When to Visit Key West for the Best Festivals
Plan Your Next Key West Visit Around the City’s Most Fabulous Festivals
A tropical town like no other, Key West is as beloved for its beautiful, shell-strewn beaches and delectable seafood as it is for its lively nightlife and festivals. With its sunny disposition and welcoming atmosphere, it should come as no surprise that the island has never been touched by frost. In fact, it’s one of the sunniest and warmest places in the entire USA.
As such, it’s also a prime party destination. Whether you’d rather watch a dazzling fireworks show on the shore, dance and mingle at a magical masquerade, or sample a dozen different kinds of key lime pie, you’ll find it all, and more, at Mile 0.
1. Key Lime Festival
Five full days of flavorful festivities in early July
Good for: Food, Families
Few events are more uniquely Key West-flavored than the annual Key Lime Festival held every July. Spanning five days and the entire island, this festival offers a veritable cornucopia of events to enjoy. Become the world’s next key lime pie-eating champion, attend a pie hop, or stroll and sip to sample desserts and drinks from all over town. Join a bike tour to burn off a few calories, then indulge in some shopping at a waterside market. If you’re into engineering, there’s even a Pie Drop contest.
While most of the festival is family-friendly, party animals are welcome, too. Venues across the Key host pool parties, pub-style trivia nights, bartending showdowns, and cabaret shows throughout the event.
Key Lime Festival
2. Summer Solstice
A celebration of all things fun in the sun throughout June
Good for: Families, Nightlife
What better place to enjoy the first day of summer than at the Sunshine State’s Summer Solstice celebration in Key West? Starting on June 1st, Mallory Square’s nightly Sunset Celebration takes on a sunny new disposition, with daily festivities ramping up as the solstice approaches (around June 21st).
Peruse art and street performances by local artists and buskers, including jugglers, musicians, magicians, and more. Sip a tropical cocktail or nibble on conch fritters while attending a live painting or craft demonstration. Feeling magical? Craft a flower crown, get a tarot reading, and make a wish. Sunset on the solstice is marked by the sound of a conch shell horn, though the fun will continue well into the night.
Summer Solstice
3. Hemingway Days
A lively late-July tribute to a literary legend
Good for: Couples, Unusual
Ernest Hemingway was born in Illinois, but he penned some of his most memorable works in Key West, where his legacy continues to be celebrated during Hemingway Days. Focused primarily on Duval Street, this five-day festival is worth the trip for literary enthusiasts.
If you’re the rugged sort, compete in the 5k run, paddleboard race, or marlin tournament, and if you look the part, consider entering the lookalike contest. Avid readers should stop by the Art & Historical Society to view rare Hemingway memorabilia, while aspiring writers can enter the Lorian Hemingway Short Story Competition. Whatever you do, don’t miss the “Running of the Bulls,” featuring Hemingway lookalikes racing pretend wooden bulls down the street.
Phone: +1 305-294-5717
Hemingway Days
4. Fantasy Fest
Magical merriment and masquerade marches every October
Good for: Photo, Couples
October is a magical time of year, but few fall festivals are as enchanting or extravagant as Fantasy Fest. Every year, as Halloween draws near, Old Town invites over 75,000 costumed merrymakers to come and party like it’s 1999 for ten full days and nights.
Order a glittering glass of liquid courage and belt out a tune at karaoke, dive into a pool party, or dance the night away at a live concert. Dress your best for the Masquerade March and level up your decorating skills for the Frightful Fantasy Façade contest. While the festival is most often associated with risque revelries like the Kinky Carnival, there are also some family-friendly events, like the Goombay Bash and Zombie Bike Ride.
Location: 922 Caroline St, Key West, FL 33040, USA
Phone: +1 305-295-9112
Fantasy Fest
5. Pride
A kaleidoscopic party and parade in June, celebrating the LGBTQ+ movement
Good for: Families, Photo
Key West’s official motto is “One Human Family,” a beautiful concept perhaps best illustrated by the city’s all-out Pride Week celebration at the end of every June. As inspiring as it is inclusive, this festival illuminates the history of the LGBTQ+ community through educational tours and exhibitions while celebrating contemporary members through Pride-themed performances and parties galore.
During the day, hop on a Gay History Trolley Tour, enjoy bottomless mimosas at a drag brunch, or browse a colorful collection of craft and snack vendors at the bustling street fair on Duval Street. Nighttime is, of course, party time, culminating in the shiniest shindig of all, the Pride Parade, on the festival’s final evening.
Pride
6. 4th July
Patriotic festivities by land and by sea
Good for: Families, Photo
Sand, sun, and sparkling water: America’s Southernmost City is a picture-perfect setting for a fun Fourth of July vacation. While venues across the Key West celebrate with patriotically themed menus and events, the heart of the party lies downtown. As the afternoon wanes, head to the Edward B. Knight Pier for carnival games, face painting, live performances, and more while waiting for nightfall.
The real star of the show is, of course, the fireworks display. Settle down with the kids by the pier for shoreside viewing or book a quick cruise ahead of time to watch the show from the comfort of a catamaran while sipping a margarita and tapping your toes to live tunes.
4th July
7. Harbor Walk of Lights
Bright lights bring a warm glow to the streets through dark December nights
Good for: Families, Nightlife
While most folks flock to South Florida during the winter for sunshine and warmth, it’s at night that Key West really shines during the Harbor Walk of Lights. Beginning in late November and lasting through the end of December, when the sun goes down in Old Town, hundreds of holiday lights go up all along the seawall every night, without fail.
Kick off the holiday season with live music and a lighting ceremony. Past years have seen holidays “trees” made from buoys and even lobster traps used as the ceremony’s centerpiece. Afterward, take a leisurely stroll from Greene Street down to the ferry terminal, sipping a mug of hot chocolate or cider while admiring the dazzling display.
Location: 201 William St, Key West, FL 33040, USA
Harbor Walk of Lights
8. New Year
A uniquely tropical take on a classic winter celebration
Good for: Nightlife, Photo
New Year’s Eve in Key West is like sunset on the beach: a riot of color and light before night falls and a new day, and new year, dawns. In fact, you can enjoy the year’s last sunset on one of two local cruises, one catering to adult partygoers and the other offering a more family-friendly experience.
Meanwhile, on land, the year’s final Sunset Celebration at Mallory Square includes a variety of street vendors and live entertainment, with many nearby venues hosting their own parties as well. Don’t worry about missing the ball drop in Times Square: you can always watch the Lowering of the Pirate Wench, the Dropping of the Conch Shell, or the Red High Heel Drop instead.
New Year
This article includes opinions of the Go Guides editorial team. Hotels.com compensates authors for their writing appearing on this site; such compensation may include travel and other costs.