Christmas Holiday Celebrations and Events At The Shops At Wailea, Maui, Hawaii

The 2019 holiday events calendar at The Shops At Wailea kicked off with the arrival of Santa today, on Black Friday here at the Shops at Wailea! The holiday festivities continue with special events and entertainment through December 24.

Today’s Santa’s Parade started at Kalama Park and progresses from Kihei to The Shops at Wailea. Santa rode 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 10am at The Shops at Wailea.

Photo by The Shops At Wailea

Following the parade, holiday photos with Santa were by the professionals at Pacific Dream Photography in the Fountain Courtyard, from 11am – 7pm. Throughout the day today the Honolulu Cookie Company will provide free holiday cookies to Santa’s visitors, while supplies last.

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

Santa’s Visiting Hours

From November 29 – December 24, photos and visits with Santa are available daily. Photo opportunities are scheduled as follows:
* November 29 – December 1: 11am – 7pm
* December 2 – December 19: 1 – 7pm
* December 19 – 24: 11am – 8pm

“Paws and Claus” pet photos with Santa will also be available Mondays from 4 – 7pm from December 2-16.

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 November 29 through December 15.

Gift wrapping will be offered from December 19 – 23 from 10am- 9pm and on Christmas Eve, December 24 from 10am – 6pm. Complimentary gift wrapping for purchases made at The Shops at Wailea is provided by Gamma Chapter of Hawaii Alpha Delta Kappa. Donations are appreciated and will go towards college scholarships for Maui high school students.

Gingerbread House Display

See some of the cutest and creative gingerbread houses on display at the Wailea Realty office (ground floor in front

Help us select the winner by voting, and get a chance to win a $100 Gift Card:
* Visit Wailea Realty Corp. office at Unit B16 The Shops at Wailea and view all the gingerbread houses on display (created by our own agents and their families)
* Each gingerbread house on display has a number.
* Pick the number of the gingerbread house you like best and go into our office and submit your entry.
* You can also vote online via Wailea Realty Facebook Page by liking the photo of your choice at Wailea Realty Facebook Page Gingerbread House Album or liking the photo on Wailea Realty Instagram
* Voting starts December 3, 2019 and ends December 30, 2019.
* Raffle draw of the voting ballots/likes will be held on December 31, 2019 –  Prize: $100 gift certificate
* Winner will be contacted via email or a phone call.
* Name of the winner will be announced here on our blog at Wailea Realty Website:

See the Gingerbread house displays from  of the previous years:  December 20142015, 2016, 2017, 2018

This year in addition to voting, we also will be encouraging the public to make a donation to the Maui Food Bank as they vote. We hope to raise some funds to bring cheers to the families in need this Christmas!

Holiday Entertainment Schedule:

* Kamehameha School’s Ukulele Band on Friday, November 29 from 6 -7:30pm
* Maui Brass Ensemble on Saturday, November 30 from 5 – 6:30pm
* Holiday Jazz with Guitarist Prem Brosio & Friends on Sunday, December 1 from 5:30 – 7pm
* Maui Community Band on Saturday, December 7 from 5 – 6:30pm
* Festival of Harps on Sunday, December 8 and Saturday December 14 and 21 from 5:30 – 7pm
* “The Joyful Hearts” sing-along caroling lead by Bonnie Newman on Sunday, December 15 from 5:30 – 7pm

Cultural Activities Schedule:

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 – 2pm
* Lei Po’o Making: Mondays 2:30 – 3:30pm and Wednesdays 1:30 – 2:30pm
* Ukulele Lessons: Mondays 5:30 – 6:30pm and Fridays 3 – 4pm
* Coconut Husking: Tuesdays 2:30 – 3:30pm
* Island Wood Carving: Wednesdays 10:30am – 1pm and Fridays 12:30 – 3:30pm
* Polynesian Show: Tuesdays and Thursdays 5:30 – 6:30pm
* Coconut Frond Weaving: Thursdays 2:30 – 3:30pm
* Pau Hana at The Shops: Fridays 4 – 6pm
* Jazz at The Shops featuring Rock Hendricks on Wednesday, December 4 from 5:30 – 7pm
* Market at The Shops: Wednesday December 11 & 18 from 4 – 6pm
* Concerts at The Shops with Napua Greig: Wednesday, December 18 from 5:30 – 7pm

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 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.  For a complete calendar of events, activities and entertainment, please visit our website at

For More HOLIDAY EVENTS and HAPPENING ON MAUI, check out blog



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