The Shops at Wailea rolls out holiday lineup, annual Instagram giveaways and more

The Shops at Wailea is spreading holiday cheer and inviting families to join in the festive fun this December with an exciting lineup of events, giveaways, and live entertainment for all ages. Throughout the month, Maui residents and Wailea visitors can enjoy these special offerings designed to celebrate the magic of the season. 

Holiday entertainment

The entire ‘ohana will be treated to special performances from Hawai‘i’s best ensembles at the Lower Valley Performance Area. The entertainment schedule includes:

• Sunday, Dec. 1, 4:30-6 p.m. – Chop Suey Jazz Orchestra
• Monday, Dec. 2, 5:30-6:30 p.m. – Maui Waena Intermediate Band
• Friday, Dec. 6, 5:30-6:30 p.m. – Kalama Intermediate Band & ʻOhana 
• Saturday, Dec. 7, 5:30-7 p.m. – Holiday Jazz at The Shops with Joe Cano
• Saturday, Dec. 14, 4-5 p.m. – Festival of Harps with Madrigal Singers in Costumes 
• Saturday, Dec. 14, 5:30-6:30 p.m. – Maui Community Band
• Friday, Dec. 20, 5:30-7 p.m. – Holiday Concert with Napua Greig & Hālau 
• Sunday, Dec. 21, 5-6:30 p.m. – Festival of Harps (4-5 harps) 

Holiday shop and dine special gift

From Monday, Dec. 2 to Sunday, Dec. 7, guests can get into the holiday spirit with a special gift when they shop and dine at The Shops at Wailea. Those who spend $750 or more at any store or restaurant will receive a $50 gift card to choose from the following signature restaurants: Wolfgang’s Steakhouse, Tommy Bahama Restaurant and Bar, Ruth’s Chris Steak House, Lineage, Waikīkī Brewing Company, or The Pint & Cork. To redeem this gift, visit The Shops at Wailea Management office from 9 a.m. to 4 p.m. between Dec. 2-7.

Mele Kalikimaka Show every Wednesday

The Shops’ weekly music series turns into the “Mele Kalikimaka Show” each Wednesday, featuring a festive lineup of Hawai‘i’s iconic musicians at the Lower Valley Performance Area.

• Dec. 4, 4:30-6 p.m. – Nevah Too Late 
• Dec. 11, 4:30-6 p.m. – Rama Camarillo 
• Dec. 18, 4:30-6 p.m. – Max Angel 
• Dec. 25, 4:30-6 p.m. – Mondokane 

Complimentary photos with Santa

Guests of all ages will have the opportunity to meet Santa and take a festive photo with him, for free! Santa’s home away from home is located between Mahina and TravisMathew on the Lower Level at The Shops. While greeting Santa, Maui Food Bank will be accepting canned good donations to help support the local community. As a special mahalo, Santa’s helper will give delicious Peppermint Macadamia Nut cookies, courtesy of the newly opened Honolulu Cookie Company. Santa Photo Schedule is as follows:

• Wednesday, Dec. 4, 4–7 p.m.
• Saturday, Dec. 7, 4–7 p.m.
• Wednesday, Dec. 11, 4–7 p.m.
• Saturday, Dec. 14, 4–7 p.m.
• Wednesday, Dec. 18, 4–7 p.m.
• Saturday, Dec. 21, 4–7 p.m.

Holiday gift with purchase

From Sunday, Dec. 8 to Sunday, Jan. 5, guests can enjoy holiday shopping with special gifts when they spend the following: 

• $250, receive a festive green holiday vanity pouch
• $750, receive an exclusive revitalization-inspired splash-proof tote bag
• $1,000, receive both the tote bag and vanity pouch, plus, an original CocoNene Lūʻau 2024 Holiday Ornament

Receipts dated from Dec. 8 to Jan. 5 can be redeemed with the following merchants at The Shops, while supplies last: CocoNene, J.McLaughlin and Sunglass Hut. 

12 Days of Christmas Instagram giveaway (open to Maui residents only)

From Wednesday, Dec. 11 to Sunday, Dec. 22, The Shops will host their annual “12 Days of Christmas” Instagram giveaway, a special opportunity for Maui residents to win delightful prizes from renowned brands. 

• To enter, participants must:
• Follow @theshopsatwailea on Instagram
• Follow the merchant tagged on the post
• Like the giveaway post
• Tag one (1) friend in the comments
• Bonus: For every friend tagged (one per line), get an extra entry

The giveaway will close at 5 p.m. HST daily and winners will be chosen at random and notified through The Shops’ Instagram story. No purchase is necessary to win and a purchase will not increase the patron’s chance of winning. 

This giveaway is not sponsored, endorsed or administered by, or associated with Instagram.

Gift wrapping at The Shops

From Thursday, Dec. 19, through Christmas Eve, guests can enjoy gift wrapping at The Shops, provided by the Gamma chapter of Alpha Delta Kappa. This international honorary organization of women educators is committed to promoting educational excellence, altruism, and global understanding. Proceeds from this event will go towards funding scholarships for graduating Maui seniors.

The dates and times are as follows:

• Thursday, Dec. 19 to Monday, Dec. 23, 10 a.m.–6 p.m.
• Tuesday, Dec. 24, 10 a.m.–5 p.m.

“As Maui’s premier destination for family-friendly entertainment, we’re honored to feature events that bring joy, connection and lasting memories to our guests and their ‘ohana. We look forward to welcoming you and your loved ones to The Shops at Wailea, where the spirit of the season is alive for all to enjoy,” said Diana Whitt, general manager and vice president property management of The Festival Companies, the management and leasing company for The Shops at Wailea. 

For more information, visit theshopsatwailea.com.