The Sailing Season – Oahu, Circumnavigating The Island

By: Destinations, Schools

ASA Outstanding Instructor Greg Martin of Sail Hawaii is very familiar with the waters around the Hawaiian Islands and he regularly sails and teaches out of Oahu. Greg has contributed to a three-part story on sailing in Hawaii.

Venturing further than Waikiki, a sailing adventure from Oahu might start with a short cruise to Keehi Lagoon. Downwind from Ala Wai, Keehi is home to La Mariana Sailing Club, the original Tiki Bar and an unofficial “dock and dine” stop with some of the best seafood dishes, local favorite rum punch, and live entertainment. After a fun night at La Mariana, Keehi Marine Center is also the place to top off on fuel at the start of your multi-day sailing adventure.

Circumnavigating Oahu, Hawaii

If the plan is to circumnavigate Oahu, with regular Trade Winds (east/ northeast, less than 25 knots), it’s best to go around the island counter-clockwise. The roughest, the upwind part will be in the beginning, passing Diamond Head buoy and beating to windward around Koko Head and Mokapu’u Point. Once you get around the point, it’s a nice reach- though likely big seas as you cruise down the windward east coast, past Waimanalo and see the other side of the twin “Mokes” (Mokulua islands) off Lanikai. Finally getting around the Marine Corps base at Mokapu Point, you can sail downwind for a bit until you have to motor through the narrow Sanpan Channel leading into Kaneohe Bay. K Bay is beautiful, circled by the Ko’olau mountain range. However, most of the bay is a lee shore with dangerous reefs everywhere, though the offshore reefs break the seas. In the middle of the bay is the popular Kaneohe Sandbar. The Sandbar is a fun place to almost ground your boat, step off and walk around and it makes a safe place to anchor for the night.

Departing the next day, you cruise past Mokoli’i Island (Chinaman’s Hat) through the north Kaneohe Bay channel, to continue your cruise along the windward coast of Oahu. Kahana Bay is one of the first options to stop and anchor tucked away in the lush cliffs of the windward side. Past Kahana Bay, you’re committed to going around the north cape of the island, around Kahuku Point. Once around Kahuku Point, it’s all downwind sailing to the beautiful Waimea Bay on the North Shore where the legendary Eddie Aikau once worked as a lifeguard. You can stay here at anchor for the night, but if you want a little bit of civilization, the North Shore town of Haleiwa is just down the coast and you can either anchor outside the harbor or you may as well just go inside the harbor and temporarily tie up at the visitor dock if there’s room.

After a comfortable night at the dock, and maybe a visit to Haleiwa Joes or the Beach House for fine dining, it’s all downwind sailing from Haleiwa to Kaena Point on Oahu’s northwest corner. This point can be a treacherous sail, but once around the point, you’re in the calm leeward side of Oahu. Just south of Kaena Point is Yokohama Beach and Makua Bay, two of the most beautiful and tranquil anchorages on Oahu. Spinner dolphins always like to hang out in this area and Makua Bay almost always has a spectacular rainbow over it. You can also cruise down the coast a little way to Pokai Bay, outside of Waianae Harbor and anchor in any of these three spots for the night. If you really want a hot shower, you can go just a little way further south to Ko’Olina Marina, the nicest private marina on Oahu, which always has visitor slips (for a price). If you’re going to dock at Ko’Olina you might as well hang out at any of the resorts in the area and be sure to stop at Monkeypod kitchen for the best lilikoi mai tais on the island. Any of these leeward side anchorages are a day sail around Barber’s Point, back upwind to our homeport at Ala Wai and the Aloha Dock at Hawaii Yacht Club.

Sailing Schools in Hawaii

Greg Martin is a recipient of the 2018 ASA Outstanding Instructor award and teaches at Sail Hawaii out of Ala Wai Harbor on Oahu. He not only teaches in Hawaii he also leads sail charters throughout the neighboring islands.