Fantasy Fest in Key West

Experience one of the most iconic events in the Florida Keys with Fantasy Fest in Key West, a 10-day celebration of creativity, costumes, and Caribbean-style revelry. Held each October, Fantasy Fest transforms Key West into a vibrant playground of parades, themed parties, live music, and unforgettable street performances along Duval Street.

Photo compliments of Nick Doll Photography.

Key West Songwriters Festival

Discover the stories behind your favorite songs at the Key West Songwriters Festival, the largest event of its kind in the world. Each spring, top country and contemporary songwriters perform in intimate venues across Key West, offering a one-of-a-kind live music experience. From waterfront stages to hidden local gems, this festival brings music lovers closer to the creative process.

Hemingway Days

Celebrate the life and legacy of Ernest Hemingway during Hemingway Days in Key West, held each July. This beloved festival features literary readings, a quirky “Running of the Bulls,” a look-alike contest at Sloppy Joe’s, and events honoring one of America’s most iconic writers.

Conch Republic Independence Celebration

Step into the spirit of the Florida Keys during the Conch Republic Independence Celebration, an annual April event commemorating Key West’s symbolic “secession” from the United States in 1982. This lively festival features bed races, mock sea battles, parades, and plenty of local flavor. It’s a uniquely Key West experience filled with humor, history, and island pride.

Mile 0 Fest Key West

Kick off the year with great music at Mile 0 Fest Key West, a premier Red Dirt and Americana music festival held each January. Featuring a curated lineup of top artists, this multi-day event blends live performances with the laid-back charm of Key West’s bars, beaches, and waterfront venues. Whether you're a devoted fan or discovering new favorites, Mile 0 Fest offers an unforgettable start to the year.

Annual Key West World Championship Superboat Races

High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing.

International Sand Art Competition

Watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving weekend. The competiton brings together incredibly talented sand sculptors from all around the world. The sculptors, each using seven tons of sand, have four days to create their works of art with just sand and water.

Lighted Boat Parades

We love our boat parades! Lighted and decorated vessels from rowboats to tall ships. Dec. 15, 2018 in Key West, 28th Annual Schooner Wharf Bar Annual Lighted Boat Parade. Dec. 9, 2018 in Marathon, Key Colony Beach Lighted Boat Parade. Dec. 8, 2018 in Marathon, Christmas By the Sea Boot Key Harbor Lighted Boat Parade. Dec. 7, 2018 in The Lower Keys, Stock Island Lighted Boat Parade

SkyDive Key West

After jumping from the plane, you will experience the thrill of falling at speeds of 120 mph or more. Once your parachute opens, your dive becomes peacefully quiet, and you will enjoy a five to seven minute ride floating quietly back to earth for a soft, pinpoint landing.

Livin' the Dream Charters

Set sail from the serene shores of Little Torch Key at Parmer's Resort and dive into a day filled with sun, sea, and endless skies. Our exclusive partnership with Livin' the Dream Charters offers private boat tours and Florida Keys fishing charters that promise not only a personal escape into the tranquil waters, but an adventure tailored just for you.

Big Pine & Lower Keys Dolphin Tournament

With over $35,000 in cash prizes and a special cash prize of $20,000 for the largest dolphin over 50 lbs

Underwater Music Festival

Join hundreds of divers and snorkelers every year for an underwater music festival on Looe Key Reef. Broadcast world-wide, many participants come in costume with their own instruments to join in.

Florida Keys Stone Crab Season

Savor one of the Florida Keys’ most celebrated culinary traditions during Stone Crab Season, running from October through May. Known for their sweet, tender meat and sustainably harvested claws, Florida stone crabs are a must-try for seafood lovers visiting the Keys. Local restaurants from Marathon to Key West feature fresh catches served chilled with signature mustard sauce, creating an authentic taste of the region.

Lobster Season

The Keys are filled with Lobster Hunters from all over looking to catch their share. Mini Lobster Season starts at Midnight, the last Wednesday and Thursday in July. Regular season starts on August 6th. Be sure to check to check dates and regulations.

Key West Butterfly & Nature Conservatory

Walk through a magical and inviting environment filled with hundreds of the most beautiful winged creatures in nature. Experience an impressive collection of flowering plants, colorful birds, cascading waterfalls and trees