Dating back for hundreds of years, the Hawaiian Islands and Hawaiian people have a storied history with sailing and navigating the oceans. The earliest arrivals to the islands came via voyaging canoe, using only the stars and trade winds to navigate the Pacific Ocean, ultimately landing at the undiscovered island chain that is now Hawaii.
Today, sailing to Hawaii is a little different, and navigating the open ocean is no longer solely dependent on the stars and trade winds. GPS alone makes getting to the islands far easier and significantly faster. Though there are still boats, like the Hokulea, that use traditional Polynesian navigation to sail the world, most vessels today utilize the technology available to them.
Sailing remains a cherished part of daily life in Hawaii, and visitors can take part in this timeless activity. Each island offers incredible options for sailing adventures, with breathtaking views and the chance to experience the islands from a new perspective. Imagine spending your first few days strolling Waikiki Beach, with Diamond Head in view, then setting out on a coastal sunset sailing cruise to see the landmark from the sea. Seeing Diamond Head from the ocean gives you the same awe-inspiring view that greeted voyagers arriving to Oahu centuries ago.
Sailing is as historic as any other Hawaiian tradition, even surfing, and time spent at sea is always memorable. Whether you’re gliding along the Na Pali Coast on Kauai’s famous sailing tours or enjoying a sunset cocktail cruise off Maui, you’ll experience one of Hawaii’s oldest and most peaceful adventures.
Each island offers distinct sailing experiences that let you connect with the ocean and the legacy of Hawaii’s first navigators. From catamaran sails to luxury charters, these trips reveal island views and hidden beaches you can’t reach by land. The islands of Hawaii are stunning from the sea — and every Hawaii Sailing Adventure is a story worth telling.
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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