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Florida Keys Events Calendar

Florida Keys Events

The Official Florida Keys and Key West Web Site is your Premier Travel Guide to the Florida Keys: Key Largo, Islamorada, Marathon, Lower Keys, Key West. Accommodations, Real Estate, Diving & Snorkeling, Fishing & Boating, Museums & Tours, Restaurants & Bars, Theaters & Art Galleries, Events and more. Brought to you by the Monroe County Tourist Development Council.

Upper Keys

  • Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music, 6-9......

  • For a refreshing start to 2023 on New Year’s Day, put on a crazy outfit and jump in the ocean for the second annual Manatee Plunge at the Tiki Bar at Holiday Isle. The bar opens at 11 a.m. and the Manatee Plunge starts at......

  • Florida Keys Brewing Co. and Island Community Entertainment (ICE) are keeping the spirit of Baygrass Bluegrass Festival alive! Enjoy three days of music blending the best of traditional bluegrass with the next generation of bluegrass and some interesting variations of the genre. This year’s festival......

  • As Redbone Gallery closes after 30 years, Florida Keys History & Discovery Center is showcasing the journey of Captain Gary, Susan and Nicole Ellis with a special exhibit highlighting their lives through Jan. 8. The remaining inventory of exceptional art is for sale in the......

  • The museum opens for a special event Saturday, Dec. 3 to support the Redbone Gallery’s mission to “Catch the Cure” for cystic fibrosis. Redbone is selling the remainder of its gallery originals and giclee artwork from some of the foremost saltwater angling artists including Millard......

  • Second in the three-pronged 2023 Gold Cup Sailfish Championship series currently underway in the Florida Keys is the Islamorada Fishing Club’s Captain’s Cup Sailfish Tournament. Participants vie for an attractive cash payout and the chance to tally points to earn the coveted Gold Cup Series......

  • Anglers are to pursue sailfish, the most plentiful billfish in the waters off the Keys, in a series of three competitions – the Islamorada Sailfish Tournament, Dec. 1-4, 2022; the Islamorada Fishing Club Captain’s Cup Sailfish Tournament, Jan.17-18, 2023; and the Cheeca Lodge Presidential Sailfish......

  • The final leg of the three-event Florida Keys Gold Cup Championship Series, the Cheeca Lodge Presidential Sailfish Tournament, is scheduled Friday through Sunday, Jan. 20-22. The tournament kick-off and awards events take place at the resort at mile marker 82 oceanside in Islamorada. A limited......

  • The Florida Keys Gold Cup Sailfish Championship triple-crown series is to open with the Islamorada Sailfish Tournament, a primary fundraiser for the Islamorada Charter Boat Association Thursday, Dec. 1 through Sunday, Dec. 4. Social events are to be headquartered at the Whale Harbor Inn and Marina......

  • 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......

  • Meditate and relax under the glow of the full moon and the twinkling stars at Postcard Inn, Islamorada from 6 to 7:30 p.m. Zenfully Aware Yoga, the Islamorada Resort Collection, and Coral Restoration Foundation™ are bringing you on an adventure – a yoga practice centered......

  • Looking for some ghoulishly good fun this month? Join the History of Diving Museum on Thursday, Oct. 27th for Treasure Treat Night! This two-hour event will include trick-or-treating inside the museum, kid’s activities, a costume contest with prizes, raffles, and a spooky exhibit experience with......

  • Sponge Hunters: Key West Hookers, Bahamian Free Divers, and the Hard Hat Divers of Tarpon Springs will be on display May 19 through December 31, 2022. Learn about the sea sponge and its uses, from the long history of fishers to modern fisheries, current restoration......

  • Join Surfrider Florida Keys and Sereia Films on Friday, December 9th for “Ocean to Everglades: Stories of the Sea” – a night of film screenings and discussion on sustainable seafood in Florida and the ocean livelihoods that depend on it. Happy hour will be from......

  • A festival of Bacon – from breakfast to dinner dishes and all that’s in between! Area restaurants will dish out bacon appetizers to desserts for your palatable pleasure. There will be arts and crafts by local artisans and music all day! This is a kid......

  • Theater of the Sea’s first annual Halloween Show takes place Friday, Oct. 28 at the park, located at mile marker 84 oceanside in Islamorada. Buy tickets online or at the door – $10 per person, kids age 3 and under get in free. Doors open......

  • Part I of the Florida Keys History & Discovery Center lecture series, “Smuggling in the Florida Keys,” features Richard Russell and Ricou Deshaw sharing details of their individual adventures and being on opposite sides of smuggling in the Florida Keys. Doors open at 5 p.m.......

  • Part II of the Florida Keys History & Discovery Center lecture series, “Smuggling in the Florida Keys,” features law enforcement officials as they share stories of Smuggling in the Florida Keys and run-ins with those involved. Panel includes Sheriff Rick Ramsay, MSO Captain Don Hiller,......

  • The Florida Keys History & Discovery Center lecture series “Smuggling in the Florida Keys” Part IV, the final panel in the series, consists of State Prosecutor Allison DeFoor speaking on what it took to convict those who were involved in Smuggling in the Florida Keys,......

  • Boogie over to the Florida Keys History & Discovery Center’s signature annual fundraising event, themed to tie into the museum’s fall lecture Series, “Smuggling in the Florida Keys.” Travel back to a boisterous time of bell bottoms and platform shoes. Your evening begins with a......

Middle Keys

  • This month’s free fishing seminar, presented by The Tackle Box, offers tips on ways to fish for and catch wahoo. The seminar takes place from 5:30 to 8 p.m. at Marathon Community Theatre, mile marker 49.5 oceanside....

  • Havana Jack’s Oceanside Restaurant at 401 East Ocean Drive in Key Colony Beach invites you to boogie into the new year with live music from The Lady A Band on New Year’s Eve starting at 4 p.m., along with dinner and drink specials starting at......

  • Celebrate the holiday season at Faro Blanco Resort in Marathon for their annual Lighting of the Lighthouse event from 4 until 9 p.m. Enjoy food, drinks, music by Abstract Radio and Santa and Mrs. Claus arriving by train. Mile marker 48.5....

  • The parade will start in from the west side of the harbor (7 mile bridge side) at 6 p.m. and slowly meander east past Lazy Days, Marathon Marina, Pancho’s and Burdines, then down to Dockside past the condo’s and turn around in the basin at......

  • The Key Colony Beach Christmas Boat Parade happens on Sunday night, Dec. 11, beginning at dusk, around 5 p.m....

  • Come out to Marathon Community Park for a fun night of Holiday fun. Enjoy live holiday music, entertainment by the Marathon Community Theater dancers and the Prodigy Dancers, face painting, bounce houses, cotton candy and other treats, and see Santa! Mile marker 49 oceanside....

  • Celtic history, culture, food and music are to be celebrated by attendees at the 10th annual Florida Keys Celtic Festival, a favorite family event in the Middle Keys. The event opens Friday, Jan. 6 from 5 to 7 p.m for the free “Kilts in the......

  • There’s a forecast for snow in the tropical forest at Crane Point Hammock Museum & Nature Trail during Winter Wonderland from 4:30 to 7:30 p.m. Bring the entire family to encounter reindeer ponies, holiday decorations, Santa and snow! Enjoy Santa stew, the chocolate fountain, roasted......

  • Start Thanksgiving Day the right way—by giving back. Participate in the Hawks Cay Turkey Trot 5K Run/Walk through the islands of Duck Key or virtually. All proceeds from the event benefit the Relay for Life—American Cancer Society. Your donation for the 5K includes a race......

  • Take a torch walk along the Crane Point Hammock nature trail to a haunted mansion. Kids can enjoy games and non-scary movies. Adult beverages for sale. 5 to 8 p.m. on Oct. 22. 5550 Overseas Hwy, Marathon....

  • Families of all ages are welcome to come and enjoy a petting zoo, hayrides, kids face painting, bubbles and more. From 4-7:30 p.m., inside Crane Point, 5550 Overseas Highway. Adult beverages and food will be available for purchase. Donation admission is $8 per adult, $5......

  • Hosted by one of the pioneers in the Cuban music scene, this all-day music fest is from 10 a.m. to 10 p.m. at Marathon Community Park’s outdoor amphitheater. Partial proceeds from this event are to support the Somos Esperanza foundation, that helps provide for sick......

  • Staged for over 60 years, this mid-Keys tournament is one of the Keys’ oldest. Registration and Captain’s meeting kick off the event at Overseas Lounge, at 4 p.m. Anglers traditionally fish 8:30 a.m. to 3:30 p.m. Friday – Sunday. Locations for cocktail parties on fishing......

  • Enjoy an evening of music and fine food with classical guitarist Mateo Jampol. Tickets are $65 each before sales tax and include a tropical three-course meal prepared by local Chef Jamie Pruitt and a Champagne Toast to end the evening’s festivities. Doors open 5 p.m.,......

  • 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,......

  • Located at Marathon Community Park, the smoked barbecue and craft beer festival-style event is to feature mouth watering BBQ, and tons of delicious craft beers to wash it down.  Highlights also are to include an amateur BBQ cooking competition with prizes, vendors, boats, live music, kids’......

  • Enjoy a family friendly Sunday from 9 a.m. to 4 p.m., with old fashioned fun, food, drinks, vendors and the famous Barracuda Races! Event celebrates the City of Key Colony Beach’s birthday, and its incorporation as a city. Admission and parking is free, at the......

  • Marathon Garden Club is to host its first butterfly garden tour from 10 a.m. to 4 p.m., for participants to tour four Marathon-area certified butterfly gardens. Tickets are $30 per person and can be purchased with a tour map at the Club, 5270 Overseas Highway,......

  • Fish for a cause! Join this festive one-day fun fishing tournament for the heaviest mahi mahi. The entire event is a fundraiser to help Habitat Middle Keys build 11 additional affordable homes in Marathon. This angler tournament includes four prize categories: Professional, Weekend Warrior, Ladies......

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

Lower Keys

  • “Come Together” for New Year’s Eve with The Beatle Band at the famous Sunset Pier at Ocean Key Resort, located at 0 Duval Street. The party starts at 9 p.m. right over the water. Enjoy a complimentary champagne toast and the annual Key Lime Drop......

  • 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......

  • Snowy Sunday, the Key West Tropical Forest & Botanical Garden’s annual winter concert, features local classical guitarist, Mateo Jampol performing songs especially for children. The event opens at 1 p.m. and Jampol’s concert starts at 1:30 p.m., followed by snow cones (while they last) and......

  • Join members of Surfrider’s Florida Keys Chapter and others for a cleanup of Smathers Beach from 9 to 11 a.m. Free, limited edition t-shirts will be given to the first 25 attendees. Gloves, buckets, grabbers, cold water and good times provided. Please wear close-toed shoes......

  • “Neil Young: Harvest Time” is a fan piece that has never before been seen. Performance and rehearsal content is intertwined into creative storytelling and includes most of the tracks from the iconic 1972 album Harvest. Created in 1971, this docu-film takes us on a journey......

  • A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Music begins at 6 p.m., parade starts at 8....

  • All are welcome to gather to celebrate the lives of friends and loved ones taken from us far too soon and honor those that we lost in 2022. There will be a processional starting at 4:30 p.m. from Key West City Hall, located at 1300......

  • The Revival is a gathering of Nashville’s biggest hit writers sharing their songs, considered some of the best music in Nashville. In 2022 the Revival took the pew on the road with some of Nashvilles greatest songwriters. The tour ends in Key West with two......

  • Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8......

  • Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street from 11 a.m. to 2 p.m. for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary....

  • The Friends of the Key West Library kick off their 50th Anniversary celebration with an event at the library, located at 700 Fleming Street, from 4 to 6 p.m. There will be a short program, tours and refreshments in the library lounge....

  • The City of Key West’s holiday tree is to be illuminated at Bayview Park, corner of Truman Avenue and Eisenhower Drive. All are invited for this free event from 6 to 7 p.m. featuring the Horace O’ Bryant School Jazz Band and an appearance by......

  • Members have decked the halls of the historic mansion at 319 Duval Street for all to enjoy at Sunday’s open house from 4 to 6 p.m. Enjoy appetizers, desserts and Amsterdam eggnog, and an appearance by Santa. Music from the Bahama Village Children’s Choir and......

  • This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members.......

  • The City of Key West’s annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.18 from 5 to 6 p.m. 1320 Truman Avenue....

  • The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from......

  • Hogfish Bar & Grill, home to fresh seafood, strong drinks, panoramic waterfront views, outdoor dining and plenty of local characters for a truly authentic Keys experience, is celebrating its 20th anniversary Sat. Nov. 19. Enjoy great food and some dynamite musical guests, including opening act......

  • Artist and astronomy buff Larry Halstead takes participants to the cosmos and back. Meet in the theater for a presentation on the first night, then use a powerful telescope on the roof for direct observation the next night. From 7 to 9 p.m. both nights......

  • Kick off the holiday season by supporting your community artists as part of Small Business Saturday. Over 20 artisans present unique and locally produced gifts: jewelry, textiles, home accessories and quality crafts. 10 a.m. to 4 p.m., 533 Eaton Street, Key West...

  • Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts and the Key West United Methodist Church unite for the annual Eaton Street Christmas Stroll. Each venue hosts a short Christmas-themed performance with caroling as you walk from......