Key West Music Events

Duval Street Party with the Landshark Band

200 Duval St, Key West, FL 33040, United States 4 Sep 2026

Cheese Burger Beach Battle and Tribute Concert

Southernmost Beach Resort 3 Sep 2026

Will Kimbrough - Live in the Chart Room

Pier House Resort & Spa 7 Sep 2026

Second Line Memorial Walking Parade

100 Duval St, Key West, FL 33040-6506, United States 6 Sep 2026

Key West's Favorite Son City Proclamation

Shrimp Boat Sounds (Jimmy Buffetts Recording Studio) 4 Sep 2026

Back to the Island Beach Party

801 Bourbon bar 5 Sep 2026

Just a Few Friends Celebration, Key West

Key West 3 Sep 2026

The Wheeland Brothers + Mike Stack & Friends at Sunset Pier

Sunset Pier, Key West, FL 33040, United States 5 Sep 2026

Landsharks Band Jimmy Buffett Tribute in Key West

Duval St Key West Florida 4 Sep 2026

Bubba Look Alike Contest

200 Duval St, Key West, FL 33040, United States 4 Sep 2026

Come Monday: Cayman & the Mango Men

Sunset Pier, Key West, FL 33040, United States 7 Sep 2026

Best Friend VIP Show ft. Nadirah Shakoor

Margaritaville Restaurant, Key West 6 Sep 2026

Keep it Going: Margaritaville Cafe After Party with Nadirah

Margaritaville Restaurant, Key West 3 Sep 2026

Last Call - After Party at Smokin' Tuna

313 Duval St, Key West, FL 33040-6565, United States 7 Sep 2026

Wind and Wine Music Sail with Caleb

255 Front St, Key West, FL 33040-8371, United States 5 Sep 2026

Sunset to Stage: Wheeland Brothers Dockside Party

S/V Argo Navis 5 Sep 2026

Mac McAnally, Will Kimbrough, Howard Livingston & the Mile Marker 24 Band in Key West

201 Duval St 6 Sep 2026

Gov't Mule & Ziggy Marley

Coffee Butler Amphitheater 30 Sep 2026

Labor Day Pool Party at The Marker Key West Harbor Resort - September 6

The Marker Key West Harbor Resort 6 Sep 2026

Keep It Going… Hog’s Breath Saloon After Party

Hog's Breath Saloon 4 Sep 2026

Bubbles Brunch Sail with Will & Jessica

S/V Argo Navis 6 Sep 2026

Commotion on the Ocean Sunset Sail

Fury Water Adventures Key West 3 Sep 2026

Roger Bartlett Show with Emily Randle

The Key West Empourium 6 Sep 2026

A Sailor's Sun Sunset Sail on Argo Navis

S/V Argo Navis 5 Sep 2026

Making Waves: The Official Womenfest Pool Party

902 Whitehead St, Key West, FL 33040-7423, United States 5 Sep 2026

A Pirate Looks Back - Jimmy Buffett Tribute

Comedy Key West 5 Sep 2026

Captain Morgan's Masquerade March

1117 Fleming St, Key West, FL 33040-6909, United States 23 Oct 2026

Gov't Mule & Ziggy Marley

Key West, Florida 30 Sep 2026

Outdoor Movie: Parrot Heads – The Essential Jimmy Buffett Documentary

Southernmost Pint Brewpub 4 Sep 2026

Through the Lens – Early Buffett Concert Photography Exhibit Meet & Greet

Pier House Resort & Spa 4 Sep 2026

BBQ Rib Battle

Ann St, Key West, FL 33040, United States 6 Sep 2026

Fantasy Fest Street Fair & Costume Promenade

Duval St, Key West, FL 33040, United States 23 Oct 2026

A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show

218 Whitehead St, Key West, FL 33040-6595, United States 2 Sep 2026

Wheeland Brothers in Key West

Sunset Pier 5 Sep 2026

Lunch Like a Local

Hogfish Bar & Grill 5 Sep 2026

Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show

Casa Marina Key West, Curio Collection by Hilton 19 Sep 2026

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

Hog's Breath Saloon 5 Sep 2026

John Frinzi & Aaron Scherz

Key West Theater 2 Sep 2026

Womenfest Kick-Off Party!

803 Emma St, Key West, FL 33040-7344, United States 2 Sep 2026

John Frinzi & Aaron Scherz

Key West Theater 3 Sep 2026

Friends of Bubba After Party featuring Aaron Luka's "Songs We Know By Heart" Piano Sing-Along

803 Emma St, Key West, FL 33040-7344, United States 6 Sep 2026

Keep It Going After Party at the EmPOURium with Claire Finley

618 Duval St, Key West, FL 33040-6555, United States 5 Sep 2026

Island Tiki Sunset & Music Cruise

200 William St, Key West, FL 33040-6645, United States 7 Sep 2026

Pirate Looks Back Tribute Show: Ultimate Friends Edition

218 Whitehead St, Key West, FL 33040-6595, United States 4 Sep 2026

The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30

TBA 30 Oct 2026

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

400 Front St, Key West, FL, United States, Florida 33040 4 Sep 2026

The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31

TBA 31 Oct 2026

The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31

TBA 31 Oct 2026

Brews & Blues

Blue Flamingo Resort Key West 2 Oct 2026

2026 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 24 Oct 2026

Chart Room Daily Hangout Headquarters

Pier House Resort & Spa 3 Sep 2026

“Open Mic / No Mic Night” at Andy's Cabana

Andy's Cabana 3 Sep 2026

Lip Sync & Lifeguards - A Fantasy Fest Pool Party

Blue Flamingo Resort Key West 17 Oct 2026

Golden Hour - A Fantasy Fest Sunset Experience

Galleon Marina 19 Oct 2026

Stories with Friends: Author Showcase & Book Signing

Books & Books at The Studios 5 Sep 2026

Friends of Bubba Outdoor Video Lounge

Southernmost Pint Brewpub 5 Sep 2026

Sloppy Joe's Comic Book Caper-ers Party

Sloppy Joe's Key West 19 Oct 2026

Summer Bingo Night (Free Entry)

Key West Theater 16 Sep 2026

Margaritaville Beach House Trivia Contest

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 5 Sep 2026

That Arena Rock Show

0 Duval Street, Key West, FL, United States, Florida 33040 18 Oct 2026

Sins & Sequins - An Official Fantasy Fest Event

Blue Flamingo Resort Key West 21 Oct 2026

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

Key West 4 Sep 2026

Buffett Through the Years

Key West Theater 30 Oct 2026

Candlelight: Coldplay vs. Imagine Dragons

Key West Theater 13 Nov 2026

Bruce Cockburn at Key West Theater

Key West Theater 8 Nov 2026

Through the Lens – Early Buffett Concert Photography Exhibit

Pier House Resort & Spa 5 Sep 2026

Bruce Cockburn & Livingston Taylor

Key West Theater 7 Nov 2026

Irish Kevin's Annual 80's Party

211 Duval St, Key West, FL, United States, Florida 33040 22 Oct 2026

A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests

Key West Theatre 14 Nov 2026

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 11 Dec 2026

Candlelight: The Best of Hans Zimmer

Key West Theater 13 Nov 2026

Songs on the Water: Best Friends VIP Harbor Sail ft. Cliff Cody

241 Front St, Key West, FL 33040-8371, United States 5 Sep 2026

Candlelight: Tribute to Fleetwood Mac

Key West Theater 11 Dec 2026

Pop Up Jazz In The Gardens to support 'Get Out The Vote' Keys Dems campaign!

526 Angela St 13 Sep 2026

Candlelight: Vivaldi's Four Seasons

Key West Theater 11 Dec 2026

Krewe de Krazy Life Meet and Greet and Costume Parts Exchange

Galleon Tiki Bar 18 Oct 2026

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

Sebago Watersports 31 Oct 2026

September's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 19 Sep 2026

Parrot Head Reef Trop Rock

Key West 4 Sep 2026

Tay-Tay Tuesday - Life of a Showgirl

0 Duval Street, Key West, FL, United States, Florida 33040 20 Oct 2026

Classic Seger: Bob Seger's Greatest Hits Live (9PM)

Key West Theater 23 Jan 2027

Old Crow Medicine Show in Key West

Truman Waterfront Park Amphitheater 26 Jan 2027

Key West Theater

Key West Theater 30 Oct 2026

Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays

Key West Theater 10 Dec 2026

Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band

Key West Theater 31 Oct 2026

Wicked Bingo

126 Simonton Street, Key West, FL, United States, Florida 33040 6 Aug 2026

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

Sebago Watersports 30 Oct 2026

The Garcia Project

Key West Theater 15 Nov 2026

The Buena Vista Orchestra

Key West Theater 22 Nov 2026

October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 17 Oct 2026

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg, Reese Dailey & Special Guests

Key West Theatre 13 Feb 2027

The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

Key West Theater 12 Dec 2026

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theater 15 Dec 2026

Fantastic Body Art & Stunning Sunsets!!

Sunset Pier, Key West, FL 33040, United States 16 Oct 2026

Bahama Village Goombay Festival - A Family Friendly Event

Petronia St, Key West, FL 33040, United States 16 Oct 2026

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band

Key West Theater 1 Jan 2027

Killer Prom (11/8)

Key West Theater 8 Nov 2026

The Fright Crawl | Key West Halloween Weekend Pass 2026 | All 4 Crawls

TBA 29 Oct 2026

Sunny Jim, Florida Days

Key West Theater 30 Oct 2026

Keller Williams Trio at Key West Theater

Key West Theater 2 Jan 2027