Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Graham Nash- Live on Tour 2026

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

Irish Kevin's 13th Annual Shamrock Shuffle

Sat, 14 Mar at 08:00 am 211 Duval St, Key West, FL, United States, Florida 33040

Schooner Wharf Wrecker's Cup Race Series

 Sun, 22 Feb at 01:00 pm 202 William St, Key West, FL, United States, Florida 33040

Changes In Latitude at Key West Theater

Tue, 03 Mar at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Jake Shimabukuro in Key West

 Tue, 10 Mar at 07:00 pm The Studios of Key West

FLO-RAW at Sloppy Joes Key West

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

Q West: Comedy Escape 2026

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

St. Patrick's Day 2026!

 Tue, 17 Mar at 11:00 am 528 Front Street, Key West, FL, United States, Florida 33040

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

 Sat, 09 May at 07:30 pm

Colin Quinn

 Thu, 26 Feb at 07:00 pm Key West Theater

Mangoes Drag Brunch Royale Pride Week

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

Parking Big Bad Voodoo Daddy (21+)

 Sun, 22 Feb at 06:00 pm Key West Theater

Jazz At Lincoln Center: Great American Crooners

 Mon, 23 Mar at 07:00 pm Tennessee Williams Theatre

Big Bad Voodoo Daddy at Key West Theater

 Sun, 22 Feb at 01:00 pm Key West Theater

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

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

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

FLO-RAW at Sloppy Joes Key West

 Sun, 05 Jul at 10:00 pm Sloppy Joe's Bar

Dusty Slay at Key West Theater

 Sat, 18 Apr Key West Theater

Changes in Latitudes - Jimmy Buffet Tribute

 Mon, 02 Mar at 07:00 pm Key West Theater

Vintners Dinner

 Sat, 21 Mar at 06:00 pm 729 Fleming St, Key West, FL 33040-6827, United States

Burgers & Buffett Tunes

 Sat, 28 Feb at 12:00 pm Comedy Key West

Scott Kirby- 35 Years of Songs & Stories

Thu, 26 Feb at 07:00 pm Key West Theater

The Studios of Key West Playlist featuring Cortadito

 Fri, 06 Mar at 07:00 pm The Studios of Key West

Yachtley Crew at Key West Theater

 Wed, 18 Feb Key West Theater

South Florida Symphony Orchestra - Rimsky - Korsakovs at Tennessee Williams Theatre

 Sat, 21 Feb Tennessee Williams Theatre

Big Bad Voodoo Daddy

 Sat, 21 Feb at 07:00 pm Key West Theater

Keith Sykes

 Fri, 03 Apr at 07:00 pm Key West Theater

The Reverend Peyton's Big Damn Band

 Sun, 22 Mar at 12:00 am Key West Theater

Golden Girls - The Tribute Show

 Sat, 14 Mar at 07:00 pm Key West Theater

Martin Sexton

 Thu, 12 Mar at 07:00 pm Key West Theater

South Florida Symphony Orchestra - Dvoraks Eight at Tennessee Williams Theatre

 Sat, 14 Mar at 07:30 pm Tennessee Williams Theatre

Dave Matthews Tribute Band

 Tue, 24 Feb at 07:00 pm Key West Theater

Scott Kirby- 35 Years of Songs & Stories

Wed, 25 Feb at 07:00 pm Key West Theater

Gold Pool Parties

 Sun, 22 Feb at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Ladies Night Out - Cayo Hueso Original Music Series

Sun, 22 Mar at 07:00 pm Key West Theater, Key West, FL

Grateful Dub: a Reggae-infused tribute to the Grateful Dead @ Ocean Key Resort | Key West, FL

 Wed, 18 Mar at 06:30 pm Ocean Key Resort & Spa

WOOF Week 2026!

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

Damon Fowler - The Green Parrot, Key West, FL

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

The Linda Ronstadt Experience

 Sat, 21 Feb at 08:00 pm Key West Theater

FLO-RAW at Sloppy Joes Key West

 Wed, 01 Jul at 10:00 pm Sloppy Joe's Bar

BoDeans

 Sat, 28 Mar at 07:00 pm Key West Theater

Paradise Big Band at Tennessee Williams Theatre

 Sun, 22 Mar at 07:30 pm Tennessee Williams Theatre

South Florida Symphony Orchestra: Dvořák’s Eighth & Sibelius’ Violin Concerto

 Sat, 14 Mar at 07:30 pm 5901 College Rd, Key West, FL, United States, Florida 33040

The 77 Experience ( A Journey Thru Rock and Roll History Plus Much More)

Sat, 28 Mar at 08:00 pm Key West Theater

Paradise Big Band

 Sun, 22 Mar at 07:30 pm 5901 College Rd, Key West, FL, United States, Florida 33040

Carson Lowe

 Thu, 19 Feb at 07:00 pm Back Stage Listening Room at Key West Theater

Dvořák | Sibelius | Schubert - Key West

 Sat, 14 Mar at 07:30 pm Tennessee Williams Theatre

Italian Movie Night at Tropic Cinema: Cinema Paradiso on Saturday March 7th

 Sat, 07 Mar at 04:00 pm Tropic Cinema

2026 Annual Author Gala: Ruth Reichl

 Mon, 23 Feb at 06:00 pm 700 Fleming St, Key West, FL, United States, Florida 33040

Larry Joe Taylor

 Wed, 18 Mar at 07:00 pm Back Stage Listening Room at Key West Theater

Key West After Dark | The Nocturnes by Sean P. Dwyer

 Fri, 20 Feb at 05:00 pm 720 Caroline Street, Key West, FL

Tommy Emmanuel

 Sat, 21 Mar at 07:00 pm Key West Theater

John Frinzi & Aaron Scherz

 Wed, 25 Mar at 07:00 pm Back Stage Listening Room at Key West Theater

A Glam Concert and Dance Party to Feed Local Kids

 Sat, 14 Mar at 07:30 pm Key West Theater

Darcy Cooke: Songs & Stories of the Silver Screen

 Fri, 20 Feb at 07:00 pm The Studios of Key West

Speaker Series: Christopher Castellani

 Mon, 16 Mar at 06:00 pm 700 Fleming St, Key West, FL, United States, Florida 33040

Scott Kirby

 Thu, 12 Feb 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

Stand-Up Comedy Extravaganza in Key West

 Sat, 28 Feb at 05:30 pm Loyal Order of Moose, Lodge 1760 USD 28

Nick Brownell, Jeff Harris and Ray Fogg – Hey, We Write Nice Songs Too!

 Wed, 18 Mar at 08:00 pm Key West Theater

Keith Sykes

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

Rick Thomas - Key West

 Wed, 04 Mar at 12:30 am Tennessee Williams Theatre

Family Movie Night: 'The Avengers'

 Fri, 27 Feb at 06:00 pm Sigsbee Community Center

Max von Essen: Spotlight Cabaret Curated by Randy Roberts

 Mon, 02 Mar at 08:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

Parking DMTB: The Dave Matthews Tribute Band

 Thu, 26 Feb at 01:00 am Key West Theater

Captain Midnight Band - Key West, FL - 3 Nights!

 Fri, 20 Mar at 09:30 pm The Alamo Key West

Great American Crooners

 Tue, 24 Mar Tennessee Williams Theatre

Bark & Brew

 Thu, 12 Mar at 05:00 pm 5950 Peninsular Avenue, Key West, FL, United States, Florida 33040

Karaoke Night

 Thu, 19 Feb at 06:00 pm Sunset Lounge bar & Grill

Speaker Series: Bob Rich

 Mon, 02 Mar at 06:00 pm 700 Fleming St, Key West, FL, United States, Florida 33040

Puppy Pals Live! - Key West

 Mon, 06 Apr Tennessee Williams Theatre

Rob Benton LIVE at The Marker Key West

 Tue, 24 Feb at 04:00 pm The Marker Key West

Cypress Gardens Water Ski Show

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

The Beach Boys in Key West

 Sun, 29 Mar at 08:00 pm Coffee Butler Amphitheater

Belle Jampol

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

Stars, Stripes & Sandbars Getaways!

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

FLO-RAW at Sloppy Joes Key West

 Tue, 07 Jul at 10:00 pm Sloppy Joe's Bar

Early Bird Clean Up Whitehead and Front Streets hosted by the Key West Aquarium

 Fri, 27 Mar at 08:00 am Key West Aquarium

Where’s Dave Band

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

Bumpin' Uglies

 Tue, 24 Mar at 07:00 pm Key West Theater

Jazz at Lincoln Center: Great American Crooners

 Mon, 23 Mar at 07:00 pm Tennessee Williams Theatre

Key West Conspiracy Game: The Outdoor Escape

 Fri, 15 Aug at 03:00 pm The Custom House USD 10 to 30

Early Bird Clean Up United Street and Varela hosted by Children's Montessori School

 Fri, 13 Mar at 08:00 am The Children's School

Early Bird Clean Up North Roosevelt & Kennedy Drive hosted by H&R Block

Fri, 20 Mar at 08:00 am H&R Block

The M**der Mystery Experience in Key West

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

DMTB: The Dave Matthews Tribute Band

 Thu, 26 Feb at 01:00 am Key West Theater

Garrison Keillor

 Mon, 23 Feb Key West Theater