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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January 2018 | February 2018 | March 2018 | April 2018 | May 2018 | June 2018 | July 2018 | August 2018 | September 2018 | October 2018 | November 2018 | December 2018

Key West 2018 Event Calendar

January 2018 Key West Events

  • January 11 – 14, 2018 – LITERATURE36th Annual Key West Literary Seminar – This year’s topic is “Writers of the Caribbean: The Literature of Politics.” Celebrated authors and numerous others gather at readings, discussions, lectures, and parties. More information and registration is available at or by calling 305-293-9291.
  • January 11 – 14, 2018 – FISHINGKey West Kingfish Mayhem – Did you know that the richest tournament prizes in saltwater fishing is for kingfish? Part of the mackeral family, this sport-fish 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
  • January 12 – 13, 2018 – ARCHITECTURE58th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $40, include Conch Train transportation, and are available at Call 305-294-9501 for more information.
  • January 13 – 14, 2018 – FOOD13th 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 or call 305-292-4501
  • January 14, 2018 – SPORTS20th 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
  • January 22 – 29, 2018 – SPORTS27th 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 – 19 has full week of events including parties). For more information, visit
  • January 24 – 28, 2018 – FOOD9th Annual Key West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”. For more information, visit or call 800-474-4319. Tickets for each even cost between $35 – $315.
  • January 24, 2018 – FOOD3rd Annual Conch Revival Picnic – Sample local Key West recipes and ingredients in this celebration of classic Florida Keys cuisine. Treasured family recipes, including Key Lime pie, conch chowder, Queen of All Puddings, conch fritters, and many more are served. $50 per person. East Martello Tower (3501 S. Roosevelt Blvd), 5:30 – 8:30pm. For more information, call 305-295-6616 ext. 111.
  • January 26 – February 3, 2018 – SAILING10th Conch Republic Cup – Sailing race and regatta to Cuba, comprised of three long-distance sails (between Key West & Cuba, between Varadaro and Havana, and between Cuba and Key West). Registration cost is $1000 per boat plus $200 per person ($500 additional if registering after Dec 31). For more information, visit
  • January 27 – 28, 2018 – ARTS33rd 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 or call 305-294-1243.
  • January 27, 2018 – 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 28, 2018 – FOOD 24th 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, 2107. 4 – 7pm. Margaritaville Resort & Marina, 245 Front Street. For more information, visit
  • January 28, 2018 – LOCAL COLOR2018 Crooks Annual Second Line – Reminiscent of the New Orlean’s funeral procession, and in celebration of those who have passed on, join hundreds of others in a marching “second line” procession from Hog’s Breath Saloon to the Green Parrot bar.  12pm – 5pm.  (noon-2pm, gathering at the Hog’s Breath; 2pm-3pm March on Duval Street; 3pm – 5pm, party at the Green Parrot). FREE TO ATTEND.  For more information, call 305-504-7664 or visit

February 2018 Key West Events

  • February 1 – 3, 2018 – 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 or call 305-360-6969 for more information.
  • February 2 – 4, 2018 – HISTORYCivil 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 3, 2018 – BENEFIT11th 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 7 – 10, 2018 – MUSICMile 0 Fest – Innaugural 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 $346.79 for 4-day festival pass. For more information and tickets, visit: or call 877-412-7658.
  • February 14, 2018 – 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 10, 2018 – BENEFIT4th 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. For more information, visit
  • February 16 – 17, 2018 – ARCHITECTURE58th 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 Call 305-294-9501 for more information.
  • February 24 – 25, 2018 – ARTS53rd 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 or call (305) 294-1243.

March 2018 Key West Events

  • March 3, 2018 – LOCAL COLOR56th 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. 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 3, 2018 – ARTS18th 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 12 – 15, 2018 – 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 or call 303-888-4546.
  • March 16 – 17, 2018 – ARCHITECTURE58th 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 Call 305-294-9501 for more information.
  • March 17, 2018 – 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 17, 2018 – BENEFITLucy’s Retired Surfers Bar & Restaurant Block Party – To benefit children’s cancer research, this block party features face painting, live music, and fund-raiding head-shaving.  Begins at 12 noon. 320 Grinnell Street.
  • March 24, 2018 – 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 24, 2018 – LGBTQ2018 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 or call 813-870-3735.

April 2018 Key West Events

  • April 1, 2018 – HOLIDAYEaster in Key West – Numerous local restaurants offer special Easter Brunch menus.
  • April 14, 2018 – RUNNING37th 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 2018. Only 1500 entries are allowed and this event quickly sells out. For more information, visit or call 305-395-7040.
  • April 15, 2018 – RUNNING5th 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. FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Registration costs $5. Race begins at noon. For more information, visit:
  • April 16, 2018 – FOOD23rd 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 17 – 21, 2017 – FISHING Final Sail in the Quest for the Crest Series – Formerly known as the Key West Sailfish Championship, this event offers three days of catch-and-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 or call 305-340-2737.
  • April 21-30, 2018 – LOCAL COLOR35th Annual Conch Republic Independence Celebration – Celebration of Key West’s brief secession from the United States. Event highlights include bed races on Duval Street (2pm April 29, Duval Street), conch shell blowing contest (7pm April 21, Schooner Wharf Bar), arts & crafts show (10am-5pm April 28, Duval Street), Duval Street Parade (7pm April 27), and the infamous bloody battle in Key West harbor (6pm April 28 Mallory Square) 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 21th, 7pm. For more information call 305-296-0213.
  • April 22, 2018 – 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 2018 Key West Events

  • May 4 – 6, 2018 – ARTS3rd 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 5 at noon in front of Customs House at 281 Front Street. For more information, call 305-295-6616 or visit
  • May 9 – 13, 2018 – MUSIC23rd 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
  • May 18 – 19, 2018 – HISTORY16th Annual Harry S. Truman Legacy Symposium – This year’s theme explores Russia & the Cold War, Truman through Reagan. For more information, call 305-294-9911 or visit
  • May 19 – 20, 2018 – RUNNING11th 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 2018 Key West Events

  • June 6 – 10, 2018 – LGBT 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 the Pride Parade along Duval Street. For more information, call (305) 292-3223 or visit
  • June 30, 2018 – 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

July 2018 Key West Events

  • June 30 – July 4, 2018 – FOOD6th Annual Key Lime Festival – Key Limes grown abundantly on the island, and 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
  • July 4, 2018 – 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.
  • July 9 – 14, 2018 – MARITIME – Mel Fisher Days – Come celebrate the day in Key West, over 30 years ago, when Mel’s crews found over $400 million in shipwrecked gold, silver and emeralds that had been sitting on the ocean floor for more than 300 years. Annual Dock Party at Schooner Wharf Bar is on Saturday, July 14th, with tours of salvaging vessels, raffle, silent and live auctions and live entertainment. Private tours of the Fisher Family Conservation Laboratory available. Enter to win an Atocha Coin.  Benefits Wesley House Family Services. For more information, visit or call 305-296-6533
  • July 15 – 18, 2018 – FISHING18th 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 or call 305-744-0903.
  • July 18 – 21, 2018 – FISHINGKey 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 $1800 per vessel for early registration, or $2100 for late registration. Only 75 boats accepted for competition. Additional fees for fun fish, extra angler, and extra banquet tickets. For more information, call 305-292-2710 or visit
  • July 19 – 22, 2018 – HEMINGWAYHemingway Days & Sloppy Joe’s 37th 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 21, 2018 – 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 or call 305-240-0727
  • July 25 – 26, 2018 – 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 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 (FWC) at 305-289-2320 for more information.

August 2018 Key West Events

  • August 9 – 12, 2018 – SEAFOOD22nd 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 or call 305-744-9804
  • August 15 – 19, 2018 – 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 or call the Key West Business Guild at 305-294-4603.

September 2018 Key West Events

  • September 1 – September 5, 2018 – PARTY9th 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 3, 2018 – HOLIDAYLabor 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 5 – 9, 2018 – LGBTWomenfest Key West 2018 – 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 or call 305-294-4603 for more information.
  • September 7 – 9, 2018 – 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, call 305-664-2002 or visit
  • September 22 – September 23, 2018 – MUSIC – Key West Musicians Festival – Some of Key West’s most talented musicians perform for the benefit of Sister Season, a local organization that helps workers, especially through tough times brought on by Hurricane Irma.  Smoking Tuna Saloon (4 Charles Street…just off Duval), 2pm – 9pm. FREE admission

October 2018 Key West Events

  • October 15, 2018 – SEAFOODOfficial 2018 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 19 – 20, 2018 – PARTY37th Annual Goombay Fest 2018 – 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 19 – October 28, 2017 – FANTASY FEST39th 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 “Oh…The Games We Play!” Last year, this festival began a “re-fresh” by a new festival organizer, and we continue to encourage artistic creativity over simple sleaze in your costume choice.  For more information, visit
  • October 25, 2018 – LOCAL COLOR – The 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. For more information, visit
  • October 25, 2018 – 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 31 – November 4, 2018 – MUSIC – 27th Annual Meeting of the Minds 2018 – 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

November 2018 Key West Events

  • October 31 – November 4, 2018 – MUSIC – 27th Annual Meeting of the Minds 2018 – 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
  • November 3, 2018 – RUNNING – 26th 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 at For more information, call 305-393-5200.
  • November 4 – 11, 2018 – BOATING – 37th 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 14 – 18, 2018 – ARTS –  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, call 941-527-9385 or visit
  • November 22, 2018 – HOLIDAY – Thanksgiving in Key West 2018 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.

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
  • December, 2018 (EXACT DATE TO BE ANNOUNCED) – 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, 2018 (EXACT DATE TO BE ANNOUNCED)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, 2018 (EXACT DATE TO BE ANNOUNCED)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
  • December, 2018 (EXACT DATE TO BE ANNOUNCED) 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, 2018 (EXACT DATE TO BE ANNOUNCED) 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 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.

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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