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.

UPDATE: As vaccination increases and covid-19 cases decrease, a post-pandemic Key West is emerging.  Events are now being added to the 2021 event calendar.  We will add dates as events are confirmed.  If you have an event you would like to add to our calendar, visit this page to submit  your event details: https://www.keywesttravelguide.com/submit-your-event-for-the-key-west-calendar/

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 January 2021  |  February 2021  |  March 2021  |  April 2021  |  May 2021  | June 2021 |  July 2021 |  August 2021 |  September 2021 |  October 2021 |  November 2021 |  December 2021

2021 Key West Event Calendar

                                

June 2021 Key West Events

  • June 2 – 5, 2021 – 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 26, 2021 – SWIMMING45th 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. Deadline to register is May 18. For more information, visit https://www.swimaroundkeywest.com

                                

July 2021 Key West Events

  • July 1 – 4, 2021 – FOOD9th 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 https://www.keylimefestival.com
  • July 4, 2021 – 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. https://www.keywesttravelguide.com/key-west-fireworks/
  • July 20 – 25, 2021 – HEMINGWAYHemingway Days & Sloppy Joe’s 41st 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 28 – 29, 2021 – 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-inch 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 2021 Key West Events

  • August 11 – 14, 2021 – 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 12 – 14, 2021 – SEAFOOD25th 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

                                

September 2021 Key West Events

  • September 2 – 5, 2021 – PARTY12th 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 6, 2021 – HOLIDAYLabor Day 2021 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.

                                

October 2021 Key West Events

  • October 15, 2021 – SEAFOODOfficial 2021 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 22 – October 31, 2021 – FANTASY FEST42nd 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 “All a Daze for a Holiday.” 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 https://www.fantasyfest.com

                                

November 2021 Key West Events

  • November 3 – 7, 2019 – MUSIC 30th Annual Meeting of the Minds 2021 – 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 7 – 14, 2021 – BOATINGPowerboat Races – 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.
  • November 25, 2019 – HOLIDAYThanksgiving in Key West 2021 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.
  • November 28 – December 6, 2021 – HOLIDAYHanukkah in Key West 2021 – 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 2021 Key West Events

  • December 25, 2021 – HOLIDAYChristmas in Key West 2021 – 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, 2021 – 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.

Things to do…everyday!

Waverunner Jet Ski Tours

  Have an absolute BLAST zooming across the water…all the way around the island of

Express Watersports Package

  Three-hour trip includes parasailing, jetskis, kayaks, big water toys, snorkel gear, and tasty snacks

Private Sunset Charters

  Wouldn’t it be nice to have your own boat in Key West? Well you

Sunset Cruise – Glass Bottom Boat

  A great view – above and below deck. Air-conditioned comfort on this Key West

Sunset Sail – Wind & Wine

  An upscale sunset cruise aboard a traditional working schooner – serving premium wine, beer,

Sunset Sails – Schooners & Tall Ships

  Hoist the sails – if you’d like to lend a hand – aboard the

Sunset Sail – Booze Cruise

  Boat trip to see the Key West sunset  – with beverages and an island

Sunset Booze Cruise Concert

  Trop-rock into the sunset on a sailboat! Includes free-flowing beer, wine, margaritas, and snacks

SNUBA

  Like snorkeling, but you can breath underwater thanks to scuba air tanks floating on

Traditional Sailboat Snorkel

  Smaller group, impressive mono-hull sailboat, offering relaxed snorkel trips to the reef This elegant

Private Snorkeling Charters

  Have the boat and Captain to yourself, allowing for custom trips to suit your

Catamaran Snorkeling Trips

  Large and stable sailboats provide comfortable and affordable reef snorkeling trips in Key West