With its balmy temperatures all year round, calm trade winds, and magnificent natural beauty, Destinations in Hawaii is a sailor’s paradise. Hawaii is a great place for sailors of all skill levels since there are so many islands to discover, each with its own distinctive landscapes and sailing conditions. Hawaii offers something to offer everyone, whether you’re an experienced cruiser or a novice sailor.

As a sailor, Maui, Kauai, Oahu, Molokai, Lanai, the Big Island, and Niihau are a few of the best Hawaii sailing places you won’t want to miss. From the protected, quiet seas of Molokai’s south shore to the exhilarating 20-foot surf on Maui’s north shore, each island boasts its own distinctive sailing conditions. Destinations in Hawaii are ideal for an unforgettable sailing adventure because there is so much to discover there.

Top 7 Destinations in Hawaii for Sailors

Because of its crystal-clear waters and breathtaking surroundings, Maui, often known as the Valley Isle, is a well-liked sailing destination. Sailors may enjoy the island’s scenic beaches, explore secret coves and reefs, and come in contact with dolphins and sea turtles.


Maui, one of Hawaii’s most well-known Destinations in Hawaii, provides a variety of activities for sailors of all skill levels. Sailors can explore the island’s breathtaking shoreline and find undiscovered coves and reefs thanks to its warm and tranquil waters. Together with great chances for scuba diving and snorkeling, Maui has a plethora of marine life, including dolphins, sea turtles, and vibrant fish. After a day of sailing, there are many possibilities for relaxation and sunbathing on the island’s lovely beaches.

A short sail from Maui separates Lanai, which offers a tranquil and isolated sailing experience. Lanai is a fantastic location for fishing, scuba diving, and snorkeling thanks to its beautiful coastline and clear waters.


A tranquil and remote sailing destination, Lanai is only a short sail from Maui. Lanai is the ideal Destinations in Hawaii for fishing, snorkeling, and scuba diving because of its immaculate coastline and crystal-clear waters. The island is a must-visit location for sailors seeking a serene and immersive experience because it also features gorgeous hiking trails and distinctive cultural experiences.

Sailing aficionados frequently travel to Kauai, sometimes known as Garden Island. While sailing the island’s waterways, the waterfalls, lush landscapes, and rocky coasts provide a stunning backdrop.


The Garden Island, Kauai, provides a distinctive and varied sailing experience. The island’s secluded coves and bays may be explored by sailors thanks to its rocky coasts, waterfalls, and beautiful sceneries. The Napali Coast, one of Hawaii’s most breathtaking coasts, is located on the island of Kauai and is accessible only by boat for an incredible sailing adventure. For those seeking excitement, the island has good surfing and hiking options.

To discover more about various sailboats, yachts, and catamaran types you can check out this Sailboat Data page. You may discover comprehensive details on different sailboat models and their performance here, making it easy for you how to pick the best boat for your requirements. 


The fifth-largest island in Hawaii, Molokai, is a secret paradise for sailors. The undeveloped shoreline and remote anchorages of Molokai make for an exceptional and peaceful sailing experience.

For those who enjoy sailing, Molokai is a hidden gem that provides a distinctive and peaceful sailing experience. Sailors can take pleasure in the solitude of this lonely island thanks to its undeveloped coastline and private anchorages. Aside from its well-preserved Hawaiian traditions, including as the hula and canoeing, Molokai is renowned for its rich cultural heritage.


Honolulu, the state capital of Hawaii, is located on the island of Oahu, which is a bustling centre of activity and a favourite sailing location. Oahu provides a wide variety of sailing experiences, from the tranquil waters of Waikiki to the world-famous surf on the North Shore.

Oahu, the centre of activity in Hawaii, provides sailors with a variety of sailing opportunities. Any sailor may find something to enjoy on Oahu, from the serene waters of Waikiki to the world-famous surf on the North Shore. The island is a must-visit location for history buffs because it is also the location of Pearl Harbor and the USS Arizona Memorial.

Big Island

The Big Island, the biggest of Hawaii’s islands, is a must-see location for any sailor. The Big Island provides a singular and spectacular sailing experience because to its active volcano, black sand beaches, and marine life including manta rays and sea turtles.

The Big Island offers a one-of-a-kind and extraordinary sailing experience with its active volcano, black sand beaches, and varied marine life. In addition to seeing marine species like manta rays and sea turtles, sailors may also explore the island’s beautiful coastline and see lava flowing into the water. The island also provides a variety of cultural events, such as contemporary art and music festivals as well as traditional Hawaiian ceremonies.


Niihau is Hawaii’s westernmost inhabited island and a quiet getaway that provides a tranquil and unspoiled sailing experience. Niihau is a must-visit location for any sailor wishing to get away from the crowds and appreciate Hawaii’s natural beauty because of its pristine seas and diverse marine life.

Niihau provides a tranquil and unspoiled sailing experience because it is a distant and secluded location. Sailors can discover the island’s secret bays and cove thanks to its clean seas and diverse marine life. The island is a must-visit Destinations in Hawaii for sailors seeking a true Hawaiian experience because of its distinctive cultural traditions, including the use of the Hawaiian language and traditional crafts.

Best time to Sail in Hawaii

Between May and October, when the trade winds are at their strongest, is the ideal time to sail in Hawaii. The best sailing conditions are created by these northeasterly breezes, and this is also the time of year when the water is the warmest. A sailboat or yacht is advised in order to truly appreciate your sailing adventure in Hawaii. Long-distance sailing is best suited to sailboats with deep keels because they offer stability in the wind. A catamaran or trimaran, on the other hand, can provide greater speed and stability in turbulent conditions, making them ideal for day sails or shorter voyages.

Visit our sailing destinations page for some incredible ideas and places to explore if you’re feeling motivated to organize your own sailing holiday. Start preparing for your upcoming sailing excursion right away with Ocean Wave Sail!

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