9 Best Key West Festivals That Need To Be On Your Bucket List

9 Best Key West Festivals That Need To Be On Your Bucket List

Key West Festivals

Get in line, festival enthusiasts! The biggest and wildest festivals in Monroe County are about to give you a run for your money.

If you are a foodie? The Key Lime Festival will be perfect for trying out the island’s favorite dish – Key Lime Pie.

Once you’ve had enough pie, although there is no such thing, wash it down with the Key Lime cocktail! Be careful; the cocktail is not your cup of tea, in the very literal sense.

Key West festivals don’t favor foodies alone. Have you heard of Ernest Hemmingway? I bet you’ve already read ‘The Old Man and the Sea’ or ‘For Whom the Bell Tolls.’ True page-turners!

You can literally walk in the author’s footsteps at the Hemmingway Days Festival. So, dress up like a pirate and let the Key West festivals paint your tapestry of Hemmingway Days in vibrant colors!

Visit Key West! Where the air is alive with the spirit of celebration and wild fun.

1) Grab Your Bib For The Key West Food And Wine Festival In January

One of the best Key West festivals happens in January for food enthusiasts and wine lovers!

The whimsical wonderland of rich wine, delicious fresh seafood, exotic tropical flavors, and unique local tastings will send you into an ecstatic frenzy.

Don’t worry if you missed this year’s festivities; the next event will be from Wednesday, January 24, to January 28, 2024. So, mark the date!

Find out what makes it hard to be on a diet in this southernmost city.

Group Of People Cheering With Wine At Key West Food And Wine Festival

2) Reenact History At The Conch Republic Independence Celebration In April

Party people, are you ready?

The wild celebration of the Conch Republic Independence in Key West, Florida, is something you can’t afford to miss.

The festival marks a day of independence from the United States on April 23, 1982. In the island’s true fashion, its independence is synonymous with a good party.

So, what do you get off on? With the street parades filled with extravagant tube men, locals dressed up as pirates, and the Caribbean rhythm swaying your hips, prepare to have the time of your life.

That’s not all! There are plenty of mock naval battles and “athletic challenges” to keep you entertained. But these competitive races are kind of different.

Fix your dental formula because you are in for a gag. It’s a bunch of men sprinting in high heels! After all these activities, it’s normal to be famished.

So why not go for the Key West lunch cruise? It’s the perfect opportunity to sneak out for a quick grab before returning to the festivities.

Perks of attending the Conch Republic Independence Celebration:

  • Live entertainment
  • Free parking
  • Historic reenactment at Mallory Square
  • Artisan displays
  • Pirate’s ball
Conch Republic Independence Celebration

3) Get Discovered At The Key West Songwriters Festival In May

Can you handle five straight days and nights of live music? If you are a music lover, you must be nodding your head already.

So why don’t you head to one of the famous Key West Songwriters Festivals?

This festival has kickstarted some household names such as Georgia Line, Jake Owen, Randy Houser, and Kacey Musgraves. Who knows, your name could be next on this list.

If you are not particularly looking for a big break in the music industry, bring your dancing shoes and sway away to live music.

You can also listen to stories from some of your favorite veteran songwriters and promising upcoming artists.

Woman Playing Guitar - Key West Songwriters Festival

4) Unleash Your Inner Diva At Key West Pride In June

Duval Street in downtown Key West is a throbbing lifeline of pure fun.

You should know that this festival is not just for LGBTQ members but anyone preaching the mantra of One Human Family. It encourages diversity, inclusivity, and pride in Key West.

Witness the 1.25-mile rainbow flag during the parade, rumored to be the longest rainbow flag in the world.

It’s one of the most-anticipated festivals in Key West; running for a week, you will have ample time to marinate in the spirit of pride.

Organized by the Key West Business Guild, you can expect the following:

  • Exciting drag shows
  • Plays
  • A street fair
  • Pool parties
  • A Big parade
Key West Pride

5) Indulge In Key Lime Pie At The Key Lime Festival In July

Think of a lemonade stand but on a much bigger and larger scale.

With five full days of culinary events, the Key Lime Festival is fun, strange, and unforgettable. Visitors and locals like participating in the Key lime pie eating contest, where you can’t use your hands, forks, or spoons.

Former winner Chris Shultz finished a whole 9-inch Key lime pie without his hands in under 1 minute and 14 seconds.

Are you ready to wiggle your face to the Key Lime Pie Championship?

If you just want to enjoy the delicious pie without pressure, the Key Lime Pie Hop tour will take you across the Conch Republic to sample some of the best pies.

However, it’s not all about eating at this festival; you must come with a few tricks up your sleeve!

If you can’t eat your way to the championship, how about throwing it away?

In the Key Lime Pie drop competition, you must drop the pie from the topmost part of the Key West Lighthouse without damaging it.

There is also the Key Lime Scavenger Hunt, a 5k race that will make you sweat off the extra calories.

But if you don’t want to eat, throw, or look for a pie, how about washing it down with a refreshing Key Lime Cocktail Sip?

Key Lime Pie

6) Write Away At The Hemingway Days Festival In July

Are you part of the Beard gang or looking for some eye candy? Get to witness more than 100 handsome bearded men at the famous Ernest Hemingway festival.

The men dress in Ernest Hemingway’s appearance to channel their inner Hemingway in the look-alike contest. You can cheer your favorite competitor every July at Sloppy Joe’s Bar.

Why this particular location? The author would frequent the Duval Street saloon for a pint or hang out. This was over 80 years ago. He also left some of his belongings in the storeroom after his second marriage crumbled in 1939. However, these items are now at Penn State. Four unpublished stories, drafts of manuscripts, and multiple boxes of Ernest Hemingway’s personal effects.

To enter the Hemingway Days contest, you should come with the complete look of safari gear or a turtle-neck sweater. This apparel is identified with the author; if you win, you will get the title “Papa.”

So it’s not all about good-looking men trotting the island. This is one of the Key West Florida festivals that pays homage to poetry readings and general writing talent.

The Hemingway Home And Museum

7) Bring Your Appetite To Key West Lobsterfest In August

Are you a sucker for big summer parties? You better mark the date for the annual Key West Lobsterfest.

Marking the beginning of the lobster season, indulge in fresh Florida lobsters, enjoy live music, and relish the great company of locals and visitors of Florida.

Why would you go to the Florida Keys instead of staying home for some lobster? The Florida lobster has sweet and tender meat that makes it simply irresistible. If you are a purist, you know how delicious steamed lobster served alongside butter is.

Don’t miss out on the Street Fair on Duval Street, where you can buy any dish, from traditional lobsters to delicious appetizers prepared by professional chefs. With free admission, all you need to carry is a big appetite. There is also free parking, so don’t worry about parking fees.

It’s more than just lobster at this festival! Buy art and crafts, dance to the free outdoor concert, and enjoy the sunset at South Beach.

Delicious Dishes - Key West Lobsterfest

8) Get Wild At The Goombay Caribbean Festival And Fantasy Fest In October

Welcome to the Wild Wild West of parties!

You have probably seen Johnny Depp or Rihanna in the most eccentric looks in Key West. This festival is so much fun that a pre-festival runs the weekend before the actual festival. The pre-festival, Goombay Caribbean Festival, offers a preview of great food and entertainment on the streets of Bahama Village in the Old Town, Key West.

So let’s get to the fun!

Fantasy Fest, an annual ten-day event in paradise, is an opportunity of a lifetime for grown-ups to let loose and enjoy themselves. Key West locals started this tradition to summon visitors to the tranquil and beautiful island. And obviously, it worked!

Pack your costume, libation, and excitement because you are in for a treat! Here is what you should expect at the Goombay Caribbean Festival and Fantasy Fest:

  • Street fair
  • Royal Coronation Ball
  • Pet masquerade
  • Costume contest
  • Live music
Key West Festival

9) Experience Silver Screen Magic At The Key West Film Festival In November

Do you love Netflix and chill or going to the theatres?

This Key West Florida festival has a special place in the heart of film aficionados. With live screenings set up outdoors, get ready to live like a movie star! Bring your whole family to experience silver screen magic and unforgettable movie experiences, from independent gems to critically acclaimed masterpieces.

That’s not all! You can get valuable insights into the art of filmmaking if you want to break into the industry. From discussions with filmmakers, panel gatherings, and Q&A sessions, you will have all you need to jumpstart your career.

So, grab your popcorn and get ready to have your mind blown away.

Group Of People Watching Movie In The Cinema

Discover The Best Festivals In Key West

You are now armed to the teeth with the best festivals in Key West. Grab your friends and family and set off to get a taste of the island’s unique and fun celebrations.

As expected, a festival aficionado can’t put a limit on fun. So why stop at the festivals? Add on to the major attractions and festivals of Key West by going for a thrilling e-foil ride.

With a two-hour battery life, carry on the celebration spirit of the island before you head back home. No need for waves; when you have Key West Boat Trips.

E-Foil Ride

Ready for your next adventure?