4 Ways Key West Celebrates Hemingway Days

Ernest Hemingway first visited Key West on a trip from Paris.  He said it felt like living in another country, so he moved in.  He sport fished and sailed, refereed boxing matches and lived his life.  He also wrote and left an impression that can still be felt today.  Key West celebrates the times Hemingway lived and wrote about each year.  Some of the celebrations have been scaled back for the times we're living today and these are four of the ways Key West will celebrate the man and the sea.

Stock Island Marina Village Key West Marling Tournament

Just like Hemingway, anglers will ply the waters he once fished, except their catches could bring in $50,000 in guaranteed cash prizes. $25,000 goes to the first-place team alone. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Annual Hemingway 5K Sunset Run/Walk 

Did you know this is the original and oldest ongoing 5K Run in Key West? The race course is a scenic flat course that runs past Key West's most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. 

Hemingway Sunset Paddleboard Race 

Paddleboarders race through a three-mile course before starting the 5k portion at 7:30 pm at the Southernmost Point in the continental U.S. 

Virtual Symposium Webinars

Hemingway Look-a-like Contest

A select stocky and bearded men resembling Ernest compete in an annual Hemingway Look-Alike Contest at Sloppy Joes, a frequent hangout for the legendary writer during his Key West years.

Ernest Hemingway's sporting lifestyle continues to be an inspiration. Come and be a part of the culture and joy.  Reserve a premier vacation rental from our luxury collection of Key West rentals. The fun you'll have depends on you visiting with us for these Hemingway Days!