Upcoming Key West Events

Check out what's happening all around Key West, FL

Duval Street Party with the Landshark Band

 Fri, 04 Sep at 06:00 pm 200 Duval St, Key West, FL 33040, United States

28th Annual Key West Lobsterfest

 Wed, 05 Aug at 06:00 pm 100-500 Blocks Duval Street, Key West, FL, United States, Florida 33040

The Key Lime Festival 2026

 Wed, 01 Jul at 12:00 pm Key West, Florida

Edgar Allan Poe Speakeasy: Chapter Two - Key West, FL

 Thu, 21 May at 06:00 pm Key West Theater USD 59 to 70

Steve Earle Solo and Acoustic at Key West Theater

 Tue, 09 Jun at 08:00 pm Key West Theater

2026 Key Lime Pie Drop

 Sun, 05 Jul at 04:00 pm Key West lighthouse

Mangoes Drag Brunch Royale Pride Week

 Sun, 07 Jun at 11:30 am Mangoes Restaurant USD 55 to 66

FLO-RAW at Sloppy Joes Key West

 Sat, 04 Jul at 10:00 pm Sloppy Joe's Bar

Mangoes Drag Brunch Royale Halloween Edition

 Sun, 01 Nov at 11:30 am Mangoes Restaurant USD 55 to 66

Second Line Memorial Walking Parade

 Sun, 06 Sep at 05:00 pm 100 Duval St, Key West, FL 33040-6506, United States

Paint the Town Proud Trolley Pub Roll

 Sat, 06 Jun at 11:00 am Bobby's Monkey Bar

Bruce Cockburn at Key West Theater

 Sun, 08 Nov Key West Theater

Running of the Chihuahuas!

 Sun, 17 May at 01:00 pm Rick's Key West

Key West Pride Brunch Sail & Swim

 Fri, 05 Jun at 11:00 am 0 Duval Street, Key West, FL, United States, Florida 33040

Lobsterfest Duval Crawl - Pub Crawl

 Fri, 07 Aug at 08:00 pm Duval St Key West Florida

Key West's Favorite Son City Proclamation

 Fri, 04 Sep at 11:00 am Shrimp Boat Sounds (Jimmy Buffetts Recording Studio)

The Rotary Club of Key West Casino Night Roaring 20's Speakeasy

 Sat, 16 May at 06:30 pm Beachside Key West

Back to the Island Beach Party

 Sat, 05 Sep at 11:00 am 801 Bourbon bar

Swim Around Key West

 Sat, 13 Jun at 06:45 am Higgs Beach Key West

Key West Pride Follies

 Sat, 30 May at 07:30 pm Key West Theater

Steve Earle

 Tue, 09 Jun at 10:00 pm Key West Theater

Sunday Fun-Day Swimsuit Shenanigans Bar Crawl

 Sun, 17 May at 01:00 pm 512 Greene St, Key West, FL

Lobsterfest Kick-Off Party at Rick's

 Wed, 05 Aug at 07:00 pm Rick's Key West

Just a Few Friends Celebration, Key West

 Thu, 03 Sep at 11:00 am Key West

Bruce Cockburn & Livingston Taylor

 Sat, 07 Nov at 07:00 pm Key West Theater

Bruce Cockburn and Livingston Taylor

 Mon, 09 Nov at 01:00 am Key West Theater

John Caparulo in Key West, FL!

 Thu, 28 May at 08:30 pm Comedy Key West

Follow The Rabbit... (9PM)

Fri, 29 May at 09:00 pm Key West Theater

Parrots and Margaritas 5k Run/Walk

 Sat, 05 Sep at 08:00 am Kaya Island Eats

The Wheeland Brothers + Mike Stack & Friends at Sunset Pier

Sat, 05 Sep at 06:30 pm Sunset Pier, Key West, FL 33040, United States

Rum Fest Key West Grand Tasting

 Sat, 15 Aug at 02:30 pm 513 Eaton St, Key West, FL 33040-6801, United States

Key West Artisan Market at the Party in the Park

 Sun, 06 Sep at 06:00 pm Truman Waterfront Park

Gold Pool Parties

 Sun, 17 May at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Key West Pride Street Fair

 Sat, 06 Jun at 04:00 pm Duval Street Key West FL

Garrison Keillor & Erica Rhodes

 Mon, 26 Oct at 07:00 pm Key West Theater

Garrison Keillor (21+)

 Wed, 28 Oct Key West Theater

Florida Keys Mini Season Getaways! (MarineMax St. Pete) - Waitlisted

 Sat, 25 Jul at 10:00 am The Perry Hotel & Marina Key West Free

Mango Madness Summer Members' Exhibit Opening

 Thu, 04 Jun at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

May's Walk On White

 Thu, 21 May at 06:00 pm 1102 White St, Key West, FL, United States, Florida 33040

Key West Pride Presents: A Mojito Masterclass at Tropicado in La Concha Key West

 Fri, 05 Jun at 04:00 pm La Concha Key West

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

 Sat, 31 Oct at 04:00 pm Sebago Watersports

International Ocean Film Festival (Florida Keys Viewing)

 Sat, 06 Jun at 05:30 pm Williams Hall

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

 Sat, 05 Sep at 04:30 pm Hog's Breath Saloon

Swim Around Key West 2026 CFK

 Sat, 13 Jun at 07:00 am The College of the Florida Keys

Tales From The Chart Room Bar

 Thu, 03 Sep Pier House Resort & Spa

Jesse Rice in Key West

 Sat, 15 Aug at 08:00 pm Key West Theater

Wheeland Brothers in Key West

 Sat, 05 Sep at 07:00 pm Sunset Pier

The BIG Pride Fundraiser

 Thu, 25 Jun at 05:00 pm 504 Angela St, Key West, FL 33040-7433, United States

Through the Lens – Early Buffett Concert Photography Exhibit Meet & Greet

 Fri, 04 Sep at 04:15 pm Pier House Resort & Spa

Truman Waterfront Farmers Market

 Thu, 03 Sep at 01:00 pm Truman Waterfront Park

Outdoor Movie: Parrot Heads – The Essential Jimmy Buffett Documentary

 Fri, 04 Sep at 09:00 pm Southernmost Pint Brewpub

Sister Season's Aqua Idol

 Tue, 28 Apr at 06:00 pm AquaPlex Key West

ALB @ Sloppy Joes Key West

Mon, 18 May at 10:00 pm Sloppy Joe's Key West

A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show

 Wed, 02 Sep at 12:30 pm 218 Whitehead St, Key West, FL 33040-6595, United States

Sloppy Joe's -Key West, FL

 Wed, 10 Jun at 10:00 pm Sloppy Joe's

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

 Fri, 30 Oct at 05:00 pm Sebago Watersports

Pool Party at La Concha

 Mon, 07 Sep at 01:00 pm La Concha Key West

Live at Margaritaville Key West

 Fri, 17 Jul at 07:30 pm Margaritaville Restaurant, Key West

Truman Waterfront Community Garage Sale "Junk in the Trunk"

 Sat, 16 May at 08:00 am 21 E Quay Rd, Key West, FL, United States, Florida 33040

Steve Earle

 Tue, 09 Jun at 08:00 pm Key West Theater

Chart Room Daily Hangout Headquarters

 Thu, 03 Sep at 01:00 pm Pier House Resort & Spa

Key West ocktoBREWfest Grand Tasting Event

 Sat, 03 Oct at 05:00 pm 1405 Duval Street

Pre-event Official Meetup at the Chart Room

 Wed, 02 Sep at 05:00 pm Pier House Resort & Spa

The Marshall Morlock Band: Summer Send-Off

 Fri, 19 Jun at 08:00 pm Key West Theater

“Open Mic / No Mic Night” at Andy's Cabana

 Thu, 03 Sep at 07:00 pm Andy's Cabana

Mamey & Mojitos Ice Cream Social!

 Sat, 27 Jun at 05:30 pm 1024 Grinnell St, Key West, FL, United States, Florida 33040

Key West Powerboat Races 2026 - VIP Tent - FRIDAY

 Fri, 06 Nov at 09:00 am Sunset Pier USD 525

Key West Powerboat Races 2026 - VIP Tent - SUNDAY

 Sun, 08 Nov at 09:00 am Sunset Pier USD 525

Friends of Bubba Outdoor Video Lounge

 Sat, 05 Sep at 08:30 pm Southernmost Pint Brewpub

The Ocean Blue

 Fri, 06 Nov at 07:00 pm Key West Theater

Sunset to Stage: Wheeland Brothers Dockside Party

 Sat, 05 Sep at 08:00 pm S/V Argo Navis

Key West Murder Mystery 2: Crime on Date Night!

 Mon, 01 Jun at 12:00 am 502 Whitehead St, Key West USD 15

Key West or BUST!

Sat, 30 May at 11:00 am Key West, Florida

KWHS-Fashion Show

 Sat, 16 May at 07:00 pm Key West High School

Stars, Stripes & Sandbars Getaways! | July 3-6, 2026

 Fri, 03 Jul at 08:00 am Galleon Marina Free

Key West Candidate Event

 Thu, 23 Jul at 06:00 pm Harvey Government Center

Landsharks Band, Key West Concert, JUST A FEW FRIENDS CONCERT WEEKEND!

 Fri, 04 Sep at 05:00 pm Key West

Summer of Rum Festival

 Sat, 15 Aug at 12:00 am Key West Theater

Southernmost Slow Ride in the Pride parade

Sun, 07 Jun at 07:00 pm Truman Waterfront Park Amphitheater

The Ocean Blue at Key West Theater

 Sat, 07 Nov at 08:00 pm Key West Theater

Island Groove Dance Studio Presents: Be Our Guest

 Sun, 17 May at 04:30 pm Key West High School

The Key Lime Festival Kick Off Party & SPIRIT Pageant!

 Wed, 01 Jul at 05:00 pm 1317 Duval St, Key West, FL 33040-3131, United States

Key West Yachts Getaways!®

 Wed, 11 Nov at 10:00 am Duval Street Free

Cypress Gardens Water Ski Show

Sat, 16 May at 02:00 pm Cypress Gardens Water Ski Team (est. 2012)

Milagro Margarita Historic Seaport Bar Stroll

 Sat, 05 Sep at 02:00 pm The Marker Key West Resort

Kids Music Tour Key West Florida

 Mon, 15 Jun at 10:00 am Key West Public Library

DanceWorks 23! at Tennessee Williams Theatre

 Sat, 16 May Tennessee Williams Theatre

Key West

 Sat, 07 Nov at 04:30 am Key West

"Shrimp Boat Sound: Echoes From the Edge" Movie Panel Discussion

 Fri, 04 Sep at 02:30 pm 729 Fleming St, Key West, FL 33040-6827, United States

Pool Party at The Marker Resort

 Sun, 06 Sep at 01:00 pm The Marker Key West Resort

Key West Landings: Paddlers, Runners and Cyclist

 Fri, 12 Jun at 04:00 pm Simonton Beach

"Island in the Works" — Young Writers Studio

 Mon, 22 Jun at 09:00 am 624 White Street, Key West, FL, United States, Florida 33040

Plogging The Keys at MCC Key West

 Fri, 29 May at 08:00 pm 1215 Petronia St, Key West, FL

Through the Lens – Early Buffett Concert Photography Exhibit

 Sat, 05 Sep at 08:00 am Pier House Resort & Spa

Just a Few Friends: Early Bird Clean Up at the Historic Waterfront

 Fri, 04 Sep at 08:00 am Reef Relief

Just a Few Friends Walking Tour

 Thu, 03 Sep Shrimpboat Sound

Key West OktoBREWfest

 Sat, 03 Oct at 03:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Childbirth Education

 Sat, 09 Aug at 10:00 am Lower Keys Medical Center Free

Dry Tortugas Camping Trip

 Fri, 09 Oct at 04:00 pm Dry Tortugas National Park

Monthly Community Yard Sale

 Sat, 25 Apr 1401 Seminary St, Key West, FL, United States, Florida 33040
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