Key West Festivals Events

28th Annual Key West Lobsterfest

100-500 Blocks Duval Street, Key West, FL, United States, Florida 33040 5 Aug 2026

Key West Fantasy Fest 2026

Key West, Florida 16 Oct 2026

Key West Powerboat Races 2026 - VIP Tent - FRIDAY

Sunset Pier 6 Nov 2026

Cheese Burger Beach Battle and Tribute Concert

Southernmost Beach Resort 3 Sep 2026

Lobsterfest Duval Crawl - Pub Crawl

Duval St Key West Florida 7 Aug 2026

Lobsterfest Kick-Off Party at Rick's

Rick's Key West 5 Aug 2026

Lobster Boil at Historic Port Mansion

Porter Mansion Key West 6 Aug 2026

Just a Few Friends Celebration, Key West

Key West 3 Sep 2026

Bubba Look Alike Contest

200 Duval St, Key West, FL 33040, United States 4 Sep 2026

Rum Fest Key West Grand Tasting

513 Eaton St, Key West, FL 33040-6801, United States 15 Aug 2026

Key West Artisan Market at the Party in the Park

Truman Waterfront Park 6 Sep 2026

Last Call - After Party at Smokin' Tuna

313 Duval St, Key West, FL 33040-6565, United States 7 Sep 2026

Summertime Stories: Original song session with Meghan Barter

Key West Theater 18 Jul 2026

Gold Pool Parties

1129 Fleming St, Key West, FL, United States, Florida 33040 17 May 2026

Experience Hemingway Days from the Water | SeaEO Luxury Boat Charters

Key West, Florida 21 Jul 2026

Lobsterfest Trivia Night

1319 Duval Street, Key West, FL, United States, Florida 33040 5 Aug 2026

FLIGHT OF THE FLAMINGOS

601 Front St, Key West, FL, United States, Florida 33040 6 Aug 2026

Early Welcome: Island Adventure Sand Bar

Fury Water Adventures Key West 2 Sep 2026

Through the Lens – Early Buffett Concert Photography Exhibit Meet & Greet

Pier House Resort & Spa 4 Sep 2026

Prix-fixe Dinner in celebration of Key West Rum Fest 2026

601 Front St, Key West, FL, United States, Florida 33040 14 Aug 2026

Rum Fest: Cliff Cody & Sharese

Key West Theater 14 Aug 2026

Lobster Roll Contest & Pool Party

Southermost Hotel At The Beach 9 Aug 2026

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band

Key West Theater 1 Jan 2027

John Frinzi & Aaron Scherz

Key West Theater 2 Sep 2026

VIP Tasting at the 3rd Annual Key West Rum Fest

Key West Theater 15 Aug 2026

Pre-event Official Meetup at the Chart Room

Pier House Resort & Spa 2 Sep 2026

BBQ Rib Battle

Ann St, Key West, FL 33040, United States 6 Sep 2026

Key West ocktoBREWfest Grand Tasting Event

1405 Duval Street 3 Oct 2026

Chart Room Daily Hangout Headquarters

Pier House Resort & Spa 3 Sep 2026

Experience Key West Rum Fest from the Water | SeaEO Luxury Boat Charters

Key West, Florida 10 Aug 2026

"Painting Paradise: A Guided Plein Air Experience Session Two: Louis Back Yard"

Louie's Backyard 5 Sep 2026

Lobster Fest Dinner @ Key West Cooking Show

Key West Cooking Show 7 Aug 2026

"Shrimp Boat Sound: Echoes From the Edge" Movie Panel Discussion

729 Fleming St, Key West, FL 33040-6827, United States 4 Sep 2026

Summer of Rum Festival

Key West Theater 14 Aug 2026

"Painting Paradise: A Guided Plein Air Experience Session One: Shrimp Boat Sound"

Shrimpboat Sound 4 Sep 2026

Parrot Head Reef Trop Rock

Key West 4 Sep 2026

Key West Body Painting Fantasy Fest Body Painter

Key West 17 Oct 2026