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.
2020 Key West Event Calendar
January 2020 Key West Events
- January 9-12, 2020 – SPORTS – Pole Vault in Paradise: Pole Vaulting Champions – Top national pole vaulters will perform their skills at the Truman Waterfront Park. FREE to attend. Begins 9am, Truman Waterfront Park (end of Southard Street)
- January 9 – 12, 2020 – LITERARY – 38th Annual Key West Literary Seminar – This year’s topic is “Reading Between the Lines: Sports & Literature.” Noteworthy and celebrated writers, including Megan Abbott, Amy Bass, Buzz Bissinger, Daniel James Brown, Anelise Chen, Billy Collins, Geoff Dyer, Paul Goldberger, Jane Leavy, David Maraniss, Ben McGrath, Michael Mewshaw, Joyce Carol Oates,Arnold Tampersad, Leanne Shapton, Lioinel Shriver, Louisa Thomas, Keving Young – and numerous others – gather at readings, discussions, lectures, and parties. Registration is now sold out, but a waitlist is available. More informationis available at http://www.kwls.org/seminar or by calling 305-293-9291.
- January 12, 2020 – MUSIC – Grace Potter in Concert – Live performance by the major recording artist. Tickets cost $55-119. 6pm doors, 7pm showtime. Sunset Green Event Lawn, 3820 North Roosevelt Blvd, Key West. Tickets available here: https://www.eventbrite.com/e/grace-potter-at-the-sunset-green-event-lawn-tickets-73877159573
- January 14, 2020 – COMEDY – Sinbad Live – Comedian and actor will have the crowd laughing out loud at the intimate Key West Theater, 512 Eaton Street. There will be two shows: 6:30pm and 9pm. Tickets cost $48.50-68.50. Tickets available here: https://www.eventbrite.com/a/sinbad-211448
- January 15 – 20, 2020 – RUNNING – 22nd Annual Key West Half Marathon & 5K Run – 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 https://www.keywesthalfmarathon.com
- January 16 – 19, 2020 – FISHING – Key West Kingfish Mayhem – Bet you didn’t know that the richest tournament prizes in saltwater fishing is for kingfish! Part of the mackeral family, this sportfish 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 https://www.meatmayhemtournamentsfl.com/key-west-kingfish-mayhem/
- January 17 – 18, 2020 – ARCHITECTURE – 60th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $45, include Conch Train transportation, or $35 ($45 on day of tour) without the train pass, and are available at http://keywesthometours.com/. Call 305-294-9501 for more information.
- January 17, 2020 – ART – Grand Opening of Jag Gallery – An exciting and highly anticipated art gallery is about to open in Key West, featuring many of the islands most important and collected artists, including: John Martini, Carol Munder, Susand Sugar, Rick Worth, Lincoln Perry, AD Tinkham, and more. 6-8:30pm, Duval Square, 1075 Duval Street (gallery space is near Simonton Street)
- January 18 – 19, 2019 – FOOD – 15th 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 http://www.floridakeysseafoodfestival.com/ or call 305-292-4501
- January 21 – 27, 2019 – SPORTS – 29th 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 – 29 has full week of events including parties). For more information, visit http://www.iwffa.com/world-challenge-game/
- January 25 – 26, 2020 – ART – 35th 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 https://keywestartcenter.com/craft-show-visitor-info or call 305-294-1243.
- January 26, 2020 – FOOD – 26th 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, 2019. 4 – 7pm. Margaritaville Resort & Marina, 245 Front Street. For more information, visit http://www.marchouse.org/masterchefsclassic/
- January 26 – February 2, 2020 – FOOD – 11th Annual Key West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”. For more information, visit https://keywestfoodandwinefestival.com/ or call 800-474-4319. Tickets for each event costs between $35 – $135.
- January 26, 2020 – MUSIC – Crooks Second Line – Traditional New-Orleans parade honoring those who have passed on and are beloved. Parade starts at 2pm at the HOg’s Breath Saloon, and goes down Duval Street. Ends at 3pm at Green Parrot, where a jazz performance will commence.
- January 28 – February 1, 2020 – MUSIC – 3rd Annual Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Acts include Shiny Ribs,Jason Isbell and the 400 Unit, Whiskey Myers, Randy Rogers Band, and Robert Earl Keen. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $399 for 4-day festival pass. This year will offer single-day passes and cost $139. For more information and tickets, visit: https://www.eventbrite.com/e/mile-0-fest-2020-tickets-63518270858 or call 877-412-7658.
- January 31, 2020 – 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 http://www.cudabowl.com or call 305-360-6969 for more information.
February 2020 Key West Events
- February 14 – 15, 2020 – ARCHITECTURE – 60th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $45, include Conch Train transportation, or $35 ($45 on day of tour) without the train pass, and are available at http://keywesthometours.com/. Call 305-294-9501 for more information.
- February 14, 2020 – HOLIDAY – 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 couples in Key West.
- February 21, 2020 – MUSIC – Kool & the Gang with the Village People, LIVE in Concert – Disco, funk, and R & B giants perform at the Key West Amphitheater, Truman Waterfront Park (end of Southart Street). Doors at 5:30, showtime at 7pm. Tickets available here: https://www.eventbrite.com/e/kool-the-gang-with-village-people-tickets-69743260971
- February 22 – 23, 2020 – ARTS – 55th 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 https://keywestartcenter.com/art-festival-visitor-info or call (305) 294-1243.
- February 29, 2020 – RUNNING – 7th 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. This year’s theme is “Pirates of the Cowibbean.” FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Registration costs $10 for bib only, or $35 with bib, shirt, and koozie. Race begins at noon. For more information, visit: http://cowkeybridgerun.com/
March 2020 Key West Events
- March 7, 2020 – LOCAL COLOR – 58th Annual Conch Shell Blowing Contest – Prizes are awarded for contestants ability to make sound and music 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 7, 2020 – ARTS – 20th 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 8, 2020 – MUSIC – George Thorogood & the Destroyers in Concert – Legendary classic rocker who has sold over fifteen million albums performs at the Sunset Green Event Lawn, part of the 24 North Hotel property, 3820 N. Roosevelt Blvd. 5:30pm doors (show starts at 7pm). Tickets cost $65-$99 and are available at https://www.eventbrite.com/e/george-thorogood-the-destroyers-at-the-sunset-green-event-lawn-tickets-84630775929
- March 9 – 12, 2020 – 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 http://www.marchmerkin.com or call 303-888-4546.
- March 13 – 14, 2020 – ARCHITECTURE – 60th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $35 in advance, $45 day of tour, and are available at http://keywesthometours.com/60th-season-home-tours. Call 305-294-9501 for more information.
- March 17, 2020 – HOLIDAY – Saint 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 28, 2020 – RUNNING – 39th 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 2019. Only 1500 entries are allowed and this event quickly sells out.
April 2020 Key West Events
- April 4, 2020 – LGBTQ – 2020 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 https://www.eqfl.org/index.php/keywestcelebration or call 305-304-5126
- April 3 – 5, 2020 – ARTS – 5th 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 April 4 at noon in front of Customs House at 281 Front Street. For more information, call 305-295-6616 or visit http://www.papioskineticparade.com/
- April 5, 2020 – MUSIC – The Tempatations in Concert – Definitive Motown band with 44 top-10 hits performs mega-hit classics like “The Way You Do the Things You Do”, “My Girl”, and “Papa Was a Rollin’ Stone”. 3820 N. Roosevelt Blvd. 5:30pm doors (show starts at 7pm). Tickets cost $85-$109 and are available at https://www.eventbrite.com/e/the-temptations-at-the-sunset-green-event-lawn-tickets-68833223023
- April 12, 2020 – HOLIDAY – Easter in Key West – Numerous local restaurants offer special Easter Brunch menus. Large Catholic mass held at St. Mary’s Star of the Sea, Truman Ave & Windsor Lane
- April 17– 26, 2019 – LOCAL COLOR – 38th Annual Conch Republic Independence Celebration – Celebration of Key West’s brief secession from the United States, triggered by a government blockade of US1. Event highlights include bed races on Duval Street, conch shell blowing contest , arts & crafts show, Duval Street Parade , 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 Friday April 17th, 7pm. For more information call 305-296-0213.
- April 20, 2020 – FOOD – 25th 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.
May 2020 Key West Events
- May 6 – 10, 2020 – MUSIC – 25th Annual Key West Song Writers Festival – Features more than two-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 https://www.keywestsongwritersfestival.com
- May 10, 2020 – HOLIDAY – Mother’s Day in Key West – Celebrate your mom in style! Local restaurant have numerous brunches available – dine indoor or outdoor, oceanfront or air-conditioned. Happy day mothers! We love you!!
- May 11, 2020 – LGBT – 37th Annual Queen Mother Pageant – Drag queens compete for title of “Queen Mother,” judged by their often hilarious, always talented performance in evening gown, talent, and interview skills. THIS YEAR’S EVENT HAS NOT BEEN CONFIRMED. Last year’s details include: Benefits Compassionate Care Hospice and One Human Family Foundations. Cost is $25 for general admission, or tables from $200-$500 (these sell out fast). Door open at 7pm, show starts at 8pm. LaTeDa, 1125 Duval Street.
- May 16 – 17, 2020 – RUNNING – 13th 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 2020 Key West Events
- June [DATE NOT YET ANNOUNCED], 2020 – FOOD – Tropical Fruit Fiesta – Held on the grounds of the Truman Little White House, this event features a display Key West’s numerous tropical fruits, including mango, papaya, Key Lime, spanish lime, jackfruit, starfruit and others. Tastings, lectures, and opportunity to purchase locally grown produce. Growers compete for award of best fruits in each category. Fun event with genuine local color. 9am-1pm, Truman Little White House, 111 Front Street. FREE to attend.
- June 3 – 7, 2020 – 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 https://www.keywestpride.org
- June 6, 2020 – SWIMMING – 44th Annual Swim Around Key West – Presented by the Key West Athletic Association, this 12.5 mile swim around the island of Key West must be completed in 8 hours and typically has 200 participants, including solo and team swimmers. Cost for registration by March 15 is $165 for a solo swimmer, $300 for two-person relay, and $420 for three-person relay. For more information, visit http://www.swimaroundkeywest.com
- June 20, 2020 – SWIMMING – FKCC 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 26, 2020 – LITERATURE – 6th Annual Mystery Fest Key West – Over twenty South Florida’s writers convene in Key West for three days of discussions and interactions. Cost is $195 for the weekend events. For more information, visit http://www.mysteryfestkeywest.com/
July 2020 Key West Events
- July 1 – 5, 2020 – LOCAL COLOR – Key West Mermaid Festival – Family-friendly event featuring mermaids in costume. Offers swimming with mermaids, parties, Duval Street parade on Saturday, vending, and more.
- July 4, 2020 – INDEPENDENCE DAY – Key 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. https://www.keywesttravelguide.com/key-west-fireworks/
- July 2 – 6, 2020 – FOOD – 8th Annual Key Lime Festival – Key Limes, grown abundantly on the island, 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 18 – 21, 2020 – FISHING – 20th 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, call 305-744-0903.
- July 18, 2020 – 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, visit https://www.keywesthalfmarathon.com/hemingway-event-details/ or call 305-240-0727
- July 23 – 26, 2020 – HEMINGWAY – Hemingway Days & Sloppy Joe’s 40th 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 29 – 30, 2020 – FISHING – Lobster 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 2020 Key West Events
- August 6 – 9, 2020 – SEAFOOD – 24th 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 https://www.keywestlobsterfest.com or call 305-744-9804
- August 12 – 16, 2020 – LBGT – 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, visit www.tropicalheatkw.com or call the Key West Business Guild at 305-294-4603.
September 2020 Key West Events
- September 2 – 6, 2020 – LGBT – Womenfest Key West 2020 – 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/ for more information
- September 3 – 7, 2020 – PARTY – 11th 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 7, 2020 – HOLIDAY – Labor Day 2020 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. Visit http://www.womenfest.com or call 305-294-4603 for more information.
October 2020 Key West Events
- October 15, 2020 – SEAFOOD – Official 2020 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 16 – 17, 2020 – PARTY – 39th Annual Goombay Fest – 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.
- October 16 – 25, 2020 – FANTASY FEST – 41st Annual Key West Fantasy Fest – CANCELLED – Week-long celebration and Key West’s biggest party of the year – with many adult-only events. This year’s theme is “Roaring 2020’s & Future Fictions.” Be creative with your costume! For more information, visit https://www.fantasyfest.com
- October 22, 2020 – LOCAL COLOR – 38th Annual 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 29 – 31, 2020 – MUSIC – 29th Annual Meeting of the Minds 2020 – Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows usually 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 2020 Key West Events
- November [DATE TO BE ANNOUNCED], 2020 – RUNNING – 28th 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. For more information, call 305-393-5200 or visit https://www.zontakeywest.com/abc-walk-2
- November [DATE TO BE ANNOUNCED], 2020 – BOATING – 39th 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 [DATE TO BE ANNOUNCED], 2020 – ARCHITECTURE – Garden Lecture Series – With the largest number of wood-framed historic structures in the United States, the architecture of Key West is a local and national treasure. This lecture, held in the garden of Key West’s oldest house, will discuss the history, form, and influences of the local architecture. Tickets cost $25 per person, 7pm start time, 322 Duval Street. Tickets are available here: https://www.showclix.com/event/Architecture
- November 26, 2020 – HOLIDAY – Thanksgiving in Key West 2020 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.
December 2020 Key West Events
- December [DATE TO BE ANNOUNCED], 2020 – HOLIDAY – Tree 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 [DATE TO BE ANNOUNCED], 2020 – HOLIDAY – Key West Lighted Bike Parade – To benefit Wesley House Family Services, this neighborhood parade features bicycles adorned with holiday lights and decoration. Ride ends on Appelrouth Lane (off Duval St), where there will be a Holiday block party. Begins at 7pm (check-in is at 5pm), Bayview Park. FREE with donation of unwrapped child’s gift.
- December [DATE TO BE ANNOUNCED], 2020 – HOLIDAY – Key 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 [DATE TO BE ANNOUNCED], 2020 – SPORTS – TRIKW Triathalon – Athletes swim, run, and bike among Key West’s ideal scenery and conditions. Up to 1000 competitors are expected. Two race distances are available: Sprint and the twice-as-long Olympic. For more information, call (954) 213-6699 or visit https://www.trikw.com
- December [DATE TO BE ANNOUNCED], 2020 – ART – Charity Art Auction – To benefit Wesley House Family Services, this auction includes pieces donated by the estate of Judge Tegan Slaton and his widow Rosemary Enright. The event begins at 5:30 p.m. with a reception featuring appetizers by the Iron Chefs, and signature rum drinks by the Hemingway Rum Company. Cost is $20 and can be applied to art purchases. Viewing of auction lots, and appetizers, at 5:30pm. Auction begins at 6:30pm. 201 Simonton Street.
- December [DATE TO BE ANNOUNCED], 2020 – HOLIDAY – 30th 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 [DATE TO BE ANNOUNCED], 2020 – HOLIDAY – 7th Annual Parade of Paws & Holiday Bazaar – Benefiting the Florida Keys SPCA, this family-friendly event features pet parade, holiday bazaar, local vendors, live music, and smooch-a-pooch booth. Santa will be there to take photos with your pets. 10am-2pm at Higgs Dog Park, White Street & Atlantic Blvd. For more information, call 305-294-4857 or visit https://fkspca.org/event/6th-annual-parade-of-paws/
- December 10 – 18, 2020 – HOLIDAY – Hanukkah in Key West 2020 – 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, 2019 – HOLIDAY – Christmas in Key West 2020 – 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 [DATE TO BE ANNOUNCED], 2020 – ARCHITECTURE – 61st Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $35 and are available at http://keywesthometours.com/. Call 305-294-9501 for more information.
- December 31, 2020 – CELEBRATION – 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
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.