Key West Festivals Events

28th Annual Key West Lobsterfest

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

Captain Morgan's Masquerade March

1117 Fleming St, Key West, FL 33040-6909, United States 23 Oct 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

Nine One Five's Fantasy Fest Parade Viewing Party

Nine One Five 24 Oct 2026

Dusty Slay:The Neighborhood Guy Tour

Key West Theater 21 Nov 2026

Golden Hour - A Fantasy Fest Sunset Experience

Galleon Marina 19 Oct 2026

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

Rick's Bar 21 Oct 2026

Just a Few Friends Celebration, Key West

Key West 3 Sep 2026

Southernmost Slow Riders in the Fantasy Fest parade

Truman Annex 24 Oct 2026

Bubba Look Alike Contest

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

Rum Fest Key West Grand Tasting

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

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

Pier House Resort & Spa 4 Sep 2026

John Frinzi & Aaron Scherz

Key West Theater 2 Sep 2026

Early Welcome: Island Adventure Sand Bar

Fury Water Adventures Key West 2 Sep 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

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

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

Pre-event Official Meetup at the Chart Room

Pier House Resort & Spa 2 Sep 2026

VIP Tasting at the 3rd Annual Key West Rum Fest

Key West Theater 15 Aug 2026

BBQ Rib Battle

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

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

Shrimpboat Sound 4 Sep 2026

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

Key West Theater 1 Jan 2027

Fantasy Fest Body Paint at Margaritaville!

Margaritaville Restaurant, Key West 18 Oct 2026

Chart Room Daily Hangout Headquarters

Pier House Resort & Spa 3 Sep 2026

Key West ocktoBREWfest Grand Tasting Event

1405 Duval Street 3 Oct 2026

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

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

Summer of Rum Festival

Key West Theater 14 Aug 2026

Just a Few Friends: Early Bird Clean Up at the Historic Waterfront

Reef Relief 4 Sep 2026

Fantasy Fest 26th Annual Living Art Expo

0 Duval Street, Key West, FL, United States, Florida 33040 23 Oct 2026

Parrot Head Reef Trop Rock

Key West 4 Sep 2026

GOOMBAY FEST IN KEYWEST (Miami Bus ride to Keywest)

Key West, Florida Keys 17 Oct 2026

Early Bird Clean Up Lower Duval Street co-hosted by Oldest House Museum & Gardens & The Saint Hotel

Oldest House & Gardens Key West 6 Nov 2026

Key West Body Painting Fantasy Fest Body Painter

Key West 17 Oct 2026