December drifts into Maui on the trade winds—where winter arrives not with snow, but with shimmering coastlines, cool upland breezes, and the soft glow of festive lights woven through island landscapes. From the pulse of hula and mele to the stillness of star-filled nights above Haleakala, December invites residents and visitors alike to gather, connect, and savor the season in a place where nature and community are inseparable.
Upcountry Winter Fest — Presented by the Kekaulike High School Foundation
November 29, 2025 — King Kekaulike High School (Upcountry Maui)
The Upcountry Winter Fest returns to Kekaulike High School with an evening of seasonal celebration, community spirit, and festive island charm. On Saturday, Nov. 29, from 3 to 8 p.m., the campus transforms into a winter-themed wonderland filled with holiday markets, live entertainment, keiki activities, and family-friendly experiences. Guests can wander through the Holiday Craft Fair hosted by Nā Aliʻi Football, browse a vibrant farmers market, enjoy an array of local food trucks, and take in performances from Nā Aliʻi Big Band, Zenshin Daiko, V.I.V. & Band, and Nuff Sedd. Children can visit Santa and Mrs. Claus, explore a walk-through holiday display brought to life by student performers, and join in games hosted by school clubs.
Hui Holidays Marketplace
December 1–24, 2025 — Hui No‘eau Visual Arts Center (Upcountry Maui)The annual Hui Holidays Marketplace transforms the historic Hui No‘eau estate into a festive gallery filled with handcrafted gifts, local artwork, jewelry, ceramics, and seasonal décor. Visitors can explore beautifully decorated rooms, participate in artist demonstrations, and enjoy the charm of Upcountry during the holiday season. This marketplace celebrates Maui’s creative community and offers a unique way to support local makers.
LOL@MACC — Jiaoying Summers
December 4, 2025 — Maui Arts & Cultural Center (Kahului)The Maui Arts & Cultural Center hosts internationally acclaimed comedian Jiaoying Summers for a lively evening of stand-up. Known for her sharp wit and fearless insights, Summers delivers a high-energy show that blends personal storytelling with global humor. It’s a fun, spirited start to the holiday season in one of Maui’s most beloved arts venues.
Kapalua Concert Series ft. ʻUlu Maika
December 5, 2025 — The Ritz-Carlton Maui, Kapalua, Alaloa Lounge On Friday, December 5 from 6:00 pm to 9:00 pm, join the island-style rhythm of the Kapalua Concert Series featuring the dynamic band ʻUlu Maika at The Ritz-Carlton Maui, Kapalua. Set in the Alaloa Lounge overlooking the sacred shores of Honokahua Bay, the evening blends live musical storytelling with handcrafted cocktails, fresh sushi and sashimi, and gourmet smash burgers. The event is open to the public at no cover charge—food and beverages are available for purchase, and complimentary valet parking adds ease to the experience.
Holiday Movies Under the Stars
December 5–28, 2025 — Whaler’s Village (Kāʻanapali)Whaler’s Village hosts free outdoor holiday movie screenings every Friday, Saturday, and Sunday in December. Guests gather near the beach to enjoy festive classics on a large outdoor screen while taking in ocean breezes and nearby dining options. It’s a relaxed, family-friendly way to get into the holiday spirit in one of West Maui’s most iconic beachfront shopping destinations. View the full schedule at the Whaler’s Village holiday guide.
7th Annual Holiday Fair & Electric Light Golf Cart Parade
December 6, 2025 — Pukalani Country Club (Upcountry Maui)This Upcountry favorite brings together local vendors, keiki activities, food booths, and holiday crafts before the evening’s highlight: a glowing electric golf cart parade rolling through the Pukalani Country Club. The event blends small-town charm with festive creativity and is a true reflection of Upcountry community spirit.
Holiday Pops — Maui Pops Orchestra
December 7, 2025 — Maui Arts & Cultural Center (Kahului)The Maui Pops Orchestra returns with its annual Holiday Pops concert, featuring full orchestral arrangements of seasonal classics and special guest vocalists. The MACC’s Castle Theater provides an elegant setting for a sophisticated afternoon performance that blends tradition, artistry, and holiday warmth.
Morro Bay to Kapalua Bay: A Coastal Collaboration — Sip & Shuck at Cliff House
December 12, 2025 — Montage Kapalua Bay (Kapalua)Montage Kapalua Bay hosts a remarkable ocean-to-ocean culinary celebration as Neal Maloney, founder of Morro Bay Oyster Company, joins the resort for an exclusive Sip & Shuck experience at sunset. Set against the dramatic cliffs overlooking Kapalua Bay, the evening features a curated oyster raw bar, coastal pupus, and Veuve Clicquot Champagne poured as the sun slips behind Molokaʻi. This intimate tasting showcases the connection between California’s cool Pacific waters and Hawai‘i’s abundant coastline, making it a standout event for seafood lovers and those seeking a refined, sensory-driven evening by the ocean.
Dec. 12, 5–7 p.m. | $195 per guest
The Nutcracker — Alexander Academy of Performing Arts
December 13–14, 2025 — Maui Arts & Cultural Center (Kahului)The beloved holiday ballet returns to the MACC as the Alexander Academy presents a full-length production of The Nutcracker. Featuring beautiful costumes, classic choreography, and talented local dancers, this show brings holiday magic to life and has become a cherished December tradition on Maui.
Jake Shimabukuro: “Holidays in Hawaiʻi”
December 20, 2025 — Maui Arts & Cultural Center (Kahului)Renowned ‘ukulele virtuoso Jake Shimabukuro steps into the holiday spotlight with Holidays in Hawaiʻi, a festive concert blending his signature style with re-imagined season classics. On December 20 at 7:30 pm at the MACC Castle Theater, guests can expect a program that includes sparkling versions of “We Three Kings,” “O Holy Night,” and “All I Want for Christmas Is You,” alongside selections from his newest album Grateful. He’ll be joined on stage by bassist Jackson Waldhoff and vocalist Justin Kawika Young, creating a night of musical craft, island soul, and aloha spirit.
Hānau Ke Aliʻi — A King Is Born
December 21, 2025 — Maui Arts & Cultural Center (Kahului)Hālau Nā Lei Kaumaka o Uka presents a powerful evening of hula, mele, and cultural storytelling in this moving performance honoring the birth and legacy of Hawaiian aliʻi. With more than 100 performers, the production is both visually stunning and culturally significant, offering audiences a deep connection to Hawaiian heritage.
Santa’s Arrival by Outrigger Canoe
December 24, 2025 — Wailea Beach (South Maui)One of Maui’s most iconic holiday traditions, Santa’s arrival by outrigger canoe draws families to Keoneopolo (Polo) Beach for a truly Hawaiian celebration. Santa paddles ashore to greet keiki against a backdrop of golden sand and turquoise water, creating an unforgettable Christmas Eve moment.