As a working captain from Hawaii, I know most of the sailing charter boats on the Big Island. The following are my recommendations of who to go with. Only boats that really sail are on this list.

There are currently no Bare Boat Sailing Charters available here, only crewed charters.

KAMANU SAILING CHARTERS - Kailua Kona.
Kamanu is a 36 foot cat. She is an excellent sailing boat and the only cat. in Kona town that really sails. Being a smaller boat means fewer people (24 max) and getting in and out of the water for snorkeling is easy. They offer snorkeling, sunset sails and a great Manta Ray night snorkel.

MAILE SAILING CHARTERS - Kawaihae
If you're looking for a live aboard sailing adventure, or just a day sail on a great boat, check out Maile. She is a 50 foot GulfStar, nicely set up for a week or two of inter-island cruising.

Holy Grail - Kailua Kona.

Holy Grail is a beautiful custom built 51' cruising sail boat. She has many miles under her keel sailing between exotic ports around the world. The owners are now settled in Kona and run day sailing trips aboard her. It's truly a pleasure to go sailing with these experienced blue water sailors. They have many fascinating sailing stories to tell.

Mauna Lani Sea Adventures - Waikoloa

This great 50' sailing cat runs out of the Mauna Lani Hotel in Waikoloa. They Sail, Snorkel, SCUBA dive and Whale Watch in some of the best waters Hawaii has to offer. They have a great crew and offer a first class product. Waikoloa is the best area on the Big Island for whale watching. (durring the winter)

Sea Paradise - Keauhou

Another great sailing cat. Sea Paradise is based in Keauhou, just south of Kona town. They offer SCUBA diving, snorkeling and a great Manta Ray night snorkel / dive.