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.

2016 Key West Calendar of Events

January 2016 Key West Events

  • January 7 – 10, 2016 – LITERARY 34th Annual Key West Literary Seminar – This year’s topic is “Shorts – Stories, Essays, & Other Briefs.”. Celebrated authors, including Ann Beattie, Billy Collins, Thomas McGuane, and numerous others gather at readings, discussions, lectures, and parties. More information and registration is available at http://www.kwls.org/seminar34 or by calling 305-293-9291.
  • January 13 – 15, 2016 – SAILING2016 Lauderdale to Key West Race – 41st annual sailing race open to single and multi-hull boats 25 feet and longer. Skippers meeting at Lauderdale Yacht Club on January 12. Race starts on January 13. For more information visit http://www.keywestrace.org or call 954-881-3094.
  • January 15 – 16, 2016 – ARCHITECTURE56th 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 16 – 17, 2016 – FOOD11th 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 is $5. 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 17, 2016 – SPORTS18th 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.
  • January 17 – 22, 2016 – SAILINGQuantum Racing Presents: Key West 2016 – 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.yachtscoring.com/emenu.cfm?eID=1390.
  • January 27 – 31, 2016 – FOOD – 6th Annual Key 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 800-474-4319.
  • January 30 – 31, 2016 – ARTS31st 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.

February 2016 Key West Events

  • February 7, 2016 – SPORTSSuper Bowl L (50) – The NFL’s 50th annual championship game is held and Key West bars offer a raucous and fun scene to watch the spectacle. Schooner Wharf Bar, at 202 William Street, has numerous large screen TV’s, food, and drink specials.
  • February 12 – 13, 2016 – ARCHITECTURE56th 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 14, 2016 – 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 lovers in Key West.
  • February 27 – 28, 2016 – ARTS51st 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.

March 2016 Key West Events

  • March 5, 2016 – LOCAL COLOR54th 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. 12pm (noon), Oldest House, 322 Duval Street. FREE to attend. For more information, call 305-294-9501.
  • March 11 – 12, 2016 – ARCHITECTURE 56th 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 14 – 17, 2016 – FISHING – Merkin 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 www.marchmerkin.com or call 303-888-4546.
  • March 17, 2016 – 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 27, 2016 – HOLIDAYEaster in Key West – Numerous restaurants has special Easter Brunch menus.

April 2016 Key West Events

  • April 6, 2016 – ARTS7th Annual Florida Keys Ocean Festival & Waterfront Craft Show – Hosted by the Florida Keys Eco-Discover Center, this two day event features live music by Howard Livingston & the Mile Marker 24 Band, 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/.
  • April 9, 2016 – RUNNING 35th 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. For more information, call 305-395-7040.
  • April 10, 2016 – RUNNING 3rd Annual Cow Key Channel Run – This 300-feet long mock marathon over the short 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. FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Race begins at noon. For more information, visit: http://cowkeybridgerun.com/.
  • April 12 – 17, 2016 – FISHING Final Sail in the Quest for the Crest Series (Formerly known as the 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.
  • April 22 – May 1, 2016 – LOCAL COLOR34th 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, 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 April 17th, 7pm. For more information visit http://www.conchrepublic.com/schedule.htm or call 305-296-0213.
  • April 22, 2016 – 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!
  • April 30, 2016 – 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 2016 Key West Events

  • May 4 – 8, 2016 – MUSIC – 21st 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 30, 2016 – HOLIDAY – Memorial Day 2015 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, at a local fish fry, or on Duval Street. Happy summer!

June 2016 Key West Events

  • June 8 – 12, 2016 – LGBT – 21st Annual Key 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 Pride Parade on Duval Street. Street fair on June 12, 10am – 7pm on Duval Street. For more information, visit www.keywestpride.org.
  • June 10 – 12, 2016  – LITERATURE – 3rd Annual Key West Mystery Writers Fest – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. Registration is $98. For more information, visithttp://www.mysterywriterskeywestfest.com/

July 2016 Key West Events

  • July 2 – 4, 2016 – FOOD4th Annual Key Lime Festival – Key Limes grown abundantly on the island, and are necessary to make true Key Lime pie.  This three 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 9 – 12, 2016 – FISHING 16th 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, visit http://www.delbrown.com or call 305-744-0903.
  • July 14 – 16, 2016 – MARITIMEMel Fisher Days – Come celebrate the day 29 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, visit http://www.melfisherdays.com or call 305-295-7929.
  • July 20 – 24, 2016 – HEMINGWAYHemingway Days & Sloppy Joe’s 36th 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 27 – 28, 2016 – FISHINGLobster 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 2016 Key West Events

  • August 11, 2016 – SEAFOODKey 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 11 – 14, 2016 – 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, visitwww.tropicalheatkw.com or call the Key West Business Guild at 305-294-4603.

September 2016 Key West Events

  • Dates have not been announced for the following regular events that occur in September, including: Key West Brewfest, WomenFest Key West, S.L.A.M. Celebrity Fishing Tournament, and Key West Poker Run.  Check back – this calendar will be updated when details become available.

October 2016 Key West Events

  • October 15, 2016 – SEAFOOD Official 2016 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 21 – 22, 2016 – PARTY36th Annual Goombay Fest 2016 – 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.
  • October 21 – October 30, 2016 – FANTASY FEST37th 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 will be announced after the conclusion of Fantasy Fest 2015.  Fantasy Fest event schedule will be posted here once it becomes available. For more information, visit http://www.fantasyfest.com

November 2016 Key West Events

  • November 2 – 6, 2016 – MUSIC25th Annual Meeting of the Minds 2016: A Salty Piece of Land – 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 24, 2016 – HOLIDAYThanksgiving in Key West 2016 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.
  • Dates have not been announced for the following regular events that occur in November, including: Key West World Powerboat Championship, Smart Ride, Key West Film Festival, and ART!KeyWest!  Check back – this calendar will be updated as more details become available.

December 2016 Key West Events

  • December 24, 2016 – January 1, 2017 – HOLIDAYHanukkah in Key West 2016 – 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 25, 2016 – HOLIDAYChristmas in Key West 2016 – 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 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, 20165 – 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.
  • Dates have not been announced for the following regular events that occur in December, including: Fort Taylor Pyrate Invasion, TRIKW Triathalon, and the Lighted Boat Parade. Check back – this calendar will be updated as more details become available.

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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