Key West Events and Festivals Ghost Stories, Literary Haunts, and the Best Month to Wander Key West Every island keeps a few secrets. Key West keeps them in plain sight — in a turret window on Eaton Street, in a coral-rock fort on the Atlantic shore, in the cottages where American literature came to spend the winter. October is when the island (read) Published on Sep 27, 2026
Key West Events and Festivals Your Guide to July in Key West: Key Lime Festival, 4th of July, & Hemingway July is when Key West turns up the color, the flavor, and the festivity. The island spends the month celebrating everything that makes it unforgettable — a sweet-tart pie, a literary legend, and the most laid-back Fourth of July in the country. (read) Published on Jun 15, 2026
Key West Events and Festivals Swap snow for sun, and a winter holiday in your own island paradise The traditional winter holiday season comes with a script: cold weather, crowded airports, tightly packed schedules, and a calendar that somehow feels both full and fleeting. But what if you rewrote it? What if this year, instead of squeezing (read) Published on Jun 07, 2026
Key West Events and Festivals Plan now for October in Key West—and one of the world’s most famous parties! If there’s one time of year when Key West comes alive, it’s October. For more than four fabulous decades, the island’s legendary Fantasy Fest has transformed Old Town into a 10-day spectacle of elaborate costumes, lively parades (read) Published on Mar 31, 2026
Key West Events and Festivals April in Key West brings springtime adventures and The Songwriters Festival Warm breezes, turquoise water and five days of unforgettable music. The legendary Key West Songwriters Festival returns this spring — celebrating 30 years as the largest festival of its kind in the world. For five days and nights, music lovers gather (read) Published on Mar 15, 2026
Key West Events and Festivals Pack your flip-flops and dancing shoes! Book now for the KWSF At its heart, Key West embraces a laid-back, tranquil vibe, but each spring the island turns up the volume for the Key West Songwriters Festival. It’s the largest festival of its kind in the world — yet one of the most intimate music experiences... (read) Published on Feb 25, 2026
Key West Events and Festivals Top Key West Festivals of Late Summer & Fall Rich in natural beauty, colorful history, vibrant culture, unique architecture and bustling nightlife, there are many reasons visitors flock to Key West. Add this to the list: Key West knows how to throw a party, with countless events scheduled each (read) Published on Aug 12, 2024