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.
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/
2023 Key West Event Calendar
May 2023 Key West Events
May 3-7, 2023 – MUSIC – 27th Annual Key West Song Writers Festival – Features more than two-hundred top songwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and a free concert on Duval Street. For more information, visit http://www.keywestsongwritersfestival.com
May 13, 2023 – MILITARY – Commissioning of USS Lenah Sutcliffe Higbee – Naval ship commissioning, a Arleigh Burke class Guided-missile Destroyer.
May 20, 2023 – HISTORY – Key West Art & Historical Society: Remember the USS Maine 125th Anniversary – Talk about the 125th anniversay of the sinking of the USS Maine in Havana Harbor.The presentation takes place from 6 to 7 p.m. at Tropic Cinema, 416 Eaton St. Tickets $15.
May 20, 2023 – RUNNING – Key West Mile Marker 0 5K Run/Walk – The Key West Mile Marker 0 5K Run/Walk is a fun and festive event that celebrates the beauty and history of Key West. The race starts and finishes at Mile Marker 0, the southernmost point in the continental United States. The course winds through Truman Waterfront Park, past the Southernmost Point Buoy Marker, Key West Lighthouse, the Hemingway Home, and other favorite visitor destinations. All participants will receive a Mile Marker 0 bottle opener medal and sticker. The top three male and female finishers in each age group will also receive awards. The post-race party will be held at Mary Ellen’s Bar, 420 Appelrouth Lane. Enjoy live music, free beer or Bloody Mary, and food for purchase. The Key West Mile Marker 0 5K Run/Walk is a fundraiser for Reef Relief, a non-profit organization dedicated to protecting and restoring coral reefs. Your registration fee will help Reef Relief continue their important work. Registration is $39 for runners and walkers, here: https://runsignup.com/Race/FL/KeyWest/EndoftheRoad5K
May 20, 2023 – ECOLOGY – Key West Tropical Forest & Botanical Garden: Speaker Series – John Bratton, Professor of Anthropology at the University of West Florida, will present a program titled “Hope and Resolve” about the garden’s Cuban Chug exhibit. The exhibit features a collection of homemade migrant boats that tell a visual story of desperate migrants seeking freedom. Bratton will also discuss artifact conservation and maritime archaeology, tracking the decades of relations between the Florida Keys and Cuba, and the Cubans who helped build Key West over the past 200 years. The talk will begin at 1 p.m. at the Key West Tropical Forest & Botanical Garden, 5210 College Rd. Admission is $10 per person; free for garden members.
May 20, 2023 – LGBTQ – Key West Business Guild: Pride Follies – The Key West Business Guild is proud to present Pride Follies, a fun evening of the best and worst of local Key West entertainment. The show will be hosted by the former Queen of Fantasy Fest, Destiny Montgomery. The show will feature a variety of acts, including singers, dancers, comedians, and drag queens. There will also be a silent auction and raffle to benefit the Key West Business Guild. Doors open at 7 p.m. and the show starts at 8 p.m. at the Key West Theater, 512 Eaton Street. Tickets are $15 to $35 and can be purchased online or at the door. More information here: https://thekeywesttheater.com/e/?event=479448
May 21, 2023 – LOCAL COLOR – 10th Annual Running of the Chihuahuas – The smallest dogs with the biggest personalities are invited to enter the Chihuahua Races at Rick’s Bar, 202 Duval Street on Sunday, May 21st. Doors open at 1 p.m.; races start at 2 p.m. There are three categories of races: Chihuahua pure and mixed breeds; senior pups; and all other small dogs. Preregistration is $25 per dog or $30 on the day of the event. Spectators are free. Proceeds benefit Florida Keys SPCA. More information here: https://fkspca.org/event/the-running-of-the-chihuahuas/
May 28, 2023 – LOCAL COLOR – Schooner Wharf Minimal Regatta – The annual Minimal Regatta is a Memorial Day Weekend tradition in the Florida Keys. Teams of six must construct a boat out of a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners, and a roll of duct tape. Caulking and adhesives are forbidden, but epoxy paint is permitted. The race begins at 11 a.m. at the Schooner Wharf Bar, 202 William St. The Minimal Regatta is a fun and wacky event that celebrates the creativity and ingenuity of the Florida Keys community. It is also a great way to get out and enjoy the beautiful weather of the Keys on Memorial Day Weekend. More information here: http://www.schoonerwharf.com/
May 30, 2023 – MUSIC – Sunset Green: Live at Sunset Concert – The Keys Collection presents a free monthly concert series called “Live at Sunset” on the last Tuesday of every month on the Sunset Green. The lawn opens at 6 p.m., and local talent performs from 7-10 p.m. Entry and parking are free, and food and drinks are available for purchase. The venue is located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels. More information here: https://www.thekeyscollection.com/events/
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.