Key West, Florida, is a Florida Keys town on the Jupiter-to-Key West coast. This guide covers 31 upcoming events, kept current from official sources. Top picks: Monday Night Jazz Jams and Burgers & Buffet Tunes: A Tribute Show at Comedy Key West. Nearest towns: Big Pine Key (28 mi) and Marathon (45 mi).

Last updated September 7, 2026. Events refresh daily; places are hand-picked and re-checked monthly.

Key West is the end of the road: Duval Street, Hemingway's six-toed cats, the nightly Sunset Celebration at Mallory Square and a race calendar that runs from the Half Marathon in January to Fantasy Fest in October. Rent a bike and skip the car.

For the live version of everything below, open the Key West page: things to do · events · where to eat.

What's on in Key West

The next 10 events on the Key West calendar (dates are America/New_York; confirm with the organizer before you go):

  • Monday Night Jazz Jams — Mon, Sep 7, 8:30 AM · American Legion Post 168 · Concerts & Live Music. Kick off your week with smooth jazz tunes every Monday night.
  • Burgers & Buffet Tunes: A Tribute Show at Comedy Key West — Mon, Sep 7, 12:30 PM · Comedy Key West · Theater & Shows. Enjoy lunch while experiencing a unique tribute show.
  • Occupational Hazard: The First Coral Reefers — Mon, Sep 7, 2:00 PM · Key West Theater · Theater & Shows. A special two-show engagement highlighting the creative heart of Old Town.
  • Glow Hours at Hugh’s Views — Mon, Sep 7, 5:00 AM · Hugh’s View · Community. Experience a unique rooftop evening with stunning views.
  • Aqua Idol at the Legion — Tue, Sep 8 · American Legion · Theater & Shows. Cheer on local singers while supporting a great cause.
  • Arts & Drafts — Wed, Sep 9, 7:00 AM · The Retro Room · Festivals & Markets. Enjoy a relaxed, social art night with local creativity.
  • Hemingway in a Funny Way at Comedy Key West — Wed, Sep 9, 5:30 AM · Comedy Key West · Theater & Shows. A playful tribute to one of Key West’s legendary literary figures.
  • Key West Farmers Market — Thu, Sep 10, 1:00 AM · Key West Farmers Market · Festivals & Markets. Discover fresh local flavors and handmade treasures in a lively setting.
  • Truman Waterfront Farmers Market — Thu, Sep 10, 2:00 PM · Truman Waterfront Park · Festivals & Markets. Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. Price: Free
  • Monroe County Sheriff's Office Animal Farm Open House — Sun, Sep 13, 1:00 PM · Monroe County Sheriff's Office Animal Farm · Community. Come visit the animals at the farm including miniature horses, pigs, goats, and many more! Price: Free

See the full list, refreshed daily: Key West.

Getting there and planning your day

Key West sits at 24.555, -81.780 in the Florida Keys. Parking rules, beach access and permits are on the City of Key West site; the Florida Keys & Key West official tourism council calendar lists county-wide festivals; check the National Weather Service Key West forecast before a beach or boat day (summer storms build after 2 pm); snorkelers and anglers should read the NOAA tides: Key West; the nearest airport is Key West International Airport (EYW); the official Fort Zachary Taylor Historic State Park page has hours and entry fees.

Nearby towns

Each has its own page in this guide:

Official sources and further reading

We link to primary sources so you can verify hours, fees and dates:

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