Matt and Britney Weidert

Matt Weidert

Sailing in Hawaii: Is a Bareboat Charter Possible?

You might, as I have, dreamed of a bareboat charter yacht trip to go sailing in Hawaii (and no, I don't mean a sunset sail on a crowded catamaran at Waikiki Beach).

Perfect year-round weather. Tropical, white-sandy beaches. Stunning, mountainous terrain. Numerous flights to the US mainland. Abundant provisioning options.

Sounds like ideal conditions for a perfect sailing trip.

But not so fast.

There’s good reason why the Hawaii bareboat charter industry doesn't exist: exposed anchorages, few marinas, and treacherous conditions in the channels are some of the contributing factors.

I'll explain more and explain how you might still be able to pull off this dream trip.

Here’s what I’ll cover:
  • Where to go sailing in Hawaii?
  • What is it like to go sailing in Hawaii
  • How you can take a Hawaii yacht charter trip
The stunning Napali Coast in Kauai

Where to go sailing in Hawaii?

I think a good strategy for a week-long trip would be to pick an island: Kauai, Oahu, Maui/Molokai/Lanai, or even the Big Island. You don’t want to spend a good portion of your trip on rough passages in between the islands (see my section on cruising conditions).

Rely on your charter company or yacht crew for itinerary advice.

So where would I go?

I’m going to circumnavigate Kauai and sail down the magnificent and Napali Coast of Kauai.

I first got to experience this 10 years ago when I kayaked the length of it down to Polihale Beach. What an experience!

It is simply the most stunning place I have ever visited.

I also want to park myself in Hanalei Bay and watch the afternoon waterfall show. This is also one of the most beautiful settings I have experienced.

With help from the Mehaffy’s Cruising Guide to the Hawaiian Islands, I was able to sketch out a plan with anchorages they have tested themselves.
Sailboats at anchor in beautiful Hanalei Bay

Week-long Kauai sailing itinerary:

Day 1: Cross Kauai Channel, anchor at Hanalei Bay

I’m going to assume that we start in Oahu, but your charter yacht might be able to pick you up in Kauai.

I, however, think a spirited channel crossing in moderate conditions would be fun (it’s downwind from Oahu to Kauai). Good chance to go fishing as well.

Day 2: Hanalei Bay

Full day to explore and relax in beautiful Hanalei Bay.

Day 3: Ha’ena and Tunnels Beach

Tunnels Beach might be the most stunning beach I’ve visited with it’s setting just below the famous Bali Hai cliffs.

There is even an anchorage inside the magnificent Makua Reef. I can’t think of a better place to enjoy a sunset.

Day 4: Off to explore Napali Coast

Slowly soak up the incredible Napali Coast scenery and stop at Nu’alolo. Along the way visit the famous Honopu Arch. You may remember it from Pirates of the Caribbean: On Stranger Tides.

This is one of the most popular attractions for day tours along the Napali Coast, but it’s possible to find some space in the evening.

Snorkeling and admiring the scenery are top attractions here.
The cliffs at Polihale Beach

Day 5: Polihale Beach

Polihale is one of the longest beach stretches in Hawaii, at ~2.5 miles. This is also where the Rugged mountains of the Napali Coast turn inland.

It’s known for the mysterious barking sands and goats you will surely hear on the cliffs above your anchorage.
Ni'ihau - the forbidden island, as seen from Kauai

Day 6: Go visit the forbidden island, Ni’ihau

Ni’ihau is actually a private island, and it’s off-limits to visitors.

But, you can still admire it’s beauty from it’s shores. How many other tourists do you think get to come here?

The fishing is supposed to be excellent here, as is the snorkeling.

Day 7: Cross back to Oahu or disembark

If conditions in the Kauai Channel are treacherous, you may want to consider disembarking and flying back to Oahu.

Remember, you will be beating upwind going back the other direction. Your charter captain may have more flexibility on timing the passage in more comfortable conditions.

Nawiliwili small boat harbor would make a convenient place to catch a taxi to the nearby airport.

Let’s read on to find out how to plan a Hawaii sailing trip.

Sailboat anchored on a roadstead off the Maui coast

What is it like to go sailing in Hawaii

The biggest reason it’s hard to pull off a Hawaii bareboat charter trip?
These islands just aren’t like the Virgin Islands with it’s numerous islands and many sheltered bays.

The cruising conditions are challenging, presenting unique risks to sailboat skippers.

Let’s dive into the details.

Hawaii cruising conditions

Hawaii anchorages & marinas

Challenge #1.

The islands of Hawaii are much larger and have fewer protected anchorages. Depths tend to drop off sharply from shore. You can sail for miles along the coastline without finding shelter.

They are also stretched out across nearly 400 miles in the middle of the Pacific Ocean.

Where anchorages do exist, many tend to be exposed roadsteads. A change in the weather or a swell can make these dangerous and untenable.

There are few moorings.

Access to marinas is also more limited - there aren’t as many available. Most also simply don’t have much drop-in slip availability.

Pacific trade winds

Challenge #2.

While the trade winds that do blow in the summer can be quite consistent, they vary in strength.

It might be light or blowing up to 30 knots. Usually they fall into a pattern, blowing strongly for a few days before backing off.

Where this can disrupt your plans would be in the channels in between islands, where the wind funnels between the mountainous terrain and strengthens.

If the trades are 15 knots, they might increase to 25 knots in the channels!

This makes treacherous conditions with 8-10 foot wind waves. Not something I want to deal with upwind on a sailing vacation.
The rugged coastline of Napali, exposed to northerly swells


Challenge #3.

If you visit between August and October, the large northerly swells can be mitigated.

But swells can occur any time of year, even in the summer.

Be prepared to adjust your plans depending on weather reports - the good news is they are well forecasted.

Take for example the recent historic summer swell that occurred in July 2022. Waves crashed over condos. A wedding was washed out. And surf breaks that have slept for years erupted.


The weather is perfect and beautiful year-round in Hawaii, that is, if you plan to park yourself at a beach resort.

If you plan to put some miles behind you on the water, you’ll need to pay closer attention.

Some suggest there are generally two seasons in Hawaii: summer and winter.

Hawaii’s summer season

This would be my preference for a yacht charter trip in Hawaii (specifically Aug-Oct). It’s also the best time to do some whale watching.

Between May and October, the trade winds blow more consistently (up to 90% of these days).

Leeward sides of the island (where you might spend much of your time) receives little rainfall.

The fabled winter swells that attract surfers from all over the world, have yet to arrive.

Hurricane’s can brush closely to Hawaii’s islands, but landfalls are rare (but you may still experience affects from the associated swells).

Hawaii’s winter season

In November through April, the trade winds don’t blow as consistently, but the temperature might be more pleasant.

Fronts can push in from the north creating heavy rain on the leeward sides.

You also get those large swells that will make northerly exposed areas off-limits at times.

Tides and current

This is generally not a big deal. It’s a small tidal range and you can expect most currents to be less than 1 knot.
Kane'ohe Bay, home of the local yacht club

How you can take a Hawaii yacht charter trip

OK, so how do we pull one of these trips off?

If you’re anything like me and my crew, we prefer to do all of the work ourselves: plan, skipper, cook, clean, etc.

But frankly speaking, I wouldn’t be comfortable sailing in Hawaii with these challenging conditions and unique risks.

I want someone with local knowledge aboard.

So a Hawaii bareboat charter is off the table for me anyway.

I've yet to find a company in Hawaii that offers a bareboat charter option. If you know one, please let me know!

The good news is there are a limited number of crewed charters available. The Hawaii charter industry is a tiny fraction of the one in the Caribbean, but, it exists.

I’ve reached out to several companies. Here’s who you might check out:

Hawaii Sailing Adventures: Broker with access to 11 yachts and coverage for all the islands

Honolulu Sailing Company: Charter company with three yachts offering inter-island sailing adventures

Hawaii Catamaran Charters: Broker offering several catamarans

Sail Hawaii: Offers a chance to go aboard as part of an ASA certification

Tradewind Charters: Charter company offering inter-island trips

Final note? Be prepared for sticker shock. Some quotes I’ve seen are much higher than what you’d expect for similar crewed charter trips in the Caribbean.

When is your next yacht charter?
Consider booking with the Yacht Warriors.

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