Key West Festivals Events

The Greeen House Presents: Party In The Park with Just a Few Friends

Truman Waterfront Park 31 Aug 2025

Second Line Memorial Walking Parade

100 Duval St, Key West, FL 33040-6506, United States 31 Aug 2025

Parrots & Margaritas 5K

211 Duval St 30 Aug 2025

2025 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 25 Oct 2025

Rum Fest Presents: Jesse Rice

512 Eaton St, Key West, FL, United States, Florida 33040 15 Aug 2025

VIP Tasting at the 2nd Annual Key West Rum Fest

Key West Theater 16 Aug 2025

Back to the Island Beach Party

801 Duval St, Key West, FL 33040-7405, United States 30 Aug 2025

Key West's Favorite Son City Proclamation

Shrimp Boat Sounds (Jimmy Buffetts Recording Studio) 29 Aug 2025

Key West Brewfest Grand Tasting!

Southernmost Beach Resort 30 Aug 2025

Jesse Rice - SOLD OUT

512 Eaton St, Key West, FL, United States, Florida 33040 15 Aug 2025

Just a Few Friends Celebration, Key West

Key West 29 Aug 2025

August's Community Swim Night!!

1319 Duval Street, Key West, FL, United States, Florida 33040 16 Aug 2025

Brews & Bites: A 4-Course Paired Experience

First Flight Island Restaurant & Brewery 29 Aug 2025

Worthy Park Master Class and Tasting

Tiki House 12 Aug 2025

Fins Up! Pool Party!!

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 30 Aug 2025

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

Hot Tin Roof Restaurant 9 Nov 2025

Meet Up at the Chart Room

Chart Room 28 Aug 2025

Artisan Market @ the Party in the Park - Just a Few Friends

Truman Waterfront Park 31 Aug 2025

Pool Floatie Chug & Race

1319 Duval St, Key West, FL 33040-3131, United States 28 Aug 2025

Pencil Thin Mustache Contest

Pier House Resort & Spa 1 Sep 2025

Steers & Queers Pool Party

1129 Fleming St, Key West, FL, United States, Florida 33040 16 Aug 2025

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

Sunset Pier ~ Key West 11 Oct 2025

Ultimate Friends Emerald Real Deal Reveal (INVITE ONLY)

Emeralds International LLC 31 Aug 2025

Key West Rum Fest Grand Tasting

512 Eaton St, Key West, FL 33040-6881, United States 16 Aug 2025

Captain Morgan's Masquerade March

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

Perla: One Night Only | A Taste of Perla at Rum Fest

430 Duval St, Key West, FL, United States, Florida 33040 12 Aug 2025

Rum Fest: Cliff Cody & Sharese

Key West Theater 13 Aug 2025

September's Community Swim Night

1319 Duval Street, Key West, FL, United States, Florida 33040 20 Sep 2025

Rum & Paradise at Four Flamingos, A Richard Blais Key West Kitchen 8/15 & 8/16 in Celebration of Rum

601 Front St, Key West, FL 33040 14 Aug 2025

October's Community Swim

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

25th Annual Living Art Expo

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

Shoreline Sessions Reggae Beach Festival

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

Phil Collins Experience at Key West Theater

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

ART + RUM | Key West Rum Fest Event!

720 Caroline Street, Key West, FL 14 Aug 2025

On Our Way To Paddy's Day Weekend Celebration!

528 Front Street, Key West, FL, United States, Florida 33040 9 Oct 2025

Official Rum Fest Event! Papa's Pilar Rum Cocktail Contest | Pool Party | Music by K Dub-Ya

200 William St, Key West, FL, United States, Florida 33040 15 Aug 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

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

Sloppy Joe's 46th Annual Toga Party

Sloppy Joe's 23 Oct 2025

Take Back The Night 2025

Bayview Park 1 Oct 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

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

Rick's Bar 22 Oct 2025

Fantasy Fest 5K Run/Walk

Duval Street 20 Oct 2025

Sloppy Joe's Slumber Party

Sloppy Joe's 22 Oct 2025

Farm Open House

Monroe County Sheriff's Office Animal Farm 26 Oct 2025

Famer's Market Mingle at the Truman Waterfront Farmers Market (sunset at 7:51 pm)

Truman Waterfront Park 28 Aug 2025

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

Sebago Key West 31 Oct 2025

Berkshire Hathaway Parade of Homes Mega Open House Event

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

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

Reef Relief 29 Aug 2025

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

Fantasy Fest 2025 Bedtime Stories & Magical Monsters

Key West, Florida 17 Oct 2025

2025 float and parade entry theme is Captain Tony's Slumber Party and Bedtime Stories

Truman Annex 25 Oct 2025

Early Bird Clean up Key West Firestation Lot on Simonton St hosted by Kenna Construction

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

Rum Fest - Cliff Cody and Sharese at Key West Theater

Key West Theater 14 Aug 2025

Midnight MAss Fantasy Fest

Island House Key West Gay Hotel & Resort 24 Oct 2025

Fantasy Fest

Key West, Florida 26 Oct 2025

AG at Fantasy Fest Sloppy Joes Key West in October!

Sloppy Joe's Bar 19 Oct 2025

AG at Sloppy Joes Key West Aug 27-Sept 2!

Sloppy Joe's Bar 27 Aug 2025

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

Sloppy Joes, Key West 8 Oct 2025