A private day-sail in Hawaii.

From sun-up to sun-down, Sail Blue Hawaii offers you the best private day-sail in Hawaii that money can buy. Feel the tradewinds blow and delight in dolphins playing in the bow wake as you set sail. Private sailing charter options are limitless: kick-back sailing, full-sail adrenaline-rushing heeling, sailing lessons, relaxing sunset cruise, a boat tour, ash scattering, life celebrations, saying “I do”, saying “I will”, multi-day charters, corporate fun(ctions), custom cruises…For Sail Blue Hawaii, the horizon is no limit.

We are the Rainbow State

and it is thrilling to sail with the awesome beauty of rainbows all around us. But, you say, where there are rainbows, there is rain. Not over Sail Blue Hawaii.

How can that be? The mountains catch the clouds, giving us blue skies while we are sailing the azure blue Pacific. It is thrilling and never tiresome.

In the case of inclement weather (Captain’s call; day of…please put the weather app/ forecast away while you are on vacation. They are very general and very misleading and don’t consider our microclimates. It’s always raining somewhere in Hawaii but seldom on Sail Blue Hawaii. I have you covered..I don’t want to be out in nasty weather either!.) every attempt will be made to re-schedule your charter. If this is not possible, there is no booking or cancellation fee.

Give Sail Blue Hawaii a call TODAY to book your private day-sail in Hawaii.

Hawaii’s 5 Best Private Sailing Charter Ideas

Oh the luxury and awe of sailing your own private yacht in Hawaii. “Kaikiwi” is the best-kept charter boat in the islands. She is a US Coast Guard approved vessel, perfect for any kind of Hawaii sailing. Whether it’s an intimate sunset sail for two, a sailing afternoon with family and friends, whale watching, entertaining business colleagues, saying “I do”, or an overnight/inter island adventure; (but that makes 6 best ideas…and I could keep going:-); the experience will most probably be the highlight of your Hawaii vacation.

When is the best time to go sailing in Hawaii?

Because this is custom sailing, we can sail any time of day you want and whatever length of time you wish. Our islands are most consistently graced with trade winds so any time of day is a good time to go sailing…✨SUNRISE, morning, afternoon, SUNSET.✨  It is all good. 

“Kaikiwi” sails from Oahu’s south (protected) shore, not far from Waikiki, past beautiful coastline in the cobalt blue blue waters of our Pacific.  Wildlife such as green sea turtles, “honu”, dolphins, “nai’a”, humpback whales, “kohola” (in winter season only), and flying fish, “malolo” are some of the critters we may see as we sail. Beautiful views of Oahu, Diamond Head and, on clear days, far in the distance, Molokai and Lanai can sometimes be seen. Please understand this is not “destination” sailing.  “Destination” is sailing.

The best first mate ever!

Waikiki private whale watching charter

Every winter we are blessed with thrilling whale watching. Humpback whales migrate from Alaska to Hawaii to calve. Where better to see them but on your own Waikiki private whale watching charter. Better yet is to capture them while sailing.

A Waikiki whale watch sailing charter to remember

Yesterday we were enjoying an unusual morning without tradewinds… we couldn’t sail. What a perfect opportunity to view whales. Captain had killed the engine (we knew whales were in the area) when a humpback mum and calf swam by just to wow us. Mum was teaching calf to breech. All of us on board were breathless as the calf kept breeching as it approached the boat. It crossed our bow continuing to display this exceptional display of strength and playfulness. Adding to this, all 40 tons of mum was swimming close behind, crossing our bow a little too close, the captain would say, while the guests said “NO WAY!”. While not all whale watching is this fantabulous (fantastic + fabulous), do sign up for a Waikiki private whale watching charter if you are in Hawaii during our winter months. You will remember this for your lifetime.