Fun Things to Do in Winter on Maui

One of the most popular times to visit the beautiful island of Maui is winter – December through February– and the reasons probably won’t surprise you! Maui offers tropical weather and a laid-back lifestyle for many people from colder climates, and there are some popular events that can make your stay even more enjoyable. If you are planning a visit, read on for some fun things to do!


Celebrate the Holidays

“Mele Kalikimaka” is Hawaiian for Merry Christmas, and you’ll find ample holiday cheer on Maui! There are many holiday activities spanning a variety of faiths and cultures. Even craft fairs are “island style” with live music and local food. And keep an eye out for Santa – he likes to make an appearance in shorts! Here are a few highlights.

Banyan Tree MauiThe Annual Lighting of the Banyan Tree in Lahaina is a can’t-miss event! The 150 year-old banyan in Banyan Tree Park is even more breathtaking when it is lit up for the holidays! The Maui Made Holiday Gift Fair will kick off at 9am in nearby Campbell Park and Santa will arrive at the North Pole around 2pm. Keiki activities will be available at Campbell Park from 12-4pm. Lahainaluna High School Band will perform 5:45pm – 6:45pm at Banyan Tree Park before the big tree is lit up. Time and Date: 9am – 7pm, Saturday, December 7,  Banyan Tree Park and Campbell Park, Lahaina (West Maui)

Santa Arrives by Outrigger Canoe  on Wailea Beach by decorated outrigger canoe on December 24th between 7am – 10am. A fun Maui tradition, sponsored by the Grand Wailea Resort.

You are not too late to experience some island holiday craft fairs! Here are just a few:

Hui Holidays
Time and Date: 9am -4pm, Dec.5 – 24th
Location: Hui No’eau Visual Arts Center, 2841 Baldwin Ave., Makawao.
A winter wonderland of local and handmade items for everyone on your list in a beautiful estate setting!
Admission: Free.

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Christmas Boutique
Sponsor: Secondhand Heaven Thrift Shop.
Time and Date: 9 a.m. to 2 p.m.,
Wednesdays and Saturdays, Dec. 4 to 21.
Location: Makawao Union Church new conference room, 1445 Baldwin Ave.
Description: Original art, handmade Christmas decorations, bags, aprons, apparel, greeting cards and fabric journals.
Admission: Free.

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Montessori School of Maui PTO Holiday Fair
Time and Date: 3:30 to 7:30 p.m. Dec. 6.
Location: Montessori School of Maui, 2933 Baldwin Ave., Makawao.
Description: Artisan goods, handcrafted items, jewelry and fresh wreaths made with native foliage. Live entertainment, keiki fun zone and bake sale.
Admission: Free.

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holiday craftsHaleakala Waldorf School 34th annual Holiday Faire
Time and Date: 9 a.m. to 4 p.m. Dec. 7.
Location: Haleakala Waldorf, 4160 Lower Kula Road.
Description: Live entertainment, silent auction, Christmas wreaths, local crafters, make-and-take crafts, bakery and coffee shop, children’s games, puppet show and food. Elf parade at 10 a.m. Children dressed as elves receive a free gift.
Admission: $5; children under 12 years free.

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Pukalani Christmas Fair and Electric Golf Cart Parade
Time and Date: 3 to 7 p.m. Dec. 7.
Location: Pukalani Country Club, 9th fairway, under the pine trees.
Description: Holiday gifts, art, jewelry, T-shirts, children’s clothing, home decor and specialty food items. Cookie contest by Lala Sweets. To enter, contact Golf cart parade and ugly sweater contest. To enter, contact Santa arrives at 4:30 p.m. Parking at Pukalani Country Club with backup parking and shuttle service at Pukalani Elementary School.

Admission: $2 per person, children under 12 years free.

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Island Style Stampers fifth annual Holiday Craft & Bake Sale
Time and Date: 9 a.m. to 2 p.m. Dec. 7 and 8.
Location: 67 Ka Drive in Kula Kai.
Description: Gift items, baked goods, multiple crafters.
Admission: Free.

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Waikapu Christmas Street Fair
Time and Date: 8 a.m. to noon Dec. 14.
Location: Ulu Kanu Street in Waikapu Gardens.
Description: Handmade crafts, jewelry, decorations, food, food trucks, clothes, skin care and essential oils. Make-and-take crafts by Friends and Faire. Maui High School Choir. Santa from 9:45 to 10:30 a.m.
Admission: Free.

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Maui Gift and Craft Fair
Time and Date: 9 a.m. to 2 p.m. Sundays.
Location: Lahaina Gateway Center.
Description: Photography, jewelry, fine art, crafts and gifts.
Admission: Free.


PGA TOUR Sentry Tournament of Champions
This event is perfect for the golfer in your family! The Plantation Golf Course in Kapalua hosts the tour, which is the televised season-opener for players who qualified to tee up by winning official PGA TOUR events during the previous year. This longstanding tour is one of the most popular things to do during the winter, and it’s a great opportunity to see some of the world’s top golfers play!
Dates: January 1-5, 2020, Kapalua (West Maui)

Chinese New YearAnnual Chinese New Year Festival
Every year, the Chinese New Year festival celebrates the Chinese culture that has been an important part of Hawaii’s culture for many generations. There are festivals at Wo Hing Museum and Cookhouse on Front Street in Lahaina, and Maui Mall in Kahului. This event features a traditional Lion Dance, Chinese Fireworks, martial arts demonstrations and music.

DATE: Chinese New Year for 2020 is January 25th, but check with venues for specific festivities dates/times


It’s Whale Month!
Pacific Humpback whaleSince 1980, Maui Whale Festival has offered a series of events to celebrate Pacific Humpback whales and promote environmental stewardship . Check out these events running all month long that are fun for resident and visitor alike!


  • Run & Walk for Whales
    Saturday, February 1
  • World Whale Day + Parade of Whales
    Saturday, February 8
  • World Whale Film Festival 
    Friday, February 14
  • The Great Whale Count
    January 25, February 29 and March 28

See for more info.


 Friday Night Town Parties: Fridays are a party on Maui! You can find the Town Parties three Friday evenings per month in varying towns throughout Maui. Town Parties are fun for both visitors and residents, and they offer entertainment, vendors and local cuisine.

So which town has a party is this week?

First Friday of the month – Wailuku
Second Friday – Lahaina
Fourth Friday – Kihei
Fifth Friday – Lāna‘i

Note: Makawao Third Friday is currently on hiatus

See for more info

Free Entertainment
Be sure to check for free entertainment and events at nearby hotels and shopping centers during your visit. You can often find free hula shows, lei making, ukulele lessons, live entertainment and more!

Maui Arts and Cultural Center
The Maui Arts and Cultural Center is a great resource for upcoming events on Maui, from local cultural programs and festivals to world-famous musicians and celebrities.

Maui OnStage at the Historic Iao Theater
Take in top notch performances year round in a theater where Charlie Chaplin once performed!

The Maui News
Check out the “Maui Scene” section in Thursday’s Maui News newspaper or the “Weekender” edition to see what’s happening around Maui each week, as well as find special offers from retailers, tours and restaurants across the island. This is a great way to keep up on fun activities and events!

And for even more fun, check out our newly updated THINGS TO DO guide.

Maui Beach

By |2019-12-02T04:37:55+00:00November 30th, 2019|Entertainment, Travel, Uncategorized|0 Comments

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