6 Ways to Enjoy the Winter Season and Holidays on Maui

While the Valley Isle is a tropical paradise, there are still plenty of ways to celebrate the holidays—and relish slightly cooler temperatures.

*This story was originally published on Dec. 24, 2024, and updated in December 2025.

With its year-round tropical climate and an endless-summer energy, it’s no surprise snowbirds flock to Maui every winter. But that doesn’t mean the island lacks holiday spirit.  

Across the Valley Isle, you can enjoy festive celebrations throughout December. From welcoming the arrival of Santa on a canoe to feasting at a Christmas lūʻau, check out these unique ways to celebrate the holidays in Hawaiʻi. And if you really miss sub-70-degree temperatures, you can climb to the higher altitudes of Haleakalā and even don a light jacket!

1. Explore Upcountry Maui

Make the gradual climb up the slopes of Haleakalā to experience Maui beyond its sunny beaches. Regardless of the month, visitors can take in sweeping views of the island. But as travelers reach Kula and venture further up the mountain, the air is noticeably cooler and crisp. At Kula Botanical Garden, visitors can enjoy the refreshing air while exploring the 8-acre property filled with proteas, orchids, native plants and more. The local business also grows and sells Christmas trees—but the trees usually sell out the first weekend of December. 

Beyond Kula, visitors can journey towards the summit of Haleakalā and experience the island’s cooler climate. The Hosmer Grove Trail is an easy 0.6-mile loop at the entrance of Haleakalā National Park. On this peaceful nature walk, you might spot the endemic ʻiʻiwi (Hawaiian honeycreeper) and white-rumped ʻapapane flitting about. 

READ MORE: 5 Ways to Enjoy the Outdoors on Maui

2. Search for Cute Gifts in Makawao Town

Lower in elevation but also known for its cool, crisp climate is Makawao Town. The area’s roots go back to the island’s paniolo (cowboy) days and remnants are still seen in the streets today. While strolling through the town, you’re bound to find unique and heartfelt Christmas gifts at the local boutiques filled with cute apparel, one-of-a-kind jewelry and island-inspired décor.  

READ MORE: Your Guide to Makawao Town, Maui

3. Go on a Whale-Watching Tour

Every winter, between 8,000 to 12,000 humpback whales migrate from Alaska to Hawaiʻi, completing a six-week voyage to the Islands’ shallow, warm waters. Known as koholā in ʻōlelo Hawaiʻi (Hawaiian language), the humpback whales return to the Hawaiian Islands to mate, raise their young and impress beach-goers with their playful shows. While humpback whales can be spotted from any of the Hawaiian Islands, Maui is considered one of the best places in the world to see these creatures. Most beach-goers can spot whales while lounging on the sand in Māʻalaea, Kāʻanapali, Kīhei and Wailea. But one of the best ways to understand the significance of these creatures is to embark on a whale-watching tour. Witnessing these creatures—which weigh between 55,000 to 66,000 pounds—flap their tails and breach is an unforgettable experience. It’s one of the reasons travelers enjoy winter in Hawaiʻi.  

READ MORE: Our Tips for Whale-Watching in Hawaiʻi 

4. Go on a Historic Kīhei Walking Tour with Christmas Carolers

Maui Walking Tours hosts historic strolls through Valley Isle towns. In December, there will be a sunset tour in Kīhei, accompanied by a local Christmas caroling troupe.  

mauiwalkingtours.com/our-tours   

5. Greet Santa on the Beach

Santa Clause is ditching his sled for a canoe! You and your entire ʻohana can greet Santa as he rides his way onto the beach.   

For the first time, Santa is paddling into Kāʻanapali Beach outside of the Outrigger Kāʻanapali Beach Resort. The inaugural event will be on Dec. 19, and include mele and hula. The celebration will continue into the event with the resort’s Aloha Friday Holiday Celebration, which features carols, dance and Island-inspired treats.  

On Christmas Eve, Mr. and Mrs. Clause will paddle into Keonepolo Beach in front of Fairmont Kea Lani. Mr. and Mrs. Clause are expected to arrive around noon. This cherished Wailea tradition is a perfect chance to capture a festive photo with the entire ʻohana. 

6. Feast at a Christmas Lūʻau

Lūʻau are exciting celebrations of Hawaiian and Polynesian culture, often including epic shows and impressive feasts of traditional and local dishes. This Christmas, you can dress in your best aloha attire and enjoy a spectacular show with ʻono food. This could end up being one of your most memorable Christmas experiences, and possibly a new tradition. The Te Au Moana Lūʻau at Wailea Beach Resort added a special Christmas day performance, too.

READ MORE: What’s in a Hawaiian Plate, Anyway?