Tips for Sailing in Hawaii

Hawaii is a destination sail for any serious racer or cruiser contemplating a Pacific crossing. Whether you’re planning a few weeks of cruising after finishing the Pacific Cup, or visiting the islands on your way to the South Pacific, here’s what you need to know about sailing in Hawaii.

Boomerang leads the fleet around Kaena Point - Day 2 of the DJ Johnson 3 Day Around Oahu race. Photo by Jenn Virskus.

We went out to Hawaii recently to join John Spadaro and his crew on his DK46 Boomerang for the DJ Johnson 3 Day Around Oahu race hosted by the Waikiki Yacht Club.

Spadaro only recently began campaigning the DK46, but has won just about every sailing trophy in Hawaii with the previous Boomerang, and collectively, this group of sailors has more than 200 years of experience racing and cruising the Hawaiian Islands.

While sitting on the leeward rail—it was an unusual year, light breeze and downwind sailing nearly all the way around the island—we chatted with crew members to collect the best tips for sailing in Hawaii.

Best yacht clubs

Kaneohe Yacht Club—the first stop on the Around Oahu race—definitely has one of the best views on Oahu, if not in all of Hawaii. The eight-mile-long bay is dotted with islands and inlets, including Coconut Island, the setting for Gilligan’s Island. From anywhere in the bay, you have spectacular views of the Pali Highway climbing up over the mountains toward Honolulu and the Stairway to Heaven hiking trail leading up a steep face of the Ko’olau mountain range. There are mooring balls near KYC and limited dock space and the club offers a pool with a view, clean showers, outdoor barbeques, and tasty Mai Tai’s.

How to avoid the coral

"Whatever you do, don’t sail into Kaneohe Bay at night," says main trimmer Dave Kelly. Kelly has been sailing in Hawaii since 1968, and jovially says he’s been on every bed of coral in Kaneohe Bay. The channel is well marked with a tight series of red and green channel markers as well as range markers on shore, however, there are small beds of coral near and even inside the channel and sometimes the coral grows beyond the channel markers. These small beds are marked by white sticks, which aren’t hard to see if you’re looking, but are also easy to miss. At night and under cloudy skies, they can be impossible to see. If your boat draws more than seven feet, do not attempt to enter via Sampan Channel, but rather take the Main Ship Channel just slightly to the northwest.

How to navigate

Reefs aren’t an issue only in Kaneohe Bay, but throughout the islands, and whether or not you can see them depends on the tide and the weather. The depth charts on the Navionics app for smartphones and tablets is a great way to make sure you’re in deep water. On the north side of Oahu, be sure to give Kaena Point a wide birth to avoid submerged rocks.

Best spots for mooring

While there are a number of hospitable yacht clubs across the Hawaiian Islands, mast man Steve Anderson says in Hawaii cruisers should skip the clubs and get themselves a mooring ball off of one of Kauai’s idyllic beaches. "You can sail into Nawiliwili Harbor and stock up on supplies, and then head out to anchor," says Anderson. In the spring and summer, the 100-mile crossing from Oahu to Kauai should be fairly pleasant, but from mid-September through January, you can expect 15-foot swells (or even higher) and strong winds, and anchoring or mooring is next to impossible. One of the best and most beautiful spots to anchor in the state is Hanalei Bay on Kauai and is a great place to leave from when returning to the mainland.

If Maui is on your list, head to Big Beach off of Makenna State Park on the southwest side of the island. The sandy bottom is perfect for setting an anchor and there’s great snorkeling nearby in the Five Caves area and the Molokini crater (a short sail from Big Beach). There are also mooring balls available at Molokini if conditions allow. If soaking up the nightlife is your thing, head to Lahaina. There are slips and moorings available just steps from the best bars and restaurants.

Best Luau

"The best luau in Hawaii is at Germaine’s," says Anderson. As we rounded Kalaeoa, we watched smoke rise from the Kalua pig. From the menu to the food to the sunset views of the Pacific, Anderson says that this luau has it all. There is no harbor right at Germaine’s; if arriving via sailboat, the closest harbors are Ko Olina Marina to the west or Rainbow Bay Marina at Pearl Harbor to the east. Rainbow Bay is for military only and not accessible to the general public. Germaine’s also offers a complimentary shuttle service from hotels in Waikiki.

Best Season for Sailing

Sailing is a year-round activity in Hawaii and the Hawaii Yacht Club hosts their Friday Night Race series 52 weeks per year—even on Christmas if it falls on a Friday. But just because you can sail all year, doesn’t mean you should. September 15 is the cut-off date for sailing on the north shore of Oahu and Kauai, according to the Boomerang crew. A 30-foot wave is fantastic for surfing, but sailboats are wise to stay away. Haleiwa Boat Harbor, located on the North Shore of Oahu in Waialua Bay, is a great spot to stop on a Hawaiian cruise, but trying to get in or out when the swell is up is a risk not worth taking, says trimmer Rich Smith.

In the summer, you can generally expect trade winds from the northeast, however, this year’s Around Oahu race is a perfect example that just like on the open ocean, in Hawaii the weather can change quickly and dramatically to be anything but typical. Smart sailing means keeping a constant eye on the weather around you, and knowing where your safe harbors are on any given route.

Best Races

Spadaro says the best race of the year is the Kalakaua Cup, and not only because he’s the current holder of the historic silver trophy. The race, officially the Hawaiian Challenge Cup, was established by His Majesty, King David La’amea Kalakaua in 1889. King Kalakaua was a great lover of sailing and wanted to create an annual race on the 4th of July. The Kalakaua previously a three-day regatta consisting of distance races between Waikiki and Kaneohe and offshore buoy racing. Today, racing starts outside of Kaneohe Bay and consists of a single day of offshore buoy racing. The race winner fills the cup with “Cubies” (rum and coke if you’re not from the islands) and shares a drink with his crew, and then typically, with the rest of the competitors.

The Boomerang crew holds up the DJ Johnson 3-Day Around Oahu trophy. - From left, Quantum Sails writer Jenn Virskus, trimmer Rich Smith, skipper John Spadaro, main trimmer Dick Kelly, Carlo Brand, Jason Virskus, Mike Beason, and Mark Knoller (other crew not pictured).

Any Pac Cup boats that opt to cruise Hawaii for a few weeks after before heading back to the mainland may want to join in the fun of the Lahaina Return race held annually in early September—a favorite of the Boomerang crew. The boats are delivered to Lahaina Yacht Club on Maui and race back to the Ala Wai Boat Harbor on Oahu. Conditions normally include big breeze and swells for one of the most exciting downwind runs of the year.

The Kauai Channel Race is specifically scheduled to give Transpac and Pac Cup boats an opportunity to race in the trade winds from Kaneohe to Nawiliwili. The race is 95 nautical miles and is usually scheduled for the week or two after the awards ceremony for the ocean crossing race from California.

Next time you’re in Hawaii, test your skills against local knowledge at one of the HYC Friday Night Races—fleet winners earn three pitchers of Cubies—or just make sure to stop by and say hello to the Boomerang crew at the club! Even if you don't plan on sailing, the view of the sunsets and Friday Night Races from the upper deck Galley at HYC are fantastic.

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