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 budget 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.
Why Trust Trip101?
✅ Over 50,000 articles reviewed and published by our experienced team
✅ Over 50 years of combined experience researching, writing and reviewing travel articles
✅ Over 40,000 hours spent on research and fact-checking from credible sources (last year’s data)
✅ Optimizing content from data-driven insights collected directly from users on our platform
✅ Focus on authentic and up-to-date information by collaborating with local guides, global travelers and other industry experts
✅ Long-standing partnerships with credible brands like Airbnb, Booking.com, Agoda, Expedia, GetYourGuide, Viator, RVShare and more
✅ Full disclosure on any partnerships or sponsored content
Trip101’s team of writers, editors, and content managers oversees the publication of all travel content, including destination guides, accommodation recommendations, and travel tips. They have extensive experience in the travel industry and no content, written or visual, gets published without a review. Many of our team’s work has also been featured in Travel+Leisure, National Today, The Indian Express, The Telegraph (India), Robb Report, The Adventure Handbook, Tripoto, Korea Tourism Organization, and Korean Ministry of Culture, Sports and Tourism. Some of them are also members of professional organizations like the Society of American Travel Writers and the International Travel Writers and Photographers Alliance.
Each member of the team follows Trip101's methodology and strict editorial guidelines to ensure accuracy, authenticity, and relevance.
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
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
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, MysteryFestKeyWest.com
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
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
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.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
