Maui Arts & Entertainment

Holidays at The Shops at Wailea: Black Friday Promotions, Santa Photos

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The Shops at Wailea has a host of 2019 holiday events. Kicking off with the arrival of Santa on Black Friday, Nov. 29, The Shops at Wailea holiday festivities continue with special events and entertainment through Dec. 24.

Visit with Santa at The Shops at Wailea. PC: courtesy.

Black Friday Promotions

Holiday celebrations commence with Santa’s Parade, which progresses from Kalama Park in Kīhei to The Shops at Wailea, starting at 9:30 a.m. Santa will ride in style in a 1963 Cadillac Eldorado convertible escorted by the Maui Classic Cruisers and Street Bikers United Maui, with an estimated arrival time of 10 a.m. at The Shops at Wailea.

Following the parade, holiday photos with Santa will be taken by the professionals at Pacific Dream Photography in the Fountain Courtyard, from 11 a.m. to 7 p.m. Throughout the day, the Honolulu Cookie Company will provide free holiday cookies to Santa’s visitors, while supplies last.

The first 100 Black Friday customers will receive a complimentary holiday gift bag from The Shops at Wailea. The holiday bag giveaway will take place at the main fountain courtyard following Santa’s arrival. The holiday bag will also be promoted as a free gift for shoppers who spend a minimum of $500 at The Shops at Wailea through Jan. 1, while supplies last.

Live entertainment on Black Friday includes a holiday hula show featuring dancers from Manutea Nui E at 10 a.m. Cultural activities including island wood carving and ukulele lessons will be available during the day, culminating with a performance from Kamehameha School’s Ukulele Band from 6 to 7:30 p.m.


Santa’s Visiting Hours: 

From Nov. 29 to Dec. 24, photos and visits with Santa are available daily. Photo opportunities are scheduled as follows:

  • Nov. 29 to Dec. 1: 11 a.m. to 7 p.m.
  • Dec. 2 to Dec. 19: 1 to 7 p.m.
  • Dec. 19 to 24: 11 a.m. to 8 p.m.

“Paws and Claus” pet photos with Santa will also be available Mondays from 4 to 7 p.m. from Dec. 2 to 16.

Holiday Happenings

A Holiday Toy Drive will be held as part of The Shops’ partnership with Friends of the Children’s Justice Center, where new, unwrapped toys will be collected to support families in need in Maui County. Collection bins for donation drop-offs will be available at all center entrances from Nov. 29 through Dec. 15.


Gift wrapping will be offered from Dec. 19 to 23 from 10 a.m. to 9 p.m. and on Christmas Eve, Dec. 24 from 10 a.m. to 6 p.m. Complimentary gift wrapping for purchases made at The Shops at Wailea is provided by Gamma Chapter of Hawaiʻi Alpha Delta Kappa. Donations are appreciated and will go towards college scholarships for Maui high school students.

Daily Entertainment for the Holidays: Through the holiday season, visitors can enjoy daily entertainment, scheduled as follows:

  • Kamehameha School’s ʻUkulele Band on Friday, Nov. 29 from 6 to 7:30 p.m.
  • Maui Brass Ensemble on Saturday, Nov. 30 from 5 to 6:30 p.m.
  • Holiday Jazz with Guitarist Prem Brosio & Friends on Sunday, Dec. 1 from 5:30 tp 7 p.m.
  • Maui Community Band on Saturday, Dec. 7 from 5 to 6:30 p.m.
  • Festival of Harps on Sunday, Dec. 8 and Saturday Dec. 14 and 21 from 5:30 to 7 p.m.
  • “The Joyful Hearts” sing-along caroling lead by Bonnie Newman on Dec. 15 from 5:30 to 7 p.m.

Free Weekly Cultural Activities

Except on Christmas Day, The Shops at Wailea’s regular free weekly cultural activities will continue throughout the holiday season, scheduled as follows:

  • Papa Hula: Mondays 1 to 2 p.m.
  • Lei Poʻo Making: Mondays 2:30 to 3:30 p.m. and Wednesdays 1:30 to 2:30 p.m.
  • ʻUkulele Lessons: Mondays 5:30 to 6:30 p.m. and Fridays 3 to 4 p.m.
  • Coconut Husking: Tuesdays 2:30 to 3:30 p.m.
  • Island Wood Carving: Wednesdays 10:30 a.m. to 1 p.m. and Fridays 12:30 to 3:30 p.m.
  • Polynesian Show: Tuesdays and Thursdays 5:30 to 6:30 p.m.
  • Coconut Frond Weaving: Thursdays 2:30 to 3:30 p.m.
  • Pau Hana at The Shops: Fridays 4 to 6 p.m.
  • Jazz at The Shops featuring Rock Hendricks on Wednesday, Dec. 4 from 5:30 to 7 p.m.
  • Market at The Shops: Wednesday Dec. 11 and 18 from 4 to 6 p.m.
  • Concerts at The Shops with Nāpua Greig: Wednesday, Dec. 18 from 5:30 to 7 p.m.

Nonprofit Beneficiaries: Hālau Ke’alaokamaile and Friends of the Children’s Justice Center


In a continued effort to give back to the community, The Shops at Wailea supports a different Maui non-profit each month with a portion of the special event parking fees going to the selected charity.

The non-profit recipient for the month of November is Hālau Ke’alaokamaile. Created by Kumu Hula Keali‘i Reichel, Hālau Ke‘alaokamaile’s mission is to perpetuate the Hawaiian tradition, culture and heritage through its arts, beliefs, dance, language and agriculture.

The non-profit recipient for the month of December is Friends of the Children’s Justice Center of Maui, whose mission is to promote community awareness of child abuse and or neglect, to support the Children’s Justice Center and to provide the much needed services to help these children recover from the damaging effects of their abuse.

The Shops’ signature events are designed to enrich the community through exploration and discovery in the arts and music, while supporting local businesses and non-profit partners. The four-hour signature event parking voucher is available for $5 and can be purchased at the non-profit’s parking table.

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