Deep Eddy Vodka 2026 Fantasy Fest Parade Sat, 24 Oct at 07:00 pm Duval St, Key West, FL 33040, United States PARADES
Captain Morgan's Masquerade March Fri, 23 Oct at 05:30 pm 1117 Fleming St, Key West, FL 33040-6909, United States PARTIES
Key West OktoBREWfest Sat, 03 Oct at 03:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040
Fantasy Fest Street Fair & Costume Promenade Fri, 23 Oct at 12:00 pm Duval St, Key West, FL 33040, United States FESTIVALS
Bahama Village Goombay Festival - A Family Friendly Event Fri, 16 Oct at 12:00 pm Petronia St, Key West, FL 33040, United States FESTIVALS
LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West Wed, 21 Oct at 08:00 pm Rick's Bar USD 36 TO 117 FESTIVALS
Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL Fri, 21 Aug Illusions the Drag Queen Show Key West USD 13 TO 914 ENTERTAINMENT
Nine One Five's Fantasy Fest Parade Viewing Party Sat, 24 Oct at 06:00 pm Nine One Five USD 59 FITNESS
2026 Fantasy Fest Parade Viewing Party @ First Flight Sat, 24 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 TO 562 PARADES
Key of Bones: Curse of the Ghost Pirate – Key West Red Carpet Premiere Fri, 02 Oct at 06:30 pm Tennessee Williams Theatre ENTERTAINMENT
The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 07:30 pm TBA USD 8 TO 82 PARTIES
Gold Pool Parties Sun, 20 Sep 1129 Fleming St, Key West, FL, United States, Florida 33040 POOL-PARTIES
Golden Hour - Sunset Experience by Electroniconch Mon, 19 Oct at 04:00 pm Galleon Marina USD 71 TO 117 FESTIVALS
Lip Sync & Lifeguards - A Fantasy Fest Pool Party Sat, 17 Oct at 12:00 pm Blue Flamingo Resort Key West FREE FESTIVALS
The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 01:00 pm TBA USD 8 TO 71 FITNESS
The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29 Thu, 29 Oct at 07:30 pm TBA USD 8 TO 71 FITNESS
That Arena Rock Show Sun, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 SPORTS
Dante's Annual Halos & Horns Pool Party Thu, 22 Oct at 12:00 pm Dante's Pool Bar & Restaurant PARTIES
Halloween Eve Bar Crawl 10/30 - KEY WEST Fri, 30 Oct at 05:00 pm La Concha Key West, Autograph Collection USD 16 TO 19 PARTIES
Halloween Bar Crawl 10/31 - KEY WEST Sat, 31 Oct at 04:00 pm La Concha Key West, Autograph Collection USD 16 TO 19 FITNESS
Sins & Sequins - An Official Fantasy Fest Event Wed, 21 Oct at 07:00 pm Blue Flamingo Resort Key West USD 31 FITNESS
Tutu Tuesday Pre-Party Bar Crawl Tue, 20 Oct at 04:30 pm 420 Applerouth Ln, Key West, FL 33040-6535, United States PARTIES
Mangoes Drag Brunch Royale Halloween Edition Sun, 01 Nov at 11:30 am Mangoes Restaurant USD 55 TO 66 FITNESS
Full Moon Party At Simonton Beach Reggae Vibes Sat, 26 Sep at 07:00 pm Lagerheads Beach Bar & Watersports USD 30 FITNESS
Key West Murder Mystery 2: Crime on Date Night! Thu, 01 Oct at 12:00 am 502 Whitehead St, Key West USD 15 TRIPS-ADVENTURES
A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests Sat, 14 Nov at 08:00 pm Key West Theatre COMEDY
KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER Sat, 14 Nov at 05:00 pm Half Shell Raw Bar USD 109 TO 215 FITNESS
Irish Kevin's Annual 80's Party Thu, 22 Oct at 10:00 pm 211 Duval St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Candlelight: Coldplay vs. Imagine Dragons Fri, 13 Nov at 06:00 pm Key West Theater USD 42 TO 91 ENTERTAINMENT
FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY Fri, 23 Oct at 06:00 pm Viva Argentinian Steakhouse USD 11 TO 111 FITNESS
Tay-Tay Tuesday - Life of a Showgirl Tue, 20 Oct at 06:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Les Greene & The Swayzees Musical Icons Pool Party Take 2 At The Marker Resort Thu, 22 Oct at 02:00 pm The Marker Key West Resort PARTIES
Krewe de Krazy Life Meet and Greet and Costume Parts Exchange Sun, 18 Oct at 12:00 pm Galleon Tiki Bar MEET-AND-GREET
SOMO Short "Cut" DEAD ZONE Block & Watch Party Sun, 18 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 PARTIES
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
Candlelight: The Best of Hans Zimmer Fri, 13 Nov at 08:30 pm Key West Theater USD 40 TO 76 ENTERTAINMENT
Swayzees Music Icons Pool Party at Shores Pool Wed, 21 Oct at 02:00 pm Southernmost Beach Resort PARTIES
Custom House Holiday Concert & Bazaar Fri, 11 Dec at 05:00 pm Key West Art & Historical Society MUSIC
2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise" Fri, 30 Oct at 05:00 pm Sebago Watersports MUSIC
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band Sat, 31 Oct at 01:00 pm Key West Theater MUSIC
Copy of Seattle Hidden Gems Experience Tue, 28 Jul at 10:00 am Mallory Square USD 23 TRIPS-ADVENTURES
October's Community Swim Sat, 17 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
Candlelight: Tribute to Fleetwood Mac Fri, 11 Dec at 08:30 pm Key West Theater USD 40 TO 76 ENTERTAINMENT
Candlelight: Vivaldi's Four Seasons Fri, 11 Dec at 06:00 pm Key West Theater USD 40 TO 80 ENTERTAINMENT
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays Thu, 10 Dec at 08:00 pm Key West Theater ART
Greatest Hits Pool Party at Winslow's Bungalows Tue, 20 Oct at 12:00 pm 725 Truman Ave, Key West, FL 33040-6423, United States PARTIES
Welcome To The Jungle Party Tue, 20 Oct at 08:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 30 TO 58 FITNESS
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers Sat, 12 Dec at 08:00 pm Key West Theater MUSIC
An Evening Aglow: A Candlelight Christmas with Marjory Lee Tue, 15 Dec at 08:00 pm Key West Theater MUSIC
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band Fri, 01 Jan at 08:00 pm Key West Theater MUSIC
Fetish Party at Captain Tony's Rubber Ball & Dungeon Mon, 19 Oct at 08:00 pm Captain Tony's Saloon Key West PARTIES
32nd Annual Hog's Breath Saloon Hog Trot 5K Sat, 28 Nov at 08:00 am 400 Front St, Key West, FL, United States, Florida 33040 SPORTS
Early Bird Clean Up United Street and Varela hosted by Children's Montessori School Fri, 19 Mar at 08:00 am The Children's School ENTERTAINMENT
Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL Sat, 22 Aug Illusions the Drag Queen Brunch Key West USD 13 TO 914 FITNESS
Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows Fri, 21 Aug Diva Royale - Drag Queen Show USD 31 TO 1,264 FITNESS
November's Community Swim Sat, 14 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
Who's Bad: The World's #1 Michael Jackson Tribute Thu, 11 Feb at 08:00 pm Key West Theater ENTERTAINMENT
December's Community Swim Sat, 12 Dec at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
Early Bird Clean Up Garrison Bight hosted by Sea Dogs Fri, 23 Oct at 08:00 am Garrison Bight Marina- Key West DOG
GOOMBAY FEST IN KEYWEST (Miami Bus ride to Keywest) Sat, 17 Oct at 12:00 pm Key West, Florida Keys FESTIVALS
Taz & Jordan's Annual Holiday Party! Sun, 13 Dec at 06:00 pm 925 Seminary St, Key West, FL 33040-4717, United States PARTIES