Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

The Beach Boys in Key West

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

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

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

Tommy Emmanuel

 Sat, 21 Mar Key West Theater

Jake Shimabukuro in Key West

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

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

Irish Kevin's 13th Annual Shamrock Shuffle

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

Echoes of Erin

 Tue, 17 Mar at 07:00 pm Key West Theater

Jake Shimabukuro - Old Town New Folk

 Tue, 10 Mar at 07:00 pm 533 Eaton 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

St. Patrick's Day 2026!

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

Crystal Gayle

 Tue, 07 Apr at 08:00 pm 512 Eaton St, 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

Let’s Get Shamrocked! Pool Party with The Skallywagz 🍀

 Sat, 14 Mar at 02:00 pm 200 William 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

Kim Gordon’s Black and Red Masquerade Ball

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

Jazz At Lincoln Center: Great American Crooners

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

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

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

Donavon Frankenreiter

 Mon, 13 Apr at 12:00 am 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

Dusty Slay at Key West Theater

 Sat, 18 Apr Key West Theater

Vintners Dinner

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

FLO-RAW at Sloppy Joes Key West

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

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

John Caparulo in Key West, FL!

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

Donavon Frankenreiter: Ask Me Anything Tour

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

Earth Day Jam with That Hippie Collective

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

FLO-RAW at Sloppy Joes Key West

 Fri, 03 Jul at 10:00 pm Sloppy Joe's Bar

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

Keith Sykes

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

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

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

Martin Sexton

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

Golden Girls - The Tribute Show

 Sat, 14 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

18th Annual Spring Social Presented By Hank's Hair of the Dog Saloon

 Fri, 13 Mar at 05:30 pm Harry Truman Little White House, Key West, Florida.

Endless Summer with Howard Livingston and Friends

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

Scott Kirby- 35 Years of Songs & Stories

Wed, 11 Mar at 07:00 pm Key West Theater

COMEDY FOR KAUFMAN

 Sun, 22 Mar at 05:00 pm Comedy Key West

The Reverend Peyton's Big Damn Band

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

- The Captain Midnight Band -

Fri, 20 Mar at 09:00 pm The Alamo Key West

TOM PETTY NIGHT!

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

A Glam Concert and Dance Party to Feed Local Kids

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

Let's Get Shamrocked at The Marker Key West

 Sat, 14 Mar at 02:00 pm The Marker Key West

Gold Pool Parties

 Wed, 18 Mar at 05:00 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

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

Beach Boys Pool Party

 Sat, 28 Mar at 11:00 am 3820 N Roosevelt Blvd, Key West, FL, United States, Florida 33040

GRATEFUL DUB Live in Key West, FL [Night 1 - St Paddy's day - FREE show! ]

 Tue, 17 Mar at 06:30 pm Ocean Key Resort & Spa Free

Paradise Big Band at Tennessee Williams Theatre

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

International Ocean Film Festival (Florida Keys Viewing)

 Sat, 06 Jun at 05:30 pm Williams Hall

BoDeans

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

April's Community Swim

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

FLO-RAW at Sloppy Joes Key West

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

FLO-RAW at Sloppy Joes Key West

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

FLO-RAW at Sloppy Joes Key West

 Mon, 06 Jul at 10:00 pm Sloppy Joe's Bar

Bark & Brew

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

Bumpin' Uglies

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

Florida Keys Mini Season Getaways!

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

Conch Country Dance Party

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

Where’s Dave Band

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

Jazz in the Gardens

Sun, 19 Apr at 05:00 pm Gardens Hotel

Scott Kirby

 Tue, 10 Mar 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

Larry Joe Taylor

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

John Frinzi & Aaron Scherz

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

Speaker Series: Christopher Castellani

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

St. Patrick’s Day Celebration

 Fri, 13 Mar at 04:00 pm Sunset Lounge Sigsbee

Keith Sykes

 Thu, 02 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

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

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

Belle Jampol

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

Paradise Big Band

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

Ladies Night Out at Key West Theater - Back Stage Listening Room

 Sun, 22 Mar at 07:00 pm Key West Theater - Back Stage Listening Room

Great American Crooners

 Tue, 24 Mar at 11:30 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

WWE Florida beach day and potluck

 Sun, 15 Mar at 02:00 pm Fort Zachary Taylor Historic State Park Beach Free

Puppy Pals Live! - Key West

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

Mckenna Carlson LIVE at Sunset Lounge Bar

 Sat, 14 Mar at 05:00 pm Sunset Lounge Sigsbee

Cypress Gardens Water Ski Show

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

Family Movie Night - 'Teenage Mutant Ninja Turtles' [2023]

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

Jazz at Lincoln Center: Great American Crooners

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

Stars, Stripes & Sandbars Getaways!

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

Liberty: Movie Night - You Pick!

 Tue, 17 Mar at 04:00 pm Regal Cinema

Sharese Nicole LIVE at Sunset Lounge Bar

 Fri, 20 Mar at 05:00 pm Sunset Lounge Sigsbee

Collette Campbell LIVE at Sunset Lounge

 Sat, 21 Mar at 05:00 pm Sunset Lounge Sigsbee

Mckenna Carlson LIVE at Sunset Lounge Bar

 Sat, 28 Mar at 05:00 pm Sunset Lounge Sigsbee

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

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 Cozumel Park hosted by the Key West Aquarium

 Fri, 27 Mar at 08:00 am Cozumel Park

Corey Hill LIVE at Sunset Lounge Bar

 Fri, 27 Mar at 05:00 pm Sunset Lounge Sigsbee

Movie Matinee: 'Wicked: For Good'

 Thu, 19 Mar at 10:00 am Sigsbee Community Center

Movie Matinee: 'Crazy Rich Asians'

 Thu, 26 Mar at 10:00 am Sigsbee Community Center

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

Movie Matinee: 'Nuremberg'

 Thu, 12 Mar at 10:00 am Sigsbee Community Center