The Key West Calendar is chock full of exicting things to do! Check out every month for cultural events, sporting events, literary events, and more. Of course our Key West Calendar strives to be complete, but there are always updates and additions.

Also, visit our Key West events page for more info. There’s so much to do we couldn’t fit it all in the Key West Calendar!

January    Impromptu Concerts featuring Gryphon Trio
January    Waterfront Playhouse – A Streetcar Named Desire
February    Key West Symphony Orchestra
February    Impromptu Concerts featuring Miami Strings
February    Library Lectures <
February    Leadership Monroe County Class X
February    Cuban American Heritage Festival Cigar Dinner
February    Heritage House Travel Writing Workshop
February    TWFAC Founders Gala Event
February    Heritage House Museum Tea & Conversation Program
February    Take Stock in Children – Donors Forum
February    Judy Drucker – Library Lecture
February    “Flamenco Vivo” Carlota Santana – TWFAC
February    Heritage House Museum Tea & Conversation
February    Red Barn Theatre
February    House & Garden Tour #2


February    Heritage House Travel Writing Workshop
February    Gordon Ross & Friends
February    Library Lecture
February    Old Island Days Art Festival
February    Impromptu Concerts featuring New Century Sax Quartet
February    Red Barn Theater
February    Library Lecture
March    Heritage Days Festival
March    Free Stroll Through Key West Botanical Gardens
March    Key West Pops
March    Library Lecture
March    TWFAC Event
March    House & Garden Tour #3
March    Impromptu Concerts
March    Waterfront Playhouse
March    Red Barn Theatre
March    Conch Shell Blowing Contest
March    Key West Woman’s Club President’s Ball
March    Key West Garden Club Garden Tours
March    Library Lecture
April    Taste of Key West
April    Key West Symphony Orchestra
April    Key West Garden Club Spring Cleaning Sale
April    Conch Republic Independence Celebration
April    Red Barn Theatre – The Big Bang
April    Annual Kick-Off Key West & Lower Keys Fishing Tournament
April    Mel Fisher Maritime Museum Casino Night “Meet me in Hong Kong”
April    Leadership Monroe County Class X
April    Leadership Monroe County Class X Graduation
April    Key West & Lower Keys Kick Off Tournament
April    Key West & Lower Keys Fishing Tournament
May    Relay For Life, American Cancer Society
May    Waterfront Playhouse
May    Key West Music Festival
May    Minimal Regatta, Schooner Wharf Bar
June    Gay Pride Week
June    Super Boat Racing Series
June    Cuban American Heritage Festival
June    Key West International Jazz Festival
June    Key West Theater Festival
June    Key West Pops
July 4    Fireworks Celebration
July 4    Hospice 4th of July Picnic
July    18th Annual Lower Keys Underwater Music Festival
July    Geiger Key Marina Dolphin Tournament
July    Hemingway Days Festival


July    Key West Marlin Tournament
July    Key West Gator Club Dolphin Derby
July    Mini Lobster Season
August    Lobster Season
August    Lobster Fest
August    Miss Hawaiian Tropic – Key West Pagent
September    Women Fest
September    Poker Run – Bike Week
October    Goombay Festival
October    Fantasy Fest
November    Key West Fishing Tournament
November    Parrotheads in Paradise
November    Key West Superboat World Championship
November    APBA Offshore World Championship
November    Pirates in Paradise
December    Holiday House Tour
December    Key West Lighted Boat Parade
December    Annual Historic Seaport Music Festival
December    World AIDS Day Annual Tree of Hope
December    Key West Woman’s Club Community Christmas Party
December    Key West Holiday Festival – Helpline Benefit