Events Calendar 2016

 A great year – 2016 in Key West & The Florida Keys

So much to do!

Come to your island paradise and

Enjoy Yourself!!

What’s life without a little pleasure?!


2016 Key West Calendar of Events


January 7 – 10, 2016 – 34th Annual Key West Literary Seminar – This year’s topic is “Shorts Stories, Essays, & Other Briefs”. Authors include Ann Beattie, Billy Collins, Thomas McGuane, and others for readings, discussions, lectures, and parties. Call 305-293-9291.

January 8 – 10, 2016  Key West Wahoo Shootout – A bluewater spearfishing tournament. Headquarters at The Waterfront Brewery. Going for Wahoo, King Mackerel and Amberjack with up to $20,000 in prizes. Adult, Junior divisions and Captain’s prize. Call 305-896-4244

January 13 – 15, 2016 – 2016 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 954-881-3094.

January 15 – 16, 2016 – 56th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30. Call 305-294-9501.

January 16 – 17, 2016 – 11th Annual Florida Keys Seafood Festival – Celebrate 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  served up. 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. 305-872-9026.

January 17, 2016 – 18th Annual Key West Half Marathon – Over 1,000 runners enjoy near perfect temperatures, flat terrain and Key West scenery in one of the most popular running races. Entry $45, $50 day of race. 305-296-7182.

January 17 – 22, 2016 – Quantum 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 mid-winter sailboat regatta.

January 27 – 31, 2016 – 6th Annual Key West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”. For more information call 800-474-4319.

January 30 – 31, 2016 – 31st Annual Key West Craft Show – Open air art market and judged show offering an amazing variety of work to include sculpture, paintings, craft, and folk art. Whitehead Street and Caroline Streets, Key West. For more information call 305-294-1243.


February 4 – 6, 2016 – Cuda Bowl – Come on and fight your barracuda. Headquarters at Hurricane Hole Marina, Stock Island. Prizes and trophies for top angler and guide in light tackle spin and fly divisions. Call 305-744-0903

February 7, 2016 – Super Bowl L (50) – The NFL’s 50th annual championship game is on and Key West bars offer the best scene to watch. Schooner Wharf Bar, at 202 William Street, has numerous large screen TV’s, food, and drink specials.

February 12 – 13, 2016 – 56th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30. Call 305-294-9501 for more information.

February 14, 2016 – Valentine’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. <3 <3 <3

February 27 – 28, 2016 – 51st 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 call (305) 294-1243.


March 5, 2016 – 54th 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 – 56th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $30. Call 305-294-9501 for more information.

March 14 – 17, 2016 –  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 call 303-888-4546.

March 17, 2016 – Saint Patrick’s Day – So many people treat every 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 – Easter in Key West – Many restaurants have special Easter Brunch menus.

Some reading for your future – Here’s a great book to get you thinking

“Quit your job and move to Key West.” 


April 6, 2016 – 7th 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.

April 9, 2016 – 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 – 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. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Race begins at noon.

April 12 – 17, 2016 – 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 call 305-340-2737.

April 22 – May 1, 2016 – 34th 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 call 305-296-0213.

April 22, 2016 – Earth 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 here.

April 30, 2016 – Key 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 4 – 8, 2016 – 21st Annual Key West Song Writers Festival – 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.

May 11 – 15, 2016 – Kamp Key West – This annual event is designed for LGBTA outdoor enthusiasts and adventurists who recall the days in summer camp.

May 13 – 15, 2016 – Papio Kinetic Sculpture Parade – Presented by The Key West Art  & Historical Society this family friendly exhibition event is also a parade powered by humans on bicycles. All ages.

May 30, 2016 – 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.


June 8 – 12, 2016 – 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.

June 10 – 12, 2016  – 3rd Annual Key West Mystery Writers Fest – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. Acclaimed authors share insights on their craft. Aspiring writers have a chance to pitch their plots to editors. Registration is $98.

June 18, 2016 – Key West Island Swim: FKCC Swim Around Key West – This event is a 12.5 miles swim around the island of Key West. Open to all ages individuals and relay teams can compete. Beginning and ending at Higgs Beach the route takes you through the Atlantic and the Gulf of Mexico. Contact 305-809-3562

June 16 – 19, 2016 – Key West West Africana Festival – Explore music, art and Key West’s Afro-Caribbean culture for this three day destination retreat.

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July 2 – 4, 2016 – 4th 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. Mouth watering!

July 9 – 12, 2016 – 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 practice, it is a feat of a lifetime, but if you have skills, pattern and luck, then you may have a chance. For more information call 305-744-0903.

July 14 – 16, 2016 – Mel Fisher Days – Come celebrate the day 29 years ago when Mel’s crews found $400 million in shipwrecked gold, silver and emeralds that was 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 20 – 24, 2016 – Hemingway 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 – Lobster Mini-Sport Season – Two-day event draws many in search of Florida lobster. 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 Saltwater 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 at 305-289-2320 for more information.

Some reading for your future – Here’s a great book to get you thinking

“Quit your job and move to Key West.” 


August 11, 2016 – Key West Lobsterfest – Party on Duval Street 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 call 305-744-9804

August 11 – 14, 2016 – Tropical 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 call the Key West Business Guild at 305-294-4603.


September 01 – 05, 2016 – Seventh Annual Key West Brewfest
More than 150 beers and micro-brews are on tap for this annual event. This benefits charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Enjoy events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event and more. Contact 800-354-4455
September 08 – 11, 2016 – Womenfest Key West – Thousands of women flock to Key West each year for this renowned celebration for lesbians and their friends. Activities to include dance parties, poolside parties, sailing and snorkeling. Contact 305-294-4603
September 19 – 11, 2016 – Robert James Sales S.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.” This event raises funds for the fight against cystic fibrosis. Contact 305-664-2002


October 15, 2016 – 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 15th is a special day for locals who eagerly await the opening of the stone crab season in Key West. You have got to try Stone Crabs!

October 21 – 22, 2016 – 36th Annual Goombay Fest 2016 – This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche is popular), vendors selling wares, and live music at the bottom of Petronia. Don’t miss the party inside Blue Heaven. This is a family friendly event so please no wearing body paint and/or showing too much skin. 10am – 11pm. Petronia Street starting at Duval Street. FREE to attend.

October 23, 2016 – Key West Halloween Half Marathon and 5K Run – A Halloween themed running event that encourages you to dress in costume.

October 21 – October 30, 2016 – 37th Annual Key West Fantasy Fest – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. Costume competitions for pets, and more than 50 other contests. Street fairs and a grand parade with amazing floats.This year’s theme will be Political Voodoo And Ballot Box Barbarians. Contact 305-296-1817


November 2 – 6, 2016 – 25th 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) it is FREE and open to the public.

November 6 – 13, 2016 – 35th Annual Key West World Championship Races – Super Boat International returns. High speed powerboats race in Key West Harbor and surrounding waters – known as the Indianapolis 500 of powerboat racing. Speeds up to and above 140 mph. Whoosh!

November 24, 2016 – Thanksgiving 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.


December 24, 2016 – January 1, 2017 – Hanukkah 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 – Christmas in Key West 2016 – Whatever gift you wish for, spending Christmas in Key West could 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. It’s magical!

December 31, 20165 – Key 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.

Check back frequently – more dates and details will be added as the seasons progress.