Entertainment events in Key West

Check out happening entertainment events all around Key West, FL

Key West Songwriters Festival Platinum Pass -2026

 Wed, 29 Apr at 10:00 am Key West Theater

Graham Nash- Live on Tour 2026

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

28th Annual Key West Lobsterfest

 Wed, 05 Aug at 06:00 pm 100-500 Blocks Duval Street, Key West, FL, United States, Florida 33040

George Thorogood & The Destroyers, The Marshall Tucker Band in Key West

 Sat, 09 May at 07:30 pm

FLO-RAW at Sloppy Joes Key West

 Sat, 04 Jul at 10:00 pm Sloppy Joe's Bar

42nd Annual SCHOONER WHARF PIRATE BALL & COSTUME COMPETITION

 Sat, 25 Apr at 07:00 pm Schooner Wharf Bar

KWSF: Thursday- Songwriters In The Round- 8PM

 Thu, 30 Apr at 08:00 pm Key West Theater

Mangoes Drag Brunch Royale Pride Week

 Sun, 07 Jun at 11:30 am Mangoes Restaurant USD 55 to 66

🎟️ LAST VVIP ACCESS: Graham Nash – Key West 2026! | Apr 26, 2026

 Sun, 26 Apr at 08:00 pm Key West, Florida Keys

Paint the Town Proud Trolley Pub Roll

 Sat, 06 Jun at 11:00 am Bobby's Monkey Bar

Just a Few Friends Celebration, Key West

 Thu, 03 Sep at 11:00 am Key West

OCEAN FEST – A COMMUNITY CELEBRATION

 Sat, 25 Apr at 10:00 am Truman Waterfront Park

Key West Pride Follies

 Sat, 30 May at 07:30 pm Key West Theater

🎟️ FINAL VVIP CALL: Graham Nash – Key West Night 1! | Apr 25, 2026

 Sat, 25 Apr at 08:00 pm Key West, Florida Keys

Live Music on South Beach Stage

Sun, 03 May at 12:00 pm 1405 Duval St, Key West, FL 33040-3133, United States

KWSF: Saturday- Songwriters In The Round- 8PM

 Sat, 02 May at 08:00 pm Key West Theater

John Caparulo in Key West, FL!

 Thu, 28 May at 08:30 pm Comedy Key West

Follow The Rabbit... (9PM)

Fri, 29 May at 09:00 pm Key West Theater

Pineapple Pool Party for the Key West Songwriters Festival

 Fri, 01 May at 12:00 pm 1319 Duval St, Key West, FL 33040-3131, United States

KEY WEST ARTISAN MARKET – CONCH REPUBLIC EDITION

 Sun, 26 Apr at 10:00 am Higgs Beach, Key West

Miss Island Queen Drag Brunch Hosted by Justin Harris

 Sun, 26 Apr at 11:00 am First Flight Island Restaurant & Brewery USD 61

Tri Knot to Rock

 Fri, 15 May at 08:00 pm Key West Theater

Mango Madness Summer Members' Exhibit Opening

 Thu, 04 Jun at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040

Damon Fowler - The Green Parrot, Key West, FL

 Fri, 15 May at 05:30 pm The Green Parrot

WOOF Week 2026!

 Tue, 21 Apr at 12:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040

International Ocean Film Festival (Florida Keys Viewing)

 Sat, 06 Jun at 05:30 pm Williams Hall

Sister Season's Aqua Idol

 Tue, 28 Apr at 06:00 pm AquaPlex Key West

"SUNSHINE" Sandbar and Sunset

 Mon, 27 Apr at 02:00 pm 701 Palm Ave, Key West, FL 33040-7031, United States

JAZZ IN THE GARDENS

 Sun, 26 Apr at 05:00 pm The Gardens Hotel Key West Florida

ALB @ Sloppy Joes Key West

Wed, 13 May at 10:00 pm Sloppy Joe's Bar

Conch Country Dance Party

 Sun, 26 Apr at 05:00 pm 319 Duval St, Key West, FL

42nd Annual SCHOONER WHARF “WRECKERS CUP RACE” 2026 SEASON AWARDS PARTY

 Sun, 26 Apr at 07:00 pm Schooner Wharf Bar

Celtic Conch - Key West Songwriter Festival

 Fri, 01 May at 01:00 pm Celtic Conch Public House

April's Community Swim

 Sat, 25 Apr at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Wheeland Brothers in Key West

 Sat, 05 Sep at 07:00 pm Sunset Pier

Talk Derby To Me!

 Sat, 02 May at 05:30 pm 526 Angela St

NEIL YOUNG TRIBUTE - RAGGED GLORY BAND

 Fri, 24 Apr at 08:30 pm The Alamo Key West

May's Community Swim

 Sat, 09 May at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040

Florida Keys Mini Season Getaways!

 Sat, 25 Jul at 10:00 am The Perry Hotel & Marina Key West Free

HiNote at General Horseplay hosts the Bathtub Gin Trio, Vintage Jam Swing

 Sat, 25 Apr at 07:00 pm HiNote Bar

Where’s Dave Band

 Sun, 26 Apr at 07:00 pm Back Stage Listening Room at Key West Theater

Independent Bookstore Day

 Sat, 25 Apr at 10:00 am 533 Eaton St, Key West, FL, United States, Florida 33040

Landsharks Band, Key West Concert, JUST A FEW FRIENDS CONCERT WEEKEND!

 Fri, 04 Sep at 05:00 pm Key West

30th Annual Key West Songwriters Festival at The Marker Key West

 Thu, 30 Apr at 05:30 pm The Marker Key West Harbor Resort

Cypress Gardens Water Ski Show

Sat, 16 May at 02:00 pm Cypress Gardens Water Ski Team (est. 2012)

Kids Music Tour Key West Florida

 Mon, 15 Jun at 10:00 am Key West Public Library

Live in Key West, FL

 Mon, 27 Apr at 07:00 pm Key West Theater

Stars, Stripes & Sandbars Getaways!

 Fri, 03 Jul at 12:00 am Galleon Marina Free

Early Bird Clean Up Garrison Bight hosted by Key West Community Sailing Center

 Fri, 15 May at 08:00 am Key West Community Sailing Center

The Devil Wears Prada 2

 Thu, 30 Apr at 07:30 pm Regal (Key West, FL)