Key West Festivals

Stay Steps from the Party at our Waterfront Resort in Key West!

Perhaps best known for it’s wild side, Key West knows how to throw a party. Explore some of the annual Key West Festivals to check out while staying at Margaritaville Key West Resort & Marina!

Fantasy Fest

October 18 - 27, 2019

Every October, the Fantasy Fest brings thousands of adults to Key West for the wildest extravaganza around. Dating back to 1979, a few local business owners decided to create an event that would bring visitors to the island in a typically quiet season and it has grown every year since. Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! Keep in mind that with the exception of the Goombay Festival (see below), a lot of these activities aren’t for kids.

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Goombay Festival

October 18 - 19 2019

In contrast to the typical Fantasy Fest events, the two-day Goombay Festival offers fun the whole family can take part in. If you’re wondering what Goombay is, it’s a form of Bahamian music and the festival is filled to the max with rhythm of all forms: gospel, reggae, calypso, soca, hip-hop, and more. Key West’s Bahamian heritage is celebrated with Caribbean food, arts, crafts, dancing, face painting, carnival rides, and parades. To top off the fun, the Junkanoo Rush, a traditional Bahamian celebration will be performed with costumed marchers and dancers!

The “Bight” Before Christmas

November - December 2019

If you are a holiday enthusiast with visions of expansive holiday lights and decorations (with a topical twist) dance in your head, you won’t want to miss a trip down to Key West’s Bight (a bend in the shoreline on the northwest side of the island that creates a naturally protected harbor, from Green Street to the Ferry Terminal). Starting on November 27th, you can see the lighting of the fresh pine Nautical Christmas Tree, the Fishing Buoy Tree, and the Original Key West Lobster trap. Holiday concerts, the Classic Car Show, and the Lighted Boat Parade are just a few of the events you won’t want to miss this holiday season. Swap out the snow for sand this Christmas season!

The Key West Literary Seminar

January 9th - 12th, 2020

Every January, Key West welcomes readers and writers from all corners and backgrounds to explore a unique literary theme over the four-day event. Presentations by some of the world’s most renowned writers - from big kahunas like Margaret Atwood and Jamaica Kincaid to fantasy writer Marlon James and young-adult-book legend Meg Cabot of Princess Diaries fame. The schedule is packed with keynote speakers, singings, readings, presentations, dinners, and film screenings that will not leave you disappointed.

Seafood Festival

January 18 - 19, 2020

The Seafood Festival is a family-friendly event that provides the oppor-tuna-ty to sample the local catch in a joyful and fun environment. The festival showcases the Key’s commercial fishing industry and local seafood. The fishermen and women in Key West offer the community a variety of seafood at reasonable prices. Boasting a weekend filled with chef demonstrations, hands-on eco-activities, boats on display and live entertainment, we know this has you hooked!

Key West Food & Wine Festival

January 26 - February 2, 2020

Love food? Love wine? Look no further! The Key West Food & Wine Festival features a series of wine and food-themed events showcasing a diverse range of wines and inventive cuisine. The festival boasts over 30 unique events including waterfront tastings, winemaker & chef collaborations, and other local events. Tickets are available starting October 1st!

The Key West Songwriters Festival

May, 2020

For those that like to groove to live music, then the Songwriters Festival is for you! This is the largest event of its kind in the world, with 50 shows and 200-plus artists across some of Key West’s most famous indoor and outdoor venues. The festival is dedicated to songwriting and offers festival-goers a sample of widespread music genres and the opportunity to hear straight from the artists about little-known events that inspired every song!

Key West Pridefest

June, 2020

Key West is consistently recognized as one of the most integrated and unique communities in the world. What better way to celebrate PRIDE and diversity than on a tropical island known for its laid-back style and accepting atmosphere! Events include dance and cocktail parties, contests, shows, tours, a street fair and the Pride Parade that runs its course along Duval Street.

Key West International Guitar Festival: Bridges to Paradise

June, 2020

Taking place in historic venues across the island, the Key West International Guitar Festival features a fusion of master guitarists performing classical, jazz, Latin, blues, folk, & contemporary music. This rockin’ festival is comprised of over twenty events, including dinner concerts, jazz brunch, and a sunset sail serenade. Relax, enjoy, and even participate in this musical event!

6th Annual Mystery Fest Key West

June, 2020

If you enjoy mystery and suspense books, this is a festival you won’t want to miss! Renowned mystery writers, aspiring authors, rue crime experts, and fans meet in the southernmost city for the 6th Annual Mystery fest. Festival-goers get the chance to meet genre-leading authors, collect signed books, and join in on workshops, panels, and presentations.

39th Annual Hemingway Days

July, 2020

Did you know that America’s literary giant, Ernest Hemingway, spent most of the 1930’s living and writing on the island of Key West? Ernest Hemingway wrote many of his best-known works in the second-story studio he lived in during his time on the island. This event brings in Ernest Hemingway look-alikes, writers, anglers and fans of the late author’s work together on Key West. One of the most noteworthy events in the look-alike contest, in which hundreds of white-bearded, cocktail slinging Papa Hemingway doppelgangers ham it up for the crowd, then take to Duval Street for a mock bull run.

23rd Annual Key West Lobsterfest

August, 2020

Are you a lobster-lover? If you answered yes - you won’t want to miss the biggest party of the summer that commemorates the start of Lobster Season! Packed with events, the long weekend starts with a lobster boil on Thursday, a pool party and pub crawl on Friday, and a street fair, concert, and brunch on the weekend. Is there a better recipe for a great weekend than fresh lobster, cold drinks, and live music?

Key West Brewfest

August - September, 2020

Do you enjoy a nice, cold beer? How about the chance to sample over 200 beers from 60 local, national, and worldwide vendors? The Brewfest has events including pairing dinners, brunches, seminars, happy hours, pool parties, and late-night after-parties. The Signature Tasting Festival Event, held just below the famous Southernmost market, features the latest crafted pieces from multiple acclaimed breweries. No matter your style, the Key West Brewfest has something on tap for everyone!