Key West Paradise

Dec 01 – Jul 31
Key West Fishing Tournament
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...More

Mar 13 – Oct 24
Monday & Tuesday Evening GLOW Hours at Hugh's Rooftop
The Studios of Key West's Hugh's Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings from 6 to 8 p.m. The bar is open, admission is free. Capacity is limited, so come early. 533 Eaton...More

Apr 28 – Oct 22
Key West Art & Historical Society: Out of the Box - The Art of the Cigar Label
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 lithograp...More

May 31 – Jun 30
Key West Art & Historical Society: Sushi in the Shoe
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 i...More

Jun 07 – 11
Key West Pride
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 high...More

Jun 09 – 11
Key West Pride Sea-to-Sea Diversity Flag Laser Light Show
Key West Pride celebrates the 20th anniversary of the Sea-to-Sea Diversity Flag being unfurled on Duval Street with an amazing laser light show depicting the flag along the entire length of Duval Street. The light show will happen from 8 to 10 p.m. F

Jun 10
Key West Pride Street Fair
Key West celebrates Pride with a vibrant street fair featuring local artists and vendors from 10 a.m. to 5 p.m. in the 700, 800 and 900 blocks of Duval Street, followed by disco dancing in the street at 5 p.m.

Jun 11
Key West Artisan Market: Summer Edition
Stop by for brunch, shopping, fresh produce, baked goods and other foods to fill your pantry, and meet local artists. Full bar with great bloody Mary's and mimosas, too. The market's summer edition takes place every other Sunday from 10 a.m. to 2 p.m...More

Jun 11
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.

Jun 16 – 18
10th Annual VFW Fishing Tournament
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...More

Jun 17
CFK Swim Around Key West
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 s...More

Jun 21
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.

Jun 22 – 25
Seventh Annual Mango Fest Key West
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 m...More

Jun 26
Sunset Green: Live at Sunset Concert
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 purc...More

Jun 30 – Jul 1
Key West Association of Realtors Charity Fishing Tournament
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,...More

Jun 30 – Jul 4
Key West Key Lime Festival
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 act...More