Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

The Greeen House Presents: Party In The Park with Just a Few Friends

 Sun, 31 Aug at 05:00 pm Truman Waterfront Park

Nautical Wheelers, a Tribute to Jimmy Buffett with Roger Bartlett

 Sat, 30 Aug at 06:30 pm Sunset Pier, Key West, FL 33040, United States

Mac McAnally in Key West

 Fri, 05 Dec at 08:00 pm Key West Theater

Outdoor Movie: Parrot Heads - The Essential Jimmy Buffet Documentary

 Sat, 30 Aug at 08:00 pm Southernmost Pint Brewpub

Cheese Burger Beach Battle and Tribute Concert by Landshark

 Fri, 29 Aug at 05:00 pm Southernmost Beach Resort

Buffett Through The Years

 Fri, 31 Oct at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Second Line Memorial Walking Parade

 Sun, 31 Aug at 05:00 pm 100 Duval St, Key West, FL 33040-6506, United States

Artisan Market @ the Party in the Park - Just a Few Friends

 Sun, 31 Aug at 05:30 pm Truman Waterfront Park

Mac McAnally in Key West

 Sat, 06 Dec at 08:00 pm Key West Theater

2025 Fantasy Fest Parade Viewing Party @ First Flight

 Sat, 25 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 to 212

Women’s Equality Day Celebration

 Wed, 27 Aug at 07:00 pm Tropic Cinema

Parrots & Margaritas 5K

 Sat, 30 Aug at 08:00 am 211 Duval St

A Sailor's Sun Sunset Cruise

 Fri, 29 Aug at 06:30 pm Sunset Watersports

Clay Walker @ Country Music Cruise in Key West

 Wed, 29 Oct at 07:00 pm Country Music Cruise

Bubba's Official After Party

 Sun, 31 Aug at 08:00 pm The Key West Empourium

Back to the Island Beach Party

 Sat, 30 Aug at 11:00 am 801 Duval St, Key West, FL 33040-7405, United States

Pajama And Lingerie Party

 Thu, 23 Oct at 10:30 pm Aqua Bar and Nightclub, Duval Street, Key West, FL, USA USD 30 to 115

Outdoor Movie: Tales From Margaritavision

 Fri, 29 Aug at 08:00 pm Southernmost Pint Brewpub

Peter Antoniou at Key West Theater

 Sat, 11 Oct at 08:00 pm Key West Theater

Tay Tay Tuesday - In Your Wildest Dreams

 Tue, 21 Oct at 06:00 pm Sunset Pier ~ Key West

Puddles Pity Party at Key West Theater

Sun, 28 Sep at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Salty Rim Social

 Fri, 29 Aug at 05:00 pm 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Just a Few Friends Pool Party @ the Marker

 Sun, 31 Aug at 01:00 pm The Marker Key West Resort

Peter Antoniou "Psychic" Comedian

 Sat, 11 Oct at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Happy Hour at the Chart Room

 Fri, 29 Aug at 05:00 pm Chart Room

Author/Photographer Book Signing: Ralph DePalma Soul of Key West

 Sat, 30 Aug at 11:00 am Books & Books at The Studios

Just a Few Friends Celebration, Key West

 Fri, 29 Aug at 08:00 am Key West

AZUR's End Of Summer Party!

 Sun, 31 Aug at 06:00 pm 425 Grinnell St, Key West, FL, United States, Florida 33040

Good Trees River Band at The Green Parrot

Fri, 12 Sep at 05:30 pm Green Parrot Key West

Fins Up! Pool Party!!

Sat, 30 Aug at 01:00 pm 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Joe's BIG Volunteer Meet & Greet

 Tue, 19 Aug at 05:00 pm Hard Rock Cafe Key West - 2nd Floor

New Moon Drum Circle

 Sat, 23 Aug at 07:00 pm 3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040

Peter Antoniou

 Fri, 10 Oct at 07:00 pm Key West Theater

Puddles Pity Party at Key West Theater

 Sun, 28 Sep at 08:00 pm Key West

That Arena Rock Show

 Sat, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

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

 Thu, 28 Aug at 07:00 pm Blue Heaven Key West

Vienna Boys Choir at Tennessee Williams Theatre

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

Rum & Sun Pool Party

 Sun, 17 Aug at 12:00 pm 3420 N. Roosevelt Blvd. , Key West, FL, United States, Florida 33040

The Brit Pack: The Ultimate British Music Experience

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

Captain Morgan's Masquerade March

 Fri, 24 Oct at 05:30 pm Fleming St, Key West, FL 33040, United States

Pencil Thin Mustache Contest

 Mon, 01 Sep at 02:00 pm Pier House Resort & Spa

Volunteer Meeting

 Mon, 25 Aug at 06:00 pm 319 Duval Street. Key West, FL 33040

Key West's Favorite Son City Proclamation

 Fri, 29 Aug at 11:00 am Shrimp Boat Sounds (Jimmy Buffetts Recording Studio)

Trivia Night at the Key West Cooking School

 Mon, 18 Aug at 06:00 pm 291 Front St Suite 207 - Upstairs, Key West, FL, United States, Florida 33040

Volunteer Party for Floyd PEPA Jenkins for Fantasy Fest King 2025

 Mon, 18 Aug at 05:00 pm 618 Duval St, Key West, FL 33040-6555, United States

Good Trees River Band @ The Greeen House 9/10

 Wed, 10 Sep at 06:00 pm 3128 N Roosevelt Blvd, Key West, FL 33040-4113, United States

Jimmy Buffett Second Line Parade - Walk with Reef Relief

 Sun, 31 Aug at 04:15 pm 631 Greene St, Key West, FL, United States, Florida 33040

Pineapple Pool Party & Belly Flop Contest

 Fri, 29 Aug at 01:00 pm Southernmost Beach Resort

Mike Stack and Friends on the BIG stage at the Sunset Pier

 Sat, 11 Oct at 05:30 pm Sunset Pier ~ Key West

Movie Trivia Night for Teens

 Sat, 13 Sep at 06:00 pm 600 Eaton St, Key West, FL, United States, Florida 33040

NightCaps and Nightgowns, a Moon Light Pajama Party

 Sat, 25 Oct at 06:00 pm 319 Duval St, Key West, FL, United States, Florida 33040

Full Moon Magic Ghost Stories

 Sun, 07 Sep at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

1st Annual USCGC Ingham Fundraising Gala

 Sat, 22 Nov at 05:00 pm Truman Waterfront Park - West end of Southhard Street, Key West, FL, United States, Florida 33040

Burger Night at Rams Head Southernmost!

 Sun, 17 Aug at 05:00 pm 804 Whitehead St, Key West, FL, United States, Florida 33040

September's Community Swim Night

 Sat, 20 Sep at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Hilariously Inappropriate Drag Queen Bingo - A Comedy Show With Balls

 Fri, 10 Oct at 06:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Good Trees River Band at General Horseplay

 Tue, 09 Sep at 09:00 pm General Horseplay

Peter Antoniou at Key West Theater

 Sat, 11 Oct at 08:00 pm Key West

Drag Brunch

 Sun, 07 Sep at 12:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

 Wed, 26 Nov at 08:00 pm Key West Theater

"Gypsies In The Palace" Buffett Tribute Band

 Fri, 29 Aug at 04:30 pm Hog's Breath Saloon

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

 Sat, 29 Nov at 08:00 pm Key West Theater

Pool Floatie Chug & Race

 Thu, 28 Aug at 01:00 pm Southernmost Beach Resort

The Phil Collins Experience - Tribute

 Sun, 25 Jan at 07:00 pm Key West Theater

Dave Matthews Tribute Band - BIG Stage / FREE Show

 Fri, 17 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

October's Community Swim

 Sat, 11 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Buffett Through The Years - Tribute to Jimmy Buffett

 Thu, 30 Oct at 07:00 pm Key West Theater

Thomas Dolby: "The Iconic 80s"

Fri, 07 Nov at 08:00 pm Key West Theater

Best of Key West Jazz Concert Series!

Wed, 27 Aug at 06:00 pm 803 Emma St, Key West, FL, United States, Florida 33040

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

🖤🎤Marjory Lee & The Misspellings: 90s Female Alt-Rock Concert🎤🖤

 Fri, 05 Sep at 05:00 pm Rams Head Southernmost

Scott Kirby- 35 Years of Songs & Stories

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

Scott Kirby- 35 Years of Songs & Stories

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

Shoreline Sessions Reggae Beach Festival

Sat, 01 Nov at 04:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

DJ Sanaris at Dante's Pool!

 Sun, 17 Aug at 12:00 pm Dante's Pool Bar & Restaurant

Early Bird Clean Up Vernon Street area hosted by The Casa Marina and the Reach

 Fri, 12 Sep at 08:00 am Casa Marina Resort

Mrs. Roper Romp

 Mon, 20 Oct at 05:00 pm Sunset Pier ~ Key West

25th Annual Living Art Expo

 Fri, 24 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Mac McAnally at Key West Theater

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

Custom House Holiday Concert & Bazaar

 Fri, 12 Dec at 05:00 pm Key West Art & Historical Society

Amazing Scavenger Hunt Adventure - Key West, FL

 Sat, 21 Jun Key West Historic Seaport, William Street, Key West, FL, USA USD 49

Pizza & Pints Pool Party at Lighthouse Hotel Friday, August 29th, 3-6pm

 Fri, 29 Aug at 03:00 pm 902 Whitehead St, Key West, FL 33040-7423, United States

Will Kimbrough Dockside Lounge

 Mon, 01 Sep at 06:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040

Phil Collins Experience at Key West Theater

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

Screaming Broccolli at Sloppy Joe's Key West!

Tue, 19 Aug at 10:00 pm 201 Duval St, Key West, FL 33040-6507, United States

On Our Way To Paddy's Day Weekend Celebration!

Thu, 09 Oct at 07:00 pm 528 Front Street, Key West, FL, United States, Florida 33040

Screaming Broccolli at Sloppy Joe's Key West!

Mon, 18 Aug at 10:00 pm 201 Duval St, Key West, FL 33040-6507, United States

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

 Tue, 21 Oct at 07:00 pm 423 Caroline street, Key West, FL, United States, Florida 33040

Performing for Key West Wedding

Sat, 29 Nov at 04:00 pm Key West Islands

Savannah Brady @ Wellen Park

 Thu, 23 Oct at 06:00 pm Wellen Park Florida

Tom Sandoval & The Most Extras

 Thu, 09 Oct at 08:00 pm Key West Theater

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

 Fri, 21 Nov at 09:00 pm The Alamo Key West

LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

 Wed, 22 Oct at 08:00 pm Rick's Bar USD 36 to 117

Key West Halloween Drag Brunch Royale

 Sun, 19 Oct at 12:00 pm Mangoes Restaurant USD 55 to 71

Sloppy Joe's 46th Annual Toga Party

 Thu, 23 Oct at 08:00 pm Sloppy Joe's

Kash'd Out at Key West Theater

 Fri, 16 Jan Key West Theater

Tap Takeover Pool Party at Winslow’s Bungalows Thursday, August 28th, 2-5pm

 Thu, 28 Aug at 02:00 pm 725 Truman Ave, Key West, FL 33040-6423, United States

Crystal Gayle

 Fri, 21 Nov at 07:00 pm Key West Theater

Anthony Rodia: Laugh Until it Hurts at Key West Theater

 Thu, 11 Dec at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

Los Lobos at Key West Theater

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