Maile Charters: Sailing in Hawaii

Sailing in Hawaii

Sailing in Hawaii has long been a dream of mine. One night while planning our next trip to the Big Island I found Maile Charters. This beautiful 50 foot Gulfstar is chartered for day and sunset cruises just off the Big Island sailing out of Kawaihae. So I was able to get in touch with the owner and manager of Maile. I asked her some questions and the following is what she told me herself and this graceful boat she loves and sails.

Maile Charters

How long have you lived on the big island? Almost 9 years

How long have you been sailing Maile? the same period of time. I came to the island to take over as managing partner.

What’s unique about your boat? Maile is a beautiful 50 foot Gulfstar, and has been carefully re-built and restored over the past few years. She has very elegant and graceful lines, and handles all conditions beautifully.

What is daily life like for you living in Hawaii and Chartering Maile? Actually, I work all the time, from sunrise until late at night, as I also put on a film festival ( Most of my day is spent in front a computer.

How much does it cost to take a ride? Our base rate is $1,097 for a sunset sail for up to 6 passengers, which is close to a break even rate relative to our maintenance and operating costs. All of our trips are private trips, which is special.

How long is the ride? It depends on the trip people choose. On average, somewhere between 2 1/2 hours and 7 hours.

Do you have different packages? Yes, and for up to 16 passengers. The price varies with the length of time, and the number of people on board.

Is there any food included on your sail? No, but we work with a fabulous chef. People can order food through him, which I pass along at cost.

sailing in hawaii


What do see on Maile that you can’t see anywhere else? Sailing out of Kawaihae on the Big Island is a special place – with five mountains in view – Haleakala, Mauna Kea, Mauna Loa, Hualalai, and Kohala Mountains – turquoise waters, dolphins, whales, turtles, and the soft colors of the sunset in the evening, or the moon rise at night, and star filled sky.

Why do you love to sail? It feels as though you enter another world as you leave the harbor behind, with only the sound the water against the hull, and rustle of the wind, and beauty all around. It feels very special.

Besides Maile, what is your favorite boat to sail? Truthfully, I only sail on Maile. It would be hard to be on another boat.

How long have been sailing in general? Since I was a little girl.

Where is your favorite place to sail on the big island and why? Sailing in Hawaii in general is nice, although you want to be with someone with local knowledge.

If you’d like more information about Maile Charters, visit their website:

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