Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Mac McAnally in Key West

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

Buffett Through The Years

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

2025 Fantasy Fest Parade Viewing Party @ First Flight

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

Mac McAnally in Key West

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

Clay Walker @ Country Music Cruise in Key West

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

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

September's Community Swim Night

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

Tay Tay Tuesday - In Your Wildest Dreams

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

Peter Antoniou "Psychic" Comedian

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

Peter Antoniou at Key West Theater

 Sat, 11 Oct at 08:00 pm Key West

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

Shoreline Sessions Reggae Beach Festival

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

That Arena Rock Show

 Sat, 18 Oct at 07:00 pm 0 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

Captain Morgan's Masquerade March

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

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

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

Macy Gray-On How Life Is 25th Anniversary Tour

 Fri, 24 Oct at 09:00 pm Key West Theater

Movie Trivia Night for Teens

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

Peter Antoniou at Key West Theater

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

Puddles Pity Party at Key West Theater

Sun, 28 Sep at 08:00 pm 512 Eaton 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

RICK KING'S BAND - Funky Soul Weekend

Fri, 19 Sep at 08:00 pm The Alamo Key West

The Brit Pack: The Ultimate British Music Experience

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

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

Sharese Nicole LIVE at Sunset Lounge Bar and Grill

 Fri, 12 Sep at 05:00 pm Sunset Lounge Sigsbee

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

Drag Brunch

 Sun, 07 Sep at 12:00 pm 291 Front St suite 207, 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

Scott Kirby- 35 Years of Songs & Stories

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

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

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

Buffett Through The Years - Tribute to Jimmy Buffett

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

10th Annual Spayghetti & No Balls Dinner

 Wed, 17 Sep at 06:00 pm La Trattoria Oceanside

ACOUSTIC SOUL IN KEY WEST!

 Fri, 03 Oct at 07:00 pm Schooner Wharf Bar

22&Co Bingo Sundays w/Qmitch - Floyd for King

 Sun, 14 Sep at 05:00 pm 22&Co

Tom Sandoval & The Most Extras

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

KWBW25: Bottoms Up Pool Party

 Sat, 01 Nov at 02:00 pm Island House Key West Gay Hotel & Resort

Jerry Kramer LIVE at Sunset Lounge Bar and Grill

 Fri, 19 Sep at 05:00 pm Sunset Lounge Sigsbee

October's Community Swim

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

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

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

25th Annual Living Art Expo

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

JWADI - Jordan David Miller

 Tue, 09 Sep at 06:30 pm 0 Duval Street, Key West, FL, United States, Florida 33040

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

Custom House Holiday Concert & Bazaar

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

The 72-Hour Film Challenge at Williams Hall

 Tue, 09 Sep at 06:00 pm 729 Fleming St, Key West, FL 33040-6827, 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

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

Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show

 Sat, 20 Sep at 10:00 am Casa Marina Key West, Curio Collection by Hilton USD 34

Mac McAnally at Key West Theater

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

November's Community Swim

 Sat, 15 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Key West Pet Masquerade 2025

Wed, 22 Oct at 05:00 pm Key West Ampitheatre

Oktoberfest

 Fri, 26 Sep at 04:00 pm Sunset Lounge Sigsbee

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, 26 Feb at 07:00 pm Key West Theater

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

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

The Garcia Project: Performing classic Jerry Garcia Band Set Lists from 1976-1995

 Sat, 15 Nov at 08:00 pm 512 Eaton St, 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

Key West Halloween Drag Brunch Royale

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

Anthony Rodia at Key West Theater

 Thu, 11 Dec at 08:00 pm Key West

Southernmost Half Marathon & 10K

 Sun, 12 Oct at 06:00 am Higgs Beach Key West, Florida

Performing for Key West Wedding

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

Mrs. Roper Romp

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

Good Trees River Band at General Horseplay

 Tue, 09 Sep at 09:00 pm General Horseplay

DJ Sanaris at Dante's Pool!

 Fri, 26 Sep at 12:00 pm Dante's Pool Bar & Restaurant

Phil Collins Experience at Key West Theater

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

22&Co Bingo Sundays w/Qmitch - All Candidate

 Sun, 12 Oct at 05:00 pm 22&Co

Changes In Latitude at Key West Theater

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

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

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

Sloppy Joe's 46th Annual Toga Party

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

Tom Sandoval and The Most Extras

 Wed, 08 Oct at 07:00 pm Key West Theater

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

 Fri, 05 Dec at 03:00 pm The Alamo Key West

Crystal Gayle

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

Cocktails for Animal Tails

 Tue, 21 Oct at 08:00 pm Rick's Bar

Sloppy Joe's Slumber Party

 Wed, 22 Oct at 11:00 am Sloppy Joe's

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

Italian Night at the Movies: The Bicycle Thief

 Wed, 05 Nov at 05:30 pm Tropic Cinema

Movie Matinee: Wreck-It-Ralph

 Thu, 25 Sep at 10:00 am Sigsbee Community Center

Sloppy Joe's Comic Book Cape-ers Party

 Mon, 20 Oct at 09:00 pm Sloppy Joe's Bar

Kash'd Out at Key West Theater

 Fri, 16 Jan at 08:00 pm Key West Theater

Captain Tony's Party In Plaid

 Tue, 21 Oct at 09:00 pm 922 Caroline Street, Key West, FL, United States, Florida 33040

Will Kimbrough

 Thu, 30 Oct 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

Thomas Dolby

 Thu, 06 Nov at 07:00 pm Key West Theater

Scott Kirby- 35 Years of Songs & Stories

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

The Phil Collins Experience - Tribute

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

Los Lobos at Key West Theater

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

Savannah Brady @ Wellen Park

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

Paradise Big Band at Tennessee Williams Theatre

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

DMTB: The Dave Matthews Tribute Band

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

Rumours ATL: A Fleetwood Mac Tribute

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

Great Gatsby NYE 2026

 Wed, 31 Dec at 08:00 pm First Flight Island Restaurant & Brewery USD 269

Femmes of Rock

 Wed, 10 Dec at 08:00 pm Key West Theater

Creative Hat Party

 Fri, 17 Oct at 08:00 pm Captain Tony's Saloon "Oldest Bar In Florida"

Femmes of Rock in Key West, FL!

 Wed, 10 Dec at 08:00 pm Key West Theater

Savannah Brady @ Wellen Park

 Thu, 06 Nov at 06:00 pm Wellen Park Florida

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

 Mon, 17 Nov at 07:30 pm Tennessee Williams Theatre

The Our Dave KW Pub Crawl

 Thu, 30 Oct at 12:30 pm 525 Duval St, Key West, FL 33040-6552, United States

Vienna Boys Choir at Tennessee Williams Theatre

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

A Date Night Adventure! - The Beauty of Key West

 Sat, 02 Nov at 08:00 am 115 Front St USD 20