Lifestyle Events in Key West

Check out happening lifestyle events all around Key West, FL

Outdoor Movie: Parrot Heads - The Essential Jimmy Buffet Documentary

 Sat, 30 Aug at 08:00 pm Southernmost Pint Brewpub

Grilled Cheese & Beer Pairing Trivia

 Thu, 28 Aug at 06:00 pm La Mer Hotel & Dewey House

Fins Up! Pool Party!!

Sat, 30 Aug at 01:00 pm 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Latitude Adjustment Sail

 Sat, 30 Aug at 06:15 pm 0 Duval Street, Key West, FL, United States, Florida 33040

NightCaps and Nightgowns, a Moon Light Pajama Party

 Sat, 25 Oct at 06:00 pm 319 Duval St, Key West, FL, United States, Florida 33040

Drag Brunch

 Sun, 07 Sep at 12:00 pm 291 Front St suite 207, Key West, FL, United States, Florida 33040

Just a Few Friends Walking Tour

 Sat, 30 Aug at 12:00 pm Shrimp Boat Sounds (Jimmy Buffetts Recording Studio)

Farm Open House

 Sun, 14 Sep at 01:00 pm Monroe County Sheriff's Office Animal Farm

Bark & Brew - Kickoff!

 Thu, 28 Aug at 05:00 pm 5950 Peninsular Avenue, Key West, FL, United States, Florida 33040

Bubbles & Brunch Sail

 Sun, 31 Aug at 10:00 am 0 Duval Street, Key West, FL, United States, Florida 33040

Plogging the Keys Early Bird Cleanup

 Fri, 10 Oct at 08:00 am 510 Greene Street, 1st Floor, Key West, FL, United States, Florida 33040

Fantasy Fest 5K Run/Walk

 Mon, 20 Oct at 06:00 pm Duval Street

DEKA MILE & DEKA ATLAS Hosted by Urban Fit, Inc - Hatfield, PA

Sun, 14 Sep at 06:30 am Urban Fit, Inc.

Bumbu Rum Mixology Class at Margaritaville Key West

 Fri, 08 Aug at 07:00 pm Margaritaville Restaurant - Key West Free

Green Drinks- Healthy Living Month

Tue, 19 Aug at 05:30 pm Club 504

Early Bird Clean Up Virginia & Watson Streets hosted by Unity of the Keys

 Fri, 07 Nov at 08:00 am Unity of the Keys

Great Gatsby NYE 2026

 Wed, 31 Dec at 08:00 pm First Flight Island Restaurant & Brewery USD 269

Captain Tony's Party In Plaid

 Tue, 21 Oct at 09:00 pm 922 Caroline Street, Key West, FL, United States, Florida 33040

Farm Open House

 Sun, 26 Oct at 01:00 pm Monroe County Sheriff's Office Animal Farm

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

 Thu, 28 Aug at 02:00 pm Truman Waterfront Park

Margaritaville at Sea Cruise Ship Special

 Mon, 15 Dec at 04:00 pm Key West Rebecca

Jay & Cynthia Ceremony

Sat, 04 Oct at 11:00 am Key West

Come Monday Breakfast Special

 Mon, 01 Sep at 08:00 am 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States

Tin Cup Sailing Adventure

 Mon, 01 Sep at 10:00 am Danger Charters Wind n Wine

KEY WEST, BABY! 🌊☀️👙🥂

 Sat, 27 Sep at 01:00 pm Key West