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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November 2016 | December 2016

January 2017 | February 2017 | March 2017 | April 2017 | May 2017 | June 2017 | July 2017 | August 2017 | September 2017 | October 2017 | November 2017December 2017

2016 Key West Calendar of Events.

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 5 – 6, 2016 – ARTSRebecca Bennett Gallery Show – One of Key West’s prized artists, Rebecca Bennett, will display here newest work of impressionist oil paintings at SALT Gallery, 830 Fleming Street, 8pm.  For more information, visit http://rebeccabennettpaintings.com
  • November 6 – 13, 2016 – BOATING36th 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 11, 2016 – MUSICReef Relief Fundraising Concert – Philadelphis band “Juliano Brothers” concert for the benefit of Reef Relief, a local organization who’s mission is to protect the coral marine habitat.  Also, silent auction and raffle will be held during the event.   Cost is $10.  5:00pm – 7:50pm, Pier House Resort, 1 Duval Street. For more information, call 305-295-3201.
  • November 16 – 20, 2016 – 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, visit http://kwfilmfest.com/ or call 941-527-9385.
  • November 18 – 19, 2016 – LGBT13th 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 20, 2016 – ARTSKey West Artisan Market “Preserve Island Life – 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.
  • November 22, 2016 – THEATERPaula Poundstone – Comedian performs live stand-up shows in intimate theater setting.  Tickets cost $50-70.  Show times are 6:30pm & 9:30pm. Key West Theater, 512 Eaton Street.  For more information, call 305-985-0433 .
  • November 23 – 26, 2016 – ARTS 3rd Annual International Sand Art Competition – Six of the world’s top sand sculpture artists compete for cash and prizes while they create master works on the beach of Casa Marina.  Free to view the competitors work each day from 9-5pm.  The final works of art will be illuminated on Friday night.  Saturday will be judging day.  1500 Reynolds Street, Key West.
  • 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.

December 2016 Key West Events

  • December 3, 2016 – SPORTS7th 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.
  • December 10, 2016 – HOLIDAYS – 26th  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. Captains’ meeting is Friday, December 9 at 8pm. To register your boat or for more information, please call (305) 292-3302.
  • December 10, 2016 – FUNDRAISER 3rd Annual Parade of Paws & Holiday Bazaar – Pet parade to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Entrants gather donations and compete for bragging-rights titles, including King, Queen, Prince, Princess, Duke, and Dutchess.   Blessing of the animals is at 9:45am.  Parade begins at 10am. After parade will be a Holiday Bazaar, with food, entertainment, and Santa photo opportunities. Higgs Beach Dog Park.For more information, visit fkspca.org or call 305-294-4857.
  • December 18, 2016 – ARTSKey West Artisan Market “Holiday/Shop Local” – 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.
  • 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 27 – 28, 2016 – ARCHITECTURE56th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 7pm. Tickets are $30 in advance, $35 the day of the tour, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
  • December 31, 2016 – 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.

2017 Key West Calendar of Events

January 2017 Key West Events

  • January 12 – 15, 2017 – LITERARY 35th Annual Key West Literary Seminar – This year’s topic is “Revealing Power: The Literature of Politics.” Celebrated authors, including Ann Beattie, Joyce Carol Oates, Billy Collins, Robert Caro, Gail Collins, Joe Klein, and numerous others gather at readings, discussions, lectures, and parties. More information and registration is available at http://www.kwls.org/seminar35 or by calling 305-293-9291.
  • January 13 – 14, 2017 – ARCHITECTURE57th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $35 in advance, $40 day of show, include Conch Train transportation, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
  • January 14 – 15, 2017 – FOOD12th 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. – 8 p.m on Saturday, 11 a.m. – 5 p.m on Sunday. Bayview Park at Truman Avenue and Eisenhower Drive, Key West. For more information, visit http://monroe.ifas.ufl.edu/environment/env_seafood_fest.shtml or call 305-362-9555
  • January 15, 2017 – SPORTS19th 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 $69.99 and $120.00, depending on when you register. Call 305-296-7182 for more information. For more information visit http://keywesthalfmarathon.com
  • January 15 – 20, 2017 – SAILINGQuantum Racing Presents: Key West 2017 – 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. This is the 30th year this event has been held.For more information and registration, visit http://www.yachtscoring.com/emenu.cfm?eID=2819
  • January 22 – February 3, 2017 – SAILING9th Edition Conch Republic Cup – This sailing race is from Key West, across the Gulf Stream and the Straits of Florida, to Cuba.  Numerous classes of sailing vessels will race to Veradero, then Havana, and back to Key West over a weeklong period.  For more information and registration, visit conchrepubliccup.org
  • January 25 – 28, 2017 – 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. Tickets for each even cost between $50 – $150.
  • January 28 – 29, 2017 – ARTS32nd 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 2017 Key West Events

  • February 3 – 4, 2017 – 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. Visit http://www.cudabowl.com or call 305-360-6969 for more information.
  • February 3 – 5, 2017 – 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 5, 2017 – SPORTSSuper Bowl LI (51) – The NFL’s 51st-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 14, 2017 – 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 17 – 18, 2017 – ARCHITECTURE 57th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.
  • February 25 – 26, 2017 – ARTS52nd 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 2017 Key West Events

  • March 4, 2017 – 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. 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 13 – 16, 2017 – 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 www.marchmerkin.com or call 303-888-4546.
  • March 17, 2017 – 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 – 18, 2017 – ARCHITECTURE57th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour, and are available at http://www.oirf.org/page.php?p=tours. Call 305-294-9501 for more information.

April 2017 Key West Events

  • April 1, 2017 – RUNNING36th 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 2017. Only 1500 entries are allowed and this event quickly sells out. For more information, visit http://7mbrun.com or call 305-395-7040.
  • April 2, 2017 – RUNNING4th 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. Registration costs $5. Race begins at noon. For more information, visit: http://cowkeybridgerun.com/.
  • April 16, 2017 – HOLIDAYEaster in Key West – Numerous restaurants has special Easter Brunch menus.
  • April 21 – 22, 2017 – HISTORY – 15th Annual Harry S. Truman Legacy Symposium – This year’s theme explores Latin and South American policies. For more information, call 305-294-9911.
  • April 22, 2017 – 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 25 – 30, 2017 – FISHINGFinal 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.bluewatermovements.com/final_sail/ or call 305-340-2737.
  • April 27 – 30, 2017 – SPORTS20th Annual Key West Paddle Classic – Race around the island of Key West aboard stand-up paddleboards. Twelve-mile course and four-mile race options. Begins at 9:30am. For more information, call 305-295-9898.

May 2017 Key West Events

  • May 5-7, 2017 – ARTS2nd 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 in front of Customs House at 281 Front Street. For more information, call 305-295-6616 or visit http://www.papioskineticparade.com/
  • May 10 – 14, 2017 – MUSIC22nd 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 20 – 21, 2017 – RUNNING10th 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.
  • May 28, 2017 – LOCAL COLOR27th Annual Schooner Wharf Minimal Regatta – Hysterical race of build-your-own boats using a minimum supply of materials, including: one sheet of plywood, two 2x4s, one pound of screws/fasteners, and one roll of duct tape. Prizes awarded for fastest team, most creative design, sinker award, sportsmanship award, best costumed, and best paint job. Vessel inspection at 12pm, Schooner Wharf Bar, 202 William Street. For more information, call 305-292-3302.

June 2017 Key West Events

  • June 7 – 11, 2017 – LGBTKey West Pridefest – Event honoring diversity, openness and freedom in the city that is consistently recognized as one of the world’s top gay and lesbian vacation destinations. Includes a mix of: dance and cocktail parties, contests, shows, forums, activities on the water, tours, street fair and the Pride Parade along Duval Street. For more information, call (305) 292-3223 or visit http://www.keywestpride.org.
  • June 10, 2017 – SWIMMINGFKCC Swim Around Key West – Swimmers, accompanied by kayakers, circumnavigate the island of Key West, a distance of over 12 miles. For more information, call 305-809-3562 or visit http://www.fkccswimaroundkeywest.com
  • June 16 – 18, 2017  – LITERATURE4th Annual Key West Mystery Writers Fest – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. For more information, visit http://www.mysteryfestkeywest.com/
  • June 22 – 25, 2017 – CULTUREKey West Africana Festival – Three-day destination retreat and festival focusing on Thought, Culture and Wellness within the African Diaspora. Thought: Academic conference on topics of cultural, physical and spiritual wellness. Culture: Music, art and cultural tourism, exploring Afro-Caribbean culture in Key West. Wellness: Workshops on healthy living, physical wellness and relationship wellness. For more information, call 786-529-8624 or visit http://www.keywestafricanafestival.com/

July 2017 Key West Events

  • July 1 – 4, 2017 – FOOD – 5th 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 www.keylimefestival.com
  • July 4, 2017 – 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 8 – 11, 2017  – FISHING 17th 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://delbrownpermit.weebly.com/ or call 305-744-0903.
  • July 14 – 15, 2017 – MARITIMEMel Fisher Days – Come celebrate the day in Key West, over 30 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 is on Friday, with tours of salvaging vessels, raffle, and live entertainment. Front Street block party is on Saturday, 6pm – 10pm, in front of the “Customs House”, and features live music and street fair food. For more information, visit http://www.melfisherdays.com or call 305-296-6533.
  • July 18 – 23, 2017 – 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 19 – 22, 2017 – FISHINGBacardi 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 $1800 per vessel for early registration, or $2100 for late registration. Additional fees for fun fish, extra angler, and extra banquet tickets. For more information, call 305-292-2710 or visit http://www.keywestmarlin.com
  • July 22, 2017 – RUNNING – Hemingway 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, call 305-240-0727
  • July 26 – 27, 2017 – 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 2017 Key West Events

  • August 10 – 13, 2017 – 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 16 – 20, 2017 – LBGTTropical Heat – All male, adults-only celebration of Key West’s gay community and lifestyle. Events include all-male themed parties and adult-oriented entertainment. For more information, visit www.tropicalheatkw.com or call the Key West Business Guild at 305-294-4603.
  • August 31 – September 4, 2017 – PARTY8th 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 2017 Key West Events

  • August 31 – September 4, 2017 – PARTY8th 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 4, 2017 – 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 6 – 10, 2017 – LGBTWomenfest Key West 2017 – Lesbians and friends converge on Key West for a week of activities, including late night dancing, pool parties, comedy shows, sunset sails, competitive bull riding, and lots of music. Visit http://www.womenfest.com or call 305-294-4603 for more information.
  • September 8 – 10, 2017 – 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 http://www.redbone.org.

October 2017 Key West Events

  • October 15, 2017 – SEAFOOD Official 2017 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 20 – 21, 2017 – PARTY36th Annual Goombay Fest 2017 – 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 20 – October 29, 2017 – FANTASY FEST38th 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 “Time Travel Unravels.”  In our opinion, Fantasy Fest is ready for a re-fresh, and we encourage you to be creative in your costume choice – not sleazy.  For more information, visit http://www.fantasyfest.com
  • October 26, 2017 – LOCAL COLORThe Smallest Parade in the Universe – Now in its third 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 http://www.thesmallestparadeintheuniverse.com

November 2017 Key West Events

  • November 1 – 5, 2017 – MUSIC26th Annual Meeting of the Minds 2017 – 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 5 – 12, 2017 – BOATING 36th 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 15 – 19, 2017 – 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 http://www.kwfilmfest.com.
  • November 23, 2017 – HOLIDAYThanksgiving in Key West 2017 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.

December 2017 Key West Events

  • December 1 – 2, 2017 – SPORTS – 8th Annual TRIKW Triathalon – Athletes swim, run, and bike among Key West’s ideal scenery and conditions. More than 500 competitors are expected. Two race distances are available: Sprint and the twice-as-long Olympic. For more information, call 305-394-3469 or visit http://www.trikw.com/.
  • December 19, 2017 – HOLIDAYS – 27th  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. Captains’ meeting is Friday, December 8 at 8pm. To register your boat or for more information, please call (305) 292-3302.
  • December 12 – 20, 2017 – HOLIDAYHanukkah in Key West 2017 – 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, 2017 – HOLIDAYChristmas in Key West 2017 – 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, 2017 – 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.

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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