
  • Website
  • Registration opens on Tuesday, January 28, 2025 beginning at 6 a.m. Anyone can register on this date, but race organizers are only able to accept 1,500 entries and the field fills very quickly. Sometimes the registration is filled within minutes, so please be online and ready. You must show a PHOTO ID when picking up your bib number that matches the same address you used to register.
Image for Key West Theater: Ben Harrison
  • Jan 29, 2025 Key West Arts & Culture
  • Key West Theater: Ben Harrison
  • Website
  • Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater's Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Image for Cirque Ma'Ceo by Cavallo Equestrian Arts
  • Jan 29, 2025 - Feb 2, 2025 Marathon Arts & Culture
  • Cirque Ma'Ceo by Cavallo Equestrian Arts
  • Website
  • Experience the magic with this emotionally charging, up close and personal experience. Step into the exclusive, custom designed Italian Big Top theater and settle back in brand-new, state of the art seating. The world of Ma’Ceo is proud to showcase mesmerizing acrobatic feats, aerial dancing, and exotic horses. Come feast your senses on the beauty and mystery through the adventure of Cirque Ma'Ceo. Showtimes vary. San Pablo Catholic Church, 550 122 Street Ocean.
Image for Swamp Guides Ball Fishing Tournament & Auction
  • Jan 31, 2025 - Feb 1, 2025 Islamorada Fishing
  • Swamp Guides Ball Fishing Tournament & Auction
  • Website
  • In this annual all-release competition, organized by the Florida Keys Fishing Guides Association, anglers target three species – bonefish, redfish and snook. The tournament benefits the Florida Keys Fishing Guides Foundation and the Guides Trust Foundation, organizations that provide funds to people in the local fishing industry in times of need. Guides are welcome to register and fish as anglers. Tournament activities take place at Safe Harbor Angler House, mile marker 80.5 bayside. The online auction is open to all, not just registered anglers.
Image for Islamorada Women's Sailfish Tournament
  • Jan 31, 2025 - Feb 2, 2025 Islamorada Fishing
  • Islamorada Women's Sailfish Tournament
  • Website
  • This challenge has female anglers facing off in Islamorada against the famous tail-dancers for trophies and prizes. The tournament kick-off takes place Friday evening at Safe Harbor Angler House, MM 80.5 bayside. Fishing takes place Saturday and Sunday, with the awards ceremony at 6:30 p.m. Sunday. Men may serve as captains and mates.
Image for Coffee Butler Amphitheater: Chicago
  • Jan 31, 2025 Key West Arts & Culture
  • Coffee Butler Amphitheater: Chicago
  • Website
  • 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.
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