If escaping a cold climate for a winter vacation on Maui is on your mind, you won’t miss out on the spirit of the holidays while on the island. We might deck the halls a bit differently- like twinkling lights up towering palm trees or tropical red anthuriums artfully interspersed among lush green foliage, with a few traditional ornaments. There is also the power and emotion of hula celebrations, with keiki to adult dancers donned in Hawaiian print colors of the season. But it all comes together in a festive atmosphere, where everyone seems to have just a bit more aloha for each other.
Of course there is also enjoying some of the most consistently pleasant weather in the country, perfect for exploring nature or just letting the stress of the year roll off you while sunning on the beach or snorkeling along the reef. Winter is also the time when we see majestic humpback whales spouting and breaching just off shore.
So yes, we think the holiday season is magical on Maui, no matter what your faith or interests, and we would love to share this special time with you.
Planning a trip to Maui? Have any questions? Follow our Destination Maui Facebook page here now! We regularly update our Facebook page with condo deals, new activities to try, and beautiful scenes from around the island.
Favorite Island Holiday Activities
There are special memory-building activities we love to do, and think you will too. Here are a few.
Your Own Art Crawl
Paia, on Maui’s Northshore, has the funky surfer town and artist vibe that is perfect for browsing galleries and unique shops, then stopping in for a brew and ono burger at Paia Fish Market. Or, just across the street is Milagros, where you can have an island style margarita with li hing mui powder on the rim- a sweet and sour island delicacy made from seasoned ground seeds. Yum!
Just a few miles up Baldwin Avenue, you’ll find Hui No’eau Visual Arts Center, a lovingly maintained mansion and estate now housing an arts and culture nonprofit, with local fine art on display across multiple mediums, and treasures for sale in the gallery and store. You might even time it right to do a hands- on wreath making class, or learn how to weave coconut tree fronds.
Keep going uphill, and you will hit historic Makawao, a very walkable town with more galleries and shops in a rustic paniolo (Hawaiian cowboy) setting- there is even an old boardwalk.
Marine Life, Culture and Shopping
Hawaii’s world-class aquarium, Maui Ocean Center, has an ongoing schedule of fun events and educational entertainment throughout the festive winter season. It is the perfect place for Christmas activities for kids and families- you might even run into Scuba Clause as you explore all the Ocean Center has to offer, including one of the absolute best retail outlets on the island, and an excellent harbor front restaurant.
Do a Family Photo Shoot on the Beach
There is nothing better than sending a photo of you and your loved ones in a beautiful tropical setting to friends and family on the mainland slogging through winter weather. Or, a less evil mission is to create a wonderful keepsake of your time together on Maui. Aubrey Hord Photography is one of the best we’ve seen for location and studio portraits, including group photos.
If you are doing a DIY shot, make sure to keep time of day in mind. Kihei lies to the South and Kaanapali is West. Mornings are generally better, where you can get a little sun on faces and the background. Without a professional photographer and lights, it is difficult to get a group sunset shot. For a simple festive touch, have all members of the group wear all white, then adorn each person with a red flower lei or green maile lei.
Free Hula Shows and More
The shopping malls on Maui are famous for free center court entertainment. It is one of the best places to catch a free hula show, which are even more festive during the holidays. Many have other ongoing events, like concerts and traditional Hawaiian crafts. Here is where to check in on mall events before visiting:
Shops at Wailea
Note: some island activities are temporarily closed or may have limited hours, including Old Lahaina Luau (reopening in February), other things to do and restaurants on the West side of Maui due to the devastating Lahaina fires August 8th. Please make sure to check directly with the company you are booking with to verify their hours, as information from other sources may be outdated.
Where to see Santa
It is a little-known fact that Santa makes his first stop in the islands on Christmas eve morning, bringing joy (and photo ops) to little ones and the young-at-heart. On Maui, Wailea Beach is the spot to be on December 24th as Santa gives the reindeers a break and arrives on the island aboard an outrigger canoe! Rumor has it Santa also takes a Maui vacation after Christmas, before heading back to the North Pole, so if you see a jolly-looking elf in an aloha shirt on the beach in January, give him a knowing wink or friendly shaka.
Santa’s Arrival by Outrigger Canoe
Sunday, December 24th 8am to 8am, Wailea Beach
You can also join Santa and a full crew of elves for a special sailing tour about Alii Nui. Just a handful of dates are available for this special afternoon filled with holiday stories, hot cocoa and tasty treats. You are also likely to see a humpback whales along the festive journey.
Find more info and book your Santa sail here.
2023 Dates are 2pm to 4pm on November 25th, December 17th, 22nd, 23rd
What to Expect from Maui’s Winter Weather
In our opinion, winter is some of the best weather on Maui. Hurricane season is over. It is still warm- averaging highs in the mid 80s on the sunny coastlines, with occasional showers to keep the island lush and green. FYI, the highest rainfall months are February and March, with most precipitation falling on the north and east sides of the island.
You can literally go from a sunny warm beach in the morning to wintery conditions at the top of a volcano in the afternoon! Pack a fleece, long pants and rain jacket if you plan to go up to Haleakala crater, as the 10,000ft summit is very chilly, and can even get snowfall during the winter!
Quick Tips to Plan Your Holiday Trip!
🏨 Accommodations: Destination Maui Vacations is locally owned and managed, and has over 100 beachy condos in boutique oceanfront resorts, at reasonable rates, AND WE STILL HAVE THANKSGIVING AND CHRISTMAS HOLIDAY AVAILABILITY!
✈️ Flights: For the cheapest flights, search for the best rates with Google Flights, then match the itinerary directly with the airline
🌋 Maui Activities: See our comprehensive Things to Do section– created by people that actually live here!
📱 Mobile Tour App: Our favorite is Shaka Guide
May we be the first to say this season, Mele Kalikimaka, we can’t wait to see you on Maui for the holidays!