
If seas were rated for sailors the way mountains are rated for skiers, Hawaii would rate black diamonds, expert, with some double black tracks.
Across 2500 miles of empty Pacific the northeast tradewinds blow at 10-15 knots. Then suddenly the Hawaiian Islands erupt from the ocean floor into dozens of mountain peaks 5,000 to 14,000 feet high, bulwarked by shoals and coral reefs. The wind funnels through the channels between the islands, doubling in velocity and building up sharp 10-15-foot seas. The seas swirl around headlands and swell into harbors, making entrance dicey. The winds gust through passes and saddles, creating holes, hurricane gulches, and sail-busting wind lines. And that’s not all. Pacific storms migrating eastward into the tradewinds generate long-period swells that interact with the trade-generated chop. They bounce off the islands and bend around points. One moment you are surfing down breakers and the next moment climbing up into them. Besides the difficulty of sailing in Hawaii, it is difficult to arrange a charter. There are few boats available for bareboat charters, and only one recognized, highly capable charter company: the Honolulu Sailing Company, run by 35-year veteran charter operator and ASA sailing instructor Mike Mickelwait.
There is a saying in Hawaii that going east (into the trades) is hard on the boat; going west is hard on the crew. The truth is, it is hard on the boat in both directions, so you can expect to spend some time on repairs during your charter. 
The Virgin Islands would mostly be rated green, for beginning bareboater, along with the Pacific Northwest. The Windwards, most of Florida, New England, and the Great Lakes would be rated green and blue, for beginner to intermediate. There are lots of bareboats in all of those places, including the other nine in the top ten, and lots of good charter operators. Moreover, there are days when the weather and the seas can provide all the challenge that an expert sailor could want.
The charter rates are higher in Hawaii, too, because of the high cost of insurance there.
So why would you even consider a bareboat charter in Hawaii?
First, there is the sheer majestic beauty of the islands and the deep blue water around them. There are sheer, soaring cliffs and peaks that milk the clouds to create the wettest places on earth. The mountains are drenched in green studded with exotic flowers and laced with water falls. You can see some of this beauty by land, but seeing it from the sea, even more than by air, up close where no roads go is an unmatched spectacle. Seeing that awesome beauty while exhilarated by mastering the wind and waves can be a peak life experience. There are beautiful beaches, too, many uncrowded and in the lee of the trades.
Then there are the wonderfully warm and charming Hawaiian people that you meet in the places where few tourists go. Being received as a visitor brought by the sea is a friendlier and more personal experience than it is for the thousands who come by bus and rental car. You are one of a very select few. It is a world apart from the crowded Caribbean anchorages.
Because of the big seas, you can expect to take enough spray to dust you with salt as the spray dries on your face and hair in the warm sun. But then a cloud will pass over you, drenching you with fresh rainwater, and washing the salt away. In a moment the sun will come out again to dry you off. That evening, at anchor in a harbor, perhaps you will drink a toast to the best sail of your life.