The Best Festivals of Key West

Annual Key West Festivals to Check Out While Staying at The Laureate Key West

For such a small island - sizing in at just 4.2 square miles - Key West sure knows how to go big when it comes to parties. There’s a festival for all walks of life to be welcomed with open arms. That’s perhaps best demonstrated in the never-ending merry-go-round of eclectic annual festivals that call this southernmost outpost home. Here’s a look at the conch-blowing contests, Hemingway look-alikes, and mind-blowing masquerades to frame a visit to The Laureate Key West around.

The Key West Songwriters Festival May 8 - 12, 2019

If you like grooving on a Sunday afternoon (and Wednesday through Saturday, too), then the Songwriters Festival is for you! Whether it’s blues on the beach in the morning, or powerhouse country rock in the afternoon, the party will be going all day long. With 50 shows and 200-plus artists across some of Key West’s most famous indoor and outdoor venues, it's no wonder this is the largest event of its kind in the world. The festival, dedicated to songwriting, had acts like platinum-selling recording artist Tyler Farr and CMT Award-winning Florida Georgia Line in 2018, and this year’s lineup surely won’t disappoint. Take in a sample of widespread music genres and enjoy as all the acts let you in on the little-known events that inspired each and every tune.

Key West Pridefest June 5 - 9, 2019

Celebrate PRIDE and discover how Key West has come to be one of the most integrated and unique communities in the world. Recognized for its laid-back style and accepting atmosphere, Key West is special place for many. Pride is an event locals and visitors enjoy year after year. With the options to spend time with friends and family or just enjoy the Key West ambiance, Pridefest is an event for all to enjoy - day and night!

Key West International Guitar Festival: Bridges to Paradise June 21- 23, 2019

Embrace your passion as the 4th annual Key West International Guitar Festival bursts on stage in June! Featuring a fusion of master guitarists, music expected to be performed ranges from classical, jazz, latin, blues, folk, and contemporary. With over twenty events, such as dinner concerts, jazz brunch, garden recital, sunset sail serenade, a blues jam, guitar stroll, art gallery concert, attendees also have the opportunity to ‘create your own music’ at the festival. Live life in song this summer!

Mystery Fest Key West June 28-30, 2019

Bringing together renowned mystery writers, aspiring authors, true crime experts and fans in the southernmost city, the 6th Annual Mystery Fest features a who’s-who of award-winning and bestselling mystery authors. Readers get the chance to meet genre-leading authors, collect signed books, and join in on workshops, panels, and presentations. If you enjoy mystery and suspense books, you won’t want to miss the chance to hear Jeffery Deaver as the keynote speaker for the event!

Hemingway Days July 18-21, 2019

Are you an English major looking to come out of your shell? If the answer to that question was yes, then this fest is for you! As many know, Ernest Hemingway spent most of his life in the 1930s writing on the island of Key West. Honoring the American literary giant’s legacy, this event is all about the sea and the old man himself. The bell that tolls loudest in festival-goers’ hearts is the look-alike contest, in which hundreds of white-bearded, cocktail slinging Papa Hemingway doppelgangers ham it up for the crowd (think of it like a beauty contest for old men), then take to Duval Street for a mock bull run. Take in Hemingway’s literary expertise and breezy Key West lifestyle during this annual festival.

23rd Annual Key West Lobsterfest August 8-11, 2019

Celebrate the opening of Lobster Season with the biggest party of the summer! Packed with events for all lobster-lovers, the long weekend starts with a lobster boil on Thursday, a pool party and pub crawl on Friday, and street fair, concert, and brunch on the weekend. Fresh lobster, cold drinks, and live music - what’s a better combination than that?

Key West Brewfest August 29-September 2, 2019

Surf and suds, anyone? Whether you’re a brewmeister with a finely honed palate or you merely love to kick back with a cold one in hand, Key West Brewfest is an event for many to enjoy. You’ll get the chance to sample over 200 beers from 60 local, national, and worldwide vendors at events such as pairing dinners, brunches, seminars, happy hours, pool parties, and late-night after-parties. The Signature Tasting Event, held just below the famous Southernmost market, features the latest craft-erpieces from multiple acclaimed breweries. Even better? This year, all proceeds benefit the Key West Sunrise Rotary of the Conch Republic and their charitable efforts. Drinking beer for a good cause - what’s better than that?!

Fantasy Fest October 18-27, 2019

Calling all Halloween lovers: the Fantasy Fest brings thousands of people to Key West every October for the stretch of 10 days. As a “Halloween warm-up,” the Fantasy Fest is one of the island’s busiest times of the year. A little history on the festival: in 1979, a few local business owners decided to stir up some action with an event that riffed on the only other party-friendly day of the month - Halloween. The once small, but outrageous, costumed march down Duval Street has grown into the 10 days of events, including a street fair, pet masquerade costume contest, drag queen contests, and glamorous balls. With the exception of the Goombay Festival (see below), a lot of these activities aren’t for kids - the full schedule of “Little Black Book” events includes “naughty” bike rides, pajama parties, burlesque shows, and the famous Fantasy Fest Kink Party. Each year there are different themes, from “Freaks, Geeks, and Goddesses” to the plays of Tennessee Williams. To make this year’s festival even better, this year’s theme is “In Tune But Off Key: Celebrating 40 Years of Fantasy!”

Goombay Festival October 18-19, 2019

If you’re looking for a more family-friendly festival, look no further than the two-day Goombay Festival. Being a festival within a festival, and the core family-friendly offering during Fantasy Fest, Goombay celebrates Key West’s Bahamian heritage with Caribbean food, arts, crafts, dancing, face painting, carnival rides, and parades. Goombay is a form of Bahamian music (it’s also the name of a goatskin drum), and the festival is filled to the max with rhythm of all forms: gospel, reggae, calypso, soca, hip-hop, and more. To top off the fun, the Junkanoo Rush, a traditional Bahamian celebration will be performed with costumed marchers and dancers! Centered around the Bahama Village, you’ll find classic Florida Conch architecture in sherbet shades in the 16-block neighborhood, just a short walk from Old Town, and a plethora of great restaurants and shops.

The “Bight” Before Christmas November 20-December 25, 2019

If you love holiday trappings, but you’re not dreaming of a White Christmas, you’ll want to take 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). During the month before Christmas, enjoy the expansive series of holiday events, including the lighting of three Christmas trees - one made with fishing buoys, another with lobster traps, and a nautically themed pine tree - the Classic Car Show, and holiday concerts. We can’t forget the most anticipated event, the Lighted Boat Parade, which takes the glow to another level, giving entrants the chance to go home with more than $20,000 in prizes. Things you can expect: brilliant displays of holiday lights, conch shells, gingerbread men, jumping dolphins, and even a few Grinches. Swap out the snow for sand, the eggnog for a margarita, and make your slice of pie key lime during this Christmas celebration!

The Key West Literary Seminar January 9-12, 2020

For serious readers who just wanna have fun - the Key West Literary Seminar is an event you do not want to miss. Every January, readers come to explore a unique literary theme over the four-day event, with 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. A packed schedule with keynotes, signings, readings, presentations, dinners, and film screenings will have you wishing you never had to leave. An added bonus? The main venue is right on Duval Street, so you won’t have to choose between the literary life and Key West nightlife. You’ll want to jump on this one fast - the January 2019 event sold out several months in advance.

Seafood Festival January 18-19, 2020

We sea food, we eat it! Sample the local catch in a joyful and fun environment at the Seafood Festival. Showcasing the Keys’ commercial fishing industry and local seafood, this family-friendly event provides the freshest seafood available. The fishermen and women in Key West are proud to offer the community a variety of reasonably priced seafood, all at reasonable prices. Between the chef demonstrations, hands-on eco activities, boats on display and live entertainment, you’ll shrimply have a great day!

Key West Food & Wine Festival January 26-February 2, 2020

Did someone say food and wine? Yep, that’s right! This festival features a series of wine and food themed events showcasing a diverse range of wines and inventive cuisine. With over 20 events to attend, such as waterfront tastings, winemaker and chef collaborations, and other local funky events, you’re bound to get a true taste of the authentic Key West. Escape the cold winter months, and get your tickets to this delectable festival starting October 1st.