Worthshop Catamaran Sail - Begin the day together on the water aboard Trilogy’s 54-foot sloop-rigged catamaran, built for comfort and open-ocean performance. Wide decks, shaded seating, and unobstructed views of Kahoʻolawe and Lānaʻi make it easy to relax side by side, soaking in the island’s beauty. Guided by an expert captain and crew, the sail offers time for snorkeling at Molokini Crater and Turtle Town, or simply leaning on the rail with new friends as the island unfolds around you.

Worthshop Surf School - Head into the lineup with local instructors and fellow Worthshop guests, sharing the thrill of Maui’s waves together. Depending on conditions, the group may head north to find the best breaks, trading encouragement and stories between sets. Whether it is your first ride or your hundredth, this is less about perfect form and more about the camaraderie of being in the water, feeling the energy of the ocean, and catching waves alongside one another.

Worthshop Land Adventure - For those who prefer to stay grounded, the Maui by Land option offers a slower start that is still rich in connection. Guests will experience the island’s landscapes and culture together — walking through hidden gardens, visiting local farms, or stepping into sites with stories best shared in a group. It is designed to be restorative, weaving personal discovery with collective moments, a chance to see Maui’s beauty while deepening bonds with your peers.