Key West Events May 2026 | Festivals, Live Music & Things to Do
April 30, 2026 • Key West Tourist
Events in the Florida Keys & Key West for May 2026
May in Key West and the Florida Keys brings one of the most balanced months of the year—live music festivals, weekly markets, waterfront events, and ideal conditions for fishing, boating, and sunset experiences. With fewer peak-season crowds and a full calendar of activities, May is one of the best times to experience the island’s energy both on land and on the water. From headline music festivals to weekly artisan markets and live performances across Old Town, visitors can expect a steady flow of events throughout the entire month.
Featured May 2026 Events in Key West
Key West Songwriters Festival (April 29 – May 3, 2026)
The largest festival of its kind transforms Key West into a live music stage across dozens of venues. Over 150 artists perform intimate sets in bars, theaters, and waterfront locations, creating one of the most immersive music experiences in the country. Explore more events: https://www.keywesttourist.com/festivals-events/
Live Music & Concert Events (May 2026)
Key West continues its daily live music tradition with performances from morning through late night across Duval Street, the Historic Seaport, and beyond. From acoustic sets to full bands and national touring acts, live music is constant throughout May. Check today’s live music schedule
Weekly & Recurring Events
The Key West Artisan Market takes place Sundays throughout May at Higgs Beach, featuring local artists, food vendors, crafts, and live entertainment. The Morada Way Art Walk in the Lower Keys offers galleries, street art, live music, and local vendors in an open-air setting. Explore more events
Holiday & Themed Events
Cinco de Mayo on May 5 is celebrated across the island with waterfront parties, themed menus, and live music. Mother’s Day weekend brings special brunches, waterfront dining, and curated experiences across Key West.
Local Culture & Theater
Key West’s arts scene continues through May with theater performances, live shows, and cultural programming throughout Old Town, including events at the Key West Theater and other venues.
Fishing & On-the-Water Season
May marks the beginning of prime offshore and reef fishing conditions in Key West. Charter availability increases, and anglers target mahi-mahi, tuna, and reef species during this early summer transition. Explore deep sea fishing charters: https://www.keywesttourist.com/deep-sea-fishing/ Explore family fishing trips: https://www.keywesttourist.com/family-fun-party-fishing-boat-charters/
Top Experiences to Book in May
With calm seas and warm temperatures, May is one of the best months for on-the-water experiences. Many of these book quickly during event weekends. Explore Key West Tours
Check Sunset Sail Availability
Explore jet ski tours
Why Visit Key West in May
May offers a rare combination of a full event calendar without peak-season crowds, excellent water conditions for tours and fishing, and nonstop live music across multiple venues. It’s one of the most well-rounded months to experience everything the island has to offer.
Plan Your May 2026 Trip
Start your day exploring local markets or taking a tour, spend afternoons on the water, and finish evenings with live music or events across Old Town. With activities happening daily, it’s easy to build a complete itinerary around both scheduled events and spontaneous island experiences.
More Events & Updates
Event schedules continue to evolve throughout the month, with additional performances and local happenings added regularly. Check back for updates and newly announced events.
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