Winter is one of the most popular times to travel to Maui.
No surprise there! Maui has perpetually warm weather, even while the rest of the United States deals with bone-chilling winter temperatures.
Plus, winter is the season of rainbows and whales on Maui.
Planning a winter getaway to Maui? Here are some of the most exciting events and fun things to do on Maui in winter.
THINGS TO DO ON MAUI IN WINTER
MAUI EVENTS IN DECEMBER
Whale Watching: Winter on Maui means one thing: whale watching!!!
Maui is the best place in Hawaii for whale watching. Every year, thousands of humpback whales migrate from Alaska to Hawaii’s warm waters to mate and give birth. The whales tend to prefer Maui’s shallow, protected waters, and they are simple everywhere in winter.
Whale watching season officially begins on December 15, the date most Maui whale watching tours start operating. A whale watching tour is the best way to observe these gentle giants in their natural habitat.
You can also see lots of whales from land and hear them singing underwater while you snorkel. Whale sightings peak from January to March, but there are still plenty of whales in December and April. Before you visit Maui this winter, take a look at these Whale Watching Tips.
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.
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.
Watch our Facebook Live of Santa’s arrival in 2021:
2024 Date: Event date was not yet announced at the time of this writing. Kaʻanapali Beach and various beaches, Lahaina (West Maui), and other beaches across Maui.
MAUI EVENTS IN JANUARY
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!
2025 Dates: January 2-5. Plantation Golf Course, Kapalua (West Maui)
Book direct Condos and Villas for rent in Kapalua
MAUI EVENTS IN FEBRUARY
Whale Tales: Whale Tales is a jam-packed three day event held every year at the Ritz Carlton in Kapalua.
Photographers, conservationists, scientists, and filmmakers come together for several days of presentations and hands-on events. The event also includes an art expo, film screenings, and fun learning experiences that connect the public with the latest research and discoveries around whales.
2025 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)
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.
2025 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.
2025 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)
MORE TIPS FOR THINGS TO DO ON MAUI IN WINTER
Year-round Activities
Fourth Friday Town Party: Every fourth Friday, Kihei hosts a town party in the Azeka Shopping Center. Come here for ono local food trucks, local vendors, live entertainment, keiki activities, and more!
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.
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!
At Mystery Maui, every second counts as you and your team dive into a thrilling escape room challenge in Wailuku. Solve intricate puzzles, uncover hidden clues, and piece together the mystery before time runs out. Perfect for friends, family, or coworkers, this locally owned experience promises excitement, teamwork, and just the right amount of suspense.
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.
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Happy Travels!
Aloha! Tiffany here. I've been blessed to call Maui home since 2011. With a background in the island's finest restaurants and hotels, guiding visitors to create unforgettable Maui memories is more than a skill I've mastered—it's a profound source of joy for me.
