Sailing in Hawaii dates back to the very beginning of the islands, when ocean voyagers crossed the Pacific using only the stars and trade winds to navigate and settle the islands. For centuries, sailing was the only means of travel to Hawaii, bringing explorers and traders from across the world to these shores. While modern travel is much easier today, sailing remains one of the top ocean activities, and Hawaii Sailing Tours continue to be among the most memorable adventures on any trip.
Every island offers unique opportunities to experience the ocean and Hawaii’s scenic coastline from a whole new perspective. You’ll depart from the harbor and head out to sea, enjoying panoramic island views that are only visible from the water — revealing a side of Hawaii few visitors ever see.
We’ve highlighted one exceptional Hawaii Sailing Tour from each island to give you a taste of what awaits. But don’t just take our word for it — book a sailing tour during your visit and experience the ocean firsthand, connecting with one of Hawaii’s oldest traditions.
Oahu – North Shore Catamaran Sunset Sail
Head to Oahu’s world-famous North Shore for a relaxing evening cruise aboard the North Shore Catamaran Sunset Sail. Enjoy snacks and refreshments as you glide past legendary surf beaches like Sunset and Waimea Bay, framed by the lush mountains of Oahu’s northern coast. It’s one of the most peaceful and picturesque ways to end a day on the island.
Maui – Pacific Whale Foundation Stargazing Cruise
There’s something magical about sailing under the stars. The Pacific Whale Foundation Stargazing Cruise offers an unforgettable nighttime sailing experience guided by a guest astronomer. Learn about the constellations while enjoying appetizers, tropical drinks, and a starlit ocean view you’ll never forget.
Kauai – Holo Holo Charters Na Pali Sunset Sail
One of Hawaii’s most iconic sailing experiences is along Kauai’s Na Pali Coast. The towering cliffs, cascading waterfalls, and vivid sunset colors make this one of the most breathtaking sights in the islands. Dinner, wine, and tropical cocktails are served on board, making it a complete luxury experience at sea.
Due to the high volume of visitors traveling to Hawaii year-round, our Hawaii tours and activities sell out quickly. In many cases, tours sell out weeks or months in advance. To ensure your spots on tour, we recommend reserving your tours today. Call our office or book online to take advantage of our low price guarantee today.
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