Top Maui Catamaran Cruises

Leave behind the crowds of Ka’anapali Beach and spend the evening on a sunset cruise off the coast of Maui. The perfect romantic evening out, this sunset cruise offers unmatched island views, photo opportunities, and even the chance to spot whales (December–April).

Board the beautiful and spacious Pride of Maui catamaran for a sunset cruise near the Molokini crater. Enjoy an open bar including craft beer and blended drinks, plus a generous buffet featuring barbecued ribs, honey-glazed chicken, stir fried vegetables, and more. Watch the sun set, take in a live hula show and if you’re lucky, you may even see humpback whales during mating season.

Unwind after a day of exploring Maui on a sunset cruise with a 4-course dinner. Enjoy delicious cuisine and included Mai Tais and other beverages against the stunning backdrop of the Pacific Ocean and surrounding islands of Lana'i and Moloka'i. With a limited number of guests aboard, this makes for the ideal romantic experience.

Snorkeling in Molokini Crater is undeniably one of the best parts about visiting Maui. Here in this crescent, submerged volcano off Maui’s southern coastline, over 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet, and swim with schools of tropical fish while cruising the vibrant reef. You can also just sit and suntan on the deck, with sweeping views of Haleakala set just off the back of the boat.

This Maalaea Harbor Sunset Dinner Cruise from Wailuku is perfect for couples or anyone looking to add a beautiful, sunset experience to their trip while in Maui. When booking, choose from multiple dinner options such as prime rib, baby back ribs, and a vegetarian penne pasta. During your cruise, sit back with tableside service and drinks included as your captain and crew take care of the rest and you take in the sunset with island-style music playing in the background.

No boat has a better view of whales than the triple-decker catamaran Calypso. The newest and most-advanced whale watching boat on Maui. Come join the fun and friendly captain and crew aboard the Calypso for this 2-hour whale watch cruise along the Pali coast of Maui. Admire the whales from the surface or go down to the underwater viewing room whenever the boat makes a stop. If the whales choose to swim beneath the vessel, you’ll be able to see them through the glass panels in the bottom of the hull. Your driver/guide will tell you some of the more popular moves that whales engage in. Enjoy comfortable seating throughout and take advantage of the bar and snack area aboard. December 16, 2021 - April 17, 2023.

Get an up-close look at Hawaii’s Humpback whales during this 3-hour cruise run by a team of marine naturalists and biologists at the Pacific Whale Foundation. Each trip is different, but you’re likely to watch mothers interacting with their calves, observe mating behavior, and listen to whale songs through an underwater hydrophone. A buffet-style lunch and two complimentary drinks are also included.

Charter-ready for sailing around the renowned waters of Maalaea, our sailing fleet provides the perfect choices for small private groups to escape the crowds. Join us and snorkel, whale watch, enjoy some cocktails, learn to sail, celebrate a special occasion, or just lay back and relax. We can customize the perfect trip to make your dreams come true. This is a small ʻohana run business. We are one of the few companies on Maui owned and operated by born and raised captains. Our hand-selected and trained staff have been on island operating boats collectively for nearly 100 years, you can rest assured that your experience will be top notch. We focus on providing genuine, thrilling, eco-friendly charters. Our goal is to ensure you have the most incredible experience that you will look forward to having again, telling all your friends about, and rebooking every time you return to Maui.

Charter-ready for sailing around the renowned waters of Maalaea, our sailing fleet provides the perfect choices for small private groups to escape the crowds. Join us and snorkel, watch the sunset, whale watch, enjoy some cocktails, learn to sail, celebrate a special occasion, or just lay back and relax. We can customize the perfect trip to make your dreams come true. This is a small ʻohana run business. We are one of the few companies on Maui owned and operated by born and raised captains. Our hand-selected and trained staff have been on island operating boats collectively for nearly 100 years, you can rest assured that your experience will be top notch. We focus on providing genuine, thrilling, eco-friendly charters. Our goal is to ensure you have the most incredible experience that you will look forward to having again, telling all your friends about, and rebooking every time you return to Maui.

Charter-ready for sailing around the renowned waters of Maalaea, our sailing fleet provides the perfect choices for small private groups to escape the crowds. Join us for a gorgeous sunset sail, whale watch, enjoy some cocktails, learn to sail, celebrate a special occasion, or just lay back and relax. We can customize the perfect trip to make your dreams come true.