Friday evening sailboat races out of Ala Wai harbor

The Hawaiian Islands from a Boater’s Perspective

The Hawaiian island chain includes over 135 islands that span over 1500 miles in the north Pacific Ocean. The 50th US state is home to just under 1.5 million people that live on seven of the Hawaiian islands: Oahu, Kauai, Maui, Molokai, Lanai and the Big Island of Hawaii. Ni’ihau is an entirely privately owned island as well. Each of the populated islands of Hawai’i have their own unique character and it’s as if you’re visiting a completely different place when you hop from one island to the next. Each island’s nickname tells you something about the unique character of the island.


Oahu is the “Gathering Place” because it is the Capitol, the most populated and by far has the most going on. Oahu is most significant because it is the Hawaiian island that has a Westmarine. Oahu also has several private marinas and Hawaii state small boat harbors. The largest, Ala Wai Small Boat Harbor is nearest to the world renowned Waikiki Beach. The waters just offshore of Waikiki are sheltered from the trade winds by the iconic Diamond Head crater, making it the most popular place for boating in the state. Everyday numerous tour boats take people for snorkel and sunset cruises, scuba diving and whale watching from October to April every year. On Friday afternoons sailboats start and finish from Ala Wai harbor for the regularly scheduled Friday night sailboat races. Some of them stay out afterwards and watch the fireworks launched from the beach in front of the Hilton. There’s an active boating scene in Kaneohe Bay, on the west side out of KoOlina and Waianae and on the north shore out of Haleiwa. For more detailed information about boating on Oahu click here


Kauai is the “Garden Island” because it is the greenest of all the islands with the most rainfall and lush jungle covered mountains. Kauai is the place where people go to get away and escape into nature so it is not very populated and therefore does not have a lot of boating. Most of the boating takes place out of Nawiliwili harbor, where there is a small but dedicated yacht club. Port Allen is another small harbor that provides access to the west side of the island. Hanalei Bay on the North shore has a few moorings for the boats that venture out to explore the beautiful Na Pali Coast. For more detailed information about boating on Kauai click here.


Maui is the “Valley Island” defined by its unique geography with two big mountains on either side. Maui is a distant second most populated and active island after Oahu. There are a few Hawaii state small boat harbors on Maui, the most active by far is Lahaina. Boats come and go from this little harbor constantly, taking people on cruises and whale watching excursions in the Auau channel between Maui and Lanai. Boats also operate out of Maalaea Bay to go diving in Molokini Crater. For more detailed information about boating on Maui click here


Molokai is the “Friendly Island” and is all about people. Just about everyone of the island’s 7000 inhabitants know each other on this island without a single traffic light. Life on Molokai is very slow paced but centers very much on nature and the sea. Fishing and paddling are very popular on Molokai so the main harbor in Kaunakakai sees a lot of activity. One very popular annual event, the Molokai Hoe is a paddling race from Lono Harbor on Molokai, across the Kaiwi Channel to Oahu. For more detailed information about boating on Molokai click here.  


Lanai is the “Pineapple Island” but they really should change their name because they really don’t grow pineapples there anymore. They should change their name to Larry Ellison’s resort island because the computer entrepreneur bought most of the island in 2012 and totally fixed up the Four Seasons resort in Manele Bay into a rich person’s hideaway. You can still visit Lanai by boat though and for more information click here

Big Island (Hawaii)

The Big Island of Hawaii is so named because it’s the biggest. As big as the Big Island is, there’s not many people that live on the Island of Hawaii. Only about 200,000 people live on the Big Island, mostly in Kona and Hilo, where there are a few state run small boat harbors. There is a dedicated boating and sailing community on both sides of the Big Island and on the Kona side there’s one of the three state wide boat maintenance facilities where you can haul out your boat if Keehi Marine Center and the Phoenician on Oahu don’t work for you. For more information about the boating scene on the Big Island click here.  


Of the inhabited islands of Hawaii, Ni’ihau is the “Forbidden Island” because it is privately owned and inhabited by about 170 relatives of the Robinson family. Visiting Niihau isn’t on the itinerary for most people unless you’re invited by a resident or on a special tour. However legally all beaches in the state of Hawaii are public and so if you visit by boat there are beautiful beaches to anchor at, just be respectful of the locals if you encounter anyone. For more information about visiting Niihau by boat, check out Needles Notes.