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 dates and details are added as the season progresses.

2014 Key West Calendar of Events

  • January 2014

    • January 5, 2014 – MUSICPrima Trio – Clarinet, Violin and Piano – Presented by Impromptu Classical Concerts of Key West, the Prima Trio is comprised of clarinet, violin, and piano. They have previously won the Grand Prize and Gold Medal in the Fischoff Chamber Music Competition. 4pm at San Carlos Institute, 516 Duval Street. Tickets cost $20 and available at http://keystix.ticketforce.com/eventperformances.asp?evt=676
    • January 9 – 19, 2014 – LITERARY32nd Annual Key West Literary Seminar – This year’s topic is “The Dark Side”, exploring mystery, crime, and the literary thriller. Celebrated authors, including Carl Hiaasen, Joyce Carol Oates, Scott Turow, and many others gather at readings, discussions, lectures, and parties. More information and registration is available at http://www.kwls.org/seminar32/ or by calling 888-293-9291.
    • January 15 – 17, 2014 - SAILING - 2014 Fort Lauderdale to Key West Race - 39th annual sailing race open to single and multi-hull boats 25 feet and longer. Skippers meeting at Lauderdale Yacht Club on January 14. Race starts at 1pm on January 15. For more information visit http://www.keywestrace.org or call 954-524-5500.
    • January 17 – 18, 2014 – ARCHITECTURE54th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30 and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
    • January 18 – 19, 2014 – FOOD9th Annual Florida Keys Seafood Festival – This festival has grown in popularity by so much that this year’s festival has expanded to TWO DAYS! The 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 is free. 11 a.m. – 9 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://monroe.ifas.ufl.edu/environment/env_seafood_fest.shtml or call 305-872-9026.
    • January 19, 2014 – MUSICShen/Berkovsky Piano Duo – Presented by Impromptu Classical Concerts of Key West, this duet of pianists promises an afternoon of musical delight. 4pm at St. Paul’s Episcopal Church, 401 Duval Street. Tickets cost $20 and are available at http://keystix.ticketforce.com/eventperformances.asp?evt=677
    • January 19 – 24, 2014 – SAILINGPremier Racing Presents: Key West 2014 – Known locally in Key West as “race week”, this world-class sailing competition hosts over 100 racing yachts that compete for class championships in this international midwinter sailboat regatta. For more information and registration, visit http://www.premiere-racing.com/ or call 781-639-9545.
    • January 19, 2014 – SPORTS16th 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 $45, $50 day of race. Call 305-296-7182 for more information. For more information visit http://keywesthalfmarathon.com/index.htm or call 305-240-0727.
    • January 20 – 27, 2014 – SPORTS23rd Annual Kelly McGillis Classic Flag Football Championship – Women and girls from around the United States and the world gather in Key West for hard-fought sporting action during the Kelly McGillis Classic International Women’s & Girls’ Flag Football Championship. Includes three days of tournament games. For more information, visit http://www.iwffa.com/kmc23.html.
    • January 22 – 26, 2014 – FOODKey West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”. For more information, visit http://www.keywestfoodandwinefestival.com or call 305-292-1622.
    • January 23 – 24, 2014 – CIRCUSWalker International Small Family Circus – Traditional circus under a big tent featuring acrobatics, trained animals, and clowns.  Two performances each day.  Truman Waterfront (end of Southard Street).  For more information, call 941-350-8282.
    • January 24 – 26, 2014 – FISHINGKing Mackerel Tournament – Using the fastest boats in competitive saltwater fishing, highly competitive anglers seek the largest and most king mackerel for cash prizes. For more information, call (305) 296-0364.
    • January 25 – 26, 2014 – ARTS –  29th 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 25, 2014 – SPORTSBone Island Triathalon – Full and half-iron distance triathalon. For more information and registration, visit http://www.boneislandtri.com.
    • January 26, 2014 – FOOD20th Annual Key West Master Chefs Classic – Key West’s talented chefs compete for top honors in this annual gourmet competition. Benefits the local organization MARC House. 4pm-7pm at Westin Resort & Marina (245 Front Street). For more information, visit http://www.marchouse.org/masterchefsclassic or call 305-294-9526 ext. 25.
    • January 26, 2014 – ARTSKey West Artisan Market – Held one Sunday each month, this open air bazaar is filled with artists, authors, chef-made cuisine, craftspeople, performers and fresh produce representing the diversity of creativity, ingenuity and locally made products of Key West. 1111 Eaton Street, 10am – 2pm. For more information, visit https://www.facebook.com/KeyWestArtisanMarket or call 305-294-7994.
    • January 27 – February 2, 2014 – SAILINGKey West Classic Regatta – This regatta features classic sailing vessels in multiple races, as well as parties, music, storytelling, and nautical fun in the sun. Historic tall ships, modern wooden and replica vessels, and those who appreciate them are welcome. For more information visit http://www.keywestclassicregatta.com/ or call 305-509-1771.
    • January 31 – February 1, 2014 – FISHINGCuda Bowl – Cooler winter temperatures bring big barracuda up onto the saltwater flats, and catching them is a regular occurrence in this tournament. Hurricane Hole Marina on Stock Island. For more information, visit www.cudabowl.com or call 305-744-0903.

  • February 2014

    • February 2, 2014 – MUSICAlexander String Quartet - Presented by Impromptu Classical Concerts of Key West and includes two viola, cello, and two violins. They have previously won the London International String Quartet Prize. 4pm at the San Carlos Institute, 516 Duval Street. Tickets cost $20 and are available at http://keystix.ticketforce.com/orderticketsarea.asp?p=1216&a=585
    • February 7 – 8, 2014 – SPORTSRagnar Relay Florida Keys, Miami to Key West - Nearly two-hundred mile running race from Miami to Key West. Teams of twelve relay runners traverse the entire length of the Florida Keys. For more information, visit http://www.ragnarrelay.com/race/floridakeys or call 877-837-3529.
    • February 14 – 15, 2014 – ARCHITECTURE54th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30 and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
    • February 15 – 16, 2014 – FOODGardenFest Key West & Beer Garden – Key West Botanical Garden Society’s annual membership meeting includes food, fun, libations, and more. For more information, visit http://kwbgs.org or call 305-296-1504.
    • February 16, 2014 – MUSICTrio Solisti - Presented by Impromptu Classical Concerts of Key West and includes violin, cello, and piano. Outstanding chamber music ensemble. – 4pm at St. Paul’s Episcopal Church, 401 Duval Street. Tickets cost $20 and are available at http://keystix.ticketforce.com/orderticketsarea.asp?p=1217&a=198
    • February 17, 2014 – HOLIDAY - President’s Day 2014 in Key West – Act like a president and visit Key West.  Four previous US presidents have visited Key West, including: Truman, Eisenhower, Franklin D.  Roosevelt, and John F. Kennedy.
    • February 22 – 23, 2014 – ARTS49th 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 http://www.keywestartcenter.com/festival.html or call (305) 294-1243.
    • February 23, 2014 – ARTSKey West Artisan Market – Held one Sunday each month, this open air bazaar is filled with artists, authors, chef-made cuisine, craftspeople, performers and fresh produce representing the diversity of creativity, ingenuity and locally made products of Key West. 1111 Eaton Street, 10am – 2pm. For more information, visit https://www.facebook.com/KeyWestArtisanMarket or call 305-294-7994.

  • March 2014

    • March 1, 2014 – LOCAL COLOR52nd Annual Conch Shell Blowing Contest – Prizes are awarded for contestants ability to coax sound from a conch shell by blowing into it like a trumpet. Oldest House, 322 Duval Street. FREE to attend. For more information, call 305-294-9501.
    • March 1, 2014 – LOCAL COLOR - 4th Annual ConchFest – Native Key Wester’s are known as Conchs, and this family-friendly festival celebrates their heritage. Mingle with the locals and enjoy local art vendors, island cuisine, and live music. FREE admission, Bay View Park, 11am – 9pm.
    • March 2, 2014 – ARTS13th 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 2, 2014 – MUSICCavatina Duo – Presented by Impromptu Classical Concerts of Key West and includes flute and guitar. This praised duo is noted for their style, sympathy, and technique. 4pm at San Carlos Institute, 516 Duval Street. Tickets cost $20 and are available at http://keystix.ticketforce.com/orderticketsarea.asp?p=1218
    • March 9, 2014 – FUNDRAISER - For the Birds - Fundraiser for the Key West Wildlife Center. This celebration will include a silent auction and an opportunity to observe native wildlife being returned to the wild. Food and Drinks generously donated by local businesses. $25 per person (children under 10 years are FREE).  3pm – 5:30pm at West Martello Tower (1100 Atlantic Boulevard).  For more information, visit keywestwildlifecenter.org or call 305-292-1008.
    • March 14 – 15, 2014 – ARCHITECTURE54th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30 and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
    • March 16, 2014 – MUSICGabriel Cabezas – Presented by Impromptu Classical Concerts of Key West, this rising star in the cello world has played with the New York Philharmonic, Chicago Symphony, and New World Symphony. 4pm at St. Paul’s Episcopal Church, 401 Duval Street. Tickets cost $20 and are available at http://keystix.ticketforce.com/orderticketsarea.asp?p=1219
    • March 17 – 20, 2014 – FISHINGMerkin Invitational Permit Tournament – Fly fishermen compete to catch the most permit, one of the most challenging fish to catch on fly. Key West Yacht Harbor Marina (Stock Island). For more information, visit www.marchmerkin.com or call 303-888-4546.
    • March 20, 2014 – ARTSScott Gruppe Art Show -  As part of the monthly “Walk on White” gallery walk, figurative expressionist painter displays his work at the Debra Butler Design Studio, 600 Frances Street, 5pm-8pm.
    • March 21, 2014 – BENEFIT - 7th Annual Florida Keys SPCA Spring Social - Outdoor dinner, music and auction at the Key West Golf  Course to benefit Florida Keys SPCA with life music, cash bar for liquor and complimentary beer and wine, live and silent auctions, and your favorite restaurants preparing a great meal. All to benefit the local animal shelter that does so much to provide animals with a forever home. Tickets available at FKSPCA keystix.com and at the door. Contact: (305) 294-4857 or www.fkspca.org.
    • March 22, 2014 – MUSIC - Keystock Music Fest – Live music performances at the Truman Waterfront (end of Southard Street), featuring Florida Keys musicians including Howard Livingston. Noon to 9:30pm. For more information, call 305-745-1079.
    • March 28 – 29, 2014 – ARTS5th Annual Florida Keys Ocean Festival & Waterfront Craft Show – Hosted by the Florida Keys Eco-Discover Center, this two day event features live music, arts & crafts with Wyland, educational displays, food & beverages, and silent auction. 11am – 6pm, end of Southard Street. FREE admission. For more information, visit http://www.keysoceanfest.org/.
    • March 29, 2014 – RUNNING2nd Annual Tuna Trot Race for the Reef – This 5 kilometer race begins at 8am at the Eco Discovery Center (end of Southard Street). For more information, call 305-292-7963.
    • March 30, 2014 – MUSICChamber Orchestra Kremlin – Presented by Impromptu Classical Concerts of Key West, Chamber Orchestra Kremlin, founded in 1991 and led by Misha Rachlevsky, has earned national and international recognition as one of Russia’s leading ensembles. 4pm at the Tennessee Williams Theatre, 5901 College Road (Stock Island). Tickets cost $30 for Regular seats, $50 for Orchestra Center seats, and are available at http://keystix.ticketforce.com/ordertickets.asp?p=1222
    • March 30, 2014 – ARTSKey West Artisan Market – Held one Sunday each month, this open air bazaar is filled with artists, authors, chef-made cuisine, craftspeople, performers and fresh produce representing the diversity of creativity, ingenuity and locally made products of Key West. 1111 Eaton Street, 10am – 2pm. For more information, visit https://www.facebook.com/KeyWestArtisanMarket or call 305-294-7994.

  • April 2014

    • April 1 – 26, 2014 – ARTS18th Annual Sculpture Key West – Sculptures are installed at three locations on the island – providing visitors a creative, unique, and thought-provoking display of one-of-a-kind art. The exhibits are well worth checking out. Visit West Martello Tower and Higgs Beach. For more information, visit sculpturekeywest.org or call (305) 295-0674.
    • April 4 – 6, 2014 – FISHINGKey West Fishing Tournament – There is always good fishing to be had in Key West, and this tournament proves it. Categories include tuna, snapper, wahoo, cobia, permit, tarpon, bonefish, barracuda, marlin, and sailfish! Holy MACKERAL that’s a lot of fish. And yes, there is a mackeral division too. For more information, visit http://www.keywestfishingtournament.com/ or call 305-295-6601.
    • April 5, 2014 – ECOLOGYMigration Mania – The Great Egg Hunt and Wild Bird Show! – This family-friendly educational event creates awareness and appreciation for the birds that visit our Garden. Features educational activities, egg hunts, arts and crafts, games, live bird presentations, and much more. $5 admission, members free. 5210 College Road, Stock Island.
    • April 12 – 13, 2014 – ECOLOGYGardens Tour – Presented by the Key West Garden Club, this event visits private gardens with local experts identifying plants. 10am – 3pm at Ft. West Martello, 1100 Atlantic Blvd. For more information, visit http://kwbgs.org/news.asp?id=188 or call 305-745-2030.
    • April 12, 2014 – LITERATUREAfter Life – Images from the Key West Cemetery - Carol Tedesco, Roberta DePiero and Jane Newhagen will present their new release at a public book launch and signing event.  With photography by Tedesco and DePiero and prose by Newhagen, After Life captures the island’s unique final resting place in all its poignance, character and eccentricity. Salute on the Beach, 1000 Atlantic Blvd., 4pm – 6pm.
    • April 14, 2014 – FOOD19th Annual Taste of Key West – For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions along the Truman waterfront – 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. Car traffic is usually heavy – so come by bike or foot and breeze on past the cars lined up. Or take the Old Town Trolley, offering free transportation for the event, starting at 5:30 pm at the Pier House (1 Duval Street), with stops at the Westin, La Concha, corner of Simonton & South Street, and the Casa Marina Resort. Trolley runs every 30 minutes until last departure from Truman Waterfront Park at 9pm. Admission to event is FREE. Food tickets sold in $1 increments. For more information, visit http://www.aidshelp.cc/taste.html or call 305-296-6196.
    • April 18 – 27, 2014 – LOCAL COLOR32nd Annual Conch Republic Independence Celebration – Celebration of Key West’s brief secession from the United States. Event highlights include drag (queen) races on Duval Street (April 19, 1-11pm), 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 (April 25, 6pm). Kick-off party at the Schooner Wharf bar on April 18th, 7pm. For more information visit http://www.conchrepublic.com/schedule.htm or call 305-296-0213.
    • April 23 – 27, 2014 – FISHINGSecond Annual Key West Sailfish Championship – Three days of catch-an-release fishing by professional and amateur anglers with big cash prizes, including $50,000 for first place in the pro division. For more information, visit http://www.keywestsailfishchampionship.com/ or call 305-340-2737.

  • May 2014

    • May 1 – 4, 2014 – SPORTSKey West Paddleboard Classic – Race around the island of Key West aboard stand-up paddleboards. Begins at 9:30am. For more information, call 305-295-9898.
    • May 7 – 11, 2014 – MUSIC20th Annual Key West Song Writers Festival - Features more than one-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 www.keywestsongwritersfestival.com.
    • May 8, 2014 – MUSIC - The Living Room Series – Truman Little White House Thanks For The Memories – A Salute to the USO – Local singer and musician perform songs from President Truman’s time.  Truman’s Little White House, 111 Front Street.
    • May 16-17, 2014 – HISTORYHarry S. Truman Legacy Symposium - Examining 14 years of the Truman Legacy, this year the Symposium partners with the Harry S. Truman Library to explore Truman’s Nuclear Legacy and the decision to drop the atomic bomb.  May 18 will feature discussion by atomic bombing survivors.
    • May 16, 2014 – FOODWines of South Africa “From BBQ to Braai” Road Trip Series – Benefiting a truly excellent and worthwhile local charity, Monroe County ReMARCable Citizens, this event will feature wines from South Africa paired with BBQ by expert chefs.  $25 gets you unlimited food and wine.  $25 per person. 7pm-10pm at West Martello Tower.  For more information, call 305-294-9526 ext. 25.
    • May 26, 2014 – HOLIDAYMemorial Day 2014 in Key West – For many people, Memorial Day is the traditional beginning of summer.  And what better way to spend it than in Key West at the beach, or at a local fish fry, or on Duval Street.  Here’s to summer!
    • May 30 – 31, 2014 – FISHINGYamaha Dolphin Masters Invitational - Dolphin fish, also known as Mahi-Mahi or Dorrado, is NOT the marine mammal with the same name. (They look very different, too.) Dolphin fish are plentiful during summer offshore of Key West, and this tournament will reward the boat that catches the biggest combined weight of three fish. $13,000 in prizes. Call 305-304-7674 for more information.

  • June 2014

    • June 7, 2014 – ARTSGretchen Mills Unveils “Night is Coming” – Local artist Gretchen Mills presents her newest works.  Specializing in mixed media of collage and painting, Mills creates remarkable, powerful, and beautiful works of art. “Each of my collage subjects represents the powerful connectivity of all life around us, which I create by building up layers of organic shapes, textures, and symbols until a single life form emerges. I make my palette by printmaking and painting vivid colors on recycled, handmade papers– then tear and layer until I create something that I love.”  929 Truman Avenue, 6-9pm. (show continues to be displayed until July 7, 2014).
    • June 21, 2014 – ARTS - The 8th Annual Midsummer’s Night Dream and Spectacle - The most magical night of summer – the Midsummer’s Night Dream and Spectacle – a night of artistic expression, music, feasting, dancing, singing, and theatrical antics celebrating the art and artists of the Keys. Co-produced by Michael Shields’ Java Studios and The Key West Tropical Forest and Botanical Garden, the event benefits the Tropical Forest and Botanical Garden. Admission is $15 for adults in advance or $20 at the door; children age 12 & under are admitted free. 5 pm to 11 pm.  5210 College Road (Stock Island).   For more information, call 305-394-3804.  To purchase advance tickets, visit www.kwbgs.org.
    • June 11 – 15, 2014 – 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. Street fair in June 8, 10am-7pm on Duval Street. For more information, visit www.keywestpride.org.
    • June 13 – 15, 2014 – LITERATUREMystery Writers Fest – Inaugural festival for writers of mystery, suspense, and crime. This year’s theme is “Murder and Mayhem in Paradise”.  Features five panels, book signings, and time with authors, editors, and publishers.  $98 to register.  Event headquarters is the Grand Key Resort, 3990 S. Roosevelt Blvd, Key West.  For more information and registration, visit http://mysterywriterskeywestfest.com/mysterywriterskeywestfestivalregistration.htm
    • June 14, 2014 – SPORTSFKCC Swim Around Key West – Swimmers, accompanied by kayakers, circumnavigate the island of Key West, a distance of over 12 miles. For more information, visit www.fkccswimaroundkeywest.com or call 305-809-3562.
    • June 20 – 22, 2014 – FISHINGDolphin Derby – Fishing tournament for Key West’s summertime offshore gamefish, the dorrado (known locally as dolphinfish). Win up to $5000 for most dorrado. For more information, visit keywest.gatorclub.com/Event.htm or call 305-304-7674.
    • June 28, 2014 – SPORTS38th Annual Swim Around Key West – Long-running, long-distance swimming competition. Each race is accompanied by a kayaker. Race begins at Smathers Beach.

  • July 2014

    • July 10 – 13, 2014 – MARITIMEMel Fisher Days – Come celebrate the day 28 years ago when Mel’s crews found $400 million in shipwrecked gold, silver and emeralds that had been sitting on the ocean floor for more than 300 years. Kick-off party at the Schooner Wharf Bar with costume contest, raffle, and live entertainment. Duval Street block party is on Saturday, 2pm – 8pm, in the 200 block of Duval Street, and features live music and street fair food. For more information, call 305-295-7929.
    • July 13 – 16, 2014 – FISHING - 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. Really, it is a feat of a lifetime, but if you have the skills, pattern, and luck, then you just may have a chance. For more information, visit http://www.delbrown.com or Call 305-744-0903.
    • July 15 – 19, 2014 – HEMINGWAY - 34th Annual Hemingway Days and Look-Alike Contest – Annual celebration of Key West’s most famous writer, Ernest Hemingway, who wrote some of his most recognized works in Key West. Short story contest, readings, and marlin fishing tournament highlight the week’s activities. There will be a Duval Street fair on July 19th. Look-alike contest is held July 17-19 at Sloppy Joe’s bar, one of Hemingway’s favorite watering holes. This competition features dozens of Hemingway look a-likes competing for prizes and bragging rights. Costs $35 to register. FREE to watch. 6:30pm at 201 Duval Street. For more information, call 305-294-2388.
    • July 16 – 19, 2014 – FISHING Drambuie Key West Marlin Fishing Tournament – Coinciding with the Hemingway Days celebration, this fishing tournament has anglers competing for the king of all gamefish – the marlin. Large cash prizes for largest fish, including marlin, dolphin fish (mahi-mahi), wahoo, and sailfish. Cost is $1500 per vessel for early registration, or $1800 for late registration. Additional fees for fun fish, extra angler, and extra banquet tickets. For more information, visit http://www.keywestmarlin.com or call 305-292-2710.
    • July 17, 2014 – HEMINGWAYSloppy Joe’s 34th Annual 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 19, 2014 – SPORTSHemingway 5k Sunset Run & Paddleboard Race – Running race through Key West. For more information, visit http://www.keywestspecialevents.com/hemingway5k-run-paddleboard.htm or call 305-240-0727.

  • August 2014

    • August 3, 2014 - LOCAL COLOR21st Annual Battle of the Bars – Bartenders and drink servers from Key West’s many bars compete in a wacky, alcohol-fueled competition for fastest drink preparation, quickest drink service, and funniest costumes.  Takes place at the Schooner Wharf Bar and provides plenty of uniquely Key West entertainment. Proceeds benefit several local charities.  Begins at 12:30pm, Schooner Wharf Bar, 202 Williams Street.
    • August 7 – 10, 2014 – SEAFOOD - 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 www.keywestlobsterfest.com or call 305-744-9804
    • August 14 – 17, 2014 – 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 28 – September 1, 2014 – PARTY5th Annual Key West Brewfest – 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, August 31 at South Beach ($75 per person for that event, advance tickets required). For more information, visit http://www.keywestbrewfest.com or call 305-295-6519.
    • August 30 – September 1, 2014 – SALEBesame Mucho’s Splendid Summer Sale – Key West’s most charming, well-curated, and unique shops is Besame Mucho, located just a few doors up from Blue Heaven in Bahama Village.  In here you’ll find the most tasteful collection of items from around the world, including exotic soaps & candles, jewelry handmade by artists, designer homegoods, linen shirts, and heart-felt gifts. Once a year they do a sale, and this is your chance to get 30% off everything storewide.  315 Petronia Street.  For more information, visit http://besamemucho.net or call 305-294-1928.

  • September 2014

      • August 30 – September 1, 2014 - SALE - Besame Mucho’s Splendid Summer Sale - Key West’s most charming, well-curated, and unique shops is Besame Mucho, located just a few doors up from Blue Heaven in Bahama Village.  In here you’ll find the most tasteful collection of items from around the world, including exotic soaps & candles, jewelry handmade by artists, designer homegoods, linen shirts, and heart-felt gifts. Once a year they do a sale, and this is your chance to get 30% off everything storewide.  315 Petronia Street.  For more information, visit http://besamemucho.net or call 305-294-1928.
    • August 28 – September 1, 2014 – PARTY5th Annual Key West Brewfest – 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, August 31 at South Beach ($75 per person for that event, advance tickets required). For more information, visit http://www.keywestbrewfest.com or call 305-295-6519.
    • September 4 – 7, 2014 – LBGTWomenfest Key West 2014 – 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. For more information, visit http://www.womenfest.com or call 305-294-4603.
    • September 5 – 7, 2014 – FISHINGS.L.A.M. Celebrity Tournament – In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis. For more information, visit http://www.redbone.org or call 305-664-2002.
    • September 18 – 21, 2014 – MOTORCYCLES42nd Annual Poker Run – Over 10,000 motorcycle riders travel down the Florida Keys, stopping at five places to pick up a poker card at each one. Prizes are awarded to the best poker hands. Duval Street will be lined with impressive bikes, many rightfully called works of art. Proceeds from the event go to local charities. For more information, visit http://www.petersonsharley.com/custompage.asp?pg=pokerrun.

  • October 2014

    • October 9 – 13, 2014 – RUNNINGSoMo Marathon & Half Marathon – Running race through Key West and up the “lower Keys” with views of the Gulf of Mexico and the Atlantic Ocean. Distances of full marathon (26.2 miles) and half-marathon (13.1 miles). Registration costs $100 for full marathon, $75 for half marathon. For more information, visit http://somomarathon.com
    • October 15, 2014 – SEAFOOD2014 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, then the crab is released back into the wild to grow new ones. Stone crab is only native to this region and is considered a delicacy.  October 15 is a special day for locals who eagerly await the opening of the stone crab season in Key West.
    • October 17 – 18, 2014 – PARTY34th Annual Goombay Fest 2014 – 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. 10am – 11pm. Petronia Street starting at Duval Street. FREE to attend. For more information, visit http://www.bahamavillagegoombay.com
    • October 17 – 26, 2014 – FANTASY FEST35th 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 “Animéted Dreams and Adventures”. Fantasy Fest event schedule will be posted here once it becomes available. For more information, visit http://www.fantasyfest.com
    • October 29 – November 2, 2014 – MUSIC23rd Annual Meeting of the Minds 2014: Havana Daydreamin’ – 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/motm.asp

  • November 2014

    • November 2 – 9, 2014 – BOATING34th 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, visit http://superboat.com/race-schedule/ or call 305-296-6166.
    • November 4 – 10, 2014 – BOATING22nd Annual Key West Powerboat Poker Run – Two-hundred powerboat teams travel from Miami to Key West, a 160 mile journey. Cost is $750 per boat, and is open only to members of the Florida Powerboat Club using vessels 25-80 feet in length. For more information, visit http://www.flpowerboat.com/key-west-poker-run.html or call 954-545-1414.
    • November 7 – 10, 2014 – ARTS3rd Annual Key West International Latin Arts Festival 2014 – Celebration of traditional Latin American cultural arts featuring folkloric dance and percussion workshops, Latin American artists’ exhibits, poetry readings, culinary surprises and a spectacular theatrical concert featuring InnerNacionalSound’s Christian Monzón and Valerie Carr, renowned Miami-based Tango Times dance luminaries Roxana Garber and Oscar Caballero and an outstanding line-up of local and visiting musicians, folk dancers and thrilling Capoeira performers. San Carlos Institute, 516 Duval Street. For more information, visit http://valnchzproductions.com/-Esperando_Nacer_.html or call 305-394-0808.
    • November 12 – 16, 2014 – ARTS 3rd Annual Key West Film Festival – Features independent cinema with awards for narrative feature film, LGBT feature film, documentary, Florida feature film, and foreign feature film. Events include movie screenings, kick-off party, and awards gala. For more information, visit http://kwfilmfest.com/ or call 941-527-9385.
    • November 28 – 30, 2014 – ARTSART!KEYWEST! - Art festival that celebrates many artists, galleries, boutiques, restaurants, and art-focused emporiums. Performance art, sculpture, interactive art, and musical performances are scheduled into the lively and coordinated art walk. For more information, visit http://www.artskeywest.com.
    • November 14 – 15, 2014 – LGBT11th Annual Smart Ride – Hundreds of bicyclists ride from Miami to Key West, a 165 mile course over two days, to raise money for the benefit of raising awareness for HIV/AIDS organizations in Florida. Cost is $95 per entrant, For more information, call 305-296-6196.
    • November 27, 2014 – HOLIDAYThanksgiving in Key West – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menu.

  • December 2014

    • December 4 – 7, 2014 – SPORTS4th 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, visit http://trikw.com or call 305-797-8361.
    • December 5 – 7, 2014 – FESTIVITIES Fort Taylor Pyrate Invasion – Pirate re-enactors transform Fort Zachary Taylor in to an English Fort, defending itself from pirate invaders. Events include traditional music, costumed pirates, and pirate battles. For more information, visit http://forttaylorpyrates.com or call 305-797-1659
    • December 25, 2014 – HOLIDAYChristmas in Key West 2014 – Whatever gift you wish for, spending Christmas in Key West should be at the top of the list. While it never snows, and sometimes a palm tree is substitued 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 31, 2014 – 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, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

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. And check back frequently – since more dates and details will be added as the season progresses.

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