The Shops celebrates 25 years with month of culture, concerts and luxury experiences

The Shops at Wailea commemorates its 25th anniversary this November with a month-long celebration that honors its legacy as both a luxury destination and cultural gathering place.

Throughout November, guests will encounter a series of special experiences that reflect The Shops’ unique role as a place where culture and luxury converge:

• Live Music in Wailea – Every Wednesday in November, from 4:30 to 6 p.m., the center will host live performances by local favorites including Nevah Too Late, Larry Endrina, Mondokane and Eric Dutter.
• Anniversary Concert with Kalani Pe‘a – Four-time Grammy Award-winning singer and songwriter Kalani Pe‘a headlines a special anniversary edition of the center’s signature Ke Kani Hone O Wailea concert on Friday, Nov. 28 from 5:30 to 7 p.m. His set blends classical, R&B and traditional Hawaiian music.
• Holiday Pop-Ups & Complimentary Gifts – Enjoy seasonal pop-ups including island lifestyle boutique Coconut Ave. Guests can also receive an exclusive 25th anniversary gift-with-purchase sheer mesh tote bag, featuring a plumeria design and complimentary vanity pouch. The tote bag and vanity pouch is available with a minimum $750 purchase.

“As we reflect on 25 years, we celebrate both the world-class brands that call The Shops at Wailea home and the cultural legacy that has made us a true gathering place for Maui,” said Diana Whitt, general manager and vice president property management of The Festival Companies, the management and leasing company for The Shops at Wailea. “This milestone is a reflection of our past and a vision for an even more dynamic future. We extend our heartfelt mahalo to our guests – near and far – and to our dedicated ʻohana at The Shops who make this Center a welcoming place filled with aloha.”

For the past 25 years, The Shops at Wailea has grown into one of Maui’s most distinguished shopping destinations, introducing first-to-market retailers and restaurants such as OluKai, Waikīkī Brewing Company and Aurum Maui, guest favorites like Tommy Bahama and Ruth’s Chris Steak House, while continuing to serve as home to longtime tenants including Louis Vuitton, Gucci, Prada, Bottega Veneta, Tiffany & Co., Na Hoku and ABC Stores.

Beyond its luxury boutiques and chef-driven restaurants, the center has hosted more than 500 complimentary cultural and community events that celebrate Hawaiʻi’s traditions and showcase its talent. Its stage has welcomed multiple major local performers—from the Brothers Cazimero and Amy Hānaialiʻi to Makana, Josh Tatofi, Keali‘i Reichel and Kalani Peʻa.

Over the years, The Shops has also become a gathering place for beloved holiday traditions like Keiki Halloween and Santa’s Arrival, drawing thousands to celebrate together. Today, it remains a cornerstone of South Maui, where residents and visitors alike can shop, dine and immerse themselves in the aloha spirit, surrounded by world-class brands and authentic island experiences.

For more information on anniversary events and offerings, visit theshopsatwailea.com.