Are you planning your next Key West adventure and want to ensure it coincides with the most exciting local events? This article aims to guide you through the very best of Key West’s yearly happenings. From the flamboyant Key West Pride Festival to the thrill of the Annual Hemingway Look-Alike Contest, prepare yourself to mark your calendar and join the locals in some memorable and truly unique celebrations. So, get ready to immerse yourself in the vibrant, fun-filled world that is the festival scene of Key West.
Fantasy Fest
Fantasy Fest is one of Key West’s most exciting, wild, and lively events. We’re talking about ten days of non-stop festivities, parades, costumes, and absolutely unforgettable experiences. And it all takes place in the charming, tinsel-laden backdrop of Key West.
History of Fantasy Fest
Fantasy Fest began in 1979. It was created to attract tourists to the island during a typically quiet, but gorgeous season. The idea was to have a Mardi Gras-style festival in October, complete with elaborate costumes, parades, and parties. The festival was a success, and it has been an October staple in Key West ever since.
Highlights of Fantasy Fest
Costume parties, street fairs, and the grand parade are the highlights of the festival. Costumes tend to be creative, and there’s always a yearly theme to inspire attendees. Perhaps the most anticipated event is the Masquerade March, where thousands dress up and celebrate.
Ideal Time to Visit During Fantasy Fest
The best time to visit is during the final weekend. That’s when you’ll get to experience the grand parade, costume competitions, and a bunch of other exciting parties.
Key West Food and Wine Festival
Let us introduce you to the gastronomic delight that is the Key West Food and Wine Festival. Think of it as a warm, sun-kissed vacation devoted entirely to exceptional food and exquisite wines.
Introduction to Key West Food and Wine Festival
This festival is a culinary trait of Key West, taking place annually every winter. It is a series of wine and food-themed events showcasing a diverse range of wines and inventive cuisine, hosted by their passionate creators.
Events and Attractions at the Festival
The attractions of the festival are the wine tastings and gourmet dinners, held at various venues throughout the island. Winemakers and chefs showcase their finest works at these events, providing a truly decadent experience for attendees.
Best Time to Enjoy Key West Food and Wine Festival
The festival usually occurs in late January or early February. It’s a fantastic time to escape the winter chill of mainland USA and indulge in the delights of food and wine under the warm Key West sun.
Hemingway Days
The Hemingway Days Festival is a tribute to the acclaimed author and former Key West resident, Ernest Hemingway.
About Hemingway Days Festival
Held annually during the last week of July, the Hemingway Days Festival celebrates and honors the literary genius and his lifestyle. It’s hosted around the author’s birthday and features a variety of events aimed at replicating the Hemingway-esque atmosphere.
Main Attractions of Hemingway Days
The most notable events of the festival include the Hemingway Look-Alike contest, short story competition, and the Running with the Bulls (a playful, local version). Literati from all over the globe gather here to celebrate and remember Hemingway.
Perfect Time to Attend Hemingway Days
Hosting Hemingway Days in July makes it a summer event, a great time to visit Key West, enjoying the warm sun, clear skies, and the many water-based activities alongside the festival.
Key West Lobsterfest
Lobster lovers assemble! The Key West Lobsterfest is all about celebrating the opening of Lobster Season.
How Key West Lobsterfest Started
As the lobster season begins in August, the fishermen of Key West started a tradition to commemorate their first plentiful catch of the year. This tradition has now morphed into the joyful Key West Lobsterfest.
Things to Do at Key West Lobsterfest
From lobster boils, brunches, and dinners, to pub crawls and concerts, the Key West Lobsterfest is a seafood foodie’s heaven. There is also a street fair and a lively parade to add to the fun.
Best Time to Come for Key West Lobsterfest
Since Lobsterfest coincides with the Lobster Season, the best time to join in is in early August. That’s when you can indulge in all the fresh lobster you can handle, straight from the ocean to your plate.
Key West Film Festival
For film enthusiasts and lovers of the arts, the Key West Film Festival is a must-visit.
What is Key West Film Festival?
Held annually each November, the Key West Film Festival showcases films that exhibit excellence in storytelling and capture Key West’s essence: Creativity, Diversity, Sustainability, and Beauty.
Film Categories and Events
The festival highlights various film categories from features, shorts, documentaries, along with showcasing Florida-made movies and LGBTQ-themed films. The film screenings are accompanied by interactive Q&As with film stars, directors, and filmmakers.
When to Attend Key West Film Festival
The Key West Film Festival is held in November. It’s a great time to combine a love of film with the mild, comfortable weather of late Autumn in Key West.
Key West Songwriters Festival
Next, let’s move on to the Key West Songwriters Festival, one of the largest events of its kind in the world.
Origin of Key West Songwriters Festival
Started in 1997, the Key West Songwriters Festival has grown over the years, now seeing more than 200 acclaimed songwriters in attendance.
Experience at the Key West Songwriters Festival
The festival features songwriters from across the musical spectrum showcasing their skills before an appreciative audience. Attendees have the opportunity to listen to songwriting legends, along with discovering new talented artists.
Ideal Time to be Part of Key West Songwriters Festival
The Key West Songwriters Festival takes place during May. It’s an excellent time to visit as the weather in Key West is warm and sunny, but not quite as hot as the summer months.
Conch Republic Independence Celebration
We cordially invite you to one of the quirkiest events in Key West – The Conch Republic Independence Celebration.
About Conch Republic Independence Celebration
This event celebrates the tongue-in-cheek secession of the Florida Keys from the USA in 1982. It’s a week-long celebration of the independent and eccentric spirit that defines Key West.
Major Highlights of the Celebration
The celebration comprises fun events like the Conch Republic Flag rising ceremony, the Naval Parade and Great Battle for the Conch Republic, and the Conch Crawl.
Perfect Time to join Conch Republic Independence Celebration
The Conch Republic Independence Celebration falls in late April.
So, if you’re in the mood for a unique blend of humor, history, and community pride, April in Key West is the time for you.
The Annual Underwater Music Festival
The Annual Underwater Music Festival gives a truly melodious splash to your vacation with an offbeat, quirky event hosted underwater!
What is the Underwater Music Festival?
It’s exactly what it sounds like! Divers and snorkelers enjoy music broadcast underwater via Lubell Laboratory speakers while they swim and explore the sea life. Held annually at Looe Key Reef, it promotes the preservation of our vital coral reef ecosystem.
Unique Experiences at the Underwater Music Festival
Apart from the music experience undersea, the participants also engage in a show-off of outrageous marine-themed costumes making it an ethereal experience underwater.
Best Time to Visit the Underwater Music Festival
This surreal underwater concert takes place in July. Apart from the music, July is also an excellent time for diving and observing the marine life in the Keys.
Goombay Festival
The Goombay Festival is a splendid introduction to the rich cultural heritage and vibrant history of the Bahamas.
Understanding the Goombay Festival
Goombay is a street party that marks the beginning of the Fantasy Fest weekend. It celebrates the Bahamian and African-American heritage of the historic Bahama Village neighborhood.
Activities and Attractions at Goombay Festival
The festival features indigenous music of the Bahamas, known as ‘Goombay’ music, along with local food stalls, crafts, and Junkanoo rush outs.
When to Enjoy the Goombay Festival
If you want to experience the rich culture of the Bahamas, along with music, food, and festivities, make sure you visit Key west in October right before the Fantasy Fest.
WomenFest Key West
Last but certainly not least is WomenFest Key West, a festival specifically geared towards women.
What is WomenFest Key West?
WomenFest is an end of summer ritual in Key West. It’s a week choc full of a variety of activities that cater to a wide range of interests, all set in a relaxed, welcoming environment.
Highlights and Events of WomenFest
Some of the most popular WomenFest activities include curated film screenings, adventurous sailing, engaging workshops, spectacular sunset shows, and pool parties.
Perfect Timing for WomenFest Key West
WomenFest happens in September, a time when the summer rush has wound down, and the relaxed Key West pace of life takes over once again. It makes the festivities all the more enjoyable and comfortable.
To wrap it up, Key West offers a year-round repertoire of grand celebrations, charming festivities, and quirky traditions that make it one of the most unique destinations to visit. Whether you’re a food lover, a movie buff, a music enthusiast, or an admirer of literature, there’s always an event that will have you planning your next visit to this vibrant and inviting island.
