Key West Calendar of Events

There is always something fun to do in Key West. This calendar of events is frequently updated.

Key West’s Most Complete Calendar of Events.

This calendar of events for Key West includes nearly every happening on the island throughout the year. Something missing? If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. Check back frequently: more events, dates, and details are added as the season progresses.

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December 2018

January 2019 | February 2019 | March 2019 | April 2019 | May 2019 | June 2019 | July 2019 | August 2019 | September 2019 | October 2019 | November 2019 |

Key West 2018 Event Calendar

December 2018 Key West Events

  • December 1, 2018 – SPORTS – 9th Annual TRIKW Triathalon – Athletes swim, run, and bike among Key West’s ideal scenery and conditions. More than 500 competitors are expected. Two race distances are available: Sprint and the twice-as-long Olympic. For more information, call 305-394-3469 or visit http://www.trikw.com/.
  • December 2, 2018 – HOLIDAYTree Trimming Party – The dock-front Schooner Wharf Bar hosts this annual holiday tree decorating party, craft fair, and toy drive.  Bring an ornament and get a free holiday cocktail; prizes for best ornaments. Features live island music by The Last Mango. 5pm, 202 William Street.  For more information, call 305-292-3302
  • December 5, 2018 – HOLIDAY – Key West Lighted Bike Parade – To benefit Wesley House Family Services, this neighborhood parade features bicycles adorned with holiday lights and decoration.  Begins at 7pm (check-in is at 6pm), Bayview Park.  FREE with donation of unwrapped child’s gift.
  • December, 2018 (EXACT DATE TO BE ANNOUNCED)SPORTSAquaX World Championship – Personal watercraft (waverunners) racers, both pro and amateur, compete for world championship title.  For more information, visit https://www.p1aquax.com/Race-Info/Key%20West/2017/84228
  • December 8, 2018  – HOLIDAYKey West Holiday Parade – Extremely popular with children due to the shower of candy given out by the parade. Parade begins at Bayview Park in Key West, then heads down Truman Ave to Duval Street. Best viewing is along Truman Ave in Old Town, Key West. FREE. Call 305-292-8100 for more information.
  • December 15, 2018 BENEFIT – 5th Annual Parade of Paws & Holiday Bazaar – For the benefit of the the animals at the local Florida Keys SPCA (FKSPCA), this pledge-parade event has pet owners competing for prizes and bragging rights. 10am – 2pm, Higgs Beach Dog Park (across from White Street pier). FREE.
  • December 2 – 10, 2018 – HOLIDAYHanukkah in Key West 2018 – Key West is home to one of Florida’s oldest Jewish communities – with Jews settling here when the City was incorporated in 1832. The first Key West Congregation, B’nai Zion was founded in 1887. Today, during Hanukkah, a large menorah is lit in from of the synagogue each night of the holiday, with Rabbi and congregants gathering for the “festival of lights”. A latke and salmon feast is held the first night. Stop by 750 United Street and celebrate. For more information, call 305-294-3437.
  • December 15, 2018 – HOLIDAY –28th Annual Key West Lighted Boat Parade – Vessels of every size and shape deck their hulls and light up the night with their creativity and originality to the delight of locals and visitors alike. Santa Claus has been spotted at the helm, ditching his sleigh for a center console or sailboat with mistletoe hanging from the mast. His first mates have included gingerbread men and the Grinch. Other times, dolphins have replaced cold-weather reindeer, ushering in Santa’s sleigh packed with lighted presents. Boats will come into the Key West Bight (Historic Seaport) and pass in front of the judges’ stand at Schooner Wharf Bar. Festivities start at 6 p.m. with the Gerald Adams Steel Your Heart Band, and the parade begins at 8 p.m. Live music all evening with yuletide favorites, plus a traditional ham dinner served from our galley. To register your boat or for more information, please call (305) 292-3302.
  • December 25, 2018 – HOLIDAYChristmas in Key West 2018 – Whatever gift you wish for, spending Christmas in Key West might be at the top of the list. While it never snows, and sometimes a palm tree is substituted for a traditional tree, there still is plenty of Christmas spirit in Key West. Look for historic homes that have added twinkle and magic with lights and displays. And to all a good night!
  • December 29, 2018 – MUSIC – JJ Grey and Mofro Concert – Outdoor concert by the Southern soul-rock band, at the new Sunset Green lawn venue, a part of The Gates Hotel property. 8pm, 3820 N Roosevelt Blvd.  Tickets cost $62.50 + tax & service fee.   For more information and tickets, visit http://www.ticketfly.com/event/1732012
  • December 31, 2018 – CELEBRATIONKey West New Year’s Eve – Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, the lowering of a Key Lime wedge on the Sunset Pier (0 Duval Street), and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

 

Key West 2019 Event Calendar

January 2019 Key West Events

  • January 5, 2019 – SPORTSPole Vault in Paradise: Pole Vaulting Champions – Top national pole vaulters will perform their skills at the Truman Waterfront Park. FREE to attend. Begins 9am, Truman Waterfront Park (end of Southard Street)
  • January 10 – 13, 2019 – LITERARY37th Annual Key West Literary Seminar – This year’s topic is “Under the Influence.” Noteworthy and celebrated writers, including Margaret Atwood, Geraldine Brooks, Meg Cabot, Marlon James, Joyce Carol Oates and numerous others gather at readings, discussions, lectures, and parties. Registration is now sold out, but a waitlist is available. More informationis available at http://www.kwls.org/seminar or by calling 305-293-9291.
  • January 17 – 20, 2019 – FISHINGKey West Kingfish Mayhem – Bet you didn’t know that the richest tournament prizes in saltwater fishing is for kingfish! Part of the mackerel family, this sportfish is known for its incredible striking speed. First-place prize is expected to be $15,000. For more information, call 954-605-8284 or visit https://www.meatmayhemtournamentsfl.com/key-west-kingfish-mayhem/
  • January 18 – 19, 2019 – ARCHITECTURE59th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $40, include Conch Train transportation, or $30 without the train pass, and are available at http://keywesthometours.com/. Call 305-294-9501 for more information.
  • January 19 – 20, 2019 – FOOD14th Annual Florida Keys Seafood Festival – This festival celebrates Key West’s abundant fresh seafood with music & beverages served up by many of the Florida Keys commercial fisherman and families. Crab, lobster, ceviche, conch chowder, and other local cuisine is served up in a picnic setting. Entrance fee is $5 (children under 12 are FREE). 11 a.m. – 8 p.m on Saturday, 11 a.m. – 5 p.m on Sunday. Bayview Park at Truman Avenue and Eisenhower Drive, Key West. For more information, visit http://www.floridakeysseafoodfestival.com/ or call 305-292-4501
  • January 20, 2019 – SPORTS 21st Annual Key West Half Marathon – Over 1000 runners enjoy near perfect temperatures, flat terrain, and Key West scenery in one of the most popular running races of the year. Entry fee costs between $50 and $120.00, depending on when you register and which race you choose. Call 305-296-7182 for more information. For more information visit https://www.keywesthalfmarathon.com
  • January 21, 2019 – HOLIDAYDr. Martin Luther King, Jr. Day – Celebrate the life, efforts, and accomplishments of one of the greatest champions of civil rights in the history of the United States. This family-friendly event will feature local food, speeches, and a parade in the historic Bahama Village neighborhood. FREE to attend. 12pm-4pm, Nelson English Park, 300 Catherine Street.
  • January 22, 2019 – MUSIC – Hot Tuna in Concert – Legendary 60’s/70’s band perform at the intimate Key West Theater.  21 and over show. Top national act performs two nights at the new Key West Amphitheater, overlooking the Key West harbor.  7:30, 21 Quay Road.   Tickets cost $60-80 + tax & service fee.  8pm show, 512 Eatcon Street. For more information and tickets https://www.ticketfly.com/purchase/event/1718752?_ga=2.70423315.249705940.1541425149-1497482828.1541425148
  • January 22 – 29, 2019 – SPORTS28th Annual Kelly McGillis Classic International Female Flag Football Championship &  World Challenge – The world’s top female flag football players compete for championship titles. (Jan. 25 – 29 are game days; Jan 22 – 29 has full week of events including parties). For more information, visit http://www.iwffa.com/world-challenge-game/
  • January 23 – 27, 2019 – FOOD10th Annual Key West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”. For more information, visit https://keywestfoodandwinefestival.com/ or call 800-474-4319. Tickets for each event costs between $35 – $135.
  • January 25, 2019 – MUSICAir Supply in Concert – National pop-rock act Air Supply performs at the Sunset Green Event Lawn, part of the 24 North Hotel property. 6:30pm (show starts at 8pm). $65, general admission; $159 VIP. Tickets and more information available at http://www.ticketfly.com/event/1735514
  • January 26, 2019 – HISTORY Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required. Call 305-304-01453 for more information.
  • January 26 – 27, 2019 – ARTS – 34th Annual Key West Craft Show – Open air art market and judged show offering an amazing variety of work, including sculpture, paintings, craft, and folk art. Whitehead Street and Caroline Streets, Key West. For more information, visit http://www.keywestartcenter.com/craft.html or call 305-294-1243.
  • January 26, 2019 – HISTORYKey West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required. Call 305-304-01453 for more information.
  • January 27, 2019 – FOOD25th Annual Master Chefs Classic – Benefiting the very worthwhile local charity ReMARCable Citizens (known locally as the MARC House), this event has many of Key West’s best local restaurants in competition for favorite dishes. Cost is $75 – $1400, depending on package selected. Usually sells out quickly. Tickets on sale November 1, 2108. 4 – 7pm. Margaritaville Resort & Marina, 245 Front Street. For more information, visit http://www.marchouse.org/masterchefsclassic/
  • January 29 – February 2, 2019 – MUSIC 2nd Annual Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $349 for 4-day festival pass. For more information and tickets, visit: https://www.eventbrite.com/e/mile-0-fest-key-west-2019-tickets-42598530351 or call 877-412-7658.
  • January 31, 2019 – FISHING Cuda Bowl – Cooler winter temperatures bring big barracuda up onto the saltwater flats, and catching them is a regular occurrence in this tournament. Last year 418 barracuda were caught and released. Tournament rules require artificial lures and flats boats only. Maximum 2 anglers per boat. Entry fee is $350 for two anglers. Hurricane Hole Marina on Stock Island. Visit http://www.cudabowl.com or call 305-360-6969 for more information.

February 2019 Key West Events

  • January 29 – February 2, 2019 – MUSIC2nd Annual Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $349 for 4-day festival pass. For more information and tickets, visit: https://www.eventbrite.com/e/mile-0-fest-key-west-2019-tickets-42598530351 or call 877-412-7658.
  • February 1 – 3, 2019 – HISTORY Civil War Days Heritage Festival – During the Civil War Key West remained in Union hands. Learn about this interesting fact and much more about Key West’s rich history. Fort Zachary Taylor State Park, located at the end of Southard Street. Begins Friday at 8am, ends Sunday 5pm. For more information call 305-292-6850
  • February 2, 2019 – BENEFIT 12th Annual Rock & Roast – Get a taste of local cooking and music at this benefit for the Basilica School. Features pork roast dinner, silent auction, and music by Doerfels. 1010 Windsor Lane. For more information, call 305-294-7031.
  • February 14, 2019 – HOLIDAYValentine’s Day in Key West – Everyone’s favorite island provides the perfect playground for lovers. Sunset sails, beach walks, and waterfront dining are popular with couples in Key West.
  • February 15 – 16, 2019 – ARCHITECTURE 58th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
  • February 23, 2019 – HISTORY Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required. Call 305-304-01453 for more information.
  • February 23 – 24, 2019 – ARTS54th Annual Old Island Days Art Festival – Open-air art show and market featuring oil paintings, watercolors, sculpture, photography and other works. 10am – 5pm on Whitehead Street & Caroline Street, Key West. For more information visit https://keywestartcenter.com/old-island-days or call (305) 294-1243.

March 2019 Key West Events

  • March 1, 2019 – BENEFIT37th Annual Radio Day – Fundraiser to benefit Zonta scholarships for Key West High School girls and local women. This is an excellent local organization truly deserving of your support.  There will be prize drawings (including a $4,500 grand prize!), silent auctions, and block party at The Side Bar, 504 Angela Street.  5:30 – 8:00pm.  For more information, visit http://www.zontakeywest.com/radioday
  • March 2, 2019 – LOCAL COLOR57th Annual Conch Shell Blowing Contest – Prizes are awarded for contestants ability to make sound and music from a conch shell by blowing into it like a trumpet. Registration is at 10am. Contest begins at 12pm (noon), Oldest House, 322 Duval Street. FREE to attend. For more information, call 305-294-9501.
  • March 2, 2019 – LOCAL COLORThe Smallest Parade in the Universe – Now in its fourth year, this event has Key West’s creative community exhibiting its artistic and satirical talents. Tiny parade floats, all must be under 18 inches long, ride down a mini Duval Street set in a hysterical exhibit of whimsy and humor. Cash prizes, including $1000 for 1st place. This event marks a continued locals’ movement to make Fantasy Fest more about creativity rather than raunch, and we welcome the effort. This event sells out early, and costs $25 to enter. 6pm at Key West Theater, 512 Eaton Street. For more information, visit http://www.thesmallestparadeintheuniverse.com
  • March 2, 2019 – ARTS19th Annual Open Air Art & Music Affair – Arts and craft vendors display their creations at one of Key West’s favorite watering holes. Live music from local performers. Schooner Wharf Bar, Lazy Way Lane (end of William Street) 10am – midnight. For more information, call 305-292-3302.
  • March 4 – 7, 2019 – FISHINGMerkin Invitational Permit Tournament – Fly fishermen compete to catch Permit, one of the most challenging fish to catch on fly. Key West Yacht Harbor Marina (Stock Island). For more information, visit http://www.marchmerkin.com or call 303-888-4546.
  • March 7, 2019 – MUSIC10,000 Maniacs in Concert – Billboard-topping rock group from the 80’s plays at the intimate Key West Theatre. Although Natalie Merchant has moved as lead singer, this talented act is sure to have you tapping your toes to the numerous big hits they produced. 8pm show, 512 Eaton Street. For more information, call 305-985-0433. Tickets cost $59.50 – $79.50 and can be purchased at https://www.ticketfly.com/purchase/selectSeats?utm_medium=destination&utm_source=eventbrite&skinName=tfly&id=1785529&seatSelectorOnly=true
  • March 15 – 16, 2019 – ARCHITECTURE59th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
  • March 17, 2019 – HOLIDAYSaint Patrick’s Day – Many people treat each day in Key West like St. Patrick’s Day. So when the holiday does actually come around, it is quite the party.
  • March 23, 2019 – HISTORY Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required. Call 305-304-01453 for more information.
  • March 30, 2019 – LGBTQ2019 Key West Gala – Benefit and fundraiser for Equality Florida, the largest LGBTQ civil rights organization in Florida. FREE to attend. 5:30pm, Truman Little White House, 111 Front Street. For more information, visit https://www.eqfl.org/index.php/keywestcelebration or call 813-870-3735.
  • March 30 – 31, 2019 – MILITARY Naval Air Station Key West Southernmost Air Spectacular 2019 – The Blue Angels air squadron will be performing their amazing acts of flight synchronicity. Air show will also feature parachute teams and other aeronautical performers. Boca Chica Naval Air Field, mile marker 7. Gates open at 9am. Blue Angels perform at 2:30pm. For more information, call 305-293-2503 or visit http://airshowkeywest.com/. FREE to attend.

April 2019 Key West Events

  • April 4, 2019 – MUSICBeach Boys in Concert – The world-famous California band performs outdoors on the Sunset Green Lawn, 3820 N Roosevelt Blvd, 6:00pm (show starts at 7:30pm). $99, general admission. Tickets and more information available at http://www.ticketfly.com/event/1746772
  • April 6, 2019 – MUSIC The Revivalists in Concert – Popular major band performs at the new Key West Amphitheater, overlooking the Key West harbor. Doors open at 5pm, showtime is 6:30 at 21 Quay Road (Truman Waterfront Park, end of Southard Street). Tickets cost $45-75 + tax & service fee. For more information and tickets visit http://www.ticketfly.com/event/1776752
  • April 6, 2019 – RUNNING38th Annual 7-Mile Bridge Run – The longest bridge in the Florida Keys, and an engineering marvel, is home to one of the most anticipated and contested running races. Each year, approximately 1500 runners traverse the bridge while surrounded by stunning ocean scenery. Registration is online only in early February 2019. Only 1500 entries are allowed and this event quickly sells out. For more information, visit https://www.facebook.com/7mbrun/ or call 305-395-7040.
  • April 7, 2019 – RUNNING6th Annual Cow Key Channel Run – This 300-foot mock marathon over the tiny Cow Key Bridge features hilarious costumed runners, walkers, relay teams, and even pets. Prizes awarded for fastest, slowest, best costumed, best theatrical performance, and many more. This year’s theme is “Pirates of the Cowibbean.” FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Registration costs $10 for bib only, or $35 with bib, shirt, and koozie. Race begins at noon. For more information, visit: http://cowkeybridgerun.com/
  • April 15, 2019 – FOOD24th Annual Taste of Key West – For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions at Mallory Square – each taste costing between $3 – $8. Always well attended, this lively event will have you bouncing from cuisine to cuisine, all the while enjoying the generous selection of fine wines available in a collectible wine glass. 6pm – 9pm, Mallory Square (400 Wall Street, Key West). Admission to event is FREE. Food tickets sold in $1 increments. For more information, call 305-296-6196.
  • April 19 – 28, 2019 – LOCAL COLOR37th Annual Conch Republic Independence Celebration – Celebration of Key West’s brief secession from the United States. Event highlights include bed races on Duval Street, conch shell blowing contest , arts & crafts show, Duval Street Parade , and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale cuban bread at Coast Guard vessels and each other in a mock secession. Kick-off party at the Schooner Wharf bar on Friday April 19th, 7pm. For more information call 305-296-0213.
  • April 21, 2019 – HOLIDAYEaster in Key West – Numerous local restaurants offer special Easter Brunch menus.
  • April 22, 2019 – ECOLOGYEarth Day in Key West – Celebrate with one of earth’s most beautiful places, Key West! Visit the coral reef, explore the mangrove islands in the backcountry, walk on the beach, and appreciate all that is unique about the local eco-system. And while you are at it, please pick up any trash that you come across; the earth thanks you!

May 2019 Key West Events

  • May 3 – 5, 2019 – ARTS – 4th Annual Papio Kinetic Sculpture Parade – In recognition of Florida Keys artist Stanley Papio, known for his re-purposing of found objects into whimsical sculpture, this event showcases Key West’s creativity and whimsy with a parade of human-powered artworks. Competition categories include art bikes and kinetic sculptures. Parade begins Saturday May 4 at noon in front of Customs House at 281 Front Street. For more information, call 305-295-6616 or visit http://www.papioskineticparade.com/
  • May 5 – 7, 2019 – HISTORY – 17th Annual Harry S. Truman Legacy Symposium – This year’s theme explores Preservation & Protection of the White Houses, big and little, as well as Truman’s legacy enacting national fire laws. For more information, call 305-294-9911 or visit https://www.trumanlittlewhitehouse.com/key-west/harry-truman-symposium/index.htm.
  • May 8 – 12, 2019 – MUSIC – 24th Annual Key West Song Writers Festival – Features more than two-hundred top songwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and a free concert on Duval Street. For more information, visit http://www.keywestsongwritersfestival.com
  • May 12, 2019 – HOLIDAYMother’s Day in Key West – Celebrate your mom in style! Local restaurant have numerous brunches available – dine indoor or outdoor, oceanfront or air-conditioned. Happy day mothers! We love you!!
  • May 13, 2019 – LGBT36th Annual Queen Mother Pageant – Drag queens compete for title of “Queen Mother,” judged by their often hilarious, always talented performance in evening gown, talent, and interview skills. Benefits Compassionate Care Hospice and One Human Family Foundations. Cost is $25 for general admission, or tables from $200-$500 (these sell out fast). Door open at 7pm, show starts at 8pm. LaTeDa, 1125 Duval Street. For more information, call Ma Evans at 305-296-741.
  • May 18 – 19, 2019 – RUNNING12th Annual Keys 100 Ultra – 100 and 50 mile ultra marathons starting near Key Largo and in Marathon FL, finishing in Key West. Cost: $150 to $275 for individuals (depending on race length and time of registration), and $720 to $840 for teams (depending on race length and time of registration). For more information, call 954-439-2800.

June 2019 Key West Events

  • June 1, 2019 – SWIMMING 43rd Annual Swim Around Key West – Presented by the Key West Athletic Association, this 12.5 mile swim around the island of Key West must be completed in 8 hours and typically has 200 participants, including solo and team swimmers. Cost for registration by March 15 is $165 for a solo swimmer, $300 for two-person relay, and $420 for three-person relay. Deadline to register is May 18. For more information, visit http://www.swimaroundkeywest.com
  • June 5 – 9, 2019 – LGBTKey West Pridefest – Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations. Includes a mix of: dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. For more information, call (305) 292-3223 or visit http://www.keywestpride.org
  • June 15, 2019 – FOOD Tropical Fruit Fiesta – Held on the grounds of the Truman Little White House, this event features a display Key West’s numerous tropical fruits, including mango, papaya, Key Lime, spanish lime, jackfruit, starfruit and others. Tastings, lectures, and opportunity to purchase locally grown produce. Growers compete for award of best fruits in each category. Fun event with genuine local color. 9am-1pm, Truman Little White House, 111 Front Street. FREE to attend.
  • June (DATE TO BE ANNOUNCED), 2019 – LITERATURE6th Annual Mystery Fest Key West – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. Cost is $195 for the weekend events. For more information, visit http://www.mysteryfestkeywest.com/
  • June 15, 2019 – SWIMMINGFKCC Swim Around Key West – Swimmers, accompanied by kayakers, circumnavigate the island of Key West, a distance of over 12 miles. For more information, call 305-809-3562 or visit http://www.fkccswimaroundkeywest.com

July 2019 Key West Events

  • July 4, 2019 – INDEPENDENCE DAYKey West 4th of July Fireworks – Dazzling fireworks show is launched from the White Street pier on the south side of the island of Key West. Begins shortly after sunset. Popular tradition is to view the fireworks from the water aboard a boat. More information and reservations for boat options at Key West July 4th Fireworks Cruises. https://www.keywesttravelguide.com/key-west-fireworks/
  • July 4 – 7, 2019 – FOOD7th Annual Key Lime Festival – Key Limes, grown abundantly on the island, are necessary to make true Key Lime pie. This four-day fest celebrates the tiny local lime, with pie-baking contests, cooking classes, and pie-eating contest. For more information, visit www.keylimefestival.com
  • July 13 – 16, 2019 – FISHING19th Annual Del Brown Permit Tournament – Considered by anglers to be the hardest and most rewarding fish to catch in shallow water on fly, this tournament is named after the early innovator of the sport Del Brown, who showed that you can catch a permit on fly – more than once in a lifetime. In practice, it is a feat of a lifetime, but if you have skills, pattern, and luck, then you just may have a chance. For more information, call 305-744-0903.
  • July 16 – 21, 2019 – HEMINGWAY Hemingway Days & Sloppy Joe’s 39th Annual Papa Look-a-Like Contest – Over 100 Hemingway look-a-likes compete for prizes and notoriety as most resembling the famous writer, judged by previous contest winners. Sloppy Joe’s Bar – 6:30 pm – 201 Duval Street.
  • July 20, 2019 – RUNNINGHemingway 5k Sunset Run & Paddle Board Race – Running race through Key West. This year, the event has expanded to include a paddleboard competition. Cost is $45-85 to register, depending on which events you participate in. For more information, visit https://www.keywesthalfmarathon.com/hemingway-event-details/ or call 305-240-0727
  • July 24 – 25, 2019 – FISHING Lobster Mini-Sport Season – Two-day event draws hundreds of often frenzied recreational boaters in search of Florida lobster. Many rules apply, including: Bag limit: 6 per person per day for Monroe County. Possession limit – on the water: equal to the daily bag limit. Possession limit – off the water: equal to the daily bag limit on the first day, and double the daily bag limit on the second day. Possession limits are enforced on and off the water. Minimum size limit: must be larger than 3? carapace, measured in the water. A reminder that possession and use of a measuring device is required at all times, and night diving is prohibited in Monroe County (only during the sport season). Florida Salwater Fishing License plus lobster endorsement/stamp required. Please respect other boaters, stay away from shorelines, ecological reserves, no-take zones, and canals, use a dive flag, and do no harm to the sensitive coral and eco-system. Call Florida Fish & Wildlife (FWC) at 305-289-2320 for more information.

August 2019 Key West Events

  • August 8 – 11, 2019 – SEAFOOD23rd Annual Key West Lobsterfest – Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street. For more information, visit https://www.keywestlobsterfest.com or call 305-744-9804
  • August 14 – 18, 2019 – LBGTTropical Heat – All male, adults-only celebration of Key West’s gay community and lifestyle. Events include all-male themed parties and adult-oriented entertainment. For more information, visit www.tropicalheatkw.com or call the Key West Business Guild at 305-294-4603.
  • August 31 – September 2, 2019 – PARTY  10th Annual Key West Brew Fest – Labor-day weekend event featuring more than 150 different beers – including many award-winning microbrews. Events include seminars, tastings, pool parties, and meals. Big event is the Signature Tasting on Saturday, September 2 at South Beach ($75 per person for that event, advance tickets required). For more information, call 305-295-6519.

September 2019 Key West Events

  • August 31 – September 2, 2019 – PARTY  10th Annual Key West Brew Fest – Labor-day weekend event featuring more than 150 different beers – including many award-winning microbrews. Events include seminars, tastings, pool parties, and meals. Big event is the Signature Tasting on Saturday, September 2 at South Beach ($75 per person for that event, advance tickets required). For more information, call 305-295-6519.
  • September 2, 2019 – HOLIDAY  Labor Day 2017 in Key West – Picnics, bar-b-que, beaches, and a day of leisure, all activities Key West is known for. Expect warm ocean temperatures, balmy nights, and a laid back crowd.
  • September 4 – 8, 2019 – LGBT – Womenfest Key West 2019 – Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. Visit http://www.womenfest.com or call 305-294-4603 for more information.

October 2019 Key West Events

  • October 15, 2019 – SEAFOOD  Official 2019 Stone Crab Season Opening – In mid-October, the most delicious local seafood becomes available, the stone crab. With a porcelain-like shell and briny meat, this crab is considered a sustainable resource in that only the claws are taken and the crab is released back into the wild to grow new ones. Stone crab is only native to this region and is considered a seafood delicacy. October 15 is a special day for locals who eagerly await the opening of the stone crab season in Key West.
  • October 18 – 19, 2019 – PARTY  38th Annual Goombay Fest 2019 – This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche made fresh is popular), vendors selling a variety of wares, and live music at the bottom of Petronia. Don’t miss the party inside Blue Heaven. This is a family-friendly event and NOT the time to be wearing body paint or showing too much skin. 12noon – 12midnight. Petronia Street starting at Duval Street. FREE to attend. (Vendor opportunities available for craft and food – contact Maria Hernandez at 786-342-3340)
  • October 18 – October 27, 2019 – FANTASY FEST40th Annual Key West Fantasy Fest – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. This year’s theme is “In Tune But Off Key” In our opinion, Fantasy Fest is ready for a re-fresh, and we encourage you to be creative in your costume choice – not sleazy. For more information, visit https://www.fantasyfest.com
  • October 24, 2019 – LOCAL COLOR –  Headress Ball – Costume contest featuring dazzling headdresses created over many months and worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. Grand prize is $1500. Truman Waterfront Amphiteater, end of Southard Street. Buy tickets early as this event sells out. Call 305-294-4603 for tickets.
  • October 30 – November 3, 2019 – MUSIC – 28h Annual Meeting of the Minds 2019 – Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public. For more information, visit http://www.phip.com/meeting

November 2019 Key West Events

  • October 30 – November 3, 2019 – MUSIC – 28h Annual Meeting of the Minds 2019 – Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public. For more information, visit http://www.phip.com/meeting
  • November 2, 2019 – RUNNING27th Annual ABC 5K Walk/Run – Sponsored by Zonta, this running race benefits women’s health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach.  Registration cost is $25 – $35, depending on when you register. For more information, call 305-393-5200 or visit https://www.zontakeywest.com/abc-walk-2
  • November (DATE TO BE ANNOUNCED) 2019 – BOATING – 38th Annual Key West World Championship – Considered the pinnacle of offshore powerboat racing. Top powerboat & superboat offshore racers compete for title of World Champion. Spectators line the Key West harbor to see the 100+ mph action. Good viewing from Fort Zachary Taylor State Park at the end of Southard Street. For more information, call 305-296-6166.
  • November 28, 2019 – HOLIDAY – Thanksgiving in Key West 2019 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.

 

If you know of any Key West calendar events that we have overlooked please let us know by filling out this short form and we’ll quickly add it. And check back frequently – since more dates and details will be added as the season progresses.

 

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