Summer Events in Key West that are worth the four-hour drive

Hemingway Days in Key West. PHOTO: Andy Newman/AP

Summer is finally here, and while South Florida is warm and sunny all year long, that doesn’t mean we don’t enjoy that stretch of time when kids are off from school, the sun is out longer, and traffic runs just a bit more smoothly. And those aren’t the only perks of summer, of course. This time of year tends to bring on a slew of fun festivals and other events, and we’re right on top of it as usual. Whether you’re a fan of seafood, booze, or Hemingway (and let’s face it, it’s hard not to be any of these when you’re in the Keys), you’re certain to find something enjoyable to do on our list of best Key West events for the season.

Key West Summer Stage

Theater fans in the Conch Republic will be pleased at the arrival of this year’s Key West Summer Stage Festival. The event, which takes place at the Red Barn Theatre, was started by a group of friends and is now in its sixth season. Locals and visitors are welcome to purchase tickets to any of the mini-festival’s offerings, including the off-Broadway hit Bad Jews and the Pulitzer Prize-winning Water By The Spoonful. It all happens June 29 through July 10. 

Key Lime Festival

As you might suspect, key limes are the preferred citrus fruit of the keys. So much so that an annual Key Lime Festival is held every year to celebrate these small, round, green goodies that are the basis for such wonderful treats as key lime pie and key lime milkshakes. From July 2 through Independence Day, you’ll be able to take part in, among other things, a key lime rum sampling, a key lime cocktail sip and stroll (where you’ll get to judge which bar has the best key lime drink), and a key lime pie eating contest. All that said, if you’re not into the sour stuff, sit this one out.

Key West Hemingway Days Celebration

Certainly one of the biggest festivals of Key West summers is the Hemingway Days Celebration. From July 19 through 24, hoards of old, bearded, white dudes (or folks dressed up like old, bearded, white dudes) invade the tiny island to party it up and uphold the spirit of the writer. Festivities included in the celebration include a Hemingway Look-Alike contest, a “running of the bulls” (don’t worry–the bulls here are man-made), a 5K and paddleboard race, a short story competition coordinated by Hemingway’s granddaughter, readings of the Pulitzer Prize-winning author’s works, and a three-day fishing tournament.

Key West Fishing Tournament

Everyone goes to the Keys for the fishing, but it’s never more exciting than during the Key West Fishing Tournament. While the tournament begins in mid-spring (April) and ends in mid-Fall (November), it’s primarily a summer event. Anglers of all ages and backgrounds are welcome to participate free of charge by entering their catches at tournament weigh stations in order to qualify for prizes. 

Key West Lobsterfest

Key West locals know how to bring in lobster season in style. The annual Key West Lobsterfest takes place August 11-14 and features a number of exciting festivities for true crustacean connoisseurs (and folks who just like to have a good time). The lobster boil kicks things off at the Sunset Tiki Bar and Grill, followed by the Reef and Ritas snorkeling trip, the Duval Crawl, street festival, free concert, and finally, their big Sunday lobster brunch. 

Key West Brewfest

Doing it up Key West style almost always includes a hefty amount of alcohol, so why not celebrate all things beer by attending this year’s Key West Brewfest Sept. 1-5? Now in its seventh year, this celebration of beer includes several options for beer-paired dinners and brunches, a pool party scavenger hunt, a bar crawl and dance party, and even a New Orleans-style second line. Featured beers will include (but will definitely not be limited to): Terrapin, Abita, Nectar Ales, Kona Beer, Florida Keys Brewing Company, Cigar City Brewing, Mile Marker Brewing, and the list goes on.

Womanfest Key West

Key West is, quite fortunately, a very LGBTQ-friendly part of the world. So it’s no surprise that one of their biggest events of the summer is the lady-centric Womanfest, a four-day non-stop party by women, for women. On the docket for this year’s festival are pool parties, wine tastings, drag shows, a bicycle parade, poker tournament, gay bingo, a trolley tour, a burlesque show, and more. Basically, every awesome thing you can think of, and all in the company of hundreds of queer and queer-friendly women.