Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

11th Annual Onesie Pub Crawl

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

Mile 0 Fest Key West: Shane Smith and The Saints Casey Donahew & The Band of Heathens - Saturday

 Fri, 30 Jan Truman Waterfront Amphitheater

Put-in-Bay Days in Key West 2026

 Wed, 11 Feb at 03:00 pm Key West, Florida

Mile 0 Fest Key West - 3 Day Pass (Thursday-Saturday)

 Wed, 28 Jan at 07:00 pm Truman Waterfront Amphitheater

George Thorogood & The Destroyers w/ The Marshall Tucker Band

 Sat, 09 May at 07:30 pm Coffee Butler Amphitheater

Mile 0 Fest - (Saturday)

 Sat, 31 Jan at 05:00 pm Coffee Butler Amphitheater

Mile 0 Fest Key West - 3 Day Pass (Tuesday-Thursday)

 Tue, 27 Jan at 07:00 pm Truman Waterfront Amphitheater

Vienna Boys Choir at Tennessee Williams Theatre

 Thu, 05 Feb at 07:30 pm Tennessee Williams Theatre

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

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

Kaitlin Butts in Key West

 Thu, 29 Jan at 05:00 pm Truman Waterfront Park Amphitheater

Mile 0 Fest Key West - Tuesday

 Mon, 26 Jan at 07:00 pm Truman Waterfront Amphitheater

Changes In Latitude at Key West Theater

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

Mangoes Drag Brunch Royale Pride Week

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

Parking Mile 0 Fest - (Wednedsay)

 Wed, 28 Jan at 05:00 pm Coffee Butler Amphitheater

Reza Edge of Illusion (6:00 pm) Added by Popular Demand!

Fri, 06 Feb at 06:00 pm Key West Theater

Arrival From Sweden: The Music of ABBA

 Mon, 26 Jan at 12:30 am Tennessee Williams Theatre

Jazz At Lincoln Center: Great American Crooners

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

Mike Ryan in Key West

 Thu, 29 Jan at 05:00 pm Truman Waterfront Park

REZA LIVE ON TOUR | KEY WEST, FL

 Fri, 06 Feb at 08:00 pm Key West Theater

7th Annual Pup Crawl Presented By Bascom Grooms Real Estate

 Sat, 14 Feb at 12:00 pm Hank's Hair Of The Dog Saloon

Big Bad Voodoo Daddy at Key West Theater

 Sun, 22 Feb Key West Theater

American Aquarium in Key West

 Wed, 28 Jan at 03:00 pm Truman Waterfront Park Amphitheater

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

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

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

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

Mike Ryan in Key West

 Wed, 28 Jan at 05:00 pm Truman Waterfront Park

FLO-RAW at Sloppy Joes Key West

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

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 at 07:30 pm Tennessee Williams Theatre

Parking Mile 0 Fest - (Thursday)

 Thu, 29 Jan at 05:00 pm Coffee Butler Amphitheater

Parking Mile 0 Fest - (Friday)

 Fri, 30 Jan at 05:00 pm Coffee Butler Amphitheater

Dusty Slay at Key West Theater

 Sat, 18 Apr Key West Theater

Tropical Luncheon & Garden Party

 Sun, 08 Feb at 12:00 pm Key West Woman's Club

Burgers & Buffett Tunes

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

David Lowery - Live in Concert at the Tropic

 Sat, 07 Feb at 07:30 pm Tropic Cinema

The Studios of Key West Playlist featuring Cortadito

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

Sugar Ray in Key West

 Wed, 28 Jan at 11:00 am Key west cruise port

Tanner Usrey in Key West

 Tue, 27 Jan at 05:00 pm Truman Waterfront Park Amphitheater

Ladies Night Out - Cayo Hueso Original Music Series

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

Scott Kirby- 35 Years of Songs & Stories

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

Special Valentine Sunset

Fri, 13 Feb at 05:30 pm Truman Waterfront Park - West end of Southhard Street, Key West, FL

Scott Kirby- 35 Years of Songs & Stories

Fri, 13 Feb at 07:00 pm Key West Theater

Changes in Latitudes - Jimmy Buffet Tribute

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

Martin Sexton

 Thu, 12 Mar 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

The Reverend Peyton's Big Damn Band

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

Somo Roots!

Sun, 15 Feb at 01:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Mac's Place Big Game Party 🏈

 Sun, 08 Feb at 05:00 pm 1605 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040

Keith Sykes

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

🎸 Rock Concert & Empress Gin Cocktail Contest with The Andy Westcott Band

 Sun, 15 Feb at 01:00 pm 200 William St, Key West, FL, United States, Florida 33040

Scott Kirby- 35 Years of Songs & Stories

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

Scott Kirby- 35 Years of Songs & Stories

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

Dave Matthews Tribute Band

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

Galentines Pilates XOXO FYT

 Fri, 13 Feb at 05:30 pm George's Bar & Spritz Free

Phil Collins Experience at Key West Theater

Mon, 26 Jan at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

WOOF Week 2026!

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

Bumpin Uglies w/ Joey Harkum

Wed, 25 Mar at 08:00 pm Key West Theater

A Night of OASIS at DURTY HARRY’S

 Wed, 28 Jan at 09:00 pm Durty Harry's

The Best of the 72-Hour Film Challenge: A Screening of Audience Favorites

 Thu, 05 Feb at 07:00 pm 729 Fleming Street, Key West, FL, United States, Florida 33040

Salt Cured Life - A Special Screening

 Sat, 07 Feb at 05:30 pm Williams Hall

Paradise Big Band at Tennessee Williams Theatre

 Sun, 25 Jan at 07:30 pm Tennessee Williams Theatre

FLO-RAW at Sloppy Joes Key West

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

Damon Fowler - The Green Parrot, Key West, FL

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

The Shanty Hounds LIVE at Sunset Lounge Bar & Grill

 Sat, 31 Jan at 05:00 pm Sunset Lounge Sigsbee

The Massacoustics at Key West Theater

 Wed, 04 Feb at 08:00 pm Key West Theater

The Linda Ronstadt Experience

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

BoDeans

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

Petals & Pearls | Celebrate 90 years in the Garden

 Fri, 30 Jan at 06:00 pm 5210 College Rd, Key West, FL, United States, Florida 33040

Key West, FL – Key West Theater

 Fri, 30 Jan at 07:00 pm Key West Theater

Dvořák | Sibelius | Schubert - Key West

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

Fighting For Laughs, Too

 Sat, 07 Feb at 06:30 pm Kaya Island Eats

The Love Party

Sat, 14 Feb at 07:00 pm 803 Emma St, Key West, FL 33040-7344, United States

Reza Edge of Illusion

 Fri, 06 Feb at 08:00 pm Key West Theater

Murder Mystery on the Dance Floor

 Tue, 10 Feb at 06:00 pm 729 Fleming Street, Key West, FL, United States, Florida 33040

Paradise Big Band

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

Speaker Series: Karen Dukess

 Mon, 09 Feb at 06:00 pm 700 Fleming St, Key West, FL, United States, Florida 33040

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

 Sat, 07 Mar at 04:00 pm Tropic Cinema

Parking Mile 0 Fest - (Saturday)

 Sat, 31 Jan at 05:00 pm Coffee Butler Amphitheater

A Glam Concert and Dance Party to Feed Local Kids

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

Nick Norman w. Shane Williams & Warren Bazemore (of Finnegan Bell)

 Sun, 01 Feb at 07:00 pm Key West Theater

Mile 0 Festival at Southernmost Beach Resort

 Wed, 28 Jan at 12:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

The Big Game Watch Party at The Marker Key West

 Sun, 08 Feb at 06:00 pm The Marker Key West

Speaker Series: Bob Rich

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

Alice Howe & Freebo - Key West Theater

 Wed, 28 Jan at 07:00 pm Key West Theater

Starfish Designs Paint Party

 Tue, 27 Jan at 06:00 pm SeaSide

Pilobolus - Key West

 Sat, 14 Feb at 12:30 am Tennessee Williams Theatre

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

Mile 0 Fest Key West - 5 Day Pass

 Mon, 26 Jan at 07:00 pm Truman Waterfront Amphitheater

🎼🎵🎤🎹Ladies Night🎼🎵🎶🎻

 Wed, 28 Jan at 06:00 pm 803 Emma St, Key West, FL

Havana Nights Salsa Dancing Lessons!

Tue, 27 Jan at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Italian Movie Night at Tropic Cinema: 3 Coins in a Fountain on February 4th

 Wed, 04 Feb at 05:30 pm Tropic Cinema

An Evening with Ralph Arlyck: I like It Here

 Wed, 28 Jan at 06:30 pm Tropic Cinema

The Massacoustics

 Thu, 05 Feb at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Darcy Cooke: Songs & Stories of the Silver Screen

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

BIG GAME Tailgate & Watch Party

 Sun, 08 Feb at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Speaker Series: Christopher Castellani

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

The Massacoustics

 Wed, 04 Feb at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Gabriel Rutledge at Key West Theater

 Sun, 15 Feb at 08:00 pm Key West