Key West Food & Drink Events

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

Truman Waterfront Park 31 Aug 2025

Cheese Burger Beach Battle and Tribute Concert by Landshark

Southernmost Beach Resort 29 Aug 2025

Outdoor Movie: Parrot Heads - The Essential Jimmy Buffet Documentary

Southernmost Pint Brewpub 30 Aug 2025

A Sailor's Sun Sunset Cruise

Sunset Watersports 29 Aug 2025

Parrots & Margaritas 5K

211 Duval St 30 Aug 2025

Bubba's Official After Party

The Key West Empourium 31 Aug 2025

VIP Tasting at the 2nd Annual Key West Rum Fest

Key West Theater 16 Aug 2025

Cowboy Ken's Pink Pool Party

1129 Fleming St, Key West, FL, United States, Florida 33040 13 Aug 2025

Back to the Island Beach Party

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

Truman Waterfront Farmers Market

21 E Quay Rd, Key West, FL, United States, Florida 33040 14 Aug 2025

Outdoor Movie: Tales From Margaritavision

Southernmost Pint Brewpub 29 Aug 2025

Key West Powerboat Races 2025 - VIP Tent - SUNDAY

Sunset Pier 9 Nov 2025

Grilled Cheese & Beer Pairing Trivia

La Mer Hotel & Dewey House 28 Aug 2025

Salty Rim Social

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 29 Aug 2025

Just a Few Friends Pool Party @ the Marker

The Marker Key West Resort 31 Aug 2025

Happy Hour at the Chart Room

Chart Room 29 Aug 2025

Just a Few Friends Celebration, Key West

Key West 29 Aug 2025

BBQ Rib Battle

Ann St, Key West, FL 33040, United States 31 Aug 2025

Brews & Bites: A 4-Course Paired Experience

First Flight Island Restaurant & Brewery 29 Aug 2025

Fins Up! Pool Party!!

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

Latitude Adjustment Sail

0 Duval Street, Key West, FL, United States, Florida 33040 30 Aug 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

Trivia Night at the Key West Cooking School

291 Front St Suite 207 - Upstairs, Key West, FL, United States, Florida 33040 18 Aug 2025

Pencil Thin Mustache Contest

Pier House Resort & Spa 1 Sep 2025

AZUR's End Of Summer Party!

425 Grinnell St, Key West, FL, United States, Florida 33040 31 Aug 2025

Steers & Queers Pool Party

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

Monthly Lodge Meeting September 2025

American Legion 10 Sep 2025

Book signing with Jameson and Mary Reeder

533 Eaton St, Key West, FL, United States, Florida 33040 16 Aug 2025

🎶Blue Heaven🎶

Blue Heaven 30 Aug 2025

Key West Rum Fest Grand Tasting

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

Dub Pool Party at The Marker Key West

The Marker Key West 15 Aug 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

Drag Brunch

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

Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Sep 2025

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

Key West Theater 26 Nov 2025

BINGO at the BAR - Sunset Lounge Bar & Grill

Sunset Lounge Sigsbee 14 Aug 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

Bubbles & Brunch Sail

0 Duval Street, Key West, FL, United States, Florida 33040 31 Aug 2025

Best of Key West Jazz Concert Series!

803 Emma St, Key West, FL, United States, Florida 33040 27 Aug 2025

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

Early Bird Clean Up Vernon Street area hosted by The Casa Marina and the Reach

Casa Marina Resort 12 Sep 2025

3 Daughters Brewing Drink & Draw @ The Marker

200 William St, Key West, FL 33040-6645, United States 31 Aug 2025

What's Brewing?: Monthly Coffee Talk

Key West Lighthouse Court Hotel 14 Aug 2025

Key West Powerboat Races 2025 - VIP Tent - FRIDAY

Sunset Pier 7 Nov 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

Pasta in Paradise/ Mimosa-ville Brunch

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 31 Aug 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Not Your Average Taco/Tequila/Tuesday at Big Cheezees

404 Southard St, Key West, FL, United States, Florida 33040 12 Aug 2025

Key West Halloween Drag Brunch Royale

Mangoes Restaurant 19 Oct 2025

Fantasy Fest 5K Run/Walk

Duval Street 20 Oct 2025

Great Gatsby NYE 2026

First Flight Island Restaurant & Brewery 31 Dec 2025

Brewfest/ Green Parrot Bar Charity Bingo to Benefit the Key West Sunrise Rotary's Scholarship Fund M

Green Parrot Bar Key West 1 Sep 2025

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

Truman Waterfront Park 28 Aug 2025

Come Monday Breakfast Special

2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States 1 Sep 2025

Early Bird Clean Up Simonton & South Streets hosted by Southernmost Beach Resort, FL Dept of Health

Southernmost Beach Resort 26 Sep 2025

Early Bird Clean Up Duval and Virginia hosted by Realty ONE Group (The Halloween edition)

Realty ONE Group Destination 31 Oct 2025

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

Key West Woman's Club 9 Jan 2026

Early Bird CleanUp Lazy Way and the historic Bight area hosted by The Marker Resort

The Marker A Waterfront Resort 21 Nov 2025

Southernmost Turkey Trot 5K

The Southernmost Point Buoy 27 Nov 2025

Tin Cup Sailing Adventure

Danger Charters Wind n Wine 1 Sep 2025

Bumbu Rum Mixology Class at Margaritaville Key West

Margaritaville Restaurant - Key West 8 Aug 2025