Celebrate Valentine’s Day with a night of island music, soulful vocals, and live energy from two standout Hawaiʻi music acts.

High Watah brings their Molokaʻi-born island reggae sound to Maui, blending smooth melodies, modern production, and high-energy live performance. Known for strong crowd connection and a growing presence across Hawaiʻi, the band delivers feel-good music that keeps the room moving from start to finish.

Jason Arcilla is a Maui-raised singer-songwriter whose sound weaves R&B, reggae, and island surf rock influences into an emotionally driven live show. He gained national recognition as a contestant on The Voice Season 24, joining Team Gwen and advancing through the Blind Auditions and Battle Rounds. Back home, Jason’s band is known for powerful vocals, tight musicianship, and undeniable stage presence.

Together, High Watah and the Jason Arcilla Band set the tone for a Valentine’s night filled with good vibes, island soul, and music meant to be felt live. Whether you’re celebrating with your partner or your crew, this is a night made for connection and energy.

Event Details

• Saturday, February 14, 2026 @ Da Playground Maui

• Doors open at 7:00 PM

• 21 & Over

Get ready to keep the celebration going at the 29th Annual Kō‘olau‘lea Official After Party  Join us for a high-energy night featuring After Party with live performances by High Watah and special guests. Happening Saturday, January 17 at The Crown Room—doors open at 9PM, music starts at 10PM. Must be 21 and over to enter. Don’t miss this late-night vibe filled with island sound, good energy, and unforgettable performance.