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Key West Festivals

No matter if you’re searching for a wild extravaganza or family-friendly celebration, Key West has a festival to suit every taste. From drag queens dropping from roof tops to calypso street music and Hemingway lookalikes, these festivals won’t let you down.

Fantasy Fest, known as “the wildest extravaganza in the world,” draws thousands of tourists each October. From parades and costume parties to floats and more, this decadent event gets bigger and naughtier every year.

Fantasy Fest

Fantasy Fest is an exhilarating, colorful and entertaining event held during the last week of October in Key West. This ten-day celebration features amazing costumed events, parties and parades throughout town; with its main attraction being Bud Light Fantasy Fest Parade which draws in tens of thousands of visitors annually.

Experience all that Key West has to offer during this festival! Enjoy events and festivities like the Beach Bash, Zombie Bike Ride, Bahama Village Goombay Festival and more.

Fantasy Fest not only offers fun, but it’s also an opportunity to support local businesses and charities. For instance, the festival hosts the popular Fantasy Facade Contest that encourages both locals and visitors alike to enter their home or business into competition for cash prizes.

Fantasy Fest provides an opportunity for people to express their creativity and imaginations. With so many unique themes spanning this celebration, dressing up as any character you please is simple!

If you’re attending Fantasy Fest, it is essential to be aware of the rules and regulations in place. These measures have been put in place for everyone’s safety and enjoyment at the festival.

Fantasy Fest is not complete without the beloved Float Parade on Duval Street. Here, hundreds of people dressed in elaborate costumes dance along the streets while being serenaded by live music from bands.

Fantasy Fest floats are created by local artists and volunteers, who strive to ensure each float looks and sounds its best. It’s an amazing opportunity for island visitors to get out and view some of the island’s finest artwork up close.

Fantasy Fest’s Zombie Bike Ride is another popular event that draws a large number of zombie fans each Sunday evening. This family-friendly evening in the Florida Keys provides plenty of activities to do while you’re there!

Hemingway Days

Hemingway Days is an annual festival that pays homage to Ernest Hemingway and his legacy. This July-long event offers competitions, literary readings, and plenty of costumed fun! It’s an excellent opportunity to learn about this renowned writer while connecting with locals.

Hemingway is renowned for his many works, such as The Old Man and the Sea and For Whom the Bell Tolls. He also enjoyed fishing and taking trips to Florida’s Keys; spending time in Key West especially, where he fell in love with its natural splendor which he wrote about in several of his books.

Hemingway’s time in Key West saw the development of his passion for deep-sea fishing. His father had introduced him to fishing at an early age, and Hemingway quickly became an avid sport fisherman there, often accompanying friends on fishing trips.

Hemingway Days are an annual celebration that honors the author’s 123rd birthday with events such as a look-alike contest, literary readings and scholarship presentations, an awards ceremony for the Lorian Hemingway Short Story Competition, museum exhibit of rare memorabilia from Hemingway’s life, humorous “Running of the Bulls” parody and three day marlin tournament to remember his deep sea passion.

Be a part of Hemingway Days by joining the Hemingway 5k Sunset Run and Paddleboard Race on Saturday, July 23rd. This 3-mile route winds along the Atlantic Ocean before arriving at Key West’s Southernmost Beach – 1405 Duval St.

Another exciting Hemingway-related activity is visiting the Key West Historic Memorial Sculpture Garden. This breathtaking garden showcases busts of numerous historical figures, including Hemingway. Spend some time here during summer and take in all that beautiful scenery that first attracted Hemingway to this island.

Hemingway lived in Key West for a brief period during the 1930s, but he remained an admirer of its unique lifestyle. While here, Hemingway wrote and drank with friends at Sloppy Joe’s Bar – one of his favorite watering holes on the island – and began developing his writing career, producing some of his best known works.

Key West Songwriters Festival

The Key West Songwriters Festival is a five-day showcase of live music bliss hosted at various bars, hotels, resorts and historic theaters around Key West. It has become one of the largest festivals worldwide since 1997 and continues to draw both tourists and island locals alike. BMI, Rams Head Presents and The Florida Keys Tourist Development Council present this world-class event each May 3-7 with more than 175 performing songwriters showcasing their chart-topping hits in over 50 shows over five days from May 3-7; presented by BMI, Rams Head Presents and The Florida Keys Tourist Development Council; presented by BMI, Rams Head Presents and The Florida Keys Tourist Development Council each May 3-7 with over 175 performing songwriters sharing their chart-topping hits during over 50 shows across 50 venues worldwide

The festival is free to enter, with most shows taking place outdoors at venues such as bars, beaches and boat restaurants. Some require ticket purchases which can be purchased online. No matter if it’s a free show or not, make sure you arrive early to guarantee yourself an ideal seat for the performance!

Ocean Key Resort’s Sunset Pier is one of the most popular places for attending the Songwriters Festival, boasting a picturesque view and always lively atmosphere. Plus, there’s an awesome Tiki Bar where you can enjoy drinks and food while watching performers.

At the Key West Songwriters Festival, there are plenty of places to listen to live music, such as the Key West Theatre and San Carlos Institute. Plus, you can take in the sunset from either a boat or beach while taking in the sounds.

At the festival, you can catch performances by country artists like Luke Combs and Florida Georgia Line, as well as up-and-coming singer Mackenzie Phillips. She has an incredible voice and will surely gain some major exposure in the near future!

Other notable acts include Jelly Roll, Mitchell Tenpenny and Elle King; as well as The Love Junkies (Hillary Lindsey, Lori McKenna and Liz Rose) who will perform at Opal Key Resort and Marina. Michael Ray will also be performing on Duval Street Main Stage while Robert Randolph will host a nightcap at Coffee Butler Amphitheater. Additionally there is free main-stage concert at San Carlos Institute followed by sunset sail aboard Fury Catamaran followed by dinner performance.

Parrot Heads in Paradise

Parrot Heads in Paradise, otherwise known as the Meeting of the Minds, is an annual event that takes place in Key West each November and draws thousands of Jimmy Buffett fans from around the world to honor his music and lifestyle.

Parrot Heads in Paradise is a group of music aficionados that likes to party responsibly while also contributing hundreds of thousands of dollars to various charities. Since 2013, Parrot Heads have raised an incredible $50.5 million and volunteered over 4,013,000 hours for local community and environmental causes across America.

The Parrot Heads in Paradise organization is a Jimmy Buffett fan club that promotes humanitarian and social causes. They host meetings, happy hours and fundraisers to raise money for various causes while participating in both local and national service projects.

In addition to raising money for various charities, they also conduct trash cleanups along local beaches and roads. Furthermore, they volunteer in animal rescue organizations and food pantries as well as participating in Alzheimer’s walks and Relay for Life events.

Parrot Heads are dedicated to Jimmy Buffett’s tropical lifestyle and have an immense admiration for the Florida Keys. Their shared enthusiasm has brought them together as one cohesive unit through their shared appreciation of Jimmy Buffett’s music and passion for the Florida Keys.

Parrot Heads in Paradise is a nonprofit organization with 200 chapters around the United States and beyond. Their motto is “party with purpose” and they organize fundraisers and service projects for various causes.

Key West Festivals and events are some of the most beloved in America. They provide an opportunity to immerse oneself in Florida Keys culture while enjoying fantastic music.

Some of the most popular festivals in Key West include Fantasy Fest, Hemingway Days and Key West Songwriters Festival. Each offers a unique way to experience the island while socializing with fellow fans.

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