I did a week in Hawaii (Oahu, Molokai, Lanai, Maui, Molokai, and back to Oahu) and having all my prior sailing experience in Puget Sound
, it was definitely an eye-opener as far as sailing conditions. The first day we crossed the Kaiwi channel to Molokai in 10 foot swells and 30kts and took a good beating (for most of the rest of the week as well). We all loved it but if anyone on board had just been looking for a leisurely cruise
, they probably would have been terrified. That said, it was probably the best week of sailing I've had in my life and easily the coolest way to see the islands.
There really aren't many charter
companies there, I'm guessing because of the conditions and insurance
, etc, so besides there being few marinas
, etc, it can be difficult to find a boat.