It’s here! The most wonderful time of the year! Everywhere you turn, trees, houses, and businesses are adorned with beautiful sparkling lights, your favorite holiday tunes have started filtering onto your radio stations, decorations are going up, and families everywhere are preparing for another holiday season.
Whether you’re a snowbird who makes the cold-weather escape every year or you’re incorporating the gift of unique experiences into your holiday traditions, a trip to Maui this time of year is magical for so many reasons. From whale watching to holiday festivities, there’s always something going on to delight and excite you! Read along as we cover the can’t-miss holiday activities in Maui!
Maui’s Merrymaking Events and Activities
The holiday season in Maui is an exciting blend of the island’s vibrant culture and community spirit of Aloha. From Thanksgiving runs to Santa’s grand entrance, there are tons of ways to get into the holiday spirit on the island. Check out our curated list of activities that will make your holiday season in Maui unforgettable.
Turkey Trot at Keokea Park
7:30 am to 11:00 am
Hosted annually by the Valley Isle Road Runners (VIRR), this Thanksgiving morning activity is fun for the whole family, and this year will be no different. With a unique twist, this year’s winners will be the runners with the best Thanksgiving costumes! Choose to participate in the 8-mile or 5K, or just come as a spectator. Donations of non-perishable food items will be collected for the Maui Food Bank.
Black Friday at Queen Kaʻahumanu Center
TBD
Score holiday deals and enjoy live entertainment at the Queen Ka’ahumana Center. The day will be filled with incredible savings on all your holiday must-haves, plus prize giveaways from gift cards to cash and more that will make the season even brighter! Don’t miss this kick-off to the Christmas season in Maui.
Arrival of Santa at The Shops of Wailea
TBD
Nothing signals the beginning of the holidays quite like a visit from the big man himself! Bring the family to the Shops of Wailea on Black Friday to meet Santa Claus! The event kicks off with a parade, a traditional Polynesian show, and free photos with Santa when you bring a canned-food donation. Give back to the area that gives so much to help make your vacation special with this beloved holiday activity.
Hana Holiday Craft Show
December 5, 2026
9:00 am to 2:00 pm
Celebrate the season with a showcase of local talent and art in stunning Hana. Shop beautiful seasonal creations that expertly blend island charm with holiday magic. Featured goods include clothing, jewelry, home goods, snacks, children's gifts, original art, personalized gifts, and more!
Hui Holidays First Night Celebration
December 3, 2026
5:00 pm to 8:00 pm
Sip, sample, and shop local artists' goods at the Kaluanui estate on December 5th. If you’re looking for one-of-a-kind goods for the perfect souvenir or something special to take home as a unique gift, you’re sure to find it here. As you wander the beautifully decorated estate, enjoy the holiday music and more than 70 vendors. You can even find a holiday ornament to always remember your Maui Christmas adventure. Let this event be a continuation of Small Business Saturday as you shop local and support the businesses and creators that make Maui so special.
Winter in Maui isn’t just about festive lights and holiday cheer; it’s also a season to enjoy some of the island’s most unique natural experiences!
Whale Watching Tours – As humpback whales make their annual migration from Alaska to the warm waters of Maui, booking a whale-watching tour is an excellent activity to incorporate into your holiday vacation. Book an exciting eco-tour with PacWhale Eco-Adventures and let their certified Marine Naturalists guide you on the most innovative and educational whale-watching tour in Hawaii.
Big Swells in Maui- Winter brings some of the biggest waves to Maui’s shores, making it a prime time for spectators to be wowed by the world’s best big wave surfers. Whether a competition is happening or you're just watching pros practice, making the drive to North Shore is worth it just for the sheer experience of seeing waves this massive.
Adding these activities to your holiday trip to Maui is guaranteed to infuse a bit of the Aloha spirit as you experience both the cultural flair of holiday classics and the mesmerizing natural wonders you can only find here.
Plan Your Perfect Maui Holiday with Bello Realty Inc.
The holidays are just around the corner, and there’s no better place to celebrate than in gorgeous Maui! With a wide variety of activities and events to choose from, your holiday itinerary will be as packed with excitement as your stocking on Christmas morning.
When it comes to finding a place to stay, be sure to book directly with Bello Realty Inc. for the best in island vacation rentals. With Bello Realty Inc., you can find the ideal home away from home to suit your needs and preferences, ensuring a comfortable and relaxing holiday experience. So, what are you waiting for?! Browse our vacation rentals and book your winter wonderland Maui vacation today.