Island Stories: The Florida Keys’ Top Live Music & Art Festivals

In the Keys, even the tide seems to sing, and every porch becomes a stage.

Festivals here aren’t designed to impress. They’re how the islands breathe. On any given night, songs are traded like stories, art is shaped by sunburned hands, and the line between performer and friend blurs smoothly.

Live music and art gatherings hold a special place in the hearts of locals, and they leave a lasting mark on visitors who stop to listen or wander through. They carry the Keys’ legacy of independence and storytelling—shared in lyrics, brushstrokes, and conversations over drinks and warm lights.

Locals and visitors gather for a lively festival on the Key West waterfront.

Top Festivals in the Keys

Here are some of the most memorable festivals and gatherings that bring the Keys to life, any time of year.

Walk on White (Every Third Thursdays – Year‑Round)
This monthly art walk lights up White Street in Key West from 6 to 9 PM. Galleries, open studios, and street musicians welcome visitors walking the corridor, with new exhibits and creative interactions every single month!

Taste of the Keys (October 1–31, 2025 – Month‑Long Event)
Restaurants and food artisans across the Keys highlight local flavors, special menus, chef collaborations, and culinary events celebrating island ingredients and cuisine.

Fantasy Fest (October 17–26, 2025)
Key West’s most famous festival brings costume parades, themed parties, live music, and a streetfair atmosphere across Duval Street. Expect spectacle, creative energy, and crowds in full display. Note: Fantasy Fest can be rowdy and is designed for adults only.

Zombie Bike Ride (October 19, 2025)
A fun, costumed parade on wheels through Key West. Riders of all ages decorate their bikes, cruise the sunset route, and enjoy live music and spontaneous performances.

Key West’s annual Zombie Bike Ride with hundreds of costumed cyclists.

Local Tips

• For Fantasy Fest, check the annual theme early so you can prepare for costumes!
• For Walk on White, arrive early. Art talks and gallery openings tend to happen before dusk.
• The Zombie Bike Ride is popular, so reserve your bike ahead, decorate it big, and join the parade early.
• During Taste of the Keys, ask for chef specials and pop‑up dinners. They often sell out or run limited hours.

Plan Your Trip

These festivals lead you through to appreciate Key West’s local gems. And to enjoy more of that, Rentalz offers curated vacation homes near the heart of the action. After a day of wandering, dancing, or discovering, a good rest will always be a relaxing reward.

The festivals may end, but their energy lingers in the music and memories the Keys leave with you.