Key West Events

Few experiences capture the spirit of the Florida Keys like lobster season in Key West. Each year, locals and visitors alike gear up for two distinct spiny lobster seasons—a two-day Mini-Season on the last Wednesday and Thursday of July (July 30–31, 2025), followed by the Regular Season, which runs August 6 through March 31. Together, they mark one of the most anticipated times of year in the Keys, when clear waters, warm weather, and the thrill of the hunt create unforgettable days on (and under) the water.

Key Dates

• Mini-Season: July 30–31, 2025
• Regular Season: August 6, 2025 – March 31, 2026

Requirements for Catching Lobster
To join in on the fun, you’ll need a Florida saltwater fishing license and a spiny lobster permit. Regulations require each lobster’s carapace to measure over 3 inches, with a daily limit of six lobsters per person during the regular season. Popular tools for the catch include a tickle stick and lobster net—essentials for a successful dive.
It’s important to stay up to date with the Florida Fish and Wildlife Conservation Commission (FWC) and state regulations, as rules, limits, and protected areas can change from season to season.

Tips for Lobstering in Key West
The most productive time to lobster is late August through October, when waters are warmest and lobsters are most active. The reefs and coral heads surrounding Key West are prime territory for spotting these crustaceans. For newcomers, consider booking a lobstering charter, such as those offered by Tailing Water Expeditions, to get expert guidance and insider tips.

A Foodie’s Paradise
Lobster season isn’t just for divers—it’s also a dream for food lovers. Throughout the season, local chefs across Key West celebrate the catch by creating signature dishes that showcase the sweet, succulent flavor of Florida spiny lobster. From fresh-grilled tails and decadent lobster mac to inventive seafood specials, it’s the perfect time to taste the island’s culinary creativity at its freshest.

Whether you’re diving into the two-day frenzy of Mini-Season, savoring a chef’s coastal creation, or enjoying the long stretch of Regular Season, lobstering in Key West is more than a pastime—it’s a celebration of island life, flavor, and adventure.

Plan your trip, grab your gear (and your appetite), and experience the thrill of lobster season in the Florida Keys.

Fantasy Fest is Key West’s iconic October celebration, transforming the island into a vibrant, anything-goes playground. Since 1979, it’s drawn crowds from around the world with outrageous costumes, themed parties, and unforgettable events.

From the wild Zombie Bike Ride to body painting contests and nightly street parties, each day offers creative chaos and nonstop entertainment. The festivities peak with Saturday night’s grand parade—featuring dazzling floats, bold costumes, and unmatched energy.

Duval Street becomes the heart of the action, buzzing with music, performers, and revelers. Whether you're going all out with a costume or just soaking it in, Fantasy Fest is where fantasy meets reality in unforgettable Key West style.

Experience the ultimate adrenaline rush at the Race World Offshore Key West World Championships, taking place November 2-9, 2025, where the ocean becomes a high-speed battleground for cutting-edge boats and fearless competitors. This world-class offshore powerboat racing event represents the pinnacle of offshore powerboat racing in the Florida Keys.

The championship launches with spectacular fanfare as the First State Bank World's Fastest Boat Parade kicks off at 4:00 PM on Sunday, November 2nd along Duval Street. Race fans can witness meticulously timed high-speed action with race starts at 10:00 AM on Wednesday, November 5th, Friday, November 7th, and Sunday, November 9th.

Watch in amazement as racers reach speeds above 140 mph through the smooth waters of Key West Harbor, with one section of the course running right through the harbor itself. Immerse yourself in the excitement at the Race Village & Truman Waterfront Park, where VIP experiences include waterfront viewing under tents on the water's edge.

The week features an exciting lineup of exclusive parties and celebrations, while the annual Duval Street Party showcases boats on display for the public to see. Spectators with private boats can enjoy the races from out on the water, offering multiple vantage points to witness this spectacular motorsport event.

General admission is attractively priced at $25 per day, with complimentary entry for kids 12 and under as well as military personnel. Don't miss the live broadcasts streaming on YouTube, Facebook, and local radio, capturing every roaring engine, strategic maneuver, and triumphant finish.

Join us for this full-throttle celebration that offers an unmatched blend of speed, style, and competitive spirit in America's southernmost paradise. The Key West World Championships deliver the most thrilling offshore powerboat racing experience in one of the world's most beautiful settings.

The Key West Film Festival—where passion meets paradise—is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community. Taking place November 12-16, 2025, this prestigious event has been named one of "The 25 Coolest Film Festivals in the World" AND a "Top 20 Destination Film Festival" by Moviemaker Magazine.

KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. "The mission of the Key West Film Festival is to showcase films that capture Key West's essence: Creativity, Diversity, Sustainability, and Beauty".

Each January, the Key West Half Marathon & Runfest transforms the island into a runner’s paradise, weaving scenic, coastal routes through historic Old Town and waterfront corridors. With multiple distance options—including 5K, 8K, 10K, and the half marathon—the festival offers something for every level of runner. In 2026, the event takes place January 17–18, complete with fun challenges like the Big Pecker Challenge (complete the 5K, 10K, and half marathon for a special medal) and the Lil’ Pecker Challenge (run the 5K, 8K, and 10K for a fun keepsake hat).

More than just a race weekend, Runfest is a community celebration of fitness, fun, and local culture. Participants get to enjoy the unique spirit of Key West—tropical breezes, cheerful spectators, vibrant neighborhoods—while course spectators and runners alike soak in island charm. The event also includes volunteer opportunities, festivities, and post-race gatherings that bring together athletes and locals.

Experience world-class sailing in paradise at The Southernmost Regatta, January 20–25, in the turquoise waters off Key West, Florida.
This premier international event unites top racing teams from around the world for five thrilling days of high-caliber competition set against the stunning backdrop of America’s southernmost waters.

Open to One Design and ORC Racing/Cruising Keelboats, the regatta features two races per day across dedicated courses—including the J/111 North American Championship, plus competitive action in the J/70 and ORC Performance classes.

The Southernmost Regatta celebrates everything that made racing in Key West legendary: blue-water sailing, island camaraderie, and the chance to reconnect with friends during the winter months. Racers and spectators alike enjoy steady January breezes, warm tropical waters, and the lively spirit that makes Key West unlike anywhere else.

With more than 30 years of sailing tradition, racing in Key West has become more than just a competition—it’s a way of life. Whether you’re on the starting line or cheering from shore, The Southernmost Regatta delivers world-class racing, island hospitality, and unforgettable moments on and off the water.

Join us this January and be part of a Key West tradition where championship sailing meets the beauty and charm of the Conch Republic.

Experience Key West's premier outdoor art celebration at the annual Key West Art and Crafts Festival, proudly sponsored by the Key West Art Center—a nonprofit community arts organization and the island's oldest art gallery.

Set against the stunning backdrop of Truman Waterfront Park in historic Old Town Key West, this juried art and craft show offers an unparalleled setting with sparkling waterfront views. The festival's picturesque location at the Quay provides ample parking for visitors and creates an inspiring atmosphere for both artists and art lovers alike.

Late February's perfect weather draws together an enthusiastic mix of tourists, winter residents, cruise ship passengers, and locals for this highly anticipated annual event. Browse works from carefully selected artists and craftspeople who showcase their talents.

Discover unique artwork while enjoying one of Key West's most beautiful outdoor spaces. Whether you're seeking one-of-a-kind pieces or simply want to appreciate fine art in a spectacular setting, the Key West Art and Crafts Festival promises an unforgettable cultural experience in paradise.

Join us for this celebration of creativity where art meets the sea in the heart of Old Town Key West.

The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. In its 29th year, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.

Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or get lost in the magic of our tropical island, rediscover Key West and discover how one island’s One Human Family philosophy has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!

Where Nashville meets the Keys! Join us for the third annual Mini Music Festival, a one-of-a-kind celebration that perfectly blends the excitement of Florida's spiny lobster mini-season with the authentic sounds of Nashville.

This isn't your typical music festival. Set against the stunning backdrop of Key West's crystal-clear waters and vibrant culture, our intimate gathering brings together talented Nashville artists for an unforgettable long weekend of music, food, and island adventure.

Experience live performances, participate in exclusive songwriting sessions, and indulge in our signature chef's table lobster dinner featuring the freshest local spiny lobster. Spend the day our famous sandbar party, where the music flows as freely as the drinks.

Since our inaugural festival in 2024, we've created a unique tradition that celebrates both the musical heritage of Nashville and the natural bounty of the Florida Keys. Whether you're a country music enthusiast, a seafood lover, or simply seeking an extraordinary island experience, Mini Music Festival offers something truly special.

Limited capacity ensures an intimate, authentic experience you won't find anywhere else. Come for the music, stay for the magic of Key West.

Step into the vibrant world of Ernest Hemingway during Hemingway Days. This annual celebration honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s, where he penned many of his best-known works including "Death in the Afternoon," "For Whom the Bell Tolls," "The Snows of Kilimanjaro," and "The Short Happy Life of Francis Macomber" in his second-story studio at 907 Whitehead Street.

Key West transforms into a vibrant literary and cultural hub during this five-day festival on iconic Duval Street, paying tribute to Ernest Hemingway's enduring legacy and island spirit. The celebration features the world-famous Hemingway Look-Alike Contest at Sloppy Joe's Bar, 201 Duval Street, a frequent hangout for the legendary writer during his Key West years.

Festival Highlights Include:

The renowned Lorian Hemingway Short Story Competition, which has supported emerging writers since 1981, coordinated by Ernest's granddaughter. Daily tours of Hemingway's historic home provide a captivating glimpse into his fascinating life.

The thrilling Key West Marlin Tournament offers $50,000 in cash prizes and attracts up to 75 registered boats and their crews, recalling Hemingway's passion for deep-sea angling. The wacky "Running of the Bulls" features past contest winners dressed in their Pamplona best with a breed of "bull" found only in Key West.

The lively Caribbean Street Fair showcases local artisans and delectable cuisine, benefiting Literacy Volunteers of America Monroe County. The festivities culminate in the Papa Birthday Bash featuring signature drinks and a spirited Hemingway Rum Bar Stroll across eight distinct Key West locations, each serving a signature rum drink.

Additional events include literary readings, a 5K run and paddleboard race that salute Hemingway's sporting interests, and a presentation on 1930s Key West commemorating the 126th anniversary of Ernest's July 21 birth.

This isn't just a contest of physical resemblance; it's a celebration of Hemingway's larger-than-life persona, where contestants are judged not only on their physical similarity but also on their embodiment of his spirit and zest for life. This Key West cultural festival seamlessly blends literary homage with island charm, offering a dynamic experience for both literary enthusiasts and adventure seekers alike.

Join us for this internationally recognized celebration where the spirit of Ernest Hemingway lives on in paradise!