Calendar of Events

Current Key West Events

Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race
Image for Key Lime Festival 2023 Image for Key Lime Festival 2023 Image for Key Lime Festival 2023 Image for Key Lime Festival 2023
Image for Key West Pride Image for Key West Pride Image for Key West Pride Image for Key West Pride
Image for Underwater Music Festival Image for Underwater Music Festival Image for Underwater Music Festival Image for Underwater Music Festival
Image for History of Diving Museum Image for History of Diving Museum Image for History of Diving Museum Image for History of Diving Museum
Image for Florida Keys Youth Summer Sailing & Windsurfing Camp Image for Florida Keys Youth Summer Sailing & Windsurfing Camp Image for Florida Keys Youth Summer Sailing & Windsurfing Camp Image for Florida Keys Youth Summer Sailing & Windsurfing Camp
Image for Key West Fishing Tournament
  • Dec 1, 2022 - Jul 31, 2023 Key West Fishing
  • Key West Fishing Tournament
  • Website
  • More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
Image for Monday & Tuesday Evening GLOW Hours at Hugh's Rooftop
Image for Key West Art & Historical Society: Out of the Box - The Art of the Cigar Label
  • Apr 28, 2023 - Oct 22, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Out of the Box - The Art of the Cigar Label
  • Website
  • The Key West Art & Historical Society presents “Out of the Box: The Art of the Cigar Label." The exhibition offers a compelling sampling and interpretation of 19th and early 20th century inner and outer cigar labels, showcasing more than 40 lithographs related to the Key West and Cuba cigar manufacturers. From the 1880s into the early 20th century, cigar manufacturers desired an avenue to market their particular cigars to consumers. Mass production of cigars in Cuba and Florida contributed to the successes of lithographic arts. Included with museum general admission. Custom House Museum, 281 Front Street, 10 a.m. to 5 p.m. daily.
Image for Key West Art & Historical Society: Sushi in the Shoe
  • May 31, 2023 - Jun 30, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: Sushi in the Shoe
  • Website
  • After 25 years of ‘dropping’ in a giant red glitter high-heeled shoe on New Year’s Eve, Key West’s legendary drag queen Sushi has hung up the heel. Since its inception, the Red Shoe Drop has become so famous that it’s often featured on national and international New Year’s Eve television programs including CNN. The commemorative exhibit includes the Gary Marion - also known as Sushi - collection of original gowns. Included with general admission. 281 Front Street.
Image for Key West Pride
  • Jun 7, 2023 - Jun 11, 2023 Key West LGBTQ
  • Key West Pride
  • Website
  • Visitors can celebrate diversity and mark the 20th “birthday” of Key West’s famed 1.25-mile sea-to-sea rainbow flag during Key West Pride 2023, scheduled Wednesday through Sunday, June 7-11. Presented by the Key West Business Guild, Pride 2023’s highlight is to be a three-night laser light show that re-creates the flag above Key West’s Duval Street, with its colors once again stretching the nearly 1.25-mile length of the renowned thoroughfare. From 8 to 10 p.m. Friday, Saturday and Sunday, visitors can walk “under the rainbow” to express their support for diversity, equality and acceptance.
Image for Sunset Green: Na Ma Sit & Stay Yoga with Your Dog
  • Jun 11, 2023 Key West
  • Sunset Green: Na Ma Sit & Stay Yoga with Your Dog
  • The Keys Collection offers Na Ma Sit & Stay Yoga with Your Dog the second Sunday of each month at 9:30 am. at the Sunset Green event lawn in Key West. Admission is free but a $10 donation is suggested, with all proceeds donated to Florida Keys SPCA. Bring your dog and your own mat. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.
Image for 10th Annual VFW Fishing Tournament
  • Jun 16, 2023 - Jun 18, 2023 Key West Fishing
  • 10th Annual VFW Fishing Tournament
  • 610-304-2392 E-mail Website
  • A family fun tournament, cash prizes are to be awarded for the heaviest catch of five target species -- mahi-mahi (dolphin fish), wahoo, tuna, snapper and grouper. Cash prizes are awarded for the heaviest catches of each including a first-place prize of 5 thousand dollars for the heaviest mahi-mahi. A "super prize" of either 20 thousand dollars or a new Toyota Corolla is to be awarded to the angler who catches the heaviest dolphin fish of 50 pounds or over. Captains and anglers can choose to fish either Saturday or Sunday, but not both. All proceeds benefit disabled and needy veterans of Monroe County. The opening captains meeting and final awards banquet will be held at VFW Post 3911, 2200 N. Roosevelt Blvd.
Image for CFK Swim Around Key West
  • Jun 17, 2023 Key West Arts & Culture
  • CFK Swim Around Key West
  • E-mail Website
  • Embark on an adventurous swim - a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.
Image for Key West Art & Historical Society: "Old Island Eats" Book Signing
  • Jun 21, 2023 Key West Arts & Culture
  • Key West Art & Historical Society: "Old Island Eats" Book Signing
  • Martha Hubbard, culinary director and executive chef of Key West’s Unity Table at Williams Hall, will be signing copies of her highly acclaimed cookbook “Old Island Eats” at the Key West Museum of Art and History at 281 Front Street from 5 to 7 p.m. The new cookbook is a collection of vintage, original Key West recipes and a selection of Hubbard’s own recipes and menus from decades of cooking for the island.
Image for Seventh Annual Mango Fest Key West
  • Jun 22, 2023 - Jun 25, 2023 Key West Environmental
  • Seventh Annual Mango Fest Key West
  • Website
  • Experience all things mango through culinary treats, education and demonstrations during this celebration of the Keys' sweet indigenous fruit and its heritage. Stroll around the Mango Mania vendor village, enter a photo contest, enjoy mouthwatering mango-themed specialties prepared by top local chefs and much more. The festival is presented by the Key West Police Athletic League and supports its local youth programs.
Image for Sunset Green: Live at Sunset Concert
  • Jun 26, 2023 Key West Arts & Culture
  • Sunset Green: Live at Sunset Concert
  • Website
  • The Keys Collection presents the "Live at Sunset" free monthly concert series on the last Tuesday of every month on the Sunset Green! The lawn opens at 6 p.m., with local talent performing from 7-10 p.m. Free entry and parking, food & drinks for purchase. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.
Image for Key West Key Lime Festival
  • Jun 30, 2023 - Jul 4, 2023 Key West Arts & Culture
  • Key West Key Lime Festival
  • Website
  • Key West's annual Key Lime Festival is set to celebrate the world’s most sensational citrus with a bountiful array of festivities across the island where Key lime pie was conceived. Over five days, lovers of the lime can indulge in a full menu of activities, from an event kick-off cookbook signing and champagne reception with festival co-founder and “Key West Key Lime Pie Cookbook” author David Sloan; delicious Key lime-centric dinner and brunch events; a wild and world famous Key lime pie eating contest; a gravity-defying Key lime pie drop competition – from the top of the Key West Lighthouse; a Key lime pie hop, and for those with a taste for limey libations, a Key lime rum tasting and a bar Sip & Stroll. There’s much more, including numerous family-friendly activities.
Image for Key West Association of Realtors Charity Fishing Tournament
  • Jun 30, 2023 - Jul 1, 2023 Key West Fishing
  • Key West Association of Realtors Charity Fishing Tournament
  • 305-296-8259 Website
  • This Key West charity fishing tournament benefits FAIR (Fair Insurance Rates in Monroe) and is based at the Perry Hotel & Marina, 7005 Shrimp Road. Eligible species including sailfish (catch/photo/release) and dolphin fish, blackfin tuna or kingfish, 15 pounds or higher, verified at a live weigh-in. Captains meeting is June 30 at the Perry, with fishing on July 1. Prizes are to be awarded for the 1st, 2nd and 3rd place boats with the highest points; biggest dolphin, kingfish and tuna; top angler and top woman angler.
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