If you’re looking for the best things to do in Key West, you have come to the right place! We’ve got a list of the top twelve incredible Key West festivals that light up the island each month!
From delicious food and wine fests to festivals all about music and fun, and everything in between, there are always amazing Key West events waiting for you no matter what time of year you visit!
Key West Food & Wine Festival – January
Prepare your taste buds for an unforgettable culinary journey at the Key West Food and Wine Festival, where Key West’s funky spirit really comes alive!
This annual extravaganza is a tantalizing celebration of all things gastronomic.
Sip exquisite wines while enjoying breathtaking waterfront views as the sun sets over the horizon and experience the magic of winemaker and chef collaborations, where innovative flavors are born through their passionate artistry. Doesn’t that sound just like what the doctor ordered? We think so too!
Key Western Fest – February
Get ready to experience the ultimate music festival with Key West’s Key Western Fest, held every February!
This four-day celebration of music, sun, and sand is a dream come true for music lovers, with the island coming alive from morning til night with the vibrant sounds of classic country tunes!
During the day, bask in the glorious sunshine while savoring delicious bites from renowned restaurants. And as the sun sets, let loose on a live-music sail aboard a comfortable catamaran or sing your heart out under the starry sky at the breathtaking Truman Waterfront Amphitheater!
St. Patrick’s Day – March
Channel your inner Irish luck and make memories that will last a lifetime during the St. Patrick’s Day festivities in Key West.
Join fellow revelers for the annual St. Patrick’s Day Bar Stroll with live-music, Irish-themed delicacies, and plenty of Guinness to go around, or attend one of the many thrilling parties and prepare for a whirlwind of laughter, joy, and merriment as the island comes alive with the true spirit of the Emerald Isle!
Explore up the Keys! Florida Keys Island Fest – April
Florida Keys Island Fest is an extraordinary weekend filled with art, music, delicious food, captivating cars, and delightful family entertainment!
Featuring a multitude of events, including The Plantation Yacht Harbor Arts and Crafts Show, the tantalizing Taste of Islamorada competition, and the All-American Road Vintage Cruisers Car Show, this festival truly offers something for everyone. There are also sand-castle competitions, kite-flying, and an array of awesome beach activities to enjoy!
The Songwriters Festival – May
With over 50 free shows featuring more than 200 talented songwriters, the Key West Songwriters Festival is a paradise for music enthusiasts, and what sets this festival apart is that 90% of the performances are free, allowing you to experience an abundance of incredible music without breaking the bank!
This festival focuses on singer-songwriters, and many former past performers have since become big-name acts thanks to the publicity this festival offers! This festival is committed to supporting local businesses and keeping the event rooted in the local community, which makes it better!
Mango Fest – June
Prepare for delicious fruity fun with Mango Fest Key West in June! This Key West event celebrates the magnificent mango in all its glory!
Take a stroll through Bayview Park, where you can peruse the offerings of local vendors, admire captivating artworks at galleries, and savor delectable mango-infused dishes that showcase the versatility of this King of Fruits!
Hemingway Days – July
Celebrate everything Ernest Hemingway at the annual Hemingway Days events in Key West every July!
The festival pays homage to Hemingway, who resided on the island during the 1930s and created some of his most iconic literary works there.
Experience the essence of Hemingway’s connection to Key West as he used the island’s backdrop for his acclaimed novel “To Have and Have Not” and visit the museum that was once Hemingway’s Key West home, where he penned several of his masterpieces!
This is a week filled with camaraderie, inspiration, and a deep appreciation for the remarkable contributions of this literary giant.
Plan Your Visit
Find the perfect place to call home during your festival adventure with Historic Hideaways! Our Key West vacation rentals put you close to all the best beaches, attractions, and festivals while still giving you all the privacy you need during your stay. Start planning your Key West getaway today and experience a vacation like no other!
Lobster Fest – August
Dive into lobster-filled fun that will leave you with unforgettable memories kicking off Lobster Season with the most incredible summer party at Key West’s August Lobster Fest!
Indulge in an authentic Lobster Boil, elevate your dining experience with a sumptuous 5-course lobster dinner, or soak in the lively Street Fair’s atmosphere as you enjoy all things lobster!
Key West Brewfest – September
Raise those glasses and celebrate the spirit of Key West at Brewfest, the ultimate beer-lovers extravaganza!
This multi-day festival is held every September and is packed with exciting events that will have you buzzing with joy.
Indulge in delectable beer pairing dinners, make a splash at the Pineapple Pool Party and Belly Flop Contest, or savor a delightful 5-course Beer Pairing Dinner with FL Keys Brewing at the Southernmost Beach Resort.
The highlight of Brewfest is the not-to-be-missed Signature Tasting Festival at South Beach, where you can explore a vast selection of over 100 beers available for tasting!
Fantasy Fest – October
Get ready for the ultimate grown-up playground as Key West transforms into a vibrant and exhilarating party paradise during the annual 10-day extravaganza known as Fantasy Fest!
What began in 1979 as a brilliant idea by a small group of locals to bring life and energy to the island during its quiet season has now evolved into an unmatched celebration of fun and imagination.
With a blend of creativity, costumes, parades, and endless excitement, this October extravaganza is an unforgettable experience you won’t want to miss out on!
Key West Film Festival – November
Prepare to be transported into a world of cinematic wonders as the Key West Film Festival brings together passion, artistry, and the breathtaking beauty of Key West for an unforgettable celebration of the silver screen!
With access to some of the biggest names in the film business, this festival is dedicated to shining a spotlight on the incredible talent of Florida filmmakers while also providing a platform for visiting filmmakers and industry leaders to share their insights through engaging discussions and enriching workshops.
Coast Is Clear Music Festival – December
Emerging in 2017 as a heartwarming response to the aftermath of Hurricane Irma’s impact on The Keys, the COAST Is Clear Concerts were born with a mission to uplift the spirits of the local community.
This cherished annual event takes place on the first weekend of December, symbolizing the official conclusion of the Atlantic Hurricane Season and the reassuring notion that the “coast is clear.”
At this festival, music, art, and unity thrive, providing a platform for both emerging talents and renowned artists to showcase their craft and inspire the community.
Book Your Key West Rental with Historic Hideaways
At Historic Hideaways, we offer luxurious rentals in Key West that will bring your getaway to life, and as a trusted local vacation rental provider for over 25 years, we bring you the best in Key West!
Dive into the refreshing tropical surroundings, soak up the sun, and indulge in peaceful evenings in our charming Key West rental accommodations. No matter what kind of vacation you plan, have the perfect rental house in Key West for your getaway. From our two-bedroom Key West rentals, perfect for a family getaway or trip with friends, to our three-bedroom Key West rentals with more than enough room for everyone in your travel group!
There’s no end to the awesome things to do in Key West, with a different fun and exciting festival every month of the year, anytime is the perfect time for a beach getaway! What are you waiting for? Book your perfect Key West vacation rental with Historic Hideaways, and make your dream vacation a reality today!