Maui Arts & Entertainment

The Shops at Wailea Welcomes the Holiday Season with Santa Arrival & Signature Events

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The Shops at Wailea kicks off the holiday season on Black Friday with a host of festivities including a Santa Parade, photos with Santa, a community food drive, and a live concert from 14-time Nā Hōkū Hanohano Award winner Mark Yamanaka.

  • Nā Hōkū Hanohano Award winning band Kanekoa.
  • Napua Grieg.
  • Festive Parade, Santa Photos, and Community Food Drive Keep Holiday Spirit Alive. PC: The Shops at Wailea
  • Center-Wide Renovation now complete. PC: The Shops at Wailea
  • Center-Wide Renovation now complete. PC: The Shops at Wailea

“We’ve put together a fun-filled holiday event schedule that we hope inspires guests of all ages to embrace the magic of the season, while serving as a reminder to enjoy each moment spent with friends and loved ones,” said Diana Whitt, General Manager and Vice President Property Manager of The Shops at Wailea. “From a festive parade and photos with Santa to live concerts and holiday performances, we welcome everyone to celebrate the joyful season here at The Shops.”

The festivities begin on Black Friday, Nov. 25, with a special parade to welcome Santa’s arrival. In partnership with Maui Classic Cruisers and Street Bikers United, Santa will be escorted from Kalama Park at 10 a.m. to The Shops in style in a vintage cruiser. To welcome Santa, a special Holiday Hula performance will take place at The Shops at 10:30 a.m. 

The celebration continues in the evening with a complimentary concert performance by 14-time Nā Hōkū Hanohano Award winner, Mark Yamanaka. The “Ke Kani Hone O Wailea” holiday concert will take place in the Lower Valley Performance Area at 5:30-7 p.m.

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Beginning Saturday, Nov. 26, families and guests can capture holiday memories with free Photos with Santa. Santa’s elf will be handing out complimentary Peppermint Macadamia Nut Cookies from Honolulu Cookie Company as an added treat. There will also be a special evening of giveaways on Thursday, Dec, 22, from 7-8 p.m., when Santa will be strolling The Shops, giving away bags of gifts and merchant gift cards to random guests.

In the spirit of the giving season, The Shops at Wailea has partnered once again with Maui Food Bank for a holiday food drive, Aloha Can Make a Difference. Most needed food items include canned meat and tuna, canned fruits and vegetables, cereal, soups with proteins, rice and pasta. In-kind donations will be accepted in conjunction with the Photos with Santa schedule. 

Photos with Santa and Holiday Food Drive schedule is as follows:

  • Saturday, Nov. 26, 4-7 p.m.   
  • Wednesday, Nov. 30, 4-7 p.m.
  • Saturday, Dec. 3, 4-7 p.m.
  • Wednesday, Dec. 7, 4-7 p.m.
  • Saturday, Dec. 10, 4-7 p.m.
  • Wednesday, Dec. 14, 4-7 p.m.
  • Saturday, Dec. 17, 4-7 p.m. 
  • Thursday, Dec. 22, 4-7 p.m.
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“In the spirit of the giving season, we invite our guests to join us in making a difference in our community,” added Whitt. “Together, we can create meaningful holiday celebrations and traditions with those around us.”

Guests can experience holiday entertainment the entire season with holiday-themed live music performances from vocalists and musicians throughout December. 

Holiday Entertainment (December)

  • Kalama Intermediate Band & Ohana – Friday, Dec. 2 | 5:30-6:30 p.m.
  • Maui Brass Ensemble Full Band Concert – Saturday, Dec. 3 | 4-5 p.m.
  • Holiday Jazz at The Shops featuring Rock Hendricks – Saturday, Dec. 3 from 5:30-7 p.m.
  • Kamehameha Ukulele Band – Friday, Dec. 9 | 5:30-6:30 p.m. 
  • Maui Waena 8th Grade Symphonic Band – Dec. 10 | 6-7 p.m. 
  • Festival of Harps – Sunday, Dec. 11 | 5-6:30 p.m. 
  • Festival of Harps with Madrigal Singers in Costumes – Saturday, Dec. 17 | 5-6:30 p.m. 
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Wailea Wednesdays, a complimentary holiday live music series featuring local artists, includes:

  • Mele Kalikimaka Performance – Alika Nako’oka – Wednesday, Dec. 7 | 4:30-6 p.m.
  • Mele Kalikimaka Performance – Tarvin Makai – Wednesday, Dec. 14 | 4:30-6 p.m.
  • Christmas Esque Performance- Anthony Pfluke – Wednesday, Dec. 21 | 4:30-6 p.m.
  • Mele Kalikimaka Performance – Ron Kuala’au – Wednesday, Dec. 28 | 4:30-6 p.m.

A special holiday concert performance featuring Napua Grieg and her Hālau will take place on Friday, Dec. 23 from 5:30-7 p.m. Grieg has received Nā Hōkū Hanohano Music Awards for Female Vocalist of the Year, Hawaiian Album of the Year and Best Female Vocalist. And on Friday, Dec. 30 from 5:30-7 p.m., the signature “Ke Kani Hone O Wailea” concert welcomes Maui’s Nā Hōkū Hanohano Award winning band Kanekoa. Powered by electric ukuleles and exotic rhythms, these ukulele masters ride the wave of Hawaiian roots with jam band energy, creating a unique sound they call Hawaiian jam-rock. 

Events are complimentary and subject to change. More than a world-class shopping and dining destination, The Shops at Wailea is a gathering place for celebrating life in Hawaii. The Center’s special events and entertainment are designed to enrich the community through exploration and discovery of arts and culture. For more information, visit www.theshopsatwailea.com.

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