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 visitor seasons on Maui. . .for obvious reasons! People who live in colder regions get just plain tired of shoveling snow and bundling up in a dozen layers of clothing, making Maui’s tropical weather and carefree lifestyle more appealing than ever. If you are planning a winter visit, here are some popular annual events and other fun things to do on Maui in winter.

(NOTE: Due to the constantly evolving impacts of COVID-19, the status of most of the events or activities mentioned in this blog are uncertain at this time. For Winter of 2021/2022, most event dates have not yet been announced. This blog will be updated with the latest information as we draw closer to Winter and plans become more definite. Meanwhile, please check directly with these places to verify access, operating status and hours. Mahalo!)




Things to do on Maui in winter: whale tail in the ocean

Whale Watching: Winter is whale season in Maui. Humpback whales migrate to Hawaii’s warm waters for the winter months, and the official Maui whale-watching season is from mid-December to mid-May, with the peak months for whale sightings being January, February, and March. Whale watching is one of the most popular things to do on Maui in winter. Whale watching cruises are a wonderful way to see these magnificent creatures, but you can also view whale activity from land. You can even hear them singing underwater! Take a look at these Whale Watching Tips.




Holiday Events: Other than the whales, December on Maui is all about the Christmas season! Santa often visits Maui in December, usually wearing shorts and plenty of sunscreen. There are many holiday events, concerts, and craft fairs featuring local hand-made artwork and handicrafts that make unique gifts. Check the local newspapers for schedules of holiday events while you’re here. 

Things to do on Maui in winter: santa's jacket, hat, and snorkel fins on the beach
Mahalo to Napili Kai Beach Resort for sharing this shot of a Santa sighting on Napili Bay.


Here are two fun annual holiday tree lighting events on Maui:

The Annual Lighting of the Banyan Tree in Lahaina. Grab a spot at Banyan Tree Park in Lahaina and watch while the massive banyan tree (almost 150 years old) is lit up for the holidays! This free event includes holiday arts and crafts, live entertainment, and children’s activities throughout the day.

2020 Date:  Not Announced at the time of this writing.   THIS EVENT MIGHT BE CANCELLED DUE TO COVID-19 PANDEMIC. Banyan Tree Park, Lahaina (West Maui)

Great book-direct places to stay nearby in Lahaina

Details & Future Dates (as they become available)


The Annual Tree Lighting at Ulupalakua. This free family-friendly event takes place upcountry (on the slopes of Mount Haleakala) on the grounds of MauiWine at Ulupalakua Ranch. The tree lighting takes place after sunset, followed by a movie under the stars. Bundle up because it can get chilly up there in the evening!

2020 Date: Not Announced at the time of this writing.   THIS EVENT MIGHT BE CANCELLED DUE TO COVID-19 PANDEMIC. Ulupalakua (Upcountry Maui)

Details & Future Dates (as they become available)


Things to do on Maui in winter: "Mele Kalikimaka" sign

 Mele Kalikimaka = Merry Christmas




Things to do on Maui in winter: Plantation Golf Course

PGA TOUR Sentry Tournament of Champions: Hello golfers…this one’s for you! Head to the Plantation Golf Course (pictured) in Kapalua for this televised season-opener event for the PGA TOUR. Only players who won official PGA TOUR events during the previous calendar year qualify to tee it up in this annual event. 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!

2021 Dates: Early January. Dates not announced at the time of this writing, due to COVID-19 pandemic.  Kapalua (West Maui)

Book-direct Condos and Villas for rent in Kapalua

Details and Tickets






Things to do on Maui in winter: Chinese Lion Dance

Annual Chinese New Year Festival: Celebrate the Chinese culture that has been part of the fabric of Hawaii’s “melting pot” community for generations! Every year, there is a Chinese New Year festival at Maui Mall in Kahului (Central Maui) and at Wo Hing Museum and Cookhouse on Front Street in Lahaina (West Maui). Enjoy music and entertainment like martial arts demonstrations, Chinese fireworks, and a traditional Lion Dance. 


2021 Dates: Not Announced at the time of this writing, due to COVID-19 pandemic.  

Details & Future Dates: Check the above links for details as they become available.



World Whale Day Run And Walk for The Whales: 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.

2021 Date: Virtual Event (due to COVID) planned for Feb 8-14

Book-direct Condos for rent in this area at Maalaea 

Details & Future Dates (as they become available)


Maui Whale Festival: Hosted by the Pacific Whale Foundation, this is a month-long celebration of our annual winter visitors–the humpback whales–with a series of events taking place throughout February. Check HERE for a schedule of events and more details as they become available.

whale leaping out of ocean
©Dee Coyle.Polinahe Photography



Year-round Activities

Things to do on Maui in winter: Front Street Town Party sign

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: The Maui Town Parties have been temporarily suspended due to COVID. 

• First Friday of the month — Wailuku Town Party (Central Maui) 

• Second Friday — Lahaina Town Party (West Maui)

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

• Fourth Friday – Kihei Town Party (South Maui)


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. And check out my list of 25 Free Things To Do on Maui for other suggestions.

Mana’o Radio: Tune in to a truly local radio station! 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. The first Sunday of every month, enjoy a great lineup of live local entertainment from 2 to 5 p.m. at Casanova Italian Restaurant in Makawao (upcountry Maui). $10 donation at the door is a fundraiser for Mana’o Radio. (COVID UPDATE: The Sunday event has been temporarily suspended.) Follow Mana’o Radio on Facebook for more on their latest shows and events. 

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 boat tours, golf, dining, and helicopter tours.

Live Webcams: When you are here 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.

Things to do on Maui in winter: Maui Arts and Cultural Center at night


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Happy Travels!

Candy Aluli, Publisher

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