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,


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…]

Dutch teenager sets sailing record

Some eighteen months after she set out to sail single-handed around the world, Dutch teenager Laura Dekker has broken an unofficial record set by  Jessica Watson of Australia  in 2010 to become the youngest person ever to sail solo around the world.

Dekker, 16 years and four months old, has cut six months off the unofficial record (Guiness book of records has dropeed the category following the controversy) set by Watson, who was  shy of her 17th birthday when she completed her voyage.

Whilst controversy surrounded this voyage regarding her age, it is a remarkable feat for anyone of any age. However rest assured that if you choose to come sailing in Hawaii we won’t  put you sea solo on one of our sailing charters.

Sailing charters on the Big Island

Looking for a  sailing charter on the Big Island of Hawaii? Well you’ve come to the right place? We offer sailing adventures from Honokohau harbor in Kailua Kona on the West Side of the Big Island. Check our website for schedule and rates, departing daily.

Finally we’ve updated the Hawaii Island Sailing website!

Well… here you are kids! The website and Hawaii Island Sailing Charters are now ready for launch. After many back and forth meetings with the DLNR the USCG and other tax and insurance bodies we are finally here! So if you are ready for a sailing adventure during your visit to Hawaii Island get in touch!