Key West Arts Events

Mac McAnally in Key West

Key West Theater 5 Dec 2025

THE MANGO MURDERS Brunch Sail *SOLD OUT*

S/V Argo Navis 14 Nov 2025

HEART LIFE MUSIC: An Evening in Conversation with Kenny Chesney

5901 College Rd, Key West, FL, United States, Florida 33040 10 Nov 2025

David Sedaris

Tennessee Williams Theatre 31 Oct 2025

Keys Choral Arts: Holiday Concert

Tennessee Williams Theatre 13 Dec 2025

Q West: Comedy Escape 2026

Key West Theater 10 Apr 2026

A work-in-progress preview screening of "The Life & Art of Eric Anfinson"

533 Eaton St, Key West, FL, United States, Florida 33040 16 Nov 2025

A Celebration of the Songs of Pete & Wayne with Pete Jarvis and Friends

Key West Theatre 21 Nov 2025

Shoreline Sessions Reggae Beach Festival

1319 Duval Street, Key West, FL, United States, Florida 33040 1 Nov 2025

The Brit Pack: The Ultimate British Music Experience

Key West Theater 17 Jan 2026

Rum Infused | Mermaids Pirates in the Garden

5210 College Rd, Key West, FL, United States, Florida 33040 22 Nov 2025

CHARITY BINGO NIGHT for the Key West Art & Historical Society

The Green Parrot 27 Oct 2025

Mac McAnally in Key West

Key West Theater 4 Dec 2025

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

Truman Waterfront Farmers Market

21 E Quay Rd, Key West, FL, United States, Florida 33040 30 Oct 2025

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

61th Annual Key West Art & Craft Festival

Truman Waterfront Park 21 Feb 2026

Freedom Flotilla Festival

Key West 19 Dec 2025

CFK Community Day 2025

5901 College Rd, Key West, FL 33040-4315, United States 1 Nov 2025

The Young Dubliners: The HOT TODDY tour at Key West Theater

Key West Theater 23 Jan 2026

Holiday Concert at Tennessee Williams Theatre

Tennessee Williams Theatre 14 Dec 2025

South Florida Symphony Orchestra - Sibelius at Tennessee Williams Theatre

Tennessee Williams Theatre 24 Jan 2026

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

Tennessee Williams Theatre 17 Nov 2025

Italian Night at the Movies: Light in the Piazza

Tropic Cinema 3 Dec 2025

Black Friday Shopping Extravaganza

Truman Waterfront Park 28 Nov 2025

Mac McAnally – Key West

Mac McAnally – Key West, FL – December 6, 2025 6 Dec 2025

The second annual Key West BookFest!

700 Fleming Street, Key West, FL, United States, Florida 33040 15 Nov 2025

Follow The Rabbit... (6PM)

Key West Theater 1 Nov 2025

Mac McAnally at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 4 Dec 2025

The Wheeland Brothers

Key West Theater 7 Nov 2025

Thomas Dolby at Key West Theater

Key West Theater 7 Nov 2025

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 15 Nov 2025

David Sedaris – Key West

David Sedaris – Key West, FL – Nov 1, 2025 1 Nov 2025

Key West Theater Welcomes The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

Key West Theater 29 Nov 2025

Crystal Gayle at Key West Theater

Key West Theater 22 Nov 2025

Key West 10th Annual Casino Night by SOS Foundation

Beachside Resort & Residences Key West 14 Nov 2025

Kash'd Out at Key West Theater

Key West Theater 16 Jan 2026

The Doo Wop Project at Tennessee Williams Theatre

Tennessee Williams Theatre 11 Mar 2026

Mac McAnally - Night 3 - SOLD OUT

512 Eaton St, Key West, FL, United States, Florida 33040 6 Dec 2025

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theatre 16 Dec 2025

Marty Stuart and His Fabulous Superlatives at Key West Theater

Key West Theater 19 Feb 2026

Follow The Rabbit... (6PM)

Key West Theater 13 Dec 2025

Mac McAnally - Night 2 - SOLD OUT

512 Eaton St, Key West, FL, United States, Florida 33040 5 Dec 2025

Anthony Rodia at Key West Theater

Key West 11 Dec 2025

Houston Ballet II at Tennessee Williams Theatre

Tennessee Williams Theatre 30 Mar 2026

Dave Matthews Tribute Band

Key West Theater 24 Feb 2026

Great American Crooners at Tennessee Williams Theatre

Tennessee Williams Theatre 24 Mar 2026

Key West Truman Waterfront Farmers Market @ Bayview Park

Bayview Park 6 Nov 2025

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 20 Dec 2025

Indoor Trick-or-Treat at Queer Keys Community Center

1100 Truman Avenue, Key West, FL, United States, Florida 33040 29 Oct 2025

The Yoga of Ceramics: Art of Nature with Nature Imprint Dishes

612 Fleming Street, Key West, FL, United States, Florida 33040 1 Nov 2025

Pilobolus - Other Worlds at Tennessee Williams Theatre

Tennessee Williams Theatre 13 Feb 2026

Paradise Big Band at Tennessee Williams Theatre

Tennessee Williams Theatre 25 Jan 2026

Puppy Pals Live at Tennessee Williams Theatre

Tennessee Williams Theatre 6 Apr 2026

An Evening with David Sedaris at Tennessee Williams Theatre

Tennessee Williams Theatre 1 Nov 2025

The Our Dave KW Pub Crawl

525 Duval St, Key West, FL 33040-6552, United States 30 Oct 2025

Italian Night at the Movies: The Bicycle Thief

Tropic Cinema 5 Nov 2025

Thomas Dolby

Key West Theater 6 Nov 2025

Spooky Paint by Number with Morgan!

504 Angela St, Key West, FL, United States, Florida 33040 29 Oct 2025

Tommy Emmanuel at Key West Theater

Key West Theater 22 Mar 2026

Asleep At The Wheel at Key West Theater

Key West Theater 15 Jan 2026

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 17 Jan 2026

Dvořák | Sibelius | Schubert - Key West

Tennessee Williams Theatre 14 Mar 2026

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 18 Apr 2026

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews

Key West Theater 25 Nov 2025

Vienna Boys Choir at Tennessee Williams Theatre

Tennessee Williams Theatre 5 Feb 2026

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 21 Mar 2026

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 21 Feb 2026

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

400 South St 28 Jun 2025

Los Lobos at Key West Theater

Key West Theater 13 Jan 2026

PATRICIA LOCKWOOD and JAMI ATTENBERG

533 Eaton St, Key West, FL, United States, Florida 33040 26 Nov 2025

Parking Wheeland Brothers

Key West Theater 9 Nov 2025

Femmes of Rock at Key West Theater

Key West Theater 10 Dec 2025

Wheeland Brothers

Key West Theater 9 Nov 2025

Gabriel Rutledge at Key West Theater

Key West 15 Feb 2026

The Linda Ronstadt Experience

Key West Theater 20 Feb 2026

South Florida Symphony Orhcestra: Dvorak & Sibelius

Tennessee Williams Theatre 13 Mar 2026

Parking Crystal Gayle

Key West Theater 23 Nov 2025

The Massacoustics

Key West Theater 3 Feb 2026

Phil Collins Experience at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 26 Jan 2026

Heart Life Music - A Conversation with Kenny Chesney at Tennessee Williams Theatre

Tennessee Williams Theatre 10 Nov 2025

A Date Night Adventure! - The Beauty of Key West

115 Front St 2 Nov 2024

Key West Heist Game: Recover the Pirate's Gold Booty!

1 Whitehead St 26 Sep 2025

Lisa Zeidner teaches: "Who Says?: Mastering Point of View"

Key West, Florida 4 Jan 2026

Marty Stuart and His Fabulous Superlatives

Key West Theater 18 Feb 2026

The Music of ABBA at Tennessee Williams Theatre

Tennessee Williams Theatre 21 Jan 2026

South Florida Symphony Orhcestra: Rimsky-Korsakov’s Capriccio Mozart & Simon and Joachim

Tennessee Williams Theatre 20 Feb 2026

The Man In Black: Tribute To Johnny Cash

Key West Theater 4 Mar 2026

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

Clay Walker in Key West

Country Cruising 29 Oct 2025

Elton Dan and the Rocket Band

Key West Theater 13 Nov 2025

Parking Femmes of Rock

Key West Theater 11 Dec 2025

Kash'd Out

Key West Theater 17 Jan 2026

BeachFront Radio and Trop Rock'N Duval presents The Margarita Brothers @ Key West Theater

Key West Theater, 512 Eaton St. Key West, FL 33040 30 Oct 2025

Cheryl Lu-Lien Tan teaches: "Telling Your Story" - for memoir writers

Key West, Florida 4 Jan 2026

Mac McAnally

Key West Theater 3 Dec 2025

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 29 Jan 2026

The Expanding Man - Tribute To Steely Dan

Key West Theater 13 Jan 2026

The Dave Matthews Tribute Band

Key West Theater 24 Feb 2026

Page Turner Adventures - The Magnificent Circus Mystery at Tennessee Williams Theatre

Tennessee Williams Theatre 28 Oct 2025