About elayne

What a Whale of a Tail!!!

WOW!!! What a whale of a tail we had this day while watching the whales here on the Kona Coast of the Big Island of Hawaii! Hawaii Island Sailing guests aboard Imagine had THE MOST EPIC visit from three humpback whales as they decided to come on over and take a look……A VERY CLOSE LOOK!! With engines off and all hands on deck standing by…..well….take a look at the video!!! The video says it all!!!

Come and experience the adventures of sailing with Hawaii Island Sailing like whale watching, snorkeling, swimming with the dolphins, sunset cruising and so much more sailing in Hawaii!!!


Thank you for a great dolphin experience!!

Hi Elayne,2016-11-21-16-43-55-1





I just wanted to say thanks again to you and Cassidy for a wonderful “sail” last week. It was nice closure for my grandmother’s passing and a once in a life time experience for the girls, swimming with dolphins…probably their most memorable part of the trip.

If you use testimonials on your website, feel free to quote us and use attached photos.

Thanks again and best wishes as we head into the holiday season,


Incredible Snorkeling!

This was one of the most incredible sailing and snorkeling tours we have ever been on! – David and Wendy

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“Too Many Dolphins”

That was the answer certified snorkel instructor and First Mate Heidi of ‘Imagine’ heard come from the mouth of our teensiest dolphin adventurer yet!

WHAT A DAY we had as the dolphin circled around us for at least an hour!! Was it because of the embryonic heart beat from inside her mother or the sweet songs of a tiny little tot having her first experience with dolphins. Either way, it was a most fantastic dolphin experience we have had so far. [Read more…]

Windy days here on the Big Island

We have sure had some windy days this winter!! Craziest winter weather I have seen here in Hawaii yet!! I want to thank our customers for their understanding when we decide to cancel their tour. Unless you are a hard core sailor who likes wearing foulies and getting soaked to your skivvies, it is not going to be enjoyable for you…..best to stay on the hard. [Read more…]

Honeymooners Unite!!!

Recently we had several honeymoon couples join us for their private romantic sunset sail, adding the finishing touch to their memorable honeymoon getaway here on The Big Island of Hawaii. All of the crew here at Hawaii Island Sailing thoroughly enjoyed the time we spent with these newlywed couples and give them our best wishes as they begin their lifelong journey together. It is our hope that they will remember us as fondly as we will remember them!!! Happy Sailing to ALL of our newlyweds!!!
Hawaii island Sailing. [Read more…]

“Imagine” your sailing dream!!!

When you jump on board Big Island charter sailboat Imagine with Hawaii Island Sailing, not only will you have the chance to experience the adventure of sailing but you will also see abundant marine life, whale watch and snorkel. You will have the opportunity to learn to sail and take the helm if you would like!! At Hawaii Island Sailing, your dreams become a reality!! Looking forward to sailing with you soon!! [Read more…]

It’s just hail

What another terrible day in paradise. It’s just hail I tell ya

….just hail!!! We had Kealakekua Bay practically to our selves. What a fun filled day for everyone and all went home with a smile on their face that lasted until well after the lights went out. Every sail with Hawaiian Island Sailing is a unique and fun adventure. We are the favorite private sailing charter here on the Big island of Hawaii!! Call us soon for your private sailing charter and add your story to our story! Happy Sailing [Read more…]

Just another beautiful Hawaiian sunset

Do you ever wonder if there is a day without an exquisite sunset here on the Big Island of Hawaii?? During each of our sunset sails here at Hawaii Island Sailing, we see the sun paint its own masterpiece!! Of course we always look for and hope to see the green flash at the final sinking of the sun during every sunset tour and some days the green flash is brilliant and bright, another day it may be a quick fleeting twinkle and other days we cannot see it at all but we all admit that the sunset we experienced on this day brought many oohs and ahhhs from our guests on board Imagine. [Read more…]