Simply put, sailing in Hawaii is a dream. Bountiful winds, gorgeous islands, friendly people, unbelievable marine life and crystal-clear water make this place a paradise, as I found out last winter while sailing from Ala Wai Harbor in Honolulu to the coastal town of Lahaina on Maui’s northwest coast. Along the way I experienced enough of Hawaii’s magic to realize that it’s one of the world’s most unsung sailing destinations.
I’ll admit a bias: I love whales. There’s just something purely magical about sailing in their presence that never fails to give me the chills. I thought I’d been privy to great marine-life theatrics before, but our first two hours out of Honolulu taught me otherwise.
Spouts and breaches were a regular occurrence as humpback whales showed off during their yearly sojourn in Hawaii to mate or give birth. Sailing off Lahaina four days later, I was stunned to spy multiple whale spouts simultaneously, from all points of the compass. As the sun set on our last evening of sailing, we were treated to one of nature’s most stunning performances: a powerful humpback shot straight up, its entire body airborne for one crystalline moment before crashing back to the briny depth with a tremendous explosion of displaced saltwater.
And then there are the sea turtles and the snorkeling and SCUBA diving opportunities. Our first night found us on the hook in Kaneohe Bay. A quick dink ride over to some nearby coral heads provided one of the most intimate encounters imaginable with big marine life. Dozens—maybe hundreds—of green turtles, some up to five feet long, were drifting among the corals. Some let us swim alongside or float nearby. Others were wary, lurking in the caves formed by the coral. Startle them, I discovered, and they’re gone in a flash, swimming faster than their physique suggests.
Hawaii’s geological features lend their own magic to sailing here. Eight major islands and hundreds of smaller ones are strewn over 1,500 miles of Pacific Ocean. Some of the big islands are flat, while others have steep hillsides and soaring, volcanic ridgelines. Steep trails ascend some of these peaks, luring the fit and the foolish. For the more sedate or sensible, Hawaii’s cities, towns and villages provide entertainment and refreshment.
One of the more energetic places we visited was Lahaina. Step ashore at the town dinghy dock, and you’ll soon encounter the massive banyan tree, which grows in Courthouse Square. The tree has 12 distinct trunks and occupies nearly two-thirds of an acre. Its sloping trunks and branches are a perfect jungle gym for children of all ages.
Hawaii sometimes suffers a bad rap among cruisers, as conditions can be a boisterous, especially in the open channels. Also, harbors and anchorages are limited compared to some island chains. While these factors may be partially responsible for the limited number of bareboat companies operating in Hawaii, the real reason that there are so few charter boats has to do with the permitting of commercial vessels. According to Ed Underwood of Hawaii’s Division of Boating and Ocean Recreation, Hawaii has strict regulations governing the number of commercial permits that are issued to companies that own and operate boats. “Since 2002, more than $70 million has been spent on harbor improvements,” Underwood said. “We have places to moor, but a business can only have two berths.”
That said, while there isn’t a huge charter presence in Hawaii, there are still a number of companies that rent boats, both crewed and bareboat. And while the sailing here is perhaps more serious than in the Caribbean, there are plenty of calm, idyllic days. Factor in dolphins, whales and some of the best snorkeling around and Hawaii quickly reveals itself as a not-to-be-missed destination.
HAWAIIAN CHARTER COMPANIES
Honolulu Sailing Company honsail.com
Maile Charters adventuresailing.com
Maui Sailing Charters scotchmistsailingcharters.com
Pacific Yacht Management pacyacht.com
Paragon Sailing Charters sailmaui.com