Big Island Living
Just in from the Big Island about 6 months ago.
You can live aboard inside of the Port Authority (USCG & Cruise Ships Dock here), but with a 3 year waiting list...
There is a nice place to anchor, Reed's Bay, just a mile North of the Basin. If you're on a Cat, you can get real close, 50 feet from shore if you draw more than three. No matter where you are in Hilo, there is little protection from the East side. And the winds do kick up plenty of chop.
The Kona side Marina (Honokohau) has plenty of slips, but none are live aboards. Nice Marina, lots of charters here.
Kawaihae is on the NW side of the Big Island and they offer slips there. I've never been too far into the marina - one time late at night to pick up my husband and his sailing buddies, came in from Oahu - so I can't tell you about slip rentals or live aboards. Protection is better here.
As far as sailing goes on the Big Island...not very popular. Sailing to Oahu is a breeze, but sailing to the Big Island from there can be tricky, it's against everything.
That's why most of the sailors -few there are - spend their time on Oahu.
By the way, living on land in Hilo is no picnic either...It rains A LOT. Kona is the dry side and if you like sunny and warm, nice beaches (not much for beaches in Hilo either), go Kona. Aloha.
Cheers & Happy Sails.