Key West Festivals Events

2025 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 25 Oct 2025

31st Annual Taste of Key West

Truman Waterfront, Key West, FL, United States, Florida 33040 23 Mar 2026

Captain Morgan's Masquerade March

Fleming St, Key West, FL 33040, United States 24 Oct 2025

Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY

Hot Tin Roof Restaurant 9 Nov 2025

25th Annual Living Art Expo

0 Duval Street, Key West, FL, United States, Florida 33040 24 Oct 2025

Meghan Barter: Human Jukebox Release Concert + Listening Party

Key West Theater 10 Oct 2025

Bangers and Mash at the Celtic Conch

Celtic Conch Public House 25 Oct 2025

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

The Alamo Key West 5 Dec 2025

Key West Pet Masquerade 2025

Key West Ampitheatre 22 Oct 2025

Cocktails for Animal Tails

Rick's Bar 21 Oct 2025

Mike Stack and Friends on the BIG stage at the Sunset Pier

Sunset Pier ~ Key West 11 Oct 2025

Classy Chic Country Western Dinner

Williams Hall 6 Oct 2025

The Fabulous Spectrelles

Kaya Island Eats 3 Oct 2025

The Greeen House Costume Swap & Sale with Hoebee Live Remote

3128 N Roosevelt Blvd, Key West, FL 33040-4113, United States 11 Oct 2025

Fantasy Fest Celebration

1000 Duval Street, Key West, FL, United States, Florida FL 33040 25 Oct 2025

Shoreline Sessions Reggae Beach Festival

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

Wheeland Brothers

Key West Theater 8 Nov 2025

October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 11 Oct 2025

61th Annual Key West Art & Craft Festival

Truman Waterfront Park 21 Feb 2026

Oktoberfest Key West

522 FRONT ST, Key West, FL, United States, Florida 33040 10 Oct 2025

Sloppy Joe's 46th Annual Toga Party

Sloppy Joe's 23 Oct 2025

The Fabulous Spectrelles

Kaya Island Eats 10 Oct 2025

Funk It Up Party

922 Caroline Street, Key West, FL, United States, Florida 33040 23 Oct 2025

Fantasy Fest 5K Run/Walk

Duval Street 20 Oct 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

423 Caroline street, Key West, FL, United States, Florida 33040 21 Oct 2025

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

Hangover Pool Party at Havana Cabana

3420 N. Roosevelt Blvd. , Key West, FL, United States, Florida 33040 26 Oct 2025

LET'S GET LOONEY! FANTASY FEST AFTER PARADE PARTY!

420 Appelrouth Lane, Key West, FL, United States, Florida 33040 25 Oct 2025

Kash'd Out at Key West Theater

Key West Theater 16 Jan 2026

Aqua Idol ~ Royal Edition "Floyd PEPA Jenkins for Fantasy Fest KING 2025

AquaPlex Key West 7 Oct 2025

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey

Key West Theatre 14 Feb 2026

Adult Costume Swap & Sale- Last Chance before Fantasy Fest!

3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040 11 Oct 2025

Freedom Flotilla Festival

Key West 19 Dec 2025

Monarch Fine Art Grand Opening Celebration

910 Duval Street, Key West, FL, United States, Florida 33040 24 Oct 2025

LUV2GLOW - VIVID DREAMS - FANTASY FEST 2025 @Rick's Key West

Rick's Bar 22 Oct 2025

Key West Fantasy Fest 2025

Sunset Pier 25 Oct 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Cupid's Chase 5K Key West

Clarence S.Higgs Memorial Beach 14 Feb 2026

Sloppy Joe's Slumber Party

Sloppy Joe's 22 Oct 2025

Post-Fest Plunge Ice Bath Social

Kava Culture Key West 26 Oct 2025

Phil Collins Experience at Key West Theater

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

Bahama Village Goombay Festival

Petronia St, Key West, FL 33040, United States 17 Oct 2025

Changes In Latitude at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 3 Mar 2026

Harvest Festival

Sigsbee Community Center 9 Oct 2025

Golf Cart Facade Viewing Tour Fantasy Fest

3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040 29 Oct 2025

CHANNEL 3 AND REGGAE LOU & THE KIND BUDZ REHAB POOL PARTY

200 William St, Key West, FL, United States, Florida 33040 26 Oct 2025

Creative Hat Party

Captain Tony's Saloon "Oldest Bar In Florida" 17 Oct 2025

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews

Key West Theater 24 Nov 2025

LES GREEENE & THE SWAYZEES PAJAMA POOL PARTY TAKE 2 AT THE MARKER!

200 William St, Key West, FL, United States, Florida 33040 23 Oct 2025

Fantasy Fest 2025 Annual Competitive Bar Crawl Sponsored by Dulce Vida Tequila!

631 Greene St, Key West, FL 33040-6624, United States 23 Oct 2025

Bare As You Dare Farewell Party

Captain Tony's Saloon Key West 26 Oct 2025

Midnight MAss Fantasy Fest

Island House Key West Gay Hotel & Resort 24 Oct 2025

Key West 250th Celebration and Time Capsule Opening 2072

Mallory Square Key West 25 Mar 2026

Fantasy Fest Duck, Duck, Booze Pool Party at Havana Cabana

3420 N. Roosevelt Blvd. , Key West, FL, United States, Florida 33040 20 Oct 2025

2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!

Sebago Key West 31 Oct 2025

Krewe de Krazy Life Meet and Greet

Galleon Tiki Bar 19 Oct 2025

Berkshire Hathaway Parade of Homes Mega Open House Event

922 Caroline Street, Key West, FL, United States, Florida 33040 23 Oct 2025

Crooks Second Line Parade

111 Olivia St (temporary during construction), Key West, FL 15 Feb 2026

THE BEATLE BAND EXTRAORDINAIRE! FANTASY FEST - 2025 GREEN PARROT

Green Parrot Bar Key West 20 Oct 2025

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY

La Concha Key West 21 Oct 2025

Fantasy Fest 2025 Bedtime Stories & Magical Monsters

Key West, Florida 17 Oct 2025

2025 Fantasy Fest Parade

Truman Annex 25 Oct 2025

Put-in-Bay Days in Key West 2026

Key West, Florida 11 Feb 2026

Early Bird Clean up KW Firestation Lot on Simonton St hosted by Kenna Construction & ShineGroup, eXp

Simonton Street City Parking Lot 24 Oct 2025

Southernmost Turkey Trot 5K

The Southernmost Point Buoy 27 Nov 2025

Key West Power Boat Races

Fury Water Adventures Key West 5 Nov 2025

Fantasy Fest

Key West, Florida 26 Oct 2025

AG at Fantasy Fest Sloppy Joes Key West!

Sloppy Joe's Bar 19 Oct 2025

Party in Plaid

Captain Tony's Saloon Key West 21 Oct 2025

RockHouse LIVE at Sloppy Joe's, Key West, FL!

Sloppy Joes, Key West 8 Oct 2025