The holidays on Maui look a little different from the ones most of our guests grew up with. Santa comes in by outrigger canoe, Christmas lights go up on palm trees and plumeria, the first humpbacks of the season are spouting off Sugar Beach, and New Year's Eve ends with firecrackers in every neighborhood and fireworks over Wailea Beach. We have spent many holiday seasons in Kihei since 2012, and this is the guide we would hand a family or a couple flying in for the last two weeks of the year: the dates to know for 2026, where to see Santa, how to plan Christmas dinner, which mornings to book Haleakala, and how locals ring in the new year with poke, mochi and a lot of noise.
What the holidays feel like in Kihei
December on the south shore is warm, green and a little festive in a low-key way. Kahului's long-term averages put December highs in the low 80s and nights in the mid 60s, and the ocean stays around 76 to 77 degrees, so a Christmas morning swim at Sugar Beach is on the table. Showers come and go quickly on this side of the island, and the West Maui Mountains are usually wearing a little cloud cap while Kihei sits in the sun.
On Christmas Day the sun comes up around 7:00 a.m. and sets around 5:52 p.m., which means sunset drinks on the lanai happen before most mainland families have started dinner. It also means the sky over Kaho'olawe goes orange early, and the evening walk along the beach is part of the plan every night.
Local families are out too. Hawaii public schools are on winter break from December 21, 2026 through January 1, 2027, so local families are at the beach parks with pop-up tents, coolers and grandparents. Kalama Park and the Kamaole beaches fill with family gatherings on the weekends, and the mood is friendly and relaxed.
The holiday weeks are also the first dates on the calendar to book. Kihei stays relaxed on a weekday morning, but it does mean the best plan is made early: the bungalow, flights, a rental car, dinner reservations and Haleakala sunrise tickets. We go through each of those below.
The season at a glance
Dates to know for the 2026 holidays
Most organizers on Maui announce December dates in November, so as of late October only a handful of 2026 events are confirmed. The table below marks each one as announced for 2026 or as last year's date, which is the best guide to when it will land this year. We will keep this post updated as more dates are posted, and the Sources list at the end links to each organizer so you can check before you go.
Two patterns hold every year. The big resort events cluster on Christmas Eve morning (Santa by canoe), Christmas Day (brunches and dinners) and New Year's Eve (parties and the midnight fireworks over Wailea Beach). The community events, from craft fairs to the Nutcracker, mostly happen on the first three weekends of December, so arriving by about December 18 lets you catch the last of them.
| Date | Event | Where | Status |
|---|---|---|---|
| Sun Dec 6, 3 p.m. | Maui Pops Orchestra holiday concert | Castle Theater, MACC, Kahului | Announced |
| Thu Dec 17, 9 a.m.-1 p.m. | Kihei Christmas market | South Maui Gardens, Kihei | Announced (listing) |
| About Fri Dec 18 | Kihei Christmas carol walk with costumed carolers | Kalama Park, Kihei | 2025 pattern |
| Weekends to about Dec 20 | Nutcracker Sweets | Historic Iao Theater, Wailuku | 2025 pattern |
| Dec 19 to Jan 2 | Holiday program, Santa by canoe, lu'au | Wailea Beach Resort | Announced |
| Thu Dec 24, 10 a.m.-noon | Santa and Mrs. Claus arrive by outrigger canoe | Polo Beach, Wailea | Announced |
| Fri Dec 25 | Christmas buffets and dinners | Wailea resorts | Announced |
| Thu Dec 31, midnight | Fireworks over Wailea Beach | Wailea | 2025 pattern, plus a 2026 resort lu'au with fireworks |
| Fri Jan 1 | New Year's Day brunches | Wailea resorts | Announced |
Santa by outrigger canoe
On Christmas Eve morning, Santa paddles in to the Wailea beaches in an outrigger canoe, steps onto the sand in his red suit and a lei, and spends the next hour or so with a crowd of kids who have been watching the water since breakfast.
For 2026, the Fairmont Kea Lani has announced that Santa and Mrs. Claus will arrive by outrigger canoe on Thursday, December 24, from 10 a.m. to noon at Keoneopolo Beach, which most people call Polo Beach. Last year the Four Seasons hosted the same kind of arrival on Wailea Beach at 10 a.m., and the Grand Wailea lists a Christmas Eve Santa arrival on Wailea Beach that is open to the public. The Wailea Beach Resort has also announced Santa's arrival by canoe as part of its holiday program from December 19 to January 2.
All of these beaches are public, and each has a public access path and parking lot, so come early on Christmas Eve to get a spot. From the bungalows it is about 15 to 20 minutes to Wailea. We would leave by 9 a.m., park at the public lot, and walk in along the Wailea Beach Path, which links the resort beaches.
Bring reef-safe sunscreen, a hat and water, and plan to stay for a swim afterward. Polo Beach and Wailea Beach are both calm, sandy and good for kids on most winter mornings. If you would rather see Santa without the canoe, last year The Shops at Wailea offered free photos with Santa on Wednesday and Saturday evenings through the last Saturday before Christmas, with canned food for the Maui Food Bank encouraged. Our Wailea neighborhood guide covers the parking and the beaches in more detail.