The Ultimate Maui Winter Bucket List: 25 Things to Do
While much of the mainland is bundled up against the cold, Maui offers warm beach days, tropical fruit, outdoor dinners—and the unforgettable arrival of humpback whales.
Whether you’re escaping the snow for a week or spending the holidays in the islands, here are 25 experiences to put on your Maui winter bucket list.
Heritage Vacation Homes Blog
At Heritage Vacation Homes, we believe Maui is best experienced slowly, with time to explore its beaches, culture, and natural beauty. Our luxury condo at Makena Surf in Wailea offers a peaceful home base for discovering the island. Through this blog, we share local insight, favorite beaches, and memorable experiences across Maui. You’ll find ideas for snorkeling, spotting sea turtles, tasting local foods, and exploring scenic coastal spots. Think of it as your trusted guide to experiencing Maui in a more meaningful way.
1. See a Humpback Whale
Winter means whale season on Maui, and seeing a humpback breach offshore is one of the island’s most unforgettable experiences. Take a whale-watching excursion for a closer look, or simply keep your eyes on the water—you can often spot whales right from shore.
Local’s tip: We love the whale watching tours that offer Zodiak pontoon boats, as you get to the whales much faster when they appear in the distance.
2. Hear a Whale Sing
Seeing a whale is incredible, but hearing one takes the experience to another level. Some whale-watching excursions use underwater hydrophones so you can listen to the haunting songs of male humpback whales beneath the surface.
Local’s tip: Anytime you are swimming or snorkeling, take a moment to pause and put your head underwater while listening. You can often hear them in the background when you stop to think about it!
3. Experience a Haleakalā Sunset
Head high above the beaches to experience an entirely different side of Maui. Watch the sun disappear from Haleakalā and stay long enough to see the night sky emerge—just remember to bring plenty of warm layers because temperatures at the summit can be surprisingly cold.
Local’s tip: No timed-entry permit is required in the evening like it is in the morning. We like to visit Paia Fish House on our way home!
4. Snorkel in Maui's Clear Water
Slip beneath the surface and discover colorful tropical fish, coral, and maybe even a sea turtle swimming by. Winter ocean conditions can change quickly, so always check current conditions and choose a snorkeling location that’s appropriate for the day.
Local’s tip: Always stay together when snorkeling, don’t swim in murky water, and be sure to use de-fogger on your snorkel mask!
5. Spot a Hawaiian Green Sea Turtle (honu)
Seeing a Hawaiian green sea turtle, or honu, in the wild belongs on every Maui bucket list. Watch for them while snorkeling or along the shoreline, and always give these special island residents plenty of space.
Local’s tip: Our condo, Makena Surf C-107, is located on the point that is fondly referred to as “Turtle Town”. Anytime you swim on the point, you are almost guaranteed to see 1-5 turtles! And our favorite place to see them sunning is at Ho’okipa Beach.
6. Eat Fish Tacos After a Beach Day
There are few lunches better suited to Maui than fresh fish tacos after a morning in the water. Come straight from the beach, sandy feet and all, and find your favorite local version.
Local’s tip: Our favorite fish tacos are from a tucked-away food truck. Email us, and we’d be happy to share the name!
7. Enjoy A Shave Ice in the Middle of Winter
There’s something particularly satisfying about eating shave ice in January while wearing flip-flops. Pick your favorite flavors, find a spot in the sunshine, and enjoy the fact that this is what winter looks like on Maui.
Local’s tip: Go ahead and try the combinations with whipped cream, sweetened condensed milk, and fresh fruit. You won’t be disappointed!
8. Try a Fresh Malasada
Malasadas are Portuguese deep-fried doughnuts without a hole, often coated in granulated sugar. While they’re delicious in their simplest form, many shops have taken these treats to the next level by filling them with custards, jams, or other sweet surprises. They’re best enjoyed fresh—and don’t worry about ending up covered in sugar.
Local’s tip: Some bakeries sell out first thing in the morning so be prepared to get there at opening!
9. Walk the Wailea Bordwalk
The Wailea Beach Path winds along a beautiful stretch of South Maui coastline and is perfect for a leisurely morning or evening walk. During whale season, keep one eye on the ocean because you never know when you’ll see a splash offshore.
Local’s tip: There isn’t much shade, so plan to do this in the morning or later afternoon/evening.
10. Spend a Day Exploring Upcountry Maui
Trade the beach for rolling hills, farms, small towns, and cooler mountain air. Upcountry shows you an entirely different side of Maui and makes a wonderful change of pace during a longer island stay.
Local’s tip: Some of our favorite art galleries are Upcountry! Email us for a few suggestions.
11. Watch Maui's Big Winter Waves
Winter swells can transform parts of Maui’s coastline into a spectacular show. Find a safe viewpoint well away from the water and watch the power of the Pacific from a distance—sometimes watching the ocean is the adventure.
Local’s tip: Drive beyond Paia to Ho’okipa Beach, where you will get to watch surfing and wind-surfing from above. This is also the best beach to see groups of green sea turtles sunning themselves in the sand.
12. Play a Round of Golf with an Ocean View
Palm trees, sunshine, and glimpses of blue Pacific water make winter golf on Maui hard to beat. Guests staying in the Wailea-Makena area are especially close to Wailea’s beautiful Blue, Gold, and Emerald courses.
Local’s tip: Our condo, Makena Surf C-107, is directly across from these beautiful courses so there’s no driving time added to your day!
13. Shop for Something Made on Maui
Bring home something that truly reminds you of your time on the island. Look for local artwork, handmade goods, foods, and other Maui-made products that support local artists, makers, and businesses.
Local’s tip: Farmers markets are a great place to find these types of treasures, and you often get to meet the artist!
14. Taste Fresh Tropical Fruit
Papaya for breakfast feels a little more exciting when it’s January. Visit a roadside stand, market, or local shop and try whatever looks best—then bring a few favorites back for breakfast the next morning.
Local’s tip: Most roadside fruit stands have the ability to open up your coconut on site, let you drink the milk, and then break the coconut apart for you.
15. Eat Every Meal Outside
Outdoor dining might not sound like a bucket-list activity until you remember what December or January feels like in much of the country. Slow down, enjoy the warm air, and appreciate the simple pleasure of eatingdinnig outside in the middle of winter.
Local’s tip: You don’t only have to look for a restaurant with outdoor dining options. Our condo’s lanai has a large teak dining table, and most restaurants do take-away meals. Email us and we’ll tell you what our favorite Hawaiian take-out is!
16. Snorkel Molokini Crater
Take a boat trip to Molokini Crater, one of Maui’s most iconic snorkeling destinations. Its location in the middle of the ocean make exploring beneath the surface an unforgettable Maui experience.
Local’s tip: There are tours that go out from Kihei, so you don’t have to drive far to get on the boat!
17. Take a Guided Maui Fishing Trip
Head out on the water for a Maui fishing adventure and see the island from a whole new perspective. Charter trips offer the chance to catch species like mahi-mahi, ono, ahi, and marlin while spending a memorable day on the Pacific.
Local’s tip: Book a morning fishing trip when winds and ocean conditions are often more favorable, and ask your charter ahead of time about its catch policy. Some Maui crews will clean or fillet part of your catch so you can bring fresh fish back to your vacation rental for dinner.
18. Go Sailing
Experience Maui from the water aboard a classic sailboat or spacious catamaran. Spend a few hours cruising along the coastline, feeling the trade winds, taking in the island views, and enjoying a beautiful day on the Pacific.
Local’s tip: Choose a smaller sailing charter if you’re looking for a quieter, more personal experience on the water. With fewer passengers, there’s often more room to relax, chat with the crew, and simply enjoy Maui’s coastline. You may even have the chance to steer the boat!
19. Cool Off with a Dole Whip
Nothing says tropical vacation quite like a cold, creamy Dole Whip. Grab this pineapple treat after a warm day at the beach for a sweet taste of the islands—and a little bit of summer in the middle of winter.
Local’s tip: You will find that each Dole Whip offered is a bit different from the rest, so we encourage people to try it at multiple shops! And we’re always happy to share which one we think is best- just shoot us an email!
20. Learn to Play the Ukulele
Take home a Maui memory you can actually keep practicing. And you don’t have to be particularly musical to have fun trying!
Local’s tip: (August 2026)- The Shops at Wailea currently host free, open lessons at 5:30
21. Drive the Road to Hāna
Waterfalls, rainforest, dramatic coastline, and countless places to stop make the Road to Hāna one of Maui’s classic adventures. Give yourself plenty of time, focus on the journey rather than checking off every stop, and always respect posted signs and private property.
Local’s tip: If your group has someone that gets carsick easily, this probably isn’t the trip for them!
22. See a Maui Waterfall
Winter’s wetter weather can make Maui’s lush landscapes and waterfalls especially beautiful. You’ll find waterfall views along several island drives and trails, with plenty of opportunities to simply stop and admire them from a safe location.
Local’s tip: Most of the waterfalls are along the Road to Hana, so if you don’t plan to do the drive then you probably won’t see a Maui waterfall.
23. Paddleboard on the Pacific
On a calm Maui morning, stand-up paddleboarding is a wonderfully peaceful way to get out on the water. Choose a protected area with appropriate conditions, and don’t be afraid to start on your knees until you find your balance.
Local’s tip: You can rent paddleboards in Kihei, and the shop owners will instruct you where to go.
24. Learn to Surf
You don’t have to tackle Maui’s famous winter waves to say you surfed in Hawaii. Take a beginner lesson in an appropriate location and let an experienced local instructor introduce you to one of Hawaii’s most iconic activities.
Local’s tip: These take place in Kihei where the surf is smaller.
25. Trade One Cold Winter Week for Maui
Maybe the ultimate Maui winter bucket-list item is the simplest one of all. Trade one cold week at home for seven days of bare feet, warm ocean air, tropical fruit, whale sightings, beach days, and mornings spent outside.
And give yourself permission not to check off everything on this list. Sometimes the best Maui winter vacation is the one where you have nowhere else you need to be.
Local’s tip: Book your trip now for this popular time of year!
Heritage Vacation Homes is a boutique collection of luxury vacation rentals along the Oregon Coast and on Maui, thoughtfully designed for families and multi-generational gatherings.
With local insight, elevated amenities, and carefully curated homes, we create beautiful spaces where meaningful memories are made.