Things to do on Maui in winter: couple swimming in the ocean with santa hats on

Things To Do on Maui in Winter (December-January-February)

Winter is one of the most popular travel seasons on Maui. And is it any wonder? ‘Tis the season of rainbows and whales. And when the rest of the nation is enduring bone-chilling temperatures, Maui’s perpetually warm weather becomes more appealing than ever. If you are planning a winter escape, here are some of the most exciting events and fun things to do on Maui in winter.

Maui In Winter






Whale Watching: Winter on Maui is synonymous with whale watching. Thousands of humpback whales make their way from the North Pacific into Maui’s summery waters to mate and give birth. Whale-watching season officially begins on December 15, the date most whale-watching boats start operating tours. This is the best way to observe these gentle giants in their natural habitat! You can also see lots of whales from the land, and you can even hear them singing underwater while you snorkel. Whale sightings peak from January to March, but there are still plenty of whales in December. Before you visit Maui this winter, take a look at these Whale Watching Tips.

Whale watching off the coast of Maui, Hawaii



Holiday Events: Other than the whales, December on Maui is all about tropical holiday cheer! Santa often visits Maui in December, usually via an outrigger canoe instead of his regular sleigh. During this time, expect holiday events, concerts, and craft fairs featuring local hand-made artwork that makes unique gifts. Check with your accommodation or browse the local newspapers for schedules of holiday events while you’re here. 

Maui In Winter Surfing Santa


One of our favorite holiday events on Maui:

Santa’s Arrival via Outrigger Canoe: Who needs reindeer and a sleigh when you’ve got a canoe?! Santa makes a grand appearance in South Maui and West via outrigger canoe to take photos with families. Pictured below is Santa’s arrival on Ka’anapali Beach in front of Hula Grill.

Hula Grill Santa Arrival

Watch our Facebook Live of Santa’s arrival in 2021:

2023 Date: Event date was not yet announced at the time of this writingKaʻanapali Beach and various beaches, Lahaina (West Maui), and other beaches across Maui.

Details & Future Dates (as they become available)




PGA TOUR Sentry Tournament of Champions: Hello, golfers…this one’s for you! The coveted PGA Sentry Tournament of Champions makes its way to Maui’s shore every January. This season-opener event takes place at the Plantation Golf Course in Kapalua. Only players who won official PGA TOUR events during the previous calendar year qualify to tee it up in this annual tournament. This longstanding event is one of the most anticipated things to do on Maui in winter, providing an opportunity to see some of the world’s top golfers in action!

Maui In Winter Plantation Course

2024 Dates: January 4-7. Plantation Golf Course, Kapalua (West Maui)

Book direct Condos and Villas for rent in Kapalua

Details and Tickets





Annual Chinese New Year Festival: Chinese culture has been part of the fabric of Hawaii’s “melting pot” community for generations. Every year, the Maui Mall in Kahului (Central Maui) and the Wo Hing Museum in Lahaina host extravagant Chinese New Year celebrations. Enjoy music and entertainment like martial arts demonstrations, Chinese fireworks, and a traditional Lion Dance. 

Wo Hing Museum in Lahaina, Maui

2024 Dates: Dates were not yet announced at the time of this writing.



World Whale Day Run And Walk for The Whales: As part of the Maui Whale Festival and World Whale Day, Pacific Whale Foundation hosts an annual fun run and walking event to support humpback whale research. Festivities start and end in the shopping center at Maalaea Harbor (Central/South Maui) and include a 1-mile, 5K, 10K, and 11.5-mile course, as well as other options for participation.

Maui In Winter Maalaea Harbor

2024 Date: The date was not yet announced at the time of this writing.

Book direct Condos for rent in this area at Maalaea

Details & Future Dates (as they become available)


The Great Whale Count: Hosted by the Pacific Whale Foundation, the Great Whale Count brings volunteers together to count whales from shore. This provides researchers with a snapshot of whale abundance in Maui’s waters. The Great Whale Count is one of the longest-running citizen science projects in the world! This event takes at various locations around Maui from 8 a.m. to 12 p.m.

Maui Great Whale Count

2024 Date: The date was not yet announced at the time of this writing.

Book direct Condos for rent in this area at Maalaea 

Details & Future Dates (as they become available)





Year-round Activities

Friday Night Town Parties: If it’s Friday, there’s a party on Maui! The Town Parties (sponsored by Maui County) take place on Friday evenings in different towns across the island. The town parties are great fun for both visitors and residents, with local food, entertainment, and vendors. More Details. NOTE: Currently, Fourth Friday in Kihei is the only town party currently in operation. Wailuku and Makawao are expected to follow suit soon!

Kihei Town Party on Maui

First Friday of the month — Wailuku Town Party (Central Maui)  – Currently on Hold

Second FridayHow to Help Lahaina

Third Friday — Makawao Town Party (Upcountry); this one takes place every other month, rather than monthly – Currently on Hold

Fourth Friday – Kihei Town Party (South Maui) – Back in operation!



Free Entertainment: When you are here, make sure you check for entertainment and events at nearby hotels and resorts, as well as island shopping centers, which often offer free hula shows, activities like lei-making and ukulele lessons, and live Hawaiian entertainment. Check out my list of 25 Free Things To Do on Maui for other suggestions.


Farmers Markets: A popular stop for locals and visitors alike, peruse the delicious local produce at a nearby farmers market. Enjoy colorful and flavorful fruits and veggies, learn about the unique produce of Maui, and support the local farmers and vendors. Often local crafters and designers are also selling their unique products like jams and jellies, clothing, jewelry, and island-themed goodies. Some of our top favorites include the Upcountry Farmers Market, Napili Farmers Market, and South Maui Farmers Market. See our ultimate guide to Maui Farmers Markets.


Live Music on Maui — Manaʻo Radio: Live music is still happening around the island, with local musicians jamming almost every night at some of the island’s best restaurants. To find out who’s performing where, check out Mana’o Radio’s Music2Nite site for a full lineup of live music on Maui.

Mana’o Radio (KMNO 91.7 FM) is Maui’s non-commercial all-volunteer radio station. Instead of a canned, pre-programmed song list, you’ll hear local people (volunteer DJs) playing an eclectic selection of the music they love best. Listen while you’re here on Maui, or live stream from their website. Tune in to a truly local radio station! Follow Mana’o Radio on Facebook for the latest word on their broadcast schedule and live events on Maui.


Grassroots Festivals and Fundraisers: Don’t be shy to buy a ticket and attend local school, church, and charity fundraisers, bazaars, and festivals. These events are a great way for visitors to experience an authentic local gathering, and the organizers will love to have you there. There is always plenty of local food (eating is a priority here on Maui!) and entertainment, and often there are fundraising auctions (silent and live) where you can snag great deals on visitor activities like luaus, golf, dining, and boat tours.  You can also help with the recovery from the Maui wildfires.

Maui In Winter Festival


Live Webcams: When you are planning your day on Maui, check out these webcams to view current weather conditions around the island. It’s not unusual for it to be overcast or rainy in one area but clear and sunny just a few minutes away!


Maui Arts & Cultural Center: This is another excellent resource you should check for upcoming events and performances on Maui, from world-famous celebrities and musicians to symphonies and ballet to local Hawaiian cultural programs and festivals. The Maui Arts & Cultural Center (pictured below) is located in Kahului.

Maui Arts and Cultural Center


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Happy Travels!

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