Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Puff Puff... Float! A 4/20 Bud Crawl

 Mon, 20 Apr at 04:20 pm The Greeen House 925 Duval Street Free

Key West Songwriters Festival Platinum Pass -2026

 Wed, 29 Apr at 10:00 am Key West Theater

Graham Nash- Live on Tour 2026

 Sun, 26 Apr at 08:00 pm Key West Theater

George Thorogood & The Destroyers, The Marshall Tucker Band in Key West

 Sat, 09 May at 07:30 pm

Q West: Comedy Escape 2026

 Fri, 10 Apr at 02:00 pm Key West Theater USD 450 to 534

Crystal Gayle

 Tue, 07 Apr at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

OPENING CEREMONY & RAISING OF THE COLORS

 Fri, 17 Apr at 04:30 pm Mallory Square Key West

FLO-RAW at Sloppy Joes Key West

 Wed, 01 Jul Sloppy Joe's Bar

42ND SCHOONER WHARF KICK-OFF PARTY & CONCH SHELL BLOWING CONTEST

 Fri, 17 Apr at 07:00 pm Schooner Wharf Bar

Mangoes Drag Brunch Royale Pride Week

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

DEAD FEST KEY WEST - April 17, 18, 19 - 2026

Fri, 17 Apr at 12:00 pm The Alamo Key West

Paint the Town Proud Trolley Pub Roll

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

🎟️ FINAL VVIP CALL: Graham Nash – Key West Night 1! | Apr 25, 2026

 Sat, 25 Apr at 08:00 pm Key West, Florida Keys

Pet Fiesta – A Block Party for Pets & Their Humans!

 Sat, 11 Apr at 11:00 am The Greeen House, North Roosevelt Boulevard, Key West, FL, USA Free

42nd Annual SCHOONER WHARF PIRATE BALL & COSTUME COMPETITION

 Sat, 25 Apr at 07:00 pm Schooner Wharf Bar

Jessimae Peluso at Comedy Key West

 Wed, 01 Apr at 08:00 pm Comedy Key West

Key West Pride Follies

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

Dusty Slay at Key West Theater

 Sat, 18 Apr Key West Theater

Donavon Frankenreiter

 Mon, 13 Apr Key West Theater

KWSF: Thursday- Songwriters In The Round- 8PM

 Thu, 30 Apr at 08:00 pm Key West Theater

THE ALAMO⚡️ DEAD FEST KEY WEST ⚡️ 3 Days Honoring The Grateful Dead Legacy

 Fri, 17 Apr at 04:00 pm The Alamo Key West USD 59 to 91

Gab Cinque Band - KEY WEST, FL (DEBUT!) @ SLOPPY JOES! 4/15-4/21

 Wed, 15 Apr at 08:00 pm Sloppy Joe's

🎟️ LAST VVIP ACCESS: Graham Nash – Key West 2026! | Apr 26, 2026

 Sun, 26 Apr at 08:00 pm Key West, Florida Keys

OCEAN FEST – A COMMUNITY CELEBRATION

 Sat, 25 Apr at 10:00 am Truman Waterfront Park

Donavon Frankenreiter: Ask Me Anything Tour w. special guest Iris & The Shade

 Sun, 12 Apr at 08:00 pm Key West Theater

John Caparulo in Key West, FL!

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

Earth Day Jam with That Hippie Collective

 Wed, 22 Apr at 08:00 pm Key West Theater

SCHOONER WHARF BAR PARADE AFTER-PARTY

 Thu, 23 Apr at 09:00 pm Schooner Warf Bar...

Endless Summer with Howard Livingston and Friends

 Sat, 11 Apr at 07:30 pm 5901 College Rd, Key West, FL, United States, Florida 33040

Miss Island Queen Drag Brunch Hosted by Justin Harris

 Sun, 26 Apr at 11:00 am First Flight Island Restaurant & Brewery USD 61

KW ARTISAN MARKET - EARTH DAY EDITION

 Sun, 19 Apr at 10:00 am Higgs Beach, Key West

Keith Sykes

 Fri, 03 Apr Key West Theater

TOM PETTY NIGHT!

 Tue, 14 Apr at 05:30 pm Green Parrot Bar Key West

GTRB: Unplugged

 Sun, 12 Apr at 05:00 pm Key West Theater

HOT HAVANA NIGHT DANCE PARTY & SILENT AUCTION

Wed, 22 Apr at 06:00 pm Kaya Island Eats

KEY WEST ARTISAN MARKET – CONCH REPUBLIC EDITION

 Sun, 26 Apr at 10:00 am Higgs Beach, Key West

Damon Fowler - The Green Parrot, Key West, FL

 Fri, 15 May at 05:30 pm The Green Parrot

WOOF Week 2026!

 Tue, 21 Apr at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Puff Puff... Float! A 4/20 Bud Crawl

 Mon, 20 Apr at 04:20 pm The Greeen House 925 Duval St

42nd Annual SCHOONER WHARF “WRECKERS CUP RACE” 2026 SEASON AWARDS PARTY

 Sun, 26 Apr at 07:00 pm Schooner Wharf Bar

JAZZ IN THE GARDENS

 Sun, 26 Apr at 05:00 pm The Gardens Hotel Key West Florida

International Ocean Film Festival (Florida Keys Viewing)

 Sat, 06 Jun at 05:30 pm Williams Hall

April's Community Swim

 Sat, 25 Apr at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Conch Country Dance Party

 Sun, 26 Apr at 05:00 pm 319 Duval St, Key West, FL

DRUNKEN SPELLING BEE

 Mon, 20 Apr at 09:00 pm Mary Ellen's Bar and Kitchen

Florida Keys Mini Season Getaways!

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

Jazz in the Gardens

Sun, 19 Apr at 05:00 pm Gardens Hotel

Keith Sykes

 Thu, 02 Apr at 07:00 pm Back Stage Listening Room at Key West Theater

Bearly Dead (Grateful Dead Party!) @ Green Parrot - Key West!

 Wed, 08 Apr at 01:00 pm Green Parrot, Key West, Florida

Where’s Dave Band

 Sun, 26 Apr at 07:00 pm Back Stage Listening Room at Key West Theater

Italian Movie Night at Tropic Cinema: Avanti! on Wednesday April 1st sponsored by The Garden's Hotel

 Wed, 01 Apr at 05:30 pm Tropic Cinema

Puppy Pals Live! - Key West

 Mon, 06 Apr at 10:30 pm Tennessee Williams Theatre

Belle Jampol

 Fri, 03 Apr at 07:00 pm Tennessee Williams Theatre

Bearly Dead (Grateful Dead Party!) @ Green Parrot - Key West!

 Thu, 09 Apr at 01:00 pm Green Parrot, Key West, Florida

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

 Fri, 04 Sep at 05:00 pm Key West

Cypress Gardens Water Ski Show

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

Sunrise Service

 Sun, 05 Apr at 06:30 am Fifth Street Baptist Church

Kids Music Tour Key West Florida

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

Stars, Stripes & Sandbars Getaways!

 Fri, 03 Jul at 12:00 am Galleon Marina Free

Early Bird Clean Up Garrison Bight hosted by Key West Community Sailing Center

 Fri, 15 May at 08:00 am Key West Community Sailing Center

The M**der Mystery Experience in Key West

 Sat, 29 Nov at 11:00 am 302 Fleming St USD 10 to 30

The Devil Wears Prada 2

 Thu, 30 Apr at 07:30 pm Regal (Key West, FL)