Top 9 Festivals In Key West, Florida - Updated 2022

festivals in key west

Belonging to the Florida Key archipelago, Key West is a breathtaking island city in the USA that is known for its gorgeous beaches, exciting watersports activities, exquisite seafood restaurants, and other upscale attractions. It features adults-only hotels and homey vacation rentals for visitors to stay in as well. It is a favorite getaway destination among Americans who want to escape the routinary city life and its toxic pollution and noise. Key West will mesmerize you with its charming conch-style houses that feature a lovely pastel color scheme. Additionally, it boasts magical underwater paradises that are popular snorkeling and diving spots. If it’s the party scene you’re after, here is a list of top festivals in Kew West, Florida. Feel free to browse below.

1. Florida Keys Island Fest

Visitors and residents will head outdoors to enjoy live music, art, food, classic cars, and fun at the 24th annual...

Posted by Island Fest in Islamorada on Tuesday, 10 March 2015

If you are planning to take a much-deserved vacation in the stunning island city of Key West in March, you might just be in time for Florida Key Island Fest. In 2020, it will be held on the 28th to 29th of the month. This two-day celebration has lots in store for festival-goers. You can expect a fabulous art show that features a hundred artists from all over the country with their diverse crafts, a car show, lots of live entertainment, music events, and delicious food and overflowing drinks. To top it all off, this festival is free for all.

Florida Keys Island Fest

Address: Founders Park, 87000 Overseas Hwy, Islamorada, FL

Website: Florida Keys Island Fest

Takes place: April

2. Hemingway Days

Source: Photo by Flickr user Erin Borrini used under CC BY 2.0

Would you happen to be in Key West in July? If that’s the case, Hemingway Days might interest you to join in the fun and festivities. In 2020, it will be in its 40th year. This is an interesting celebration that revolves around Ernest Hemingway—an American literary icon. One of the highlights of the event is a friendly competition wherein many men try to imitate the legendary writer’s look, from the way he dressed up to his trademark beard. Also, as he was a literary master, poem and prose writing contests are also included during the event. Plus, a commemoration of his legacy is another activity to look out for.

Hemingway Days

Address: 201 Duval St, Key West, FL

Website: Hemingway Days

Takes place: July

3. Key West Fantasy Fest

Fantasy Fest 2012 Key West FL Parade Float
Source: Photo by user Cayobo used under CC BY 2.0

Happening every October of the year, Key West Fantasy Fest is another unmissable event in Key West, Florida. It is a festival that is overwhelming with grand parades, marvelous floats, colorful costumes, delightful music, and a lot more. Lots of tourists join this event to unleash their inner social butterflies and party to their hearts’ content. In 2020, the theme will be “Roaring 2020s & Future Fiction.” This festival lasts for 10 days, and it is exclusive for adults only. Note that the gathering bills itself as a wild extravaganza.

Key West Fantasy Fest

Address: 922 Caroline St, Key West, FL

Website: Key West Fantasy Fest

Takes place: October

4. Lobster Fest

There’s no such thing as “too much lobster.” ?? #AmericanLobsterFest

Posted by The Great American Lobster Fest on Friday, 30 August 2019

A festival for seafood lovers, Lobster Fest is a fantastic event that will treat you to a sumptuous culinary escapade that you will never forget. This exciting festival is considered to be one of the biggest and grandest seafood celebrations in the whole United States. Expect overflowing seafood dishes, especially mouthwatering lobsters. Also, live music will be present to amp up the festivity feels in the air. Plus, there will be games and activities in a well-curated program that the whole family can enjoy. Further, you can bag home some souvenir items from trade fairs at the festival.

Lobster Fest

Address: Key West, FL

Website: Lobster Fest

Takes place: August

5. Mystery Fest [Last event in 2019]

Mystery Fest Key West 2019, Photo by Carol Tedesco,

Posted by Mystery Fest Key West on Tuesday, 9 July 2019

Visit Key West in June, and be able to take part in the marvelous Mystery Fest. This fantastic fair has started not long ago. It’s only in its sixth year, but it has made its mark in the city’s social scene. It is a celebration of the country’s top mystery writers, crime experts, budding authors, and most importantly, the fans of the genre. This event is hosted by prominent people, and some distinguished guests are invited to give a talk about their crafts and literature.

Mystery Fest

Address: 926 Truman Ave, Key West, FL

Website: Mystery Fest

Takes place: June

Price: 195 USD

6. Womenfest Key West

The Swim Race Contest begins in 15 minutes!!!

Posted by Womenfest Key West on Friday, 7 September 2018

A celebration of womanhood, Womenfest Key West is a fascinating event wherein women, regardless of sexual orientation and preference, gather to socialize, enjoy live music, and savor delicious eats and superb drinks. Spearheaded by Key West Business Guild, this event is a party like no other. There will be lots of games, activities, and photobooths during the festival. Depending on the venue, guests might also be able to soak in stunning pools and bask in the warmth of the summertime sun.

Womenfest Key West

Address: 808 Duval St, Key West, FL

Website: Womenfest Key West

Takes place: September

7. Del Brown Permit Tournament

Many thanks to Christopher Bladen Sculpture for our Grand Champion awards @christopherbladen #delbrownpermittournament #permitonfly #bronzesculpture #lostwaxcasting #keywestfishingtournament

Posted by Del Brown Permit Tournament on Tuesday, 17 July 2018

Enjoy the waters of Key West and be mesmerized by picturesque natural views at Del Brown Permit Tournament. Aside from that, this exciting celebration is like a one big angle party where the best fishers compete in a friendly fishing contest. Attendees will start the celebration with a sumptuous dinner for all. This three-day event covers food and lodging. A party at the local grill is organized for the participants as well. Plus, expect delightful prizes for the winners.

Del Brown Permit Tournament

Address: Key West, FL

Website: Del Brown Permit Tournament

Takes place: July

8. Seven Mile Bridge Run

Seven Mile Bridge, Florida
Source: Photo by user SimonMGC used under CC BY-SA 4.0

Whether you are a fitness enthusiast or a regular Tom who wants to enjoy cardio, Seven Mile Bridge Run might pique your interest. This fun-filled marathon will cover 7 miles (11km) without the presence of vehicle traffic. For a complete experience, you can purchase T-shirts with a logo of the event. First-aid stalls are positioned in several sites along the course. Parking space will not be a problem as there will be enough for participants.

Seven Mile Bridge Run

Address: 9805 Overseas Hwy, Marathon, FL

Website: Seven Mile Bridge Run

Takes place: April

9. Marathon Seafood Festival

Posted by The Original Marathon Seafood Festival on Monday, 25 February 2019

A different kind of marathon compared to Seven Mile Bridge Run, Marathon Seafood Festival might be the weakness of fitness enthusiasts. Ideal for people with a big appetite and those who like eating during vacations, more than sightseeing and museum visits, this delightful festival will treat you to a delicious banquet of seafood dishes that will make you cry happy tears. Yearly, almost 20,000 attendees gather for Marathon Seafood Festival. Aside from food, expect good music that makes festivalgoers dance on their feet.

Marathon Seafood Festival

Address: Marathon Community Park, 200 Ocean, 36th St, Marathon, FL

Website: Marathon Seafood Festival

Takes place: March

Delve deep into the festival scene of Key West

Key West is a breathtaking and vibrant city that is a popular hideaway destination among tourists who want to enjoy leisure activities. Its breathtaking beaches, upscale attractions, and delicious food are what draw people to this side of Florida. But not only that—its captivating party scene is another reason to enjoy a day or two in the city. For some fun things to do in Key West, rent one of the top party boats and enjoy a fun cruise. If you are planning to experience the offerings of Key West, use this list as your guide in creating an itinerary.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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