Key West Festivals Events

Deep Eddy Vodka 2026 Fantasy Fest Parade

Duval St, Key West, FL 33040, United States 24 Oct 2026

Key West Fantasy Fest 2026

Key West, Florida 16 Oct 2026

Captain Morgan's Masquerade March

1117 Fleming St, Key West, FL 33040-6909, United States 23 Oct 2026

Fantasy Fest Street Fair & Costume Promenade

Duval St, Key West, FL 33040, United States 23 Oct 2026

Bahama Village Goombay Festival - A Family Friendly Event

Petronia St, Key West, FL 33040, United States 16 Oct 2026

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

Rick's Bar 21 Oct 2026

2026 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 24 Oct 2026

Brews & Blues

Blue Flamingo Resort Key West 2 Oct 2026

Party Like a Rockstar

319 Duval St, Key West, FL 24 Oct 2026

Gold Pool Parties

1129 Fleming St, Key West, FL, United States, Florida 33040 20 Sep 2026

Golden Hour - Sunset Experience by Electroniconch

Galleon Marina 19 Oct 2026

Nine One Five's Fantasy Fest Parade Viewing Party

Nine One Five 24 Oct 2026

Lip Sync & Lifeguards - A Fantasy Fest Pool Party

Blue Flamingo Resort Key West 17 Oct 2026

VIP Parade Viewing Party At The New Smokin Tuna!

Smokin' Tuna Saloon 24 Oct 2026

Cocktails for Animal Tails - A Fantasy Fest Party!

Rick's Key West 20 Oct 2026

A Green Parrot Beatle Tribute

The Green Parrot 19 Oct 2026

33rd Annual Homemade Bikini Contest

Irish Kevin's 21 Oct 2026

Key West Powerboat Races 2026 - VIP Tent - FRIDAY

Sunset Pier 6 Nov 2026

Southernmost Slow Riders in the Fantasy Fest parade

Truman Annex 24 Oct 2026

Southernmost Scavenger Hunt's 7th Annual Fantasy Fest Bar Crawl

Conch Republic Seafood Company 22 Oct 2026

Pirate Night

Captain Tony's Saloon Key West 23 Oct 2026

Creative Hat Party

Captain Tony's Saloon "Oldest Bar In Florida" 16 Oct 2026

Sins & Sequins - An Official Fantasy Fest Event

Blue Flamingo Resort Key West 21 Oct 2026

Key West ocktoBREWfest Grand Tasting Event

1405 Duval Street 3 Oct 2026

Fantasy Fest Royal Campaign All Candidate Event at The Gardens Hotel!

Gardens Hotel 14 Oct 2026

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Half Shell Raw Bar 14 Nov 2026

Floatapalooza Fantasy Fest at The Reach

1435 Simonton St, Key West, FL 33040 22 Oct 2026

Key West Pet Masquerade 2026

Key West Ampitheatre 21 Oct 2026

Fantasy Fest Body Paint at Margaritaville!

Margaritaville Restaurant, Key West 18 Oct 2026

Dirty Doctors Naughty Nurses Party

Southernmost Pint Brewpub - Blast Beer Company Brewery 24 Oct 2026

Krewe de Krazy Life Meet and Greet and Costume Parts Exchange

Galleon Tiki Bar 18 Oct 2026

Fantasy Fest 26th Annual Living Art Expo

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

Rockin' it as Cowboys, Cowgirls, and Indians

Captain Tony's Saloon Key West 22 Oct 2026

Wine Festival

Wellen Park Florida 14 Nov 2026

Greatest Hits Pool Party at Winslow's Bungalows

725 Truman Ave, Key West, FL 33040-6423, United States 20 Oct 2026

Trivia Night

1319 Duval Street, Key West, FL, United States, Florida 33040 4 Nov 2026

Put-in-Bay Days in Key West 2027

Key West, Florida 10 Feb 2027

Photo Op Fest Letters All Day

631 Greene St, Key West, FL 33040-6624, United States 16 Oct 2026

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

Key West Theater 1 Jan 2027

2027 Cupid's Chase 5K Key West

Higgs Beach Pavilion, 1000 Atlantic Boulevard, Key West, FL US 33040 13 Feb 2027

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

Who's Bad: The World's #1 Michael Jackson Tribute

Key West Theater 11 Feb 2027

Wienerpalooza 2027!

U.S. Customs House Museum 10 Jan 2027

GOOMBAY FEST IN KEYWEST (Miami Bus ride to Keywest)

Key West, Florida Keys 17 Oct 2026