Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

New Year's Eve at Four Marlins

 Wed, 31 Dec at 05:00 pm 1435 Simonton St, Key West, FL 33040

11th Annual Onesie Pub Crawl

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

Scott Kirby- 35 Years of Songs & Stories

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

THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!

 Wed, 07 Jan at 07:30 pm 319 Duval Street, Rear, 33040

Scott Kirby- 35 Years of Songs & Stories

Fri, 02 Jan at 07:00 pm Key West Theater

Scott Kirby- 35 Years of Songs & Stories

Sat, 03 Jan at 07:00 pm Key West Theater

The Brit Pack: The Ultimate British Music Experience

Sat, 17 Jan at 08:00 pm Key West Theater

IAN MAKSIN in KEY WEST, FL: Songs of Love & Peace

 Sat, 03 Jan at 07:00 pm Williams Hall

🍀 You're Invited! Lucky 13 Anniversary Party & Fundraiser

 Sat, 24 Jan at 05:00 pm 1024 Grinnell St, Key West, FL, United States, Florida 33040

Fighting For Laughs, Too

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

Justin Angelo at Sunset Tiki

 Sun, 04 Jan at 06:00 pm Sunset Tiki

Scott Kirby- 35 Years of Songs & Stories

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

Terri white,Larry Baeder & friends

Thu, 01 Jan at 06:00 pm 803 Emma St, Key West, FL

Scott Kirby- 35 Years of Songs & Stories

Thu, 15 Jan at 07:00 pm Key West Theater

Q West: Comedy Escape 2026

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

Given to Fly- A Tribute to Pearl Jam

Sat, 10 Jan at 08:00 pm Key West Theater

Put-in-Bay Days in Key West 2026

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

Matt Gardi LIVE at Navigator's Bar

 Sat, 10 Jan at 04:00 pm Sunset Lounge Sigsbee

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

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

The Linda Ronstadt Experience

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

Ian Maksin: New Album Release Tour

 Sat, 03 Jan at 07:00 pm 729 Fleming Street, Key West, FL, United States, Florida 33040

Colin Quinn

 Fri, 27 Feb at 08:00 pm Key West Theater

Matt Gardi LIVE at Navigator's Bar

 Sat, 24 Jan at 04:00 pm Sunset Lounge Sigsbee

Key West Buying Event

 Fri, 23 Jan at 10:00 am Doubletree By Hilton Grand Key - Key West

Dvořák | Sibelius | Schubert - Key West

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

Gabriel Rutledge at Key West Theater

 Sun, 15 Feb at 08:00 pm Key West

FRLA Monroe Cheers to 2026!

 Thu, 15 Jan at 05:00 pm Casa Marina Key West, A Waldorf Astoria Resort USD 18 to 23

DMTB: The Dave Matthews Tribute Band

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

A Night of OASIS at DURTY HARRY’S

 Tue, 27 Jan at 09:00 pm Durty Harry's

Scott Kirby- 35 Years of Songs & Stories

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

Havana Nights Salsa Dancing Lessons!

Tue, 06 Jan at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

🎤🎵Larry Smith's Monday Night Jazz Jams 🎶🎤🎼🌴

 Mon, 05 Jan at 06:00 pm 803 Emma St, Key West, FL

7 Bridges : The Ultimate EAGLES Experience - Key West, FL

 Fri, 27 Mar at 08:00 pm Key West Theater

South Florida Symphony Orchestra - Sibelius at Tennessee Williams Theatre

 Sat, 24 Jan at 07:30 pm Tennessee Williams Theatre

Key West, FL – Key West Theater

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

The Reverend Peyton's Big Damn Band

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

Mckenna Carlson LIVE at Sunset Lounge Bar & Grill

 Sat, 03 Jan at 05:00 pm Sunset Lounge Sigsbee

Rumours ATL: A Fleetwood Mac Tribute

 Wed, 21 Jan at 08:00 pm Key West Theater

Peter Mayer & Friends- Album Release: Songs & Stories from the 12 Volt Man (7PM)

 Sat, 17 Jan at 07:00 pm Key West Theater

REZA LIVE ON TOUR | KEY WEST, FL

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

Reza Edge of Illusion

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

OC3ANDS BAND! January 2 & 3

Fri, 02 Jan at 09:30 pm The Alamo Key West

Graham Nash- Live on Tour 2026

 Sun, 26 Apr at 08:00 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

Big Bad Voodoo Daddy (Matinee)

Sun, 22 Feb at 01:00 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

MONDAY NIGHT FOOTBALL SUNSET RUN

 Mon, 05 Jan at 06:15 pm Fit2Run, The Runner's Superstore- Key West (Key West)

Punk Rock Thursdays 🤘

 Thu, 01 Jan at 07:00 pm 423 Caroline street, 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

Flamy Grant in Concert

 Tue, 06 Jan at 07:00 pm 533 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

The Shanty Hounds LIVE at Sunset Lounge Bar & Grill

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

Darcy Cooke Celebrates Great Women of Song: Timeless Voices, Unforgettable Music

 Fri, 23 Jan at 08:00 pm Williams Hall

Corey Hill LIVE at Sunset Lounge Bar & Grill

 Fri, 23 Jan at 05:00 pm Sunset Lounge Sigsbee

Changes In Latitude at Key West Theater

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

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

 Sat, 21 Feb at 07:30 pm Tennessee Williams Theatre

The Expanding Man: An Original Tribute To Steely Dan & Beyond

 Wed, 14 Jan at 08:00 pm Key West Theater

BIG GAME Tailgate & Watch Party

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

Alice Howe & Freebo - Key West Theater

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

SNEEZY - at Sunset Pier Key West - Free Show

 Mon, 05 Jan at 05:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Tropical Luncheon & Garden Party

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

Italian Movie Night at Tropic Cinema: Buona Sera, Mrs. Campbell

 Wed, 07 Jan at 05:30 pm Tropic Cinema

Phil Collins Experience at Key West Theater

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

🎸 The Marshall Morlock Band: Wednesdays at General Horseplay

 Wed, 07 Jan at 08:00 pm 423 Caroline street, Key West, FL, United States, Florida 33040

🎶 Pre-Concert Tailgate Party w/ Scott Kirby & Friends 🎶

 Fri, 16 Jan at 02:00 pm 804 Whitehead St, Key West, FL, United States, Florida 33040

Mike Ryan in Key West

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

Boys & Bubbly Pool Party

 Thu, 01 Jan at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

Jimmy Buffet’s The Coral Reefer Band at Coffee Butler Amphitheater

 Fri, 16 Jan at 08:00 pm Coffee Butler Amphitheater

Bumpin Uglies w/ Joey Harkum

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

Paradise Big Band at Tennessee Williams Theatre

 Sun, 25 Jan 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

King Master

Wed, 28 Jan at 06:00 pm Sloppy Joe’s Bar, Key West

Asleep At The Wheel at Key West Theater

 Thu, 15 Jan at 08:00 pm Key West Theater

Scott Kirby- 35 Years of Songs & Stories

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

Paradise Big Band

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

BoDeans: 40 Years of Love & Hope & Sex & Dreams... and Good Things

 Sun, 29 Mar at 08:00 pm Key West Theater

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

 Sat, 07 Mar at 04:00 pm Tropic Cinema

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

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

Big Bad Voodoo Daddy in Key West

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

Max von Essen: Spotlight Cabaret Curated by Randy Roberts

 Mon, 02 Mar at 07:00 pm 533 Eaton St, 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

Speaker Series: Bob Rich

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

Mile 0 Festival at Southernmost Beach Resort

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

Vienna Boys Choir at Tennessee Williams Theatre

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

Los Lobos at Key West Theater

 Tue, 13 Jan at 08:00 pm Key West Theater

Billy Stritch and Gabrielle Stravelli: Spotlight Cabaret Curated by Randy Roberts

 Mon, 16 Feb at 07:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

Island Groove Pub Crawl - Chris is 60 and still rockin!

 Sat, 10 Jan at 03:00 pm 22&Co Key West

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

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

Tommy Emmanuel

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

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

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

Speaker Series: Christopher Castellani

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

Mile 0 Fest Key West - Tuesday

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

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

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

Bumpin' Uglies

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

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

 Fri, 30 Jan Truman Waterfront Amphitheater

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

The Band Of Heathens in Key West

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

New Year's Week in Key West with Screaming Broccolli

 Wed, 31 Dec at 10:00 pm Sloppy Joe's Bar

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

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