Plan Ahead: Upcoming Key West Events in September and October
With comfortable weather, crystal clear water, and exciting annual events, September and October are the perfect months to plan a visit (and fall in love) with Key West—specifically, the vibrant energy of Duval Street. This main drag of downtown Key West is the place to be in September and October, home to must-see attractions, extravagant celebrations, and lively culture. And with Parrot Key’s ideal location close to this popular destination and its upcoming events, it’s the perfect homebase for your Floridian adventure, complete with a complimentary shuttle service to get you to and from.
Whether it’s your first time visiting or you’re a return traveler looking to fill your itinerary with the most memorable experiences, Parrot Key has got you covered. Discover upcoming celebrations and events you won’t want to miss, for Labor Day weekend and beyond.
“It’s 5 o’clock Key West” Jimmy Buffet Memorial Event
August 29-September 2 | Duval St. Key West, FL
Kick off your Labor Day weekend honoring the pioneer of the Trop Rock movement at a city-wide celebration of rum, music, and stories. This vibrant weekend-long event is dedicated to celebrating the life and legacy of music icon Jimmy Buffett. To commemorate Buffet’s legacy and recognize his influence on Key West’s cultural fabric, an incredible lineup of events are hosted around the island, many of which hold significance for Buffet and his fans. Prepare for paradise perfection with themed events, honorary tours, scenic sailing excursions, incredible food, live entertainment, and special tributes encapsulating the essence of Key West and Buffett’s spirit, including the epic Second Line Procession.
Annual Second Line Procession for Jimmy Buffet
September 1 | Duval St. Key West, FL
The highlight of the memorial weekend extravaganza is the annual Second Line Procession, a lively walking parade complete with a marching band procession. Gear up for a celebratory event featuring a unique procession down Duval Street, culminating with a free “friends of Jimmy” concert experience and fun festival activities.
Brewfest
August 29 – September 2 | Duval St. Key West, FL
For beverage lovers and party seekers alike, Brewfest is a must-add to your Labor Day weekend itinerary. This multi-day festival features beer pairing dinners, pool parties, live music performances and tap takeovers—all leading up to a signature tasting event with over 150 beers available to sip and savor. Many of the scheduled events take place around town at local restaurants, hotels, and bars, making Brewfest an incredible way to experience the best Key West has to offer.
Labor Day
September 2 | Roosevelt Boulevard, Key West, FL
The Florida Keys truly come alive over the holiday weekend, but if you’re looking to trade in your rum runner for waverunners, Labor Day is the perfect time! Escape the festival scene and soak up the sun on the water—the perfect mild weather makes for an unbeatable day. Discover exciting water sports and experiences at Parrot Key Hotel & Villas, from dolphin swims, jet ski and snorkel tours, sunset cruises and so much more. In partnership with Sunset Watersports, we offer exhilarating onsite and nearby excursions that allow you to make the most of your tropical, waterfront Labor Day in Key West.
Fantasy Fest
October 18 – 27 | Duval St. Key West, FL
The biggest party of the year in the Florida Keys happens to be during its quieter season! For an experience unlike any other, get tickets to Fantasy Fest, an annual 10-day party made for fun-loving revelers. What started as a small event of locals has blossomed into an extravagant show of creativity and imagination from travelers around the world, featuring over 60 parties, masked costumes, lively street fairs, and endless libations. The event is best known for its show-stopping Fantasy Fest parade down Key West’s iconic Duval Street. This year’s theme is ‘90s Neon Cosmic Carnival, so prepare your costume and plan accordingly!
Plan Your Ultimate Getaway at Parrot Key
Whether you’re looking to relax and unwind once the celebrations are over or nestle into your own form of paradise, we invite you to sink into the comforts of spacious Key West accommodations at Parrot Key Hotel & Villas this September and October. With incredible waterfront views and lush native landscaping, there’s plenty to admire before and after the day’s events.
Plan your stay in Key West with one of these special offers.
