In wintertime, the Hawaiian Islands come alive. As the holidays approach, Maui starts busting with visitors- and we're not simply talking about vacationers from the mainland. December ushers in the arrival of scores of humpback whales to Hawaii's waters. With them comes massive winter swells that will periodically hammer northern facing shores (to many surfer delight). The occasional winter storm will also roll through, battering the islands with rain, wind, and sometimes even snow! It's safe to say that Maui is buzzing with energy during these months. If you find yourself on the Valley Isle this coming season, here are the top 10 things to do on Maui this winter.
1 - Go whale watching.
Whale watching is hands down one of the most popular Maui activities in the wintertime. Maui County is a favorite among humpback whales, who prefer Maui Nui's shallow channels and calm waters over other islands like Oahu and Kauai. Maui is said to have the largest humpback whale population, with the highest concentration being in the Auau channel off of Lahaina. And wouldn't you know it, one of the best whale watching tours departs directly from Lahaina Harbor. Hawaii Ocean Project boasts one of Maui's most comfortable, stable, and spacious whale watching boats. In whale season, they run several daily two-hour tours.
2 - Go on a holiday sail.
While celebrations for holidays like New Year's Eve might be up in the air for the foreseeable future, Kai Kanani has their NYE festivities locked down. Kai Kanani is south Maui's only catamaran with exclusive permission to load from the sand at Maluaka Beach. Their NYE tour (which is sold out, but you can call to be on the waitlist at (808) 879-7218) gives visitors and residents a chance to ring in the new year at sea while watching the blazing firework display that's taking place onshore. The night includes a five-course meal (plus dessert!) from The Market Maui, local beer, wine, spirits, and live entertainment. Alternatively, Kai Kanani also hosts a Valentine's Day Sunset Sail for all you romantics out there. 
If you don't find yourself on Maui during one of these holidays, Kai Kanani also hosts daily sunset sails featuring drinks, dinner, and entertainment.
3 - Visit the neighboring island of Lanai.
Typically, the only way to day-trip to another island involves hopping on a plane. And with TSA lines likely growing to be hours long in peak season, a day trip might be too much of a bother. Fortunately, Lanai, one of Maui's nearest neighbors, is a short boat ride away. While you could opt to take the ferry and then try to score a rental car, there is no easier way to discover Lanai than with Trilogy. Trilogy's 'Discover Lanai' tour has been introducing visitors to the Pineapple Isle for over four decades- so it's safe to say they're experts.
Most tours to Lanai only skirt the coastline, but Trilogy has sole permission to access the Hulopo'e Marine Preserve. Here you can spend the day exploring the Hulopo'e/Manele area- snorkeling, hiking, and beach volleyball are all on offer. This tour even offers a cultural experience led by a Hawaiian cultural practitioner. To top it off, breakfast, a delicious lunch, and beverages are included.
4 - Learn to fly a plane.
Yes, you read that right- you can learn to fly a plane out of OGG with Maui's only flight school, Fly Maui. Fly Maui's "Discovery Flights" serve as an introduction to flight school, and feature a short flight out to Hana and back with a certified instructor. This is an excellent opportunity for anyone interested in flight school or adventurous souls looking to try something new. A discovery flight can also make a great Christmas gift for a budding aviator.
5 - Explore Upcountry.
Many visitors eschew an Upcountry trip, favoring the sun and sand instead. But Upcountry offers a different side of the island and grants a peek into country living, Maui style. Upcountry encompasses the towns of Makawao, Pukalani, Kula, Ulupalakua and is also the gateway to the famous Haleakala National Park. This region is home to many activities, from ziplining through a high elevation forest to simply window shopping and cruising the streets in Makawao Town. There is so much to do and see in Upcountry; it can be worth spending a night. Especially if you're planning on seeing the sunrise at Haleakala. Spending the night at North Shore Lookout in Makawao can shave 1-2 hours off your drive time to the summit. And, not to mention, this boutique bed and breakfast is one of the chicest on the island.
If you're not one of the few who the universe has smiled upon and granted tickets to the sunrise at Haleakala, here's a hot tip: take a tour with Haleakala Eco Tours. The early wake-up call can be hard, so having someone else behind the wheel for the drive through the dark is a real luxury.
6 - Watch the surfers on the North Shore.
For surfers on the north shore, winter means one thing: waves. Ho'okipa Lookout near Pa'ia is a great stop to watch some shredders, or if you find yourself in Pa'ia Town, head to Pa'ia Bay to watch bodyboarders and surfers alike. Over on the west side, stop by the famous Honolua Bay. Honolua Bay is one of the best waves in the world, and on the right swell, it turns into a right-hand point break. There is a small lookout on the west side of the bay with a food truck and some fruit stands, where you can also peer directly into the waves. Looking for more to do and see on the North Shore?
Check out the North Shore podcast episode by the Aloha 360. They share restaurants, activities, and best beaches.
7 - Take a whale-watching kayak tour.
Okay, okay, if you're on Maui in the wintertime, chances are good you already have a whale watch planned. But can you ever really get sick of watching whales?! This Maui kayak tour heads out into the deep blue early morning when the wind and water are calm. This means it's prime time for spotting whales. Under federal law, humpback whales must not be approached within 100 yards. However, as many seasoned kayakers can attest, humpbacks can sneak up on you sometimes- especially if you're not on a tour boat with a loud engine. You never know where they might pop up for air. This tour also hits one of south Maui's best snorkeling spots. If you dive down deep, you'll probably hear some of the whales you spotted along the way singing their bellowing song.
8 - Attend a painting cocktail party with your friends.
Island Art Party is precisely what it sounds like- a party where you make art. At Island Art Party, everyone is a painting virtuoso. Chalk it up to the master instructors who give step-by-step instructions on creating your masterpiece or the liquid confidence (i.e., beer, wine, and cocktails) that are served up in-house. Island Art Party is one of Maui's most unique experiences, and it's a great activity to do with friends or family.
9 - Snorkel the famous Molokini Crater at sunrise - Redline
Winter is Hawaii's peak season for tourism. Fair enough, considering a good chunk of the country is blanketed in a layer of snow and ice at this time of year. However, this means that top attractions like Molokini Crater can get a touch crowded. Redline Rafting has crafted an effective solution to combat the crowds: simply beat the rest of the boats to the crater. Redline can do this because a) their home base is located at Kihei Boat Ramp, closer to Molokini than Ma'alaea Harbor, where most of the other boats depart from, and b) because their tours employ a speedy raft that can reach the crater in 15 minutes flat.
With Redline, you'll be checking in for your tour at 6:30 am and exploring the magical underwater world at Molokini no more than 45 minutes later. Not to mention, the views of the sun rising over looming Haleakala are hard to beat.
10 - Take an island road trip in a classic car.
Busy season is sure to bring some rental car woes. If you don't score the car you wanted, don't sweat it. You can still cruise the island in style with Maui Roadsters. Maui Roadsters has a fleet of fully restored classic 1957 convertible Porsche Speedsters. Jeeps and Mustangs are a dime a dozen, but if you cruise along the west side or out to Hana in a '57 Porsche, you're sure to turn some heads.
Looking for more to do?
Maui has plenty of more specific events (golf tournament, tree lightings, festivals, and more) which are outlined by our friend Candy on her Maui winter events article. She updates this article every year, so bookmark it. Have a great winter and ALOHA!