Key West Arts Events

Arts events Happening Next in Key West, FL

Mac McAnally in Key West

Key West Theater 5 Dec 2025
CONCERTS

THE MANGO MURDERS Brunch Sail *SOLD OUT*

S/V Argo Navis 14 Nov 2025
BRUNCH

HEART LIFE MUSIC: An Evening in Conversation with Kenny Chesney

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

David Sedaris

Tennessee Williams Theatre 31 Oct 2025
ART

Keys Choral Arts: Holiday Concert

Tennessee Williams Theatre 13 Dec 2025
CONCERTS

Q West: Comedy Escape 2026

Key West Theater 10 Apr 2026
COMEDY USD 450 TO 534

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
ART

Shoreline Sessions Reggae Beach Festival

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

The Brit Pack: The Ultimate British Music Experience

Key West Theater 17 Jan 2026
MUSIC

Rum Infused | Mermaids Pirates in the Garden

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

Mac McAnally in Key West

Key West Theater 4 Dec 2025
SPORTS

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025
MUSIC

Truman Waterfront Farmers Market

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

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025
FESTIVALS

61th Annual Key West Art & Craft Festival

Truman Waterfront Park 21 Feb 2026
ART

Freedom Flotilla Festival

Key West 19 Dec 2025
FESTIVALS FREE

CFK Community Day 2025

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

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

Key West Theater 23 Jan 2026
TRIPS-ADVENTURES

Holiday Concert at Tennessee Williams Theatre

Tennessee Williams Theatre 14 Dec 2025
ART

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

Tennessee Williams Theatre 17 Nov 2025
ENTERTAINMENT

Italian Night at the Movies: Light in the Piazza

Tropic Cinema 3 Dec 2025
ENTERTAINMENT

Black Friday Shopping Extravaganza

Truman Waterfront Park 28 Nov 2025
BLACK-FRIDAY

Mac McAnally – Key West

Mac McAnally – Key West, FL – December 6, 2025 6 Dec 2025
LIVE-MUSIC

The second annual Key West BookFest!

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

Follow The Rabbit... (6PM)

Key West Theater 1 Nov 2025
PERFORMANCES

Mac McAnally at Key West Theater

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

The Wheeland Brothers

Key West Theater 7 Nov 2025
ART

Thomas Dolby at Key West Theater

Key West Theater 7 Nov 2025
ART

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 15 Nov 2025
ART

David Sedaris – Key West

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

Crystal Gayle at Key West Theater

Key West Theater 22 Nov 2025
TRIPS-ADVENTURES

Key West 10th Annual Casino Night by SOS Foundation

Beachside Resort & Residences Key West 14 Nov 2025
NONPROFIT USD 18 TO 135

Kash'd Out at Key West Theater

Key West Theater 16 Jan 2026
ART

The Doo Wop Project at Tennessee Williams Theatre

Tennessee Williams Theatre 11 Mar 2026
ART

Mac McAnally - Night 3 - SOLD OUT

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

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theatre 16 Dec 2025
CHRISTMAS

Follow The Rabbit... (6PM)

Key West Theater 13 Dec 2025
PERFORMANCES

Mac McAnally - Night 2 - SOLD OUT

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

Anthony Rodia at Key West Theater

Key West 11 Dec 2025
PERFORMANCES

Houston Ballet II at Tennessee Williams Theatre

Tennessee Williams Theatre 30 Mar 2026
ART

Dave Matthews Tribute Band

Key West Theater 24 Feb 2026
MUSIC

Great American Crooners at Tennessee Williams Theatre

Tennessee Williams Theatre 24 Mar 2026
ART

Key West Truman Waterfront Farmers Market @ Bayview Park

Bayview Park 6 Nov 2025
FARMERS-MARKETS

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 20 Dec 2025
ART

Indoor Trick-or-Treat at Queer Keys Community Center

1100 Truman Avenue, Key West, FL, United States, Florida 33040 29 Oct 2025
TRICK-OR-TREAT

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

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

Pilobolus - Other Worlds at Tennessee Williams Theatre

Tennessee Williams Theatre 13 Feb 2026
ART

Paradise Big Band at Tennessee Williams Theatre

Tennessee Williams Theatre 25 Jan 2026
ART

Puppy Pals Live at Tennessee Williams Theatre

Tennessee Williams Theatre 6 Apr 2026
ART

An Evening with David Sedaris at Tennessee Williams Theatre

Tennessee Williams Theatre 1 Nov 2025
ART

The Our Dave KW Pub Crawl

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

Italian Night at the Movies: The Bicycle Thief

Tropic Cinema 5 Nov 2025
ENTERTAINMENT

Thomas Dolby

Key West Theater 6 Nov 2025
ART

Spooky Paint by Number with Morgan!

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

Tommy Emmanuel at Key West Theater

Key West Theater 22 Mar 2026
TRIPS-ADVENTURES

Asleep At The Wheel at Key West Theater

Key West Theater 15 Jan 2026
ART

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 17 Jan 2026
ART

Dvořák | Sibelius | Schubert - Key West

Tennessee Williams Theatre 14 Mar 2026
MUSIC

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 18 Apr 2026
ART

Vienna Boys Choir at Tennessee Williams Theatre

Tennessee Williams Theatre 5 Feb 2026
ART

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 21 Mar 2026
ART

Nature is Art: Children’s Art Workshop

5210 College Rd, Key West, FL 21 Feb 2026
ART

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

400 South St 28 Jun 2025
ART USD 10 TO 20

Los Lobos at Key West Theater

Key West Theater 13 Jan 2026
ART

PATRICIA LOCKWOOD and JAMI ATTENBERG

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

Parking Wheeland Brothers

Key West Theater 9 Nov 2025
CONTESTS

Femmes of Rock at Key West Theater

Key West Theater 10 Dec 2025
ART

Wheeland Brothers

Key West Theater 9 Nov 2025
CONTESTS

Gabriel Rutledge at Key West Theater

Key West 15 Feb 2026
ENTERTAINMENT

The Linda Ronstadt Experience

Key West Theater 20 Feb 2026
ART

South Florida Symphony Orhcestra: Dvorak & Sibelius

Tennessee Williams Theatre 13 Mar 2026
ART

Parking Crystal Gayle

Key West Theater 23 Nov 2025
ART

The Massacoustics

Key West Theater 3 Feb 2026
ART

Phil Collins Experience at Key West Theater

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

A Date Night Adventure! - The Beauty of Key West

115 Front St 2 Nov 2024
TRIPS-ADVENTURES USD 20

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

1 Whitehead St 26 Sep 2025
ART USD 6 TO 22

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

Key West, Florida 4 Jan 2026
WORKSHOPS

Marty Stuart and His Fabulous Superlatives

Key West Theater 18 Feb 2026
ART

The Music of ABBA at Tennessee Williams Theatre

Tennessee Williams Theatre 21 Jan 2026
ART

The Man In Black: Tribute To Johnny Cash

Key West Theater 4 Mar 2026
ART

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026
CONTESTS

Clay Walker in Key West

Country Cruising 29 Oct 2025
LIVE-MUSIC

Elton Dan and the Rocket Band

Key West Theater 13 Nov 2025
MUSIC

Parking Femmes of Rock

Key West Theater 11 Dec 2025
ART

Kash'd Out

Key West Theater 17 Jan 2026
ART

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
ART

Mac McAnally

Key West Theater 3 Dec 2025
ART

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 29 Jan 2026
CONCERTS

The Expanding Man - Tribute To Steely Dan

Key West Theater 13 Jan 2026
ART

The Dave Matthews Tribute Band

Key West Theater 24 Feb 2026
MUSIC