Whale Watching & Sailing with Maui Custom Charters

Located along the southwestern coastline of Maui in Maalaea Bay, Maui Custom Charters offers an intimate window into the Pacific’s vibrant marine world. This area, known for its sheltered waters and scenic ocean vistas, provides the perfect launching point for private sailing and whale-watching trips, making it an essential addition to anyone’s Maui outdoor itinerary.

Maui’s unique geography creates rich marine habitats where humpback whales migrate every winter, turning these waters into one of the planet’s premier whale-watching destinations. Maui Custom Charters operates beautiful, well-maintained catamarans like the Artemis, outfitted with snorkel and fishing gear, giving visitors a versatile adventure experience—whether spotting breaching whales or slipping beneath the surface to swim alongside sea turtles.

Guests repeatedly praise the attentive crew, including Captains Ana and Tim, alongside crew members like Marcella and Makana, who infuse each trip with expert local knowledge, safety, and genuine warmth. Their ability to blend education with enjoyment ensures each outing feels personalized and memorable. One standout feature is the private charter format, allowing groups—whether family, friends, or couples—to soak in Maui’s ocean spectacle away from crowded tour boats.

The trips range from half-day whale watches during the peak season, commonly from late December through April, to sunset cruises that reveal the island’s coastline in changing light and colors. These experiences unveil encounters with not only whales but also hawksbill sea turtles, spinner dolphins, and unique coastal rock formations shaped by volcanic activity.

Maui Custom Charters is more than a boat company; it’s a gateway to understanding Maui’s coastal ecosystem while enjoying luxury, comfort, and personalized attention. Whether watching whales breach against a backdrop of volcanic peaks or sailing calm bays under a glowing Hawaiian sunset, these charters deliver a rare blend of adventure, relaxation, and connection to Hawaii’s natural heritage.