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15 Best Florida Keys Festivals & Events

florida keys festivals

Boasting a vibrant community, the Florida Keys festivals are like no other. If you haven’t attended any of them, this is your sign to do so!

Rich in culture and tradition, Florida Keys festivals and events play a significant role in shaping the region and its people’s identity and attracting visitors from around the world. We have listed some of the most popular and the ones you must try joining in! These are from the Florida Keys Events Calendar.

Note: The festivals and events below are arranged in chronological order.

Dive Into Art at The History of Diving Museum (Islamorada)

“Dive Into Art: Coral Creations” Exhibit by TV88 MarathonFlorida com

  • Location: 82990 Overseas Hwy (MM83), Islamorada, FL 33036
  • Website: divingmuseum.org

 

Take an artistic “surface interval” between dive trips to see the recently opened exhibit, “Dive Into Art: Coral Creations,” at the History of Diving Museum. The exhibit runs through from January 17 to April 17, 2024. The museum collaborated with Keys artists from the Art Guild of the Purple Isles and students from Key Largo to Key West to produce artwork with a coral conservation theme. 

Visiting the museum is one of the most fun things to do in Islamorada. It’s open from 10 AM to 5 PM every day. Here’s the ticket information:

Admission

Fees

Adults

$15

Seniors (62+)

$13

Children 6-11

$7

Children 5 and Under

FREE

For more information, click here.

Indulge at The Islamorada Seafood Festival & Art Show (Islamorada)

florida keys festivals islamorada

 

The family-friendly Islamorada Seafood Festival & Art Show has grown since its founding. Islamorada Moose Lodge #2151 members created the festival to highlight the fine handcrafts of local and regional artisans and the seafood-focused cuisine of Islamorada restaurants. It draws thousands of visitors from the Florida Keys, South Florida, and beyond. 

The festival’s goal is to raise money for Moose Charities, Local Charities, and Scholastic Scholarships.

Admission: A $5pp donation is appreciated.

Discover hidden-gem beaches,  explore the Florida Keys food scene, find the perfect accommodation, experience the Keys’ stunning waters, and much more.

Dash Through the Seven Mile Bridge Run (Marathon)

Scenes from the 2023 Seven Mile Bridge Run by FloridaKeysTV

  • Location: Packet Pickup – The Faro Blanco Resort and Yacht Club (1996 Overseas Hwy)
  • Website: 7mbrun.com

 

If you’re interested in participating in this event, you can register online, but be quick. They can only accept 1,500 entries. 

For this race, the Seven Mile Bridge will close in both directions from 6 AM to 9 AM on the day of the event. After that, law enforcement will open the bridge to traffic. For the 1,500 runners that compete, the race is an experience of a lifetime.

Learn more about race day details here.

Registration Fee: $100. All proceeds go to children’s organizations.

Commemorate The Conch Republic Days (Key West)

Celebrating Conch Republic Days by Buffer the Tourist

 

Conch Republic enthusiasts and supporters will be able to enjoy a number of events to commemorate the irreverent “nation’s” 42nd birthday. It runs for a couple of days, and here’s a sneak peek of what you can experience during this event:

  •  A tall ship pirate adventure
  • A classic shrimp boil
  • A sunset boat parade
  • A tour of the USCGC Ingham Floating Maritime Museum
  • A staging of the Great Sea Battle of the Conch Republic
  • Performances of “Conch Republic— The Musical”
  • The World’s Longest Parade
  • Drag races on Duval Street

 

The Conch Republic Independence Celebration, held annually, honors the Keys’ momentous 1982 breakaway from the US and subsequent rebirth as the eccentric republic. Get your event tickets and fill out signup forms here.

Catch Rising Stars During Key West Songwriters Festival Week (Key West)

Key West Songwriters Festival 2023 by Rams Head Presents

 

Prominent country music artists often begin their careers at the Key West Songwriters Festival, the biggest event of its sort worldwide. Well-known performers like Randy Houser, Florida Georgia Line, Jake Owen, Michael Ray, Kacey Musgraves, and Maren Morris got their start in music thanks to the event. 

Recently, KWSF has developed into a premier attraction for music enthusiasts who travel to Key West for five days and nights of in-person performances by established songwriters and up-and-coming stars. Tickets are $55 per person. You can book your tickets here.

Wager Through the Skippers Dolphin Tournament (Key Largo)

Skippers Key Largo Dolphin Tournament by Xtreme Outdoors

 

The headquarters of this competition are located at mile marker 100, behind Key Largo’s Holiday Inn, at Skippers Dockside Restaurant. Over $50,000 in cash prizes are up for grabs, including a $20,000 first-place payout plus additional awards for the top six teams, top female anglers, and junior anglers.

Here are the tournament entry fees:

Skippers Dolphin Tournament Entry

Price

Angler Entry – There is no limit to the number of anglers allowed per boat.

$225

Daily Day One

$250

Daily Day Two

$250

Overall

$500

You can register your team or add an angler here.

Celebrate and Support Key West Pride (Key West)

Key West LGBTQ by FloridaKeysTV

 

Celebrate LGBTQ+ rights in Key West, a beautiful island known for its free-spirited vibe and welcoming community. Rediscover Key West and learn how the island has produced one of the most cohesive and distinctive communities in the world, whether your goals are to travel with family, have a good time at the party, or just lose yourself in the allure of the world’s southernmost city.

Read more about dates and ticket information here.

Experience the Tropics at Mango Fest Key West (Key West)

 

This celebration of the sweet indigenous fruit of the Keys and its history offers a chance to experience all mangoes through food delicacies, educational activities, and demonstrations. Enjoy delectable mango-themed delights during special dining events, stroll through Bayview Park’s Mango Mania vendor village, attend lectures, and more. 

The Key West Police Athletic League hosts the festival to raise money for its community-based youth initiatives. This is one of the top free things to do in Key West, but you must register to attend.

Savor a Staple at Key West Key Lime Festival (Key West)

The Key Lime Festival by FloridaKeysTV

 

Every year, Key West hosts the Key Lime Festival, which honors the most amazing citrus in the world. It has an abundance of events held all around the island where Key lime pie originated. 

Lime lovers can enjoy a full schedule of events over the course of five days, which includes a world-famous Key lime pie eating championship at the Southernmost Beach Cafe, located at 1405 Duval St.; a Key lime cocktail sip and stroll; Key lime brunches and dinners; and more.

Check the websites regularly, as tickets will be on sale soon!

Witness the Underwater Music Festival (Big Pine & the Lower Keys)

The 2019 Underwater Music Festival by FloridaKeysTV

 

Learn about coral restoration initiatives at Mote Marine, 24244 Overseas Highway on Summerland Key, at a free welcome event and tour on Friday evening in honor of the Underwater Music Festival’s anniversary. Then, dive and snorkel Looe Key Reef, which is located in the Florida Keys National Marine Sanctuary approximately 6 miles south of Big Pine Key. 

You can come as you are or join the underwater “musicians” dressed in costume. Diver operators in the vicinity can arrange trips. 

Every year, music with an underwater theme is piped in while dressed divers pretend to play fake musical instruments in the underwater setting. The ocean festival, which is being hosted by the Lower Keys Chamber of Commerce and the local radio station U.S. 104.1 FM, promotes ecologically conscious diving, the preservation of the world’s coral reefs, and an underwater experience that is sure to make any diver’s bucket list.

Participants can secure a spot on boats operated by Lower Keys dive operators or launch their own vessels from nearby marinas and public ramps.

Venture Through the Key West Marlin Tournament (Key West)

 

The 42nd annual Key West Marlin Tournament, scheduled for July 17–20, 2024, offers $50,000 in cash prizes for the Marlin Division and additional prizes for the Fun Fish Division. The competition is a world-class fishing event that attracts anglers anxious to try the waters on “The Wall.” It takes place in conjunction with the annual Hemingway Days Celebration in Key West, Florida. 

The event includes nighttime entertainment, such as the iconic Captains dinner, meals on location, an awards banquet, and fantastic fishing and prizes. Only the first 75 boats will be allowed to enter, so sign up immediately to guarantee your spot.

Admission

Fees

Boat Entry (a captain, a mate, two anglers, and four social privileges)

$2,250

Additional social privileges

$150

Additional angler including social privileges (there is no maximum number of anglers per boat)

$250

Boats to compete in the Marlin Division

$450

Taste Test Beers at Key West Brewfest (Key West)

  • Location: Southernmost Beach Resort – 1319 Duval Street, Key West, FL 33040
  • Website: keywestbrewfest.com

 

Southernmost Beach Resort is the host of the multi-day Brewfest event! Dinners paired with beer, pool parties, tap takeovers, and a hallmark tasting event with more than 150 beers are all part of the schedule. Key West visitors should not miss Brewfest since it features events at various restaurants, lodging facilities, and nightclubs across the area!

Fundamentally, Brewfest is a fundraiser organized by the Key West Sunrise Rotary Club in the Conch Republic, a nonprofit organization that addresses local and global problems. The event’s proceeds benefit the Take Stock in Children initiative and local scholarships.

Admission

Fees

General

$45

VIP

$100

Join The Swim for Alligator Lighthouse (Islamorada)

Swim for Alligator Lighthouse in the Florida Keys by FloridaKeysTV

 

One of the world’s hardest swim challenges, the eight-mile round-trip loop around Alligator Reef Lighthouse requires swimmers to finish in as little as seven hours. This tropical open-water swimming event concludes shoreside with an in-water start and a beach finish. 

The 151-year-old structure is situated in the Atlantic Ocean off the coast of Islamorada, and the tournament raises money for its restoration. What a great initiative for Florida Keys lighthouses, right?

Ticket information here:

Events

Registration Fees

Solo Swimmer & Support Kayaker

$240

2-Person Relay

$230

3-Person Relay

$220

4-Person Relay

$210

Get Festive at Key West Fantasy Fest (Key West)

Fantasy Fest 2023 in 4K: The Ultimate Party In Key West by Visit Florida

 

During the two weekends closest to Halloween, Fantasy Fest has filled hotel rooms and showcased local companies, restaurants, and pubs, thereby continuously boosting the economy since its inception. It’s an event that brings adults out to play and celebrates the Florida Keys culture, drawing up to 75,000 revelers annually. 

Fantasy Fest is dedicated to encouraging guests to stay longer by promoting the development of a wide range of events throughout the 10-day celebration. Participants and visitors from the area become excited about the chance to showcase the creative and inventive attitude that characterizes the Keys.

Visit the website regularly and secure tickets once available.

Prepare for a Movie Marathon at The Key West Film Festival (Key West)

Key West Film Festival in the Local News by Key TV

  • Location: 82990 Overseas Hwy (MM83), Islamorada, FL 33036
  • Website: keywestff.com

 

The Key West Film Festival was named one of the top 25 coolest film fests in the world by Moviemaker magazine. It honors modern film every year in a historically significant, artistically dynamic, and culturally varied island community.

With access to some of the largest names in the film industry, KWFF aims to promote the best Florida filmmaking talent while also showcasing visiting filmmakers and industry leaders through discussions and workshops. The festival also aims to provide scholarships and other significant incentives to the next wave of local student filmmakers.

Ticket Pass: $399 per person

Have Fun at The Most Popular Florida Keys Events & Festivals

Overall, the festivals and events of the Florida Keys play a crucial role in preserving and promoting the region’s culture and heritage while also providing a boost to the local economy through tourism. Whether you’re a music lover, foodie, or simply someone looking to experience the laid-back charm of island life, you’ll definitely find something to enjoy in the vibrant Florida Keys community.

So pack your bags, prepare for the road trip (or your plane ride, depending on where you’ll be coming from), and attend the biggest Florida Keys events and festivals!

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Florida Keys Festivals FAQs

The Florida Keys are popular for a variety of reasons. Firstly, they offer stunning natural beauty, with crystal-clear waters perfect for diving, snorkeling, and fishing. The laid-back island lifestyle, rich history, and vibrant culture appeal to visitors seeking relaxation and adventure.

The Keys also boast unique attractions such as the Overseas Highway, which offers breathtaking views as it stretches across the ocean, and iconic landmarks like the Southernmost Point Buoy in Key West.

The big festival in Key West is Fantasy Fest. Held annually in October, Fantasy Fest is a wildly popular event known for its elaborate costumes, lively street parties, and vibrant atmosphere. The festival features a wide range of events, including costume competitions, parades, live music performances, and art exhibitions.

The famous parade in Key West is the Fantasy Fest Parade. As the culmination of the week-long Fantasy Fest celebration, the parade is a highlight for both locals and visitors alike. Participants deck themselves out in elaborate costumes, often adhering to the year’s theme, and march down Duval Street, Key West’s main thoroughfare.

Janelle
Author: Janelle

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