Festive choices for the holidays
December on Maui blends warm ocean days with holiday lights, concerts, family events, and island style traditions. The dates and details below reflect the 2025 holiday calendar as it stands now, but it is always smart to confirm with each venue before you go.
December 5 to 7: Opening weekend holiday events
The first full weekend of December 2025 sets the tone for the season. In Kahului, the Maui Pops Orchestra is scheduled to present its Holiday Pops concert at the Maui Arts and Cultural Center’s Castle Theater on Sunday, December 7 at 3:00 pm. It is a matinee show that usually mixes classic holiday music with guest vocalists, and it tends to draw residents from all over the island, from Wailuku and Kahului over to Kihei and Wailea.
Up in Kā‘anapali, Holiday Movies Under the Stars at Whalers Village are set to run from December 5 through December 28 on Friday, Saturday, and Sunday evenings, just after sunset. A temporary outdoor screen is set up near the beach, and families spread out on the lawn with beach chairs and blankets while seasonal films play with the sound of the ocean in the background. Because it takes place right in the heart of the resort area, it is easy to walk over from many nearby condos and hotels.
December 12 to 15: Theater, lights, and family fun
Mid month is when holiday theater and light displays start to line up on the calendar. In Kihei, the Pro Arts Theater is scheduled to run “The Reluctant Elf” from December 12 to 15, 2025. It is a small, intimate playhouse just off South Kihei Road, so guests staying in nearby condo communities can usually arrive in a matter of minutes for an evening show after a day at the beach.
At the same time, Maui Ocean Center in Mā‘alaea is planning its Festival of Lights evenings, transforming the aquarium into a nighttime holiday experience with illuminated marine themed displays. For 2025, these nights are slated for Saturday, December 13 and Saturday, December 20 from 6:00 to 9:00 pm. It is a nice option for families who want a holiday outing that still keeps the focus on the ocean and local marine life.
December 16 to 21: Markets, concerts, and classic traditions
Wailea takes center stage on December 16, when the Grand Wailea’s Holiday Marketplace and Tree Lighting Ceremony are scheduled to kick off the resort’s festive season. The lobby market is planned from 4:00 to 8:00 pm and features Made on Maui vendors, while the tree lighting and entertainment along the front drive typically begin around 6:00 pm with the lighting itself closer to 7:00 pm. For owners and guests staying along the Wailea coastline, it is one of the easiest ways to step into the holiday mood without leaving the resort area.
In Wailuku, the historic ʻĪao Theater plans to host “Nutcracker Sweets” with performances spread across December 13 to 21, 2025. The show keeps the familiar Nutcracker story and music but formats it into a more relaxed, island style run that still feels special without being overly formal. It is a good option for anyone staying in central Maui or upcountry who does not want to drive to the resort side for every holiday outing.
Back at the Maui Arts and Cultural Center, Jake Shimabukuro’s “Holidays in Hawaiʻi” concert is on the calendar for Saturday, December 20, 2025 at 7:30 pm. The show brings his signature ‘ukulele style to holiday music and usually includes special guests. Many South Maui owners plan an early dinner in Kahului, then head to the Castle Theater to finish the evening with the concert.
December 22 to 25: Christmas week on Maui
As Christmas week begins, Wailea and South Maui generally become a hub for visitors and second home owners. The Fairmont Kea Lani is planning its “12 Days of Festive” schedule from December 22, 2025 through January 2, 2026 with a rotating mix of cultural activities, poolside events, and special holiday dining experiences. Even if you are not staying on property, it is worth checking their public offerings if you will be in the Wailea area during that time.
On Christmas Eve, Santa’s arrival by outrigger canoe at Wailea Beach is one of the island’s most recognizable December traditions. Instead of a sleigh, Santa glides in over the water, usually late morning or midday, greeted by keiki on the sand and visitors lining the shoreline. For owners in nearby Wailea condo communities, it often becomes a yearly ritual to walk down the coastal path, grab a spot on the beach, and enjoy the mix of holiday music and ocean views.
Christmas Day itself brings a few special meals and outings. In Lahaina, there is a Christmas Morning Oceanfront Brunch Buffet scheduled for Thursday, December 25, 2025 from 9:00 to 11:30 am at 200 Nohea Kai Drive. The setting looks out over the water, and it can be a nice match for families staying in Kā‘anapali or central Lahaina who want to mark the holiday with a meal rather than cooking in their condo or vacation rental.
December 26 to 30: Community nights and island evenings
The day after Christmas falls on the fourth Friday of the month in 2025, which means the Kihei Fourth Friday Town Party becomes a post holiday gathering spot. Held in the evening at Azeka Mauka Shopping Center, this monthly event brings live music, food trucks, local artisans, and a keiki zone together in one walkable area. Because it is right in the middle of town, owners and visitors staying in many Kihei condo communities can often leave the car at home and walk or take a short rideshare to the event.
During this window between Christmas and New Year’s, many resorts also schedule additional live music, sunset activities, and smaller scale holiday events. It is a good time to check the event calendars for properties in Wailea, Kā‘anapali, Kapalua, and central Maui if you enjoy a busy social calendar during your stay.
December 31: New Year’s Eve celebrations on Maui
New Year’s Eve on Maui tends to center around the ocean. One of the more popular options is the Alii Nui Royal Sunset Dinner cruise, scheduled for December 31, 2025 from 5:00 to 7:30 pm. Guests board in Mā‘alaea Harbor and enjoy a plated dinner and open bar while watching the sun set over the water. Because December is the start of peak whale season, it is common to see humpbacks during the cruise, which adds another layer to the evening.
In Wailea, the Grand Wailea’s Festive program typically includes a New Year’s Eve movie night on the chapel lawn followed by a midnight fireworks show over Wailea Beach. The fireworks are visible from many oceanfront resorts, the public beach access, and much of the Wailea Beach Path, so it is very easy to combine dinner at one resort with a walk along the shoreline as midnight approaches.
Across the island, other hotels and restaurants, from Kā‘anapali to Kapalua and back toward central Maui, tend to announce special dinners and live music as the date gets closer. Reservations fill quickly, so it is worth checking individual resort and restaurant sites if you have a specific neighborhood or dining style in mind.
Thinking about owning on Maui while you enjoy the holidays
Spending December here often gets people thinking about what it would be like to have a home base on the island. Some prefer the resort energy of Kā‘anapali and Wailea, others gravitate toward quieter pockets of Kihei, Napili, or upcountry neighborhoods that sit above the coastline but still keep all of these events within reach. If you would like to see how current listings line up with the parts of the island you enjoy most, you can always start with our main Maui real estate section or reach out directly to talk through neighborhoods, budgets, and rental possibilities.
When you are ready to explore property options that match the way you actually spend time here during the holidays, contact Roger and the team. We are happy to answer questions, share local insight, and help you compare homes and condos across Maui so your next visit feels a little more like coming home.
Posted by Roger Pleski R(S) on
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