Oahu has a fairly high concentration of sailing boats in the Ala Wai. There has been a continuing derelict problem in the State section though much better than it was 40 years ago. Waikiki Yacht Club has mostly sailboats in its slips as does the much smaller Hawaii Yacht Club fleet. Though nothing like the number of sailboats you'd expect with the population. With nearly a million people on the island, there are few marinas and one of them is in a really crappy location both for environment and resident population. Moorage is a problem on all the islands. As an example, Honokohau is the only pleasure boat harbor on the Big Island. There are a few moorings in Keauhou Bay, Kawaehai and Hilo Harbors. Honokohau Harbor had to be blasted out of the lava. Currently only the first two phases have been built with almost no hope of another phase ever being built. Harbor is largely populated with fishing boats, a large number of them commercial charter boats with locked in slips. I've been on the list going on 5 years for a 30'-40' slip and am probably still years away from getting a slip in Honokohau. Virtually no hope of getting a slip larger than 40' or smaller than 27'. Only good thing is slip rental is dirt cheap, $150 a month for a 35' boat. There is a fledgling sailing club with mast-up storage for trailerable boats though currently almost no boats over 25' actually racing or spending much time in the water. Most competitive fleet is the Corsair Trimarans with something like 4 that race regularly. It's priobably the same in the other out islands though no direct experience. Strangely, waiting list in the Ala Wai in the heart of Waikiki is less than here in Kona. Was offered a 45'-55' slip after only two years on the list. Waiting time for smaller slips is quite a bit longer, unfortunately

As far as sailing, it sucks anywhere within a days sail of Honokohau here in Kona. We are in the lee of two 13,000 foot mountains so wind is strictly thermally generated ranging from flat calm in the early morning and late afternoon building to a rousing Force 2 at the height of the day. Power out in the morning and back in the afternoon with a couple hours of light air sailing in between is typical. Other than the summer months, there is no place to sail to easily. During the summer you can anchor along the coast in fairly comfortable conditions and explore some deserted beaches. Other times of the year, it's a lee shore with waves sometimes exceeding 20' and almost always too rough for comfortable anchoring. Sailing farther afield is frustrating because of the lack of wind along the Kona side of the Island and way too much wind to the north and on the windward side without any protected water except in Hilo Harbor. Travelling between the Islands makes for exhilarating sailing. You've got 2,000 miles of waves and wind funneled through the channels between the islands. Seas typically run 10' or more with very steep faces and tradewinds often gusting above 30k. Sailing east to west is a surfing sleigh ride. Speeds well in excess of theoretical hull speed are common. Unfortunately, to get back home, you've got to beat into those same wind and waves that were so much fun going the other way. Green water over the bow is the rule and pounding into the waves will test the strength of your hull and bonding of the interior. Better have a third reef point as you are likely to need it. After having sailed the East and West Coast of the US, to French Polynesia and to Hawaii twice, by far the worst conditions I've encountered have been the channels between the Islands going the wrong way.

With the exception of Haleakala on Maui, the mountains on the other islands are considerably lower so wind shadows are way smaller. There is usually good sailing in relatively calm waters as long as you don't stick your nose into the channels. Sailing off Waikiki, for instance, is glorious almost every day of the year. Have to be careful of strong gusts coming out of the valleys but that just adds a little excitement to a day on the water. With the exception of the summer there are few places to sail to if you want to take a little cruise. The Lahaina area on Maui and Hanalei Bay on Kauai are great little getaways.

FWIW, if anyone wants to spend the summer exploring the islands and then head south, this is a boat to do it in. Boat is thoroughly equipped, and I do mean thoroughly, by an experienced sailor to cruise the world. Not cheap but way cheaper than you could do it buying a boat and equipping it. http://honolulu.craigslist.org/big/boa/3854490882.html