Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Running of the Elves

 Sat, 20 Dec at 06:00 pm Key West

Key West Lighted Boat Parade 🎄

 Sat, 13 Dec at 07:30 pm 631 Greene 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

Scrooge Macbeth - Opening Night

 Tue, 09 Dec at 07:30 pm 319 Duval Street, Rear, 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West, Floirda

Scott Kirby- 35 Years of Songs & Stories

 Fri, 26 Dec at 07:00 pm Key West Theater

December' Community Swim

 Sat, 13 Dec at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Scott Kirby- 35 Years of Songs & Stories

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

Steven Rogers at Comedy Key West

 Sun, 07 Dec at 08:30 pm Comedy Key West

The Brit Pack: The Ultimate British Music Experience

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

Tim Palmieri & Friends at The Green Parrot

 Fri, 12 Dec at 05:30 pm The Green Parrot

Winter Party & Holiday Lights Trolley

 Fri, 12 Dec at 06:30 pm May Sands Montessori School

Anthony Rodia at Key West Theater

 Thu, 11 Dec at 08:00 pm Key West

An Evening Aglow: A Candlelight Christmas with Marjory Lee

 Tue, 16 Dec at 06:30 pm Key West Theatre

Q West: Comedy Escape 2026

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

The Reverend Peyton's Big Damn Band

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

Rumours ATL: A Fleetwood Mac Tribute

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

IAN MAKSIN in KEY WEST, FL: "Lullaby for the World" New Album Release Tour

 Sat, 03 Jan at 07:00 pm Williams Hall

Scott Kirby- 35 Years of Songs & Stories

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

Follow The Rabbit... (9PM)

 Sat, 13 Dec at 09:00 pm Key West Theater

Sonic Sanctuary Sound Healing Journey

Fri, 19 Dec at 07:00 pm 508 Southard Street #107, Key West, FL, United States, Florida 33040

Freedom Flotilla Festival

 Fri, 19 Dec at 05:00 pm Key West Free

December Duo Holiday Concert: Irie Monte and Crispin Campbell

 Sat, 13 Dec at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

Scott Kirby- 35 Years of Songs & Stories

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

Family Movie Night - A Polar Express Adventure

 Fri, 19 Dec at 06:00 pm Sigsbee Community Center

Put-in-Bay Days in Key West 2026

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

The Linda Ronstadt Experience

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

Given to Fly- A Tribute to Pearl Jam

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

Book Release Party: How Key West Killed JFK

 Wed, 10 Dec at 05:00 pm The Alex Vega Key West Firehouse Museum

Scott Kirby- 35 Years of Songs & Stories

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

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

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

Sharese Nicole LIVE at Sunset Lounge Bar & Grill

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

Duo Holiday Concert

 Fri, 12 Dec at 06:00 pm The Studios of Key West

Phil Collins Experience at Key West Theater

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

Snowy Days Children’s Holiday Concert

 Sun, 14 Dec at 12:00 pm 5210 College Rd, Key West, FL

Scott Kirby- 35 Years of Songs & Stories

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

New Year's Eve at Four Marlins

 Wed, 31 Dec at 05:30 pm 1435 Simonton St, Key West, FL 33040

Sibelius | Ravel | Vaughan Williams - Key West

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

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

 Sat, 17 Jan at 07:00 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 - Sibelius at Tennessee Williams Theatre

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

SAM KAUFMAN FUN! RAISER - Sam Kaufman for Mayor of Key West

 Sun, 21 Dec at 02:00 pm Salute! On The Beach

Keys Choral Arts: Holiday Concert

 Sat, 13 Dec at 07:00 pm Tennessee Williams Theatre

Robert Albury “Key West’s King of Soul” - A Night of Christmas Soul

 Thu, 11 Dec at 07:00 pm Williams Hall

Tropical Luncheon & Garden Party

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

Flowing Nectar: Yoga + Live Music Sound Bath with Gina & Gershone

 Thu, 11 Dec at 09:00 am 612 Fleming Street, Key West, FL, United States, Florida 33040

THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!

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

Changes In Latitude at Key West Theater

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

FRLA Monroe Cheers to the Holidays!

 Tue, 09 Dec at 05:00 pm Opal Key Resort & Marina USD 19 to 25

Christmas Dining at Four Marlins

 Wed, 24 Dec at 05:30 pm 1435 Simonton St, Key West, FL 33040

A Night of OASIS at DURTY HARRY’S

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

New Years Eve at The Bali Bar with Cliff Cody & guest Aloha Steve

 Wed, 31 Dec at 06:00 pm The Key West Hotel USD 55

DMTB: The Dave Matthews Tribute Band

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

Vienna Boys Choir at Tennessee Williams Theatre

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

New Years Eve, Eve Celebration with Mike Stack & Friends!

 Tue, 30 Dec at 06:00 pm Blue Flamingo Resort Key West USD 0 to 145

Los Lobos at Key West Theater

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

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

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

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

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

Graham Nash- Live on Tour 2026

 Sun, 26 Apr at 08:00 pm Key West Theater

Key West New Year's Eve Sunset Cruise 🥂

 Wed, 31 Dec at 04:00 pm 631 Greene St, Key West, FL, United States, Florida 33040

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

 Wed, 07 Jan at 05:30 pm Tropic Cinema

Movie Matinee: 'The Santa Clause 2'

Thu, 18 Dec at 10:00 am Sigsbee Community Center

FRLA Monroe Chapter: Cheers to the Holidays - Food Drive and Holiday Party

 Tue, 09 Dec at 05:00 pm Opal Key West, 245 Front Street Key West, FL

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

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

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

 Fri, 30 Jan at 07:00 pm Truman Waterfront Amphitheater

Holiday Concert at Tennessee Williams Theatre

 Sun, 14 Dec at 04:00 pm Tennessee Williams Theatre

Scott Kirby- 35 Years of Songs & Stories

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

Mile 0 Fest Key West: Randy Rogers Band Kaitlin Butts & Tanner Usrey - Thursday

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

Asleep At The Wheel at Key West Theater

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

Speaker Series: Karen Dukess

 Mon, 09 Feb at 06:00 pm 700 Fleming St, Key West, FL, United States, Florida 33040

Monday Rock Night - Gerd Rube

 Mon, 22 Dec at 08:00 pm Bull and Whistle

The Band Of Heathens in Key West

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

Italian Movie Night at Tropic Cinema: 3 Coins in a Fountain on February 4th

 Wed, 04 Feb at 05:30 pm Tropic Cinema

Foreigner, Lou Gramm in Key West

 Thu, 23 Apr at 08:00 pm Coffee Butler Amphitheater

Jazz At Lincoln Center: Great American Crooners

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

Mike Ryan in Key West

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

Key West M**der Mystery: Catch the Killer!

 Sat, 28 Jun at 10:00 am 400 South St USD 10 to 20

Mike Ryan in Key West

 Wed, 28 Jan at 05:00 pm Truman Waterfront Park

South Florida Symphony Orchestra: Vaughan Williams - Sibelius' Symphony No. 2 & Ravel's Piano Concerto

 Fri, 23 Jan at 07:00 pm Tennessee Williams Theatre

Silverada in Key West

 Tue, 27 Jan at 06:00 pm Truman Waterfront Park Amphitheater

The Massacoustics at Key West Theater

 Wed, 04 Feb at 08:00 pm Key West Theater

Margaritaville at Sea Cruise Ship Special

 Mon, 15 Dec at 04:00 pm Key West Rebecca

Southernmost Republican Club Holiday Party and Elections

 Mon, 15 Dec at 05:30 pm Key West Yacht Club

Dave Matthews Tribute Band

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

Kaitlin Butts in Key West

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

The Expanding Man - Tribute To Steely Dan

 Tue, 13 Jan at 07:00 pm Key West Theater

The Dave Matthews Tribute Band

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

The Coral Reefer Band

 Sat, 17 Jan at 01:00 am Coffee Butler Amphitheater

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

Anthony Rodia at Key West Theater

 Thu, 11 Dec at 08:00 pm Key West Theater

The Massacoustics

 Thu, 05 Feb at 08:00 pm 512 Eaton St, Key West, FL, United States, Florida 33040

The Reverend Peyton's Big Damn Band

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

American Aquarium in Key West

 Wed, 28 Jan at 03:00 pm Truman Waterfront Park Amphitheater

Tanner Usrey in Key West

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

Randy Rogers Band in Key West

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

Anthony Rodia

 Wed, 10 Dec at 07:00 pm Key West Theater

Changes in Latitudes - Jimmy Buffet Tribute

 Mon, 02 Mar at 07:00 pm Key West Theater

Sugar Ray in Key West

 Wed, 28 Jan at 11:00 am Key west cruise port