Island Sotheby’s International Realty is thrilled to welcome back Maeghan Pocock, a seasoned Broker Associate whose career is rooted in a passion for people, community, and exceptional service. With years of hands-on experience working alongside Maui’s top agents and a strong foundation built on education and client care, Maeghan returns to ISIR with fresh energy and a deep sense of purpose. Her love for Maui’s Upcountry lifestyle, commitment to continuous growth, and belief in the power of connection shine through in every relationship she builds. As Maeghan embarks on this exciting new chapter, she remains dedicated to helping clients achieve their real estate dreams—delivering trusted guidance, heartfelt service, and the spirit of aloha at every

May on Maui is a time of renewal, connection, and celebration. From time-honored cultural traditions to lively music festivals and community fundraisers, the island comes alive with events that reflect the aloha spirit and the diversity of our community. Whether you're stringing flowers on Lei Day, enjoying classical music in historic churches, or sipping craft beer under the stars, there's something for everyone to experience.

May 1 – Lei Day Celebrations

Various locations across Maui

All day

Lei Day is a cherished Hawaiian tradition celebrated annually on May 1st. Established in 1929, the day honors the cultural significance of the lei, symbolizing love, friendship, and the aloha spirit. Festivities include lei-making workshops, hula

Spring and summer in South Maui bring warm breezes, golden hour sunsets, and the kind of island ambiance that makes every meal feel like a mini vacation. Whether you’re sipping mai tais at happy hour, indulging in a locally sourced brunch, or enjoying a romantic dinner under the stars, Kihei and Wailea offer a vibrant lineup of al fresco dining experiences that highlight the beauty and flavor of Maui. Here are eight of the best outdoor dining spots to check out when you're craving fresh air and flavorful fare. 

1. Monkeypod Kitchen by Merriman – Wailea

10 Wailea Gateway Place Kihei

Open everyday: 11am - 10pm

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A staple in the Wailea dining scene, Monkeypod Kitchen delivers a lively atmosphere with an expansive