The Wheeland Brothers + Mike Stack & Friends at Sunset Pier

There’s no better place in Key West to watch the sun go down than Sunset Pier—and on Saturday, it comes with a soundtrack.

As a VIP badge holder perk, early access begins at 5:00 PM—giving you first shot at table seating and time to ease into the evening ahead of the crowd. Come early, grab one of their signature frozen drinks, order from the full menu, and take in the sunset as the night begins to build. Souvenir charity Event Badge holders follow at 5:30 PM, with doors opening to the general public at 6:00 PM.

At Just a Few Friends, honoring Jimmy’s legacy also means embracing the next wave of artists who carry that same spirit of independence and storytelling—even when it doesn’t fit neatly into a single genre. Mike Stack represents that evolution. His breakout track “I’m From Key West” has become a local anthem, capturing the pride, personality, and cultural mix of the island in a way that resonates with both longtime locals and new fans.

That energy takes the stage at 6:30 PM as Mike Stack & Friends kick off the night with a fresh, high-energy set that reflects where the Key West sound is headed—not just where it’s been. Blending hip hop, island vibes, and country influences, Mike is joined by Shareese, Marjory Lee, Pierce August, and D-Lew for a collaborative set full of genre-crossing moments, unexpected mashups, and individual spotlights that build momentum for the night ahead.

As the sun drops, the Wheeland Brothers take the stage, bringing their signature blend of surf rock, reggae, and acoustic storytelling to the waterfront. Part of a new wave shaping the next chapter of the genre, they carry forward that familiar coastal spirit while making it distinctly their own.

You might catch a familiar nod or a Buffett cover woven in, but the heart of the set is their original music—songs built for sunshine, salt air, and living life a little more barefoot. Known for their high-energy performances and natural connection with the crowd, they deliver a sound that feels right at home in Key West while pushing the scene forward.

Different sounds, same setting—sunset, good company, and a night that builds from the first note to a full-on dance floor.

This set is an invitation to lean into something different, discover new sounds, and enjoy the kind of laid-back, anything-goes energy that defines both Key West and this weekend.