Calendar of Events
Current Key West Events




- Sponsored Event
- Jun 02, 2023 - Jun 04, 2023 The Lower Keys
- 30th Annual Dolphin Tournament Lower Keys Chamber of Commerce
- Website Kiki’s Sandbar
- 183 Barry Ave Little Torch Key FL 33042
- Lower Keys Chamber of Commerce 305-872-2411 E-mail
- View video
- The 30th Annual Lower Keys Chamber of Commerce Dolphin Tournament is coming up June 2nd! Enter to win over $35,000 in cash & prizes. Friday the 2nd is registration & appetizers at 5pm and Sunday the 4th is dinner & awards at 6pm. Largest Dolphin Wins!!!
- Buy tickets!




- Sponsored Event
- Jun 07, 2023 - Jun 11, 2023 The Florida Keys LGBTQ
- Key West Pride
- Website Key West Business Guild
- 808 Duval Street Key West FL 33040
- 305-294-4603 E-mail
- Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Show us your pride, we will show you our Key West Pride!
- Buy tickets!




- Sponsored Event
- Jul 07, 2023 - Jul 08, 2023 The Lower Keys Fishing
- Underwater Music Festival
- Website Marine Sanctuary at Looe Key
- Looe Key Reef Ramrod Key FL 33042
- Lower Keys Chamber of Commerce 305-872-2411 E-mail
- View video
- Divers & snorkelers can promote reef protection & explore the continental United States’ only living coral barrier reef during the 39th Annual Underwater Music Festival concert on Friday July 7th & Saturday July 8th. Music broadcast by local radio station




- Sponsored Event
- Jul 22, 2023 - Jul 25, 2023 Key West
- Hemingway 5k Sunset Run & Paddleboard Race
- Website Southernmost Point
- United & Duval Street Key West FL 33040
- Key West Half Marathon E-mail
- Runners, walkers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 23, 2022 during the Hemingway 5k Sunset Run and Paddleboard Race. The athletic challenges are part of Hemingway Days!
- Buy tickets!




- Sponsored Event
- Jun 30, 2023 - Jul 04, 2023 Key West Arts & Culture
- Key Lime Festival 2023
- Website
- Key West Key West FL 33040
- Key Lime Festival 305-295-9112 E-mail
- America’s Favorite Citrus Celebration! We like to celebrate the things that make our islands unique. Our celebrations are fun, odd & unforgettable. Come on down to the birthplace of Key Lime Pie for a little taste and you’ll see what we mean Love & Limes!
- Buy tickets!




- Sponsored Event
- May 30, 2023 - Aug 04, 2023 Key Largo
- Florida Keys Youth Summer Sailing & Windsurfing Camp
- Website Mark Sorenson Youth Sailing Program / Upper Keys Sailing Club
- 100 Ocean Bay Dr Key Largo FL 33037
- Rosa Lamela 305-747-2600 E-mail
- Our summer programs range for ages 8-18. Learn to Sail, Intro to Windsurfing, Adventure & Club 420 Sailing. Day visits to Everglades National Park and Nest Key. Kayaking and paddle boarding to Pelican Island. Marine focused Florida Keys experience!
- Buy tickets!




- Sponsored Event
- May 01, 2023 - Dec 31, 2023 Islamorada
- History of Diving Museum
- Website History of Diving Museum
- 82990 Overseas Highway (MM83), Islamorada FL 33036
- 305-664-9737 E-mail
- Open daily. Be amazed by over 4,000 years of “the quest to explore under the sea” and celebrate the special role South Florida and the Florida Keys had in this untold story. Dive in to see “Aquanauts to Astronauts” a limited-time featured exhibit.
- 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.
- Mar 13, 2023 - Oct 24, 2023 Key West Arts & Culture
- Monday & Tuesday Evening GLOW Hours at Hugh's Rooftop
- Website
- 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 Street.
- 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.