Key West Parties Events

2025 Fantasy Fest Parade Viewing Party @ First Flight

First Flight Island Restaurant & Brewery 25 Oct 2025

Murder at the Hard Rock Cafe

Hard Rock Cafe Key West 9 Oct 2025

Pajama And Lingerie Party

Aqua Bar and Nightclub, Duval Street, Key West, FL, USA 23 Oct 2025

2025 KWPD Love Fund Annual Ball

Opal Key Resort & Marina 20 Sep 2025

Tay Tay Tuesday - In Your Wildest Dreams

Sunset Pier ~ Key West 21 Oct 2025

Puddles Pity Party at Key West Theater

Key West 28 Sep 2025

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

AquaPlex Key West 23 Sep 2025

The Fabulous Spectrelles

Kaya Island Eats 3 Oct 2025

Shoreline Sessions Reggae Beach Festival

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

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

Thomas Dolby at Key West Theater

Key West Theater 7 Nov 2025

2nd Saturday Celebration - Upstairs at Shops at Mallory Square

The Shops at Mallory Square 13 Sep 2025

Macy Gray-On How Life Is 25th Anniversary Tour

Key West Theater 24 Oct 2025

First Sunday Open Mic Monthly Reading

327 Elizabeth St., Key West, Florida 33040 7 Sep 2025

Movie Trivia Night for Teens

600 Eaton St, Key West, FL, United States, Florida 33040 13 Sep 2025

The Fabulous Spectrelles

Kaya Island Eats 12 Sep 2025

The Fabulous Spectrelles

Kaya Island Eats 19 Sep 2025

Puddles Pity Party at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 28 Sep 2025

Full Moon Magic Ghost Stories

1319 Duval Street, Key West, FL, United States, Florida 33040 7 Sep 2025

Sunset Moonrise Sail

0 Duval Street, Key West, FL, United States, Florida 33040 7 Sep 2025

1st Annual USCGC Ingham Fundraising Gala

Truman Waterfront Park - West end of Southhard Street, Key West, FL, United States, Florida 33040 22 Nov 2025

Sharese Nicole LIVE at Sunset Lounge Bar and Grill

Sunset Lounge Sigsbee 12 Sep 2025

4th Annual Tat’s for Ta-Ta’s 2025

512 Greene St, Key West, FL 15 Oct 2025

Back at the Backyard!!!

The Backyard Bar key west 20 Sep 2025

Dave Matthews Tribute Band - BIG Stage / FREE Show

0 Duval Street, Key West, FL, United States, Florida 33040 17 Oct 2025

Drag Brunch

291 Front St suite 207, Key West, FL, United States, Florida 33040 7 Sep 2025

Good Trees River Band at The Green Parrot

Green Parrot Key West 12 Sep 2025

The Fabulous Spectrelles

Kaya Island Eats 26 Sep 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

10th Annual Spayghetti & No Balls Dinner

La Trattoria Oceanside 17 Sep 2025

ACOUSTIC SOUL IN KEY WEST!

Schooner Wharf Bar 3 Oct 2025

All Candidate Drag Queen Bingo with QMitch!

22&Co 7 Sep 2025

22&Co Bingo Sundays w/Qmitch - Floyd for King

22&Co 14 Sep 2025

KWBW25: Bottoms Up Pool Party

Island House Key West Gay Hotel & Resort 1 Nov 2025

Wesley House Holiday Village & Bike Ride

Coffee Butler Amphitheater 5 Dec 2025

Jerry Kramer LIVE at Sunset Lounge Bar and Grill

Sunset Lounge Sigsbee 19 Sep 2025

The Fabulous Spectrelles

Kaya Island Eats 10 Oct 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

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

Good Trees River Band @ The Greeen House 9/10

3128 N Roosevelt Blvd, Key West, FL 33040-4113, United States 10 Sep 2025

BINGO at the BAR - Sunset Lounge Bar & Grill

Sunset Lounge Sigsbee 11 Sep 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

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

Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show

Casa Marina Key West, Curio Collection by Hilton 20 Sep 2025

November's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 15 Nov 2025

Key West Pet Masquerade 2025

Key West Ampitheatre 22 Oct 2025

On Our Way To Paddy's Day Weekend Celebration!

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

NightCaps and Nightgowns, a Moon Light Pajama Party

319 Duval St, Key West, FL, United States, Florida 33040 25 Oct 2025

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

Key West Theater 26 Nov 2025

Cupid's Chase 5K Key West

Clarence S.Higgs Memorial Beach 14 Feb 2026

Key West Halloween Drag Brunch Royale

Mangoes Restaurant 19 Oct 2025

Southernmost Half Marathon & 10K

Higgs Beach Key West, Florida 12 Oct 2025

Mrs. Roper Romp

Sunset Pier ~ Key West 20 Oct 2025

Good Trees River Band at General Horseplay

General Horseplay 9 Sep 2025

DJ Sanaris at Dante's Pool!

Dante's Pool Bar & Restaurant 26 Sep 2025

New Moon Magic w/Mermaid Dorian

1319 Duval Street, Key West, FL, United States, Florida 33040 21 Sep 2025

22&Co Bingo Sundays w/Qmitch - All Candidate

22&Co 12 Oct 2025

Changes In Latitude at Key West Theater

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

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

Rick's Bar 22 Oct 2025

Sloppy Joe's 46th Annual Toga Party

Sloppy Joe's 23 Oct 2025

Tom Sandoval and The Most Extras

Key West Theater 8 Oct 2025

Post-Fest Plunge Ice Bath Social

Kava Culture Key West 26 Oct 2025

Cocktails for Animal Tails

Rick's Bar 21 Oct 2025

Sloppy Joe's Slumber Party

Sloppy Joe's 22 Oct 2025

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

AquaPlex Key West 9 Sep 2025

Fantasy Fest 5K Run/Walk

Duval Street 20 Oct 2025

Italian Night at the Movies: The Bicycle Thief

Tropic Cinema 5 Nov 2025

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

AquaPlex Key West 16 Sep 2025

Sloppy Joe's Comic Book Cape-ers Party

Sloppy Joe's Bar 20 Oct 2025

Kash'd Out at Key West Theater

Key West Theater 16 Jan 2026

Captain Tony's Party In Plaid

922 Caroline Street, Key West, FL, United States, Florida 33040 21 Oct 2025

Thomas Dolby

Key West Theater 6 Nov 2025

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

AquaPlex Key West 30 Sep 2025

DMTB: The Dave Matthews Tribute Band

Key West Theater 25 Feb 2026

MARGARITA BROTHERS @ Jimmy Buffett's Margaritaville Key West, Just added.

Margaritaville Key West 31 Oct 2025

Great Gatsby NYE 2026

First Flight Island Restaurant & Brewery 31 Dec 2025

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

AquaPlex Key West 7 Oct 2025

Creative Hat Party

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

The Our Dave KW Pub Crawl

525 Duval St, Key West, FL 33040-6552, United States 30 Oct 2025

Early Bird Clean Up Duval & Eaton Streets hosted by Berkshire Hathaway Knight & Gardner Realty

Berkshire Hathaway Home Services Knight & Gardner Realty 17 Oct 2025

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

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

Parking Diva Royale - Key West

Diva Royale Drag Queen Show - Key West 5 Sep 2025

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

Sebago Key West 31 Oct 2025

SSP Powerboat Races 2025 - WED - Locals Only VIP Tent

0 Duval Street, Key West, FL, United States, Florida 33040 5 Nov 2025

Berkshire Hathaway Parade of Homes Mega Open House Event

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

THE BEATLE BAND EXTRAORDINAIRE! FANTASY FEST - 2025 GREEN PARROT

Green Parrot Bar Key West 20 Oct 2025

Farm Open House

Monroe County Sheriff's Office Animal Farm 28 Sep 2025

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

Margaritaville at Sea Cruise Ship Special

Key West Rebecca 15 Dec 2025

Jay & Cynthia Ceremony

Key West 4 Oct 2025

BeachFront Radio and Trop Rock'N Duval presents The Margarita Brothers @ Key West Theater

Key West Theater, 512 Eaton St. Key West, FL 33040 30 Oct 2025

Mac McAnally

Key West Theater 3 Dec 2025

4th Annual MAC Patriots Golf Tournament

Key West Golf Club 7 Dec 2025

Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows

Diva Royale - Drag Queen Show 6 May 2022

The Expanding Man - Tribute To Steely Dan

Key West Theater 13 Jan 2026

FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY

La Concha Key West 21 Oct 2025

Page Turner Adventures - The Magnificent Circus Mystery at Tennessee Williams Theatre

Tennessee Williams Theatre 28 Oct 2025

Early Bird CleanUp along Flagler Ave hosted by Mount Sinai Primary Care & Diagnostic Center

2505 Flagler Ave, Key West, FL 33040-3934, United States 19 Sep 2025

Early Bird Clean Up Duval & Eaton Streets hosted by Key West Woman's Club

Key West Woman's Club 9 Jan 2026