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 FITNESS
Captain Morgan's Masquerade March Fri, 23 Oct at 05:30 pm 1117 Fleming St, Key West, FL 33040-6909, United States PARTIES
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
Fantasy Fest Street Fair & Costume Promenade Fri, 23 Oct at 12:00 pm Duval St, Key West, FL 33040, United States FESTIVALS
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
The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30 Fri, 30 Oct at 07:30 pm TBA USD 8 TO 71 FITNESS
Paparazzi Row Block Party Fri, 23 Oct 1129 Fleming St, Key West, FL, United States, Florida 33040 PARTIES
Friday Night Fever Fantasy Fest Party at Hog's Breath *FREE EVENT* Fri, 23 Oct at 07:00 pm 400 Front St, Key West, FL, United States, Florida 33040 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
Lip Sync & Lifeguards - A Fantasy Fest Pool Party Sat, 17 Oct at 12:00 pm Blue Flamingo Resort Key West FREE FITNESS
Golden Hour - Sunset Experience by Electroniconch Mon, 19 Oct at 04:00 pm Galleon Marina USD 82 TO 128 FITNESS
NINA STYLY X ELECTRONICONCH RECORDS - FASHION THROGHT SOUND Fri, 23 Oct at 10:00 pm Viva Argentinian Steakhouse ART
Halloween Bar Crawl 10/31 - KEY WEST Sat, 31 Oct at 04:00 pm La Concha Key West, Autograph Collection USD 20 TO 25 FITNESS
Halloween Eve Bar Crawl 10/30 - KEY WEST Fri, 30 Oct at 05:00 pm La Concha Key West, Autograph Collection USD 20 TO 25 FITNESS
Sins & Sequins - An Official Fantasy Fest Event Wed, 21 Oct at 07:00 pm Blue Flamingo Resort Key West USD 31 FITNESS
That Arena Rock Show Sun, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 SPORTS
WE LOVE DOLLY! 💖 A Dolly Parton Tribute Party Tue, 20 Oct at 04:00 pm 431 Front St, Key West, FL 33040-6663, United States FESTIVALS
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 40 TO 76 ENTERTAINMENT
Mamma Mia’s Margaritaville Pool Party Mon, 19 Oct at 11:00 am 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States PARTIES
Candlelight: The Best of Hans Zimmer Fri, 13 Nov at 08:30 pm Key West Theater USD 40 TO 91 ENTERTAINMENT
Dirty Doctors Naughty Nurses Party Sat, 24 Oct at 09:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 41 TO 75 FITNESS
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
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
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 ENTERTAINMENT
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
Masquerade Monday Wine Dinner Presented by Bogle Wines Mon, 19 Oct at 06:00 pm A&B Lobster House MUSIC
Swayzees Music Icons Pool Party at Shores Pool Wed, 21 Oct at 02:00 pm Southernmost Beach Resort PARTIES
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
GLAMOROUS DEAD & UNDEAD POPSTARS PARTY - at Viva's Thu, 22 Oct at 06:00 pm Viva Argentinian Steakhouse USD 19 TO 111 FITNESS
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
Krewe de Krazy Life Meet and Greet and Costume Parts Exchange Sun, 18 Oct at 12:00 pm Galleon Tiki Bar MEET-AND-GREET
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band Sat, 31 Oct at 01:00 pm Key West Theater MUSIC
2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise" Fri, 30 Oct at 05:00 pm Sebago Watersports MUSIC
STUDIO 69 DISCO PARTY - at Viva's Wed, 21 Oct at 06:00 pm Viva Argentinian Steakhouse USD 11 TO 111 FITNESS
Custom House Holiday Concert & Bazaar Fri, 11 Dec at 05:00 pm Key West Art & Historical Society MUSIC
Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22 Thu, 22 Oct at 02:00 pm The Marker Key West Harbor Resort FREE FESTIVALS
Powerboat Village in the Historic Seaport! Wed, 04 Nov at 11:30 am Conch Republic Seafood Company SPORTS
October's Community Swim Sat, 17 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour Wed, 11 Nov at 07:30 pm Congregation B'nai Zion USD 18 TO 29 MUSIC
Candlelight: Vivaldi's Four Seasons Fri, 11 Dec at 06:00 pm Key West Theater USD 40 TO 88 ENTERTAINMENT
Fantastic Body Art & Stunning Sunsets!! Fri, 16 Oct at 12:00 pm Sunset Pier, Key West, FL 33040, United States ART
Candlelight: Tribute to Fleetwood Mac Fri, 11 Dec at 08:30 pm Key West Theater USD 40 TO 76 ENTERTAINMENT
Fantasy Fest Greatest Hits Pool Party Tue, 20 Oct at 12:00 pm Winslow's Bungalows - Key West Historic Inns FESTIVALS
Bunny Pool Party - Official Fantasy Fest Event Fri, 23 Oct at 10:30 am 1400 Duval St, Key West, FL, United States, Florida 33040 FESTIVALS
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers Sat, 12 Dec at 08:00 pm Key West Theater MUSIC
December Duo Holiday Concert: Irie Monte and Crispin Campbell Sat, 12 Dec at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
An Evening Aglow: A Candlelight Christmas with Marjory Lee Tue, 15 Dec at 08:00 pm Key West Theater MUSIC
SING • SYNC • SLAY Karaoke Pool Party Wed, 21 Oct at 01:00 pm 2401 N Roosevelt Blvd, Key West, FL, United States, Florida 33040 MUSIC
A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg, Reese Dailey & Special Guests Sat, 13 Feb at 08:00 pm Key West Theatre ART
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band Fri, 01 Jan at 08:00 pm Key West Theater MUSIC
Third Annual Key West Woman's Club Bougie Afternoon Tea Party Sat, 16 Jan at 03:00 pm 319 Duval St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Double Duran "The Ultimate Duran Duran Experience" Mon, 18 Jan at 08:00 pm Key West Theater ENTERTAINMENT
Thanksgiving at Four Marlins Thu, 26 Nov at 05:30 pm 1435 Simonton St, Key West, FL, US 33040 THANKSGIVING
Scott Kirby - 36 YEARS OF SONGS AND STORIES with Gabriel Donohue Sat, 26 Dec at 07:00 pm Key West Theater MUSIC
November's Community Swim Sat, 14 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
DMTB: The Dave Matthews Tribute Band- Burnin’ One Tour Wed, 24 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