Events & Festivals
Due to the coronavirus crisis, most near-term Florida Keys special events have been or are likely to be canceled. If you see an event listed, please check the event’s website or call its organizer for more details.
Nov 30, 2020 – Jan 1, 2021
2020 Harbor Walk of Lights
The “Harbor Walk of Lights” stretches along the seawall past Greene St, William St, and Margaret St. to the K.W. Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harborwalk area in the Key West Historic Seaport is to glimmer with holiday displays from Elizabeth to Grinnell streets throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.
Dec 4, 2020 – Dec 23, 2020
Holiday Lights & Sights Tours with Old Town Trolley Tours
The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West’s best decorated historic neighborhoods, buildings and homes. Tours at 6:30 p.m. and 7:15 p.m. Capacity is limited. COVID-19 safety protocols in place.
Dec 4, 2020 – Dec 23, 2020
Conch Tour Train Holiday Light Tours
During its annual holiday lights tours of the southernmost island in the continental United States, the Conch Train travels past decorated historic homes, buildings and neighborhoods. Tours are offered at 6:30 p.m. and 7:15 p.m. with departures from Key West High School, 2100 Flagler Ave. Capacity is limited. COVID-19 safety protocols in place.
Dec 8, 2020 – Dec 24, 2020
Holiday Artisan Market with The Studios of Key West
Kick off the holiday season with The Studios of Key West by supporting community artists and small businesses. This season, TSKW is temporarily transitioning to an online platform, helping you find the perfect gifts. Their online shop will be available to browse through Christmas Eve. It will still be a one-stop-shopping experience with links to 25 unique local artisans who create jewelry, textiles, home accessories and more.
Dec 13, 2020 – Dec 27, 2020
Cocktails and Carols, Key Choral Arts’ Virtual Concert
Singing for in-person audiences this holiday season is not possible. Instead, Keys Choral Arts has prepared a virtual concert, their only fundraiser of the year, to premier on December 13, at 4PM. The hour-long concert is to include several musical pieces performed by 40 regular KCA performers in virtual choir fashion. Enjoy solos, duets and small groups of singers from the KCA performers. Performances online for 14 days. Tickets $20/viewer.
Jan 5, 2021 – Jan 7, 2021
Islamorada Sailfly Tournament
This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in a tough yet exciting angling event to kick off the year.
Jan 7, 2021 – Jan 9, 2021
Pole Vault in Paradise
Pole Vault in Paradise is an all-comers pole vault competition. The main event is on Saturday, January 9, 2021 at the Truman Waterfront Park in Key West. Key West’s average high temperature in January is 75 degrees and the average nighttime low is 65 degrees. Winds are likely and runways will be aligned for a fast downwind approach. Pole Vault in Paradise is likely the first outdoor event in the US. US and World marks will be established.
Jan 8, 2021 – Jan 9, 2021
Fish for Holly Sailfish Tournament
Created to raise monies for Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Headquartered out of Whale Harbor Marina, participants are to compete for top male, female and junior angler awards as well top offshore, bay boat, and fun fish categories.
Jan 14, 2021 – Jan 17, 2021
Key West Kingfish Mayhem
Headquartered at Stock Island Marina Village, this four-species event enhances what was formerly a king mackerel tournament by adding tuna, mahi and wahoo. Anglers are to vie for cash prizes.
Jan 15, 2021 – Jan 16, 2021
61st Annual Key West Home Tours
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 1 to 5 p.m. each day. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs. For each tour, the number of visitors allowed inside each home will be limited, masks will be required and hand sanitizers will be provided. Reservations for tour time slots are required and tickets must be purchased in advance.
Jan 17, 2021
23rd Annual Key West Half Marathon & 5k Run
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Named as one of the United States’ leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by Competitor.com. COVID-19 safety protocols are to be in place.
Jan 19, 2021 – Jan 25, 2021
30th Annual Kelly McGillis Classic, Flag Football Championships
The championship is named for and endorsed by the Golden Globe-winning actress, director, and former Key West resident who starred in “Top Gun” and “Witness” — and it includes pre- and post-tournament team-building activities and three days of challenging competition.
Jan 22, 2021 – Jan 24, 2021
Island Boat Show
Boating and watersports aficionados can browse among top boat brands at the event, staged at Hawks Cay Resort, mile marker 61 on Duck Key. Boat brands and vendors expected to be featured in the open-air show include Worldcat, Contender, Robalo, Sailfish, Cobia, Twin Vee, Hell’s Bay Boatworks, Stingray, Wellcraft, Bob Hewes, Century and Grady White. The show is to take place 1-5 p.m. Friday, 9 a.m. to 5 p.m. Saturday and 9 a.m. to 3 p.m. Sunday.
Jan 22, 2021 – Jan 24, 2021
Cheeca Lodge Presidential Sailfish Tournament
The Presidential is one of the most prestigious offshore tournaments in the Florida Keys, and serves as the third and final leg of the three-pronged Florida Keys Gold Cup Championship.
Jan 27, 2021 – Jan 31, 2021
Key West Food and Wine Festival
Adventurous aficionados of fine food and vintages can explore creative cuisine, premium wines and unique events in a subtropical island setting during the annual celebration. Whet your appetite for island-style excellence, showcasing local chefs’ culinary flair and favorite indigenous ingredients, intriguing libations and distinctive Florida Keys atmosphere. Ticket sales to be available Nov. 4, 2020.
Jan 28, 2021 – Jan 30, 2021
NEW DATES: Sugarloaf Showdown
Postponed from Nov. 2020. Angling teams are to pit their skills against the Lower Florida Keys’ wiliest in-water inhabitants. Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. According to tournament organizers, participants are to follow Monroe County COVID-19 health safety protocols throughout, including social distancing and wearing facial coverings when appropriate.
Jan 28, 2021 – Feb 3, 2021
Sundance Film Festival 2021 Satellite Screens: Tropic Cinema
This year, Sundance Film Festival is doing things differently by bringing the Fest to Key West audiences with a Sundance Satellite screen in the local community, at the Tropic Cinema, 416 Eaton St. Offered digitally via a custom-designed online platform alongside drive-ins, independent art-houses and a network of local community partnerships in select cities, the Utah festival’s characteristics remain the same: celebrating independent film, visionary artists, unique perspectives, and adventurous audiences.
Feb 4, 2021 – Feb 6, 2021 Location: The Lower Keys
Shallow-water flats anglers and guides are invited to hook up and fight their barracuda rivals. The event is headquartered at Hurricane Hole Marina on Stock Island. Prizes are awarded to the top angler and guide in light-tackle, spin and fly divisions.
Feb 6, 2021 – Feb 12, 2021
Florida Keys Cycling with Timberline Adventures
Ready for a spectacular February ride in 70 degree weather? Ride the entire 113-mile length of the famed Overseas Highway from Key Largo to Key West, with more adventures built in. These islands are a special place whether it is your first time to the famous islands or you are a regular. This unique and beautiful tour includes all lodging, breakfasts, dinners, leaders, snacks, support van, park entrance fees, airport transfers, ferry transfers, tour maps and narratives. Register online, double and single occupancy available.
Mar 5, 2021 – Mar 7, 2021
Sombrero Beach Run Weekend
This annual event’s motto is ‘come for the run, stay for the sun and fun!’ Florida Keys sunshine and family togetherness are what have attracted hundreds of avid runners and walkers from around the country to the Middle Keys for the Sombrero Beach Run, a mixture of athleticism and beach fun. For Saturday’s main event, kids and adults of all ages can participate in a 5k, 10k or 15k. Prizes and medals are awarded, and proceeds support KAIR, a Marathon-based nonprofit organization that provides Keys residents valuable emergency services, housing assistance and relocation services in addition to a food pantry. Register online.
Mar 8, 2021 – Mar 11, 2021
March Merkin Invitational Permit Tournament
This charity flats-and-fly-only tournament challenges anglers to catch, tag and release silvery permit to vie for elite titles. The event is held at the Key West Harbour Yacht Club on Stock Island, and features a silent online auction.
Mar 13, 2021 – Mar 14, 2021
Original Marathon Seafood Festival
Shrimp, spiny lobster, stone crab claws and fish, all “fishermen-to-fork fresh,” are to headline the attractions for attendees. For over 40 years, the taste bud–tempting outdoor feast has drawn seafood lovers and Keys families to gather at the Marathon Community Park, mile marker 49 oceanside. Commercial fisheries and markets catch, clean and cook the nearly 15,000-pound spread of fresh Florida Keys seafood, bushels of oysters from the west coast of Florida and tasty smoked fish dip prepared according to tightly guarded recipes.
Apr 17, 2021
40th Annual Seven Mile Bridge Run
The annual race is staged on the longest of 43 bridges along the Florida Keys’ renowned Overseas Highway. The race is one of the most popular running events in the southeast United States, attracting a field of 1,500 runners from around the world.
Apr 27, 2021 – May 1, 2021
Fourth Annual Mile 0 Fest Key West
This annual fest brings the best of Americana and Red Dirt Music to the island paradise for five full days of bands, acoustic jams and songwriter swaps. Event organizers are to have safety protocols in place per COVID-19 guidelines.
Apr 30, 2021 – May 2, 2021
Nick Sheahan Dolphin Rodeo
Fishing for a cause! Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $170,000 to date. Hosted at Tavernier Creek Marina, the event features cash prizes and $25,000 to the angler with a dolphin fish that beats the state record.
May 5, 2021 – May 9, 2021
Key West Songwriters Festival
Since 1997, BMI has been a presenting sponsor of the festival, the largest festival of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.
Jun 4, 2021 – Jun 6, 2021
28th Annual Original Big Pine & Lower Keys Dolphin Tournament
The Lower Keys Chamber of Commerce presents this annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in open, ladies and youth divisions.
Jun 4, 2021 – Jun 6, 2021
Seventh Annual Skippers Dolphin Tournament
This tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn. Cash prizes of over $60,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.
Jun 11, 2021 – Jun 12, 2021
Eighth Annual Ladies Dolphin Tournament
Hosted by the Florida Keys Elks Lodge, this event welcomes female angler teams to compete for the highest aggregate weight of three dolphin fish. Cash and prizes are awarded to first- through third-place finishers, and for the largest dolphin caught.
Jun 23, 2021 – Jun 27, 2021
Mango Fest Key West
Experience all things Mango through shopping, education and demonstrations. Stroll through Truman Waterfront Park to visit vendors, shop local shops, visit galleries, and order great food.
Jul 1, 2021 – Jul 5, 2021
Key Lime Festival
Enjoy a full 4 days of culinary events for every taste, including favorites from past years such as the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers like a Key Lime Scavenger Hunt and Key Lime University! Organizers have also added a few intimate culinary events for VIP Key Lime lovers!
Jul 10, 2021
37th Annual Underwater Music Festival
This annual event for both divers and snorkelers is staged at Looe Key Reef, an area of the Florida Keys National Marine Sanctuary about 6 miles south of Big Pine Key. Hosted by the Lower Keys Chamber of Commerce and a local radio station, US1 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs. While the festival’s primary purpose is to promote reef protection and eco-conscious diving, it also offers a bucket-list underwater experience. Some participants might even spot “mermaids” and other costumed characters swaying beneath the waves, adding visual excitement to the unique conservation concert.
Jul 18, 2021 – Jul 21, 2021
Del Brown Permit Tournament
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.
Aug 12, 2021 – Aug 15, 2021
25th Annual Key West Lobsterfest
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.
September, October, November & December currently don’t have any events scheduled. Please feel free to check out the Florida Keys Tourism Council Website for update to events.