Wailea, Maui, Hawaii (December 2, 2025)
Following Santa’s arrival on Black Friday, The Shops at Wailea continues the holiday season throughout December with a full lineup of festive celebrations. Guests can enjoy free Santa photos, complimentary gift wrapping and family-friendly activities, along with weekly concerts and special performances that bring the community together in the heart of Wailea.
Free Photos with Santa
Guests can capture holiday memories with Santa between Mahina and Travis Mathew on the Lower Level. Canned-good donations to the Maui Food Bank are encouraged.
- Wednesday, Dec. 3, 4–7pm
- Saturday, Dec. 6, 4–7pm
- Wednesday, Dec. 10, 4–7pm
- Saturday, Dec. 13, 4–7pm
- Wednesday, Dec. 17, 4–7pmSaturday, Dec. 20, 4–7pm
Mele Kalikimaka Shows | Wednesdays, 4:30–6pm
Weekly holiday concerts fill the Center with island favorites throughout December:
- Dec. 3 – Nevah Too Late
- Dec. 10 – Tarvin Makia
- Dec. 17 – Rama Camarillo
- Dec. 24 – Max Angel
- Dec. 31 – Shane Kahalehau and Hammah House Band
Special Evening Performances | Fridays
Friday evenings feature festive performances from local musicians:
- Dec. 5, 5–6pm – Maui Madrigale
- Dec. 12, 5–7pm – Chop Suey Jazz Orchestra & King Kekaulike High School’s Jazz Band
- Dec. 19, 5:30–7pm – Kamaka Kukona & Hālau
Kūlanihākoʻi High School Band and Choir | Saturday, Dec. 13, 5–6pm
The holiday celebrations continue with a special performance by the Kūlanihākoʻi High School Band and Choir at the Lower Valley Performance Area. Guests can enjoy uplifting tunes from one of Maui’s rising young ensembles.
Festival of Harps | Saturday, Dec. 20, 5–6pm
The beloved Festival of Harps returns with a serene sunset performance featuring local harpists sharing holiday classics and island melodies.
Complimentary Gift Wrapping
Guests may enjoy free gift wrapping, courtesy of the Gamma chapter of Alpha Delta Kappa on the Upper Level next to Tommy Bahama. Donations are welcome and will be used to fund scholarships for graduating Maui seniors.
- Thursday, Dec. 18, 10am–3pm
- Friday, Dec. 19, 10am–6pm
- Saturday, Dec. 20, 10am–6pm
- Sunday, Dec. 21, 10am–6pm
- Monday, Dec. 22, 10am–6pm
- Tuesday, Dec. 23, 10am–6pm
- Wednesday, Dec. 24, 10am–5pm
12 Days of Christmas Instagram Giveaway
The Shops at Wailea will celebrate the season with its annual “12 Days of Christmas” Giveaway on Instagram, running from Dec. 5–16. Open exclusively to Maui residents, the giveaway offers daily opportunities to win gifts from participating merchants, highlighting the Center’s diverse retail, dining and lifestyle offerings.
Each day, @theshopsatwailea will feature a new prize from a different merchant. To enter, participants must:
- Follow @theshopsatwailea
- Follow the featured merchant’s Instagram account
- Like the giveaway post
- Tag one friend in the comments (Bonus: Additional tagged friends, one per comment, count as extra entries.)
The giveaway will close at 5pm 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. Please note, this giveaway is not sponsored, endorsed or administered by, or associated with Instagram.
The Shops at Wailea Holiday Hours
- Christmas Eve: 10am–9pm
- Christmas Day: 10am–6pm
- New Year’s Day: 10am–9pm
“We’re delighted to offer meaningful experiences that bring guests of all ages together this time of year,” said Diana Whitt, General Manager and Vice President of Property Management at The Festival Companies, the management and leasing firm for The Shops at Wailea. “From photos with Santa and free concerts to gift wrapping and supporting local organizations, we hope each visit offers a chance to rejoice in the holiday spirit that makes this season so special at The Shops at Wailea.”
For more information about holiday events at The Shops at Wailea, visit theshopsatwailea.com.
About The Shops at Wailea
The Shops at Wailea is Maui’s premier shopping and dining gathering place with more than 80 offerings of unique retail, boutiques, restaurants and galleries. It is nestled in the heart of the Wailea resort community at 3750 Wailea Alanui Drive and is managed by The Festival Companies. Current open hours are from 10am to 9pm daily. For more information, visit our website at theshopsatwailea.com or call (808) 891-6770. Follow @TheShopsAtWailea on Instagram and @ShopsAtWailea on Twitter and “Like” us on Facebook.
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