Sailing in Hawaii: Everything You Need to Know

The ocean surrounding the Aloha State beckons all to sail its waters. For those who take the call, they will find ample steady breezes, the sun, and calm seas awaiting their adventure. However, the calm and beautiful ocean can be deceiving to the inexperienced. 

If you want to go sailing in Hawaii, you must come prepared with a plan, a doable destination, and enough supplies if something goes wrong. This is because the trade winds and currents near the islands can change from calm to turbulent in an instant. 

To solve some of the riddles of sailing in Hawaii, the American Sailing Association established a list of tips and accredited sailing schools so you can learn the ropes. By reading further, you will learn what these tips and schools are so you can implement them as needed.

The Art of Sailing Among the Islands of Hawaii

There is no better way to see Hawaii than by sailing. The trade winds surrounding the islands make nearly perfect sailing conditions without ceasing. Plus, you can enjoy the calm waters and warm breeze all year long, especially on the western side of the archipelago. You can take out your boat or rent one to see all the islands offer, such as the Kohala Coast and Kealakekua Bay.

While the lure of the water splashing onto your boat's hull sounds inviting, the islands are notoriously challenging to sail. The breeze may be steady, but it is not a constant everywhere. The shapes of the islands create a chaotic storm of everchanging ocean currents and weather. The conditions are so bad, sailors boast that if you can sail in Hawaii, you can sail anywhere.

Each island has its unique character traits. The winds are so specific that ancient Hawaiians have 30 names for the winds around the island of Maui alone. It also takes an expert navigator to chart around the swells, currents, and rotating stars. The ancient Polynesian navigators were the best in the world for a reason. 

Therefore, you must come prepared before you embark on your journey through the waters surrounding these volcanic islands. 

Hawaiian Sailing Education Resources

Most people get the taste for sailing around Hawaii on some sunset cruise and believe they are already skilled enough to handle the Hawaiian trade winds. They feel the moist air passing over the West Maui Mountains and over the boat, forcing it to move with purpose. They think they can handle the waters and embark to go off the typical visitor tours. 

However, the Hawaiian straits can get challenging beyond the shores. General sailing skills are not enough; you need local expertise if you want to avoid Hawaii's legendary surf breaks or a free trip to Tahiti. 

You can gather this expertise by hiring a guide for a private tour of the islands, or you can attend classes at one of the three American Sailing Association (ASA) sailing schools on the island of Oahu:

You will find all three schools centrally located at the Kewalo and Ala Wai harbor near the world-famous Waikiki Beach. 

All three schools provide instructions that lead to ASA certifications 101 and 106 using a classic Pearson Ariel 26 keelboat. You will learn your way around Hawaii with practical applications such as a liveaboard Pacific Offshore Challenge sailing adventure around the islands. They even offer courses for ASA 105 and 107 (Celestial Navigation) certifications. 

Best Places to Sail in Hawaii

With your new Hawaii sailing certification, you will want to get out on the open sea. Every Hawaiian island has unique vistas and challenges that will keep you coming back for more. If you set out with a guide, they will point you towards exciting destinations and how to get to them. If you are taking the seas alone, you will want to plan out your excursions before leaving the shore. 

Sailing Around Maui

Around Maui county's islands, the tradewinds generally come from the northeast but can have different effects if they flow from the north versus the east. Either way, they will lead you to the Auau and Pailolo Channels and Maalaea Bay which are often labeled as the best sailing places in Maui. 

The Pailolo Channel

The Pailolo Channel offers the most consistent sailing conditions of the archipelago. Situated between the mountains of the Maui and Molokai islands, the strait forms a 9-mile-wide funnel that keeps the winds going in the same path regardless of their direction. 

Reaching the channel requires knowing how the winds are blowing. With an east wind, your best bet is to start sailing towards Eastern Molokai, then turn towards Maui once you reach the middle of the channel. The winds would then cross your boat from the port side. 

With a north wind, you can go straight through the middle of the channel with the free-running breeze. You will crawl at a consistent 15-25 knots, but you will have a riveting sailing experience. 

Honolua Bay should be available to you regardless of the trade winds. 

Auau Channel

As the Pailolo Channel becomes the Auau Channel near Lanai, the winds get complicated. For example, you can cross the channel from Manele Harbor to Lahaina without much effort with a good north wind. However, crossing the channel with an east wind can challenge even native experts. 

With an east wind, your best chance is to find wind convection or a light breeze caused by the nearby hot land. Though, the occasional south wind can help as well. 

On the South Side of Maui

Maui's volcanoes turn the island into a wind funnel aimed directly at Maalaea Bay. This funneling makes the bay the windiest spot in Hawaii. As such, the bay is continuously whitecapped from dawn to dusk. To make matters worse, the north wind arrives early, rendering snorkeling and other water activities impossible. 

You also must reach the bay traveling upwind. Because of this, even the seasoned veterans will not sail into the bay and recommend using a motor along the coastline. You can bring out the sails again once you reach North Kihei. You can only sail to McGregor Point and Maalaea Harbor during light or westerly winds. Just be ready for the jump from 10 knots to 25 as you pass North Kihei. 

Cruising the Leeward Seas

The leeward side of the islands is the calmer side with much more manageable water and winds. Partly shielded from the tradewinds, these waters provide an unforgettable and unique way to see Hawaii and all that the islands offer. You can sail anywhere with little effort, even upwind. 

Kaiwi Channel

For instance, you can cross the Kaiwi Channel between Oahu and Molokai in less than half a day. Once there, you can spend the rest of the day and night enjoying life in Lono Harbor, a deserted but protected hideaway. You can then take the short-day trip to the Nanahoa pinnacles, an interesting rock formation with a nice anchoring spot for swimming and lunches. 

Lanai Island

Toward the south from Nanahoa, you will find the Island of Lanai and the Auau Channel with a more leisurely approach towards Manele Bay. The bay is Lanai's only recreational marina and has no guest slips, but it does give you access to Hulopoe Beach and the nearby hiking cliff trails. 

The only other interesting spot on the island is Lahaina Harbor. The Lahaina Yacht Club privately owns the historic harbor. As such, you need permissions from the club to dock. Even then, most of the time you will find yourself mooring your boat to a visitors' buoy or anchoring in the bay, using their provided dinghy to reach the bars on the shore. 

Luckily, ASA Hawaiian classes provide Lahaina Club membership, giving full access to the club's other amenities, including hot showers, fish taco shops, and the best view in town. 

Molokai Island

Across the channel from Lanai is Maui, which has nothing special for boaters, but beyond Maui is Molokai. Reaching Molokai requires crossing the Pailolo Channel, but you will find a reef that will lead you towards the calmer lee side of the island. 

Fortunately, there are no harbors or anchorages along Molokai's north shore. So, you can avoid most of the tradewinds and travel down the lee side until you reach Kaunakakai. Kaunakakai is the main town on Molokai, and its harbor is fully equipped. There is a guest dock with end ties and enough room in the harbor in case you must anchor offshore. 

As for the island itself, Molokai has the most native Hawaiians in the state, who prefer a more traditional lifestyle. The "Friendly Island" feels like a time capsule with only a few modern amenities. The island's major attraction is the Paddler's Inn. The popular restaurant serves as the central meeting spot for locals and visitors alike. It is open every day except Sunday and serves Molokai's famous hot bread.

The Open Sea Between Molokai and Oahu

When sailing around the Hawaiian Islands, you rarely venture out into the open ocean. Most travels keep you near the islands or in the semi-protected channels between them. The only time you will travel through the open Pacific is when you go directly between Oahu and Molokai. 

The course will take you past migrating Humpback whales as they play with spinner dolphins. However, we only recommend that you take the route going in the westward direction. This way, you will travel the 45 nautical miles with the trade winds and not against them. 

Sailing Between Hawaii and Mainland U. S.

When people talk about Sailing in Hawaii, they only mention traversing the waters between the islands. However, the open ocean between the archipelago and the mainland offers a gratifying experience on its own. Many sailors prefer the ventures so they can bring their boats with them instead of renting once they get to Hawaii. 

General Hawaii-Bound Sailing Route

Regardless of your starting location, your trip to Hawaii will be essentially the same, with a few deviations. You generally head south along the coastline until you are between 35 degrees North and 25 degrees North. From there, you can head straight westerly for Hilo. The trip will take about 2-4 weeks. While there are more direct routes, this passage is the quickest with the fewest chances for failure. 

Los Angeles is a good staging point. The city ranges from 38 degrees and 34 degrees North. From the south, you want to remain offshore and out of the surf as much as possible, but you can start heading west as soon as you see the city. 

From the north, you must choose from three different routes: 

  • Slowest route: Reach Los Angeles through San Francisco. You can hop from port to port until you reach the Bay Area before heading southeasterly to join the northern route to Hawaii.
  • Fastest route: Head directly towards Los Angeles, approximately 20 to 40 miles from the shore. This route lets you take advantage of the coastal current and winds. 
  • Safest Route: Same as the fastest route, except you remain 50 to 100 miles out. You will find smoother sailing the farther out you are, but try to avoid the Pacific High. 

Regardless of the route you take, you want to avoid:

  • Point St George
  • Cape Flattery
  • Cape Blanco
  • Rocky Point/Honda Point
  • Cape Arago

Make Sure You Always Remain South of the Pacific High

Regardless of how you plan to reach Hawaii, you want to avoid the Pacific High. This semi-permanent depression in the North Pacific gives Hawaii its tradewinds, and you need those tradewinds for your trip. The High also has light winds and rain, which will make your trip a miserable experience. 

Therefore, all recommended routes towards Hawaii send you south before you head west. However, the Pacific High moves. It shifts towards the equator in the winter and back north in the summer. The Los Angeles route is only suitable for summer sailing because of this. During any other time of the year, you must head further south before you start heading for the Hawaiian Islands. 

A general rule of thumb is:

  • 20 degrees North during winter
  • 30 degrees North during spring
  • 35 degrees North during summer

Once you reach your travel latitude, it will take you a few days before you pick up the tradewinds for smooth sailing to Hilo. Just note that the optimal wind zone will remain small and narrow throughout the trip. 

Best Time to Sail to Hawaii

Because of the Pacific High, your best time to sail to Hawaii is in June. Setting out in June lets you take the Los Angeles route in relative comfort while avoiding the hurricane season. After June, you must deal with the hurricanes, while your trip will get cold if you venture out during the winter and spring. 

Just note that you may still deal with the occasional hurricane. Fortunately, hurricanes are easily spotted. So, you should have plenty of time to prepare for them. Pacific hurricanes tend to stay south of 20 degrees North Latitude, far away from the summer Hawaii route. 

Heading Back to the Mainland

After your many adventures around Hawaii, you take a different route back to the mainland. The tropical tradewinds only move west, and you need the jet stream which moves easterly, so you must head north of the Pacific High to reach them. 

Therefore, the only route available to you is to head straight north from Hilo until you pass the High's northern edge. This path should take you to around 47 degrees North, which is the latitude of Seattle. From there, you can turn towards the east and sail until you reach the coast. You can then travel south until you reach your home base. The 2,600-mile trip to Seattle will take you 4 to 5 weeks.

Plan for the Journey

As with any long voyages, you must prepare for your trip before setting sail to or from Hawaii. You are looking at a several-week journey through cold nights, rain, and slow winds. These conditions grow worse as you drift near the Pacific High, but you should get through the worst of it after five days of sailing. 

Once you catch the trade winds, the air gets warmer and dryer, and with winds pick up to something respectable. This part of the journey will take about two weeks, but it should be a pleasant ocean voyage. 

However, you will spend all that time on your own. There will be nothing on the horizon to break the monotony. As such, you need to bring your knowledge of sea sailing, courage to remain focused, a strong stomach, and a plan for anything that might go awry. A part of that planning is establishing a time to sleep and change the sail, as well as fixing any leaks that might spring up. Because of this, you may not want to make the journey alone. 


Sailing among the Hawaiian Islands is a fun way to enjoy the sun and the sights from the Aloha State. However, the waters around these islands can challenge even seasoned sailing veterans. To enjoy your voyages while remaining safe, you must come prepared and understand how the winds and water current flow around the islands. Only then can you sail around the archipelago with your friends.

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