Key West Parties Events

Deep Eddy Vodka 2026 Fantasy Fest Parade

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

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

Duval Street Party with the Landshark Band

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

LobsterFest Beats & Brunch 2026

First Flight Island Restaurant & Brewery 9 Aug 2026

Key West Powerboat Races 2026 - VIP Tent - FRIDAY

Sunset Pier 6 Nov 2026

Key West Powerboat Races 2026 - VIP Tent - SUNDAY

Sunset Pier 8 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

Will Kimbrough - Live in the Chart Room

Pier House Resort & Spa 7 Sep 2026

Party Like a Rockstar

319 Duval St, Key West, FL 24 Oct 2026

Second Line Memorial Walking Parade

100 Duval St, Key West, FL 33040-6506, United States 6 Sep 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

Back to the Island Beach Party

801 Bourbon bar 5 Sep 2026

Mangoes Drag Brunch Royale Christmas Show

Mangoes Restaurant 20 Dec 2026

Key West OktoBREWfest

1319 Duval Street, Key West, FL, United States, Florida 33040 3 Oct 2026

Just a Few Friends Celebration, Key West

Key West 3 Sep 2026

Parrots and Margaritas 5k Run/Walk

Kaya Island Eats 5 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

Come Monday: Cayman & the Mango Men

Sunset Pier, Key West, FL 33040, United States 7 Sep 2026

Tropical Heat's Five-Alarm Pool Party

1129 Fleming St, Key West, FL, United States, Florida 33040 15 Aug 2026

Keep it Going: Margaritaville Cafe After Party with Nadirah

Margaritaville Restaurant, Key West 3 Sep 2026

Garrison Keillor & Erica Rhodes

Key West Theater 27 Oct 2026

Sunset to Stage: Wheeland Brothers Dockside Party

S/V Argo Navis 5 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

Wind and Wine Music Sail with Caleb

255 Front St, Key West, FL 33040-8371, United States 5 Sep 2026

Keep It Going… Hog’s Breath Saloon After Party

Hog's Breath Saloon 4 Sep 2026

A Sailor's Sun Sunset Sail on Argo Navis

S/V Argo Navis 5 Sep 2026

Liberty: Commotion on the Ocean

Fury Water Adventures Key West 28 Aug 2026

Cowboy Ken’s PINK Pool Party AND Tropical Heat Kick-off

1129 Fleming St, Key West, FL, United States, Florida 33040 12 Aug 2026

Summer Bingo Night (Free Entry)

Key West Theater 17 Jun 2026

Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show

Casa Marina Key West, Curio Collection by Hilton 19 Sep 2026

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

Sebago Watersports 31 Oct 2026

Outdoor Movie: Parrot Heads – The Essential Jimmy Buffett Documentary

Southernmost Pint Brewpub 4 Sep 2026

Tales From The Chart Room Bar

Pier House Resort & Spa 7 Sep 2026

Keep It Going After Party at the EmPOURium with Claire Finley

618 Duval St, Key West, FL 33040-6555, United States 5 Sep 2026

Margaritaville Beach House Brunch

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 6 Sep 2026

Pool Party at The Marker Resort

The Marker Key West Resort 6 Sep 2026

Pencil Thin Mustache Contest

Pier House Resort & Spa 7 Sep 2026

Pool Party at La Concha

La Concha Key West 7 Sep 2026

New Moon Magic w/Mermaid Dorian

South Beach, Key West 11 Sep 2026

Tay-Tay Tuesday - Life of a Showgirl

0 Duval Street, Key West, FL, United States, Florida 33040 20 Oct 2026

Lobster Roll Contest & Pool Party

Southermost Hotel At The Beach 9 Aug 2026

Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys!

Key West Aquarium 14 Nov 2026

The Gold Party of Key West Tropical Heat!

1129 Fleming St, Key West, FL, United States, Florida 33040 16 Aug 2026

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

Hog's Breath Saloon 5 Sep 2026

ZaneCrawl • Key West • 11/13-11/15

Key West 13 Nov 2026

BBQ Rib Battle

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

Full Moon Ghost Show

1319 Duval Street, Key West, FL, United States, Florida 33040 26 Sep 2026

An Evening Aglow: A Candlelight Christmas with Marjory Lee

Key West Theater 15 Dec 2026

A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show

218 Whitehead St, Key West, FL 33040-6595, United States 2 Sep 2026

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

Shrimpboat Sound 4 Sep 2026

Pirate Looks Back Tribute Show: Ultimate Friends Edition

218 Whitehead St, Key West, FL 33040-6595, United States 4 Sep 2026

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

Key West Theater 1 Jan 2027

Latitude Adjustment Sunset Sail

S/V Argo Navis 7 Sep 2026

Meet the Author - Jimmy Buffett: A Little Golden Book Biography by Donna Rocco

Books & Books at The Studios 6 Sep 2026

Fantasy Fest Body Paint at Margaritaville!

Margaritaville Restaurant, Key West 18 Oct 2026

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

Sebago Watersports 30 Oct 2026

Chart Room Daily Hangout Headquarters

Pier House Resort & Spa 3 Sep 2026

Paddle Out Tribute

Smathers Beach 5 Sep 2026

Key West Murder Mystery 2: Crime on Date Night!

502 Whitehead St, Key West 1 Sep 2026

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

Key West, Florida 10 Aug 2026

Stories with Friends: Author Showcase & Book Signing

Books & Books at The Studios 5 Sep 2026

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

Louie's Backyard 5 Sep 2026

Business After Hours

Keys Dermatology 11 Aug 2026

Summer of Rum Festival

Key West Theater 14 Aug 2026

October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 17 Oct 2026

80s & 90s Trivia Night!

126 Simonton Street, Key West, FL, United States, Florida 33040 9 Aug 2026

Mrs. Roper Romp

Sunset Pier ~ Key West 19 Oct 2026

Will Kimbrough

Key West Theater 30 Oct 2026

Happy Hour with the Historian | Remember the Maine: Explosion, Mystery, and the Road to War

Comedy Key West 13 Aug 2026

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

Reef Relief 4 Sep 2026

Copy of Seattle Hidden Gems Experience

Mallory Square 28 Jul 2026

Fence fairy Paint & Sip!

526 Angela St 15 Aug 2026

Fantasy Fest 26th Annual Living Art Expo

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

September's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 19 Sep 2026

Songs on the Water: Best Friends VIP Harbor Sail ft. Cliff Cody

241 Front St, Key West, FL 33040-8371, United States 5 Sep 2026

Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL

Illusions the Drag Queen Show Key West 22 Apr 2022

Tarot & Tea | DONATION-BASED with Jolie

508 Southard Street #107, Key West, FL, United States, Florida 33040 15 Aug 2026

Liberty: Private Lobstering Charter

Sigsbee Marina 15 Aug 2026

Dinner with Entrepreneurs: Small Town, Small Business Edition | Key West

Restaurant of the Week 13 Dec 2025

Wicked Bingo

126 Simonton Street, Key West, FL, United States, Florida 33040 6 Aug 2026

GOOMBAY FEST IN KEYWEST (Miami Bus ride to Keywest)

Key West, Florida Keys 17 Oct 2026

Liberty: Movie Night

Regal (Key West, FL) 11 Aug 2026

Ultimate Friends Farewell Happy Hour

Chart Room 7 Sep 2026

Early Bird Clean Up Simonton & South Streets hosted by Southernmost Beach Resort, Tobacco Free FL

Southernmost Beach Resort 25 Sep 2026

Key West Body Painting Fantasy Fest Body Painter

Key West 17 Oct 2026

Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL

Illusions the Drag Queen Brunch Key West 20 Mar 2022