Top Winter Activities in Maui: Whale Watching, Road to Hana, and Kayaking Adventures
Escape winter's chill with Maui's sun, surf, and sand. Maximize your island getaway with these expert-recommended excursions for an unforgettable tropical experience.
Whale Watching Tour
Humpback whales migrate to Maui's warm waters from Alaska each winter, peaking from January to late March. These majestic creatures seek sheltered bays for rest and calf-rearing before their northward journey.
Join the Pride of Maui for a premier 360° viewing experience on a spacious vessel with over 2,500 feet of deck space and a glass-bottom section. Capture stunning photos of breaching whales during this two-hour cruise, complete with complimentary barbecue lunch, waterslide, and open bar.
The Road to Hana
The Hana Highway, a 52-mile scenic marvel, showcases cascading waterfalls, lava arches, lush flora, and dramatic cliffs—often ranked among America's most beautiful drives.
Navigate its challenging twists safely with Valley Isle Excursions' expert drivers, trained extensively on the route. Elevated cruisers provide optimal photo vantage points without guardrail obstructions, ensuring memorable shots and heartwarming memories.
Kayaking in West Maui
Hawaiian Paddle Sports (HPS) offers intimate, eco-friendly kayak tours emphasizing cultural insights, history, and marine life—free from crowded boat noise.
Choose from four options: a three-hour whale watching tour (December-April), Olowalu's coral gardens and green sea turtle habitats, Honolua Bay (part of the Jean-Michel Cousteau Ambassadors of the Environment program), or a challenging paddle to Molokini Crater's underwater wonders.
Where to Stay on Maui
We've visited Maui twice in the past two years and stayed at the Sheraton Maui both times. This resort captivated us with Black Rock's world-class diving and snorkeling, a relaxing lazy river through manicured grounds, and exceptional dining—perfect for water enthusiasts.
All featured adventures are a short drive from Sheraton Maui in Kaanapali. Renting a car is highly recommended for flexibility.
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
