Calendar of Events
Current Key West Events




- Sponsored Event
- Oct 20, 2023 - Oct 29, 2023 Key West
- Fantasy Fest 2023
- Website Key West
- 305-295-9112 E-mail
- This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, and over 30 cleverly themed Parties and performances. Togas, Tutu’s, Body Paint and Burlesque, Halo’s, and Homemade Bikinis. Join the fun!




- 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.




- Sponsored Event
- Oct 19, 2023 - Oct 22, 2023 Key Largo
- REEF Fest - A Celebration of Marine Conservation
- Website Hosted by Reef Environmental Education Foundation
- 98300 Overseas Hwy Key Largo FL 33037
- 305-852-0030 E-mail
- Calling all ocean lovers! Join us for diving, snorkeling, kayaking, educational ocean presentations, and more. Explore the marine life of the Florida Keys, learn from ocean experts, and celebrate marine conservation.
- Buy tickets!




- Sponsored Event
- Nov 25, 2023 - Nov 25, 2023 The Lower Keys Arts & Culture
- Island Art Festival 2023
- Website Lower Keys Chamber Grounds MM31
- 31020 Overseas Hwy Big Pine Key FL 33043
- Lower Keys Chamber of Commerce 305-872-2411
- View video
- Come from 9am-3pm to celebrate the holiday season at this family-friendly event. Enjoy local arts and crafts with live music and delicious food at MM 31. Experience original one-of-a-kind Island art and a wide array of crafts. FREE ADMISSION & PARKING!




- Sponsored Event
- Oct 19, 2023 - Oct 19, 2023 Key West Arts & Culture
- The Black Crowes
- Website Coffee Butler Amphitheater
- 21 Quay Road Key West FL 33040
- Rams Heads Presents 305-985-0433 E-mail
- Get ready to rock the amp as The Black Crowes perform their hit singles "Jealous Again," Twice As Hard," "She Talks To Angels," and the break-through cover of Otis Readding's "Hard To Handle!". Doors open at 5:30P, show starts at 7:00P.
- Buy tickets!
- Mar 13, 2023 - Oct 31, 2023 Key West Arts & Culture
- 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 Tuesday evenings from 6 to 8 p.m. through Oct. 31. Stay tuned for new hours beginning Nov. 7th after the time change when sunset will be earlier. The bar is open and 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. Included with museum general admission. Custom House Museum, 281 Front Street, 10 a.m. to 5 p.m. daily.
- Jul 14, 2023 - Nov 5, 2023 Key West Arts & Culture
- Key West Museum of Art & History: Don Pinder - Eyes on the Island
- Website
- The Key West Museum of Art & History's Custom House Museum's latest exhibition—Don Pinder: Eyes on the Island—is the first exhibition devoted exclusively to the work created by Key West Citizen photographer Don Pinder (1925-2003) during his long career in Key West—including many works never before published or shown. The show, on display through Nov. 5, includes more than 50 black-and-white and color photographs made during his 35-year career of documenting Key West history and culture. 10 a.m. to 5 p.m. daily, 281 Front St.
- Sep 30, 2023 Key West
- Key West Paddle Classic
- Website
- The 26th annual Key West Paddle Classic is a 12-mile open-water distance race around Key West that is open to paddlers on stand-up and prone paddleboards, outrigger canoes, surf skis, kayaks, pedal-craft kayaks, row and dory boats. Events are headquartered at Higgs Beach, 1000 Atlantic Blvd. Start time for the race is 9 a.m. Paddlers have up to five hours to complete the race, with a lunch and awards celebration starting at 1 p.m.