In the winter, the surf can be very high (30'+). Since there are virtually no natural harbors or protected anchorages
in the Islands, you pretty much have to sail out of a marina from October till April. Most of our Marinas
are run by the State and are poster childs for privatization so don't expect luxury accomodations. Lahaina and Kailua-Kona are in the lee of the islands so are somewhat protected, but rolly most of the time. They are not safe when the big surf rolls in, however. We lose at least one boat a year off the moorings here in Kailua-Kona and sometimes 2 or more a day. To try and anchor
out would be very very iffy over the winter. Kaneohe Bay may be your best bet but I don't know what the restrictions are.
During the summer, the Pacific mostly lives up to its name. You can anchor off both windward and leeward sides of the islands much of the time. They are not protected anchorages
, however, so can be a little rolly even in the best of conditions. There are occasional large southern swells that come up from storms in the South Pacific
but they are relatively infrequent.
Passages between the islands are delightful reaches going West. You can pretend you're in the TransPac and surf your way between Islands. Have done the 175 miles from Kona to Honolulu in less 24 hours a number of times. Going East is another story. The Venturi effect intensifys the trade
winds and squares off the waves in the channels. It's a wet, bumpy, uncomfortable, and not very fast ride beating into it. The trades are almost always blowing so winds are ENE from 15 to 20mph. There are significant holes in the wind
on the lees of the Islands, however. We've always managed to sail through them, but plan your route
to pick up the wind
Having said the above, one of my must do's is to cruise
the windward coasts of Molokai, Lanai, and Kauai
. These are largely uninhabited and scenery is spectacular.
and wave forecasting is excellent so there is no reason to get caught by surprize at an anchorage. Usually, even in the worst of conditions, the sun is shining, it's always 80 degrees and open ocean sailing may be lumpy but not dangerous.