Things to Do on a Winter Trip to Maui

Things to Do on a Winter Trip to Maui

Sun, surf, and sand: three things we all wish we could have during the colder months! If you’re lucky enough to enjoy a Maui winter vacation, make sure you make the most of your adventure. These excursions will help you wring every last drop of sunshine out of your trip for an unforgettable experience.

Things to Do on a Winter Trip to Maui


Whale Watching Tour

It turns out humans aren’t the only mammals attracted to Maui’s warm, sunny weather in the colder months of winter.

Maui’s prime whale watching season falls snugly in between January and late March. Each winter, pods of Humpback whales come to relax in Maui’s temperate waters, which offer ideal protection for relaxation, before they make the long swim back to Alaska. The Pride of Maui offers a perfect 360° viewing deck from which to watch them fluke and swim.

With more than 2500 feet of deck space and a glass bottom for improved viewing, you are guaranteed to have ample chance to take that perfect picture. The two-hour cruise comes with a complimentary barbecue lunch, access to a waterslide and, for the older folks, an open bar.

winter maui activities whale watching
Whale watching in Maui


The Road to Hana

The Hana Highway is one of the most breathtaking roadways in America. Every single one of its 52 miles is rife with breathtaking waterfalls, natural lava arches and formations, local crafts, sheer cliff views, and lush Hawaiian flora and fauna.

The road’s complicated twists and surprising hairpin turns, however, make for little time to enjoy the driving experience—at least, not if you want to avoid an accident. Instead, let Valley Isle Excursions chauffeur you along this fantastic roadway in comfort, safety, and style.

Each tour cruiser driver-and-guide has been meticulously trained on the Hana Highway until they are completely familiar with the highway. This not only assures your safety in the cruiser, but gives them intimate knowledge about the best places for memorable photos!

The cruiser itself is made to allow passengers the extra height needed to take stunning snapshots without fear of a guard rail blocking half the shot. Bring home memories to warm your heart even in the coldest winter.

winter activities in maui


Kayaking in West Maui

Hawaiian Paddle Sports tours aren’t your typical tours of Maui. Their kayak tours are intimate and eco-friendly.

Not only do their small, private tours involve more time for the guides to answer your one-on-one questions about the culture, history, and sea life around the island, but they allow you to enjoy the beauty of the island uninterrupted and unimpeded by the loud engines of the average crowded cruise. Let nothing stand in between you and the serene awe of your surroundings!

HPS offers four kayak tours in total: a three-hour whale watching tour from December to April, a guide of the coral gardens off Olowalu beach (including visits to spots known for their green sea turtle activity,) a tour of the Honolua Bay area which is also part of the Jean-Michael Cousteau “Ambassadors of the Environment” program, and a challenging paddle trip to the breathtaking underwater landmark of Molokini Crater.


Where to Stay on Maui:

We’ve been to Maui twice in the last two years and during both visits, we stayed at the Sheraton Maui. We fell in love with everything about this resort and I don’t think there is another place we would stay on the island. With the top-notch diving and snorkeling at Black Rock, the lazy river that winds through the resort’s well-manicured grounds, and stellar cuisine at their restaurants, it’s the ideal location for any water lover.

The water adventures mentioned above are all within a short drive from the Sheraton Maui in Kaanapali — and I highly recommend renting a car while visiting the island.


For more Hawaii travel resources, visit these pages:

The Ultimate Guide to Maui on a Budget

5 Amazing Water Adventures on Maui

Fear of Heights? Try Paragliding in Maui

Is Molokai the Real Hawaii?

First Impressions of Lana’i

Why Molokai Should Be On Your Bucket List


Photo Credit: Buck via Creative Commons.


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  1. No Quarter says:

    The Sheraton!? You fly all the way to Maui to stay at the most fake type of accommodation possible. Plastic fake white people Hawaii. The author of this article missed the best of Maui and got herded to all the typical tourist things with the rest of the cattle. Actually, its better that way. Stay with the tourists. Don’t come into our island. Better yet, go home.

    1. Wow an to think I wanted to come an get married there put deposits down but now don’t worry I will never visit after your comment I had over 37000 dollars invested on coming there but getting it all back

  2. The Hana Highway is a great location visit. Each tour planned is a big success everytime there.

    1. Ordinary Traveler says:

      We love the Hana Highway. It’s on our list every time we visit the island.