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Address: 74-380 Kealakehe Pkwy, Honokohau Harbor Slip H-5, Kailua-Kona, Island of Hawaii, HI 96740-2721
Phone Number:
+1 808-938-7272
Website
Recommended length of visit: 2-3 hours
Description:

Hawaii Island Sailing offers private, customized sailing adventures on the...

Hawaii Island Sailing offers private, customized sailing adventures on the beautiful yacht, “Imagine”. We personalize your destination, food and refreshments. Choose to snorkel, fish, whale watch, learn sailing, take the helm, a Zodiac beach excursion or all of the above! Sit back and relax while experiencing the romance of cruising the Kona-Kohala Coast of Hawaii under sail. Sea kayaks and paddle boards are also available. We are conveniently located at Honokohau Harbor.

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TripAdvisor Reviewer Highlights

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Perfect Sail

This was the perfect choice for us and we couldn't have asked for better hosts. We wanted a private boat for a family excursion and the Imagine was excellent. Elayne and Erik... read more

Reviewed 11 April 2017
sailingdad
,
Centerport, NY
via mobile

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59 Reviews from our TripAdvisor Community

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Showing 59: English reviews
San Ramon, California
Level Contributor
100 reviews
55 attraction reviews
common_n_attraction_reviews_1bd8 109 helpful votes
Reviewed 2 weeks ago

Me and family enjoyed a 'late morning' private sail & snorkeling trip along the Kona coast with Captain Elayne on her excellent 40 footer Catalina. Elayne was very responsive (mostly email) as soon as we made reservations, clarifying & answering questions. We had booked the morning sail, but as winds were quite low early in the day I asked if... More 

Helpful?
1 Thank johnmani
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Thank you for your review!! Yes, we can usually be flexible as to your sail time, not always but we do our best!! Imagine is a large heavy blue water cruiser so if the wind is less than seven knots we do have to hoist the "D Sail"!! (Diesel) There are many power boat experiences available in our area that... More 

Centerport, NY
Level Contributor
10 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 11 April 2017 via mobile

This was the perfect choice for us and we couldn't have asked for better hosts. We wanted a private boat for a family excursion and the Imagine was excellent. Elayne and Erik were very professional and accommodated all our needs. We spent a great three hours sailing and snorkeling off the beautiful Hawaiian coast. I am a sailor myself and... More 

Helpful?
Thank sailingdad
Elayne W, Manager at Hawaii Island Sailing, responded to this review

We had blast with you guys!! We love it when we can share our time on the water with avid sailors, share tips and tricks, fun and munchies and have a super fun time doing it!! Thank you for choosing us and getting us out on the water doing what we love to do!! Looking forward to sailing with you... More 

Seattle
Level Contributor
4 reviews
Reviewed 10 April 2017

Elayne and her crew are knowledgeable and friendly. They love being out on the boat introducing visitors to what they love about their island paradise.

Helpful?
Thank Tosyjeloma
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Thank you for sailing with us!! We smiled as much as you smiled!! Without guests like you guys we would not have been able to get out on our crystal waters and sail so we thank you!!! Looking forward to next time!!! More 

New York City, New York
2 reviews
Reviewed 9 April 2017

Had a beautiful sail with Elayne on the Imagine sailboat - saw some dolphins swimming along with us as we were heading out to sea . Very knowledgeable and had a smooth ride in and out for our private sail experience Would highly recommend ! Water was beautiful

Helpful?
Thank smileandwave68
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Thank you for choosing us!! Please be assured we had just as much fun sailing with you and are very grateful to have shared our love of sailing with you!! More 

Anchorage, Alaska
Level Contributor
3 reviews
Reviewed 21 March 2017

Fine 40 foot sailboat with experienced, highly competent captain and mate. All gear well maintained and efficiently handled. Quick to turn off the engine and hoist sails. We sailed down to Kona to jump in with dolphins. Muffins on the way down and bagels, cream cheese, fresh fruit on the way back hit the spot. Every one who wanted to... More 

Helpful?
Thank Tangolinas
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Tons of fun sailing with you guys!! Next time you are here visiting let's do it again!! We needed some hat overboard maneuver practice so we enjoyed fishing your hat out of the water but it is only as easy as the crew and spotters make it!! You are good sailors......All y'all!!! Steered a straight course and kept those telltales... More 

Colorado Springs, Colorado
Level Contributor
49 reviews
13 attraction reviews
common_n_attraction_reviews_1bd8 19 helpful votes
Reviewed 20 March 2017

We did two sunset sails with Captain Elayne on the 40' Catalina Imagine and both were excellent. They accommodated one passenger in a wheelchair. Very friendly. Great food. Bring your own adult beverages. Comfortable. Very willing to adapt. Totally overcast on one sail so we diverted to watch dolphins and whales. A perfect way to spend a few hours with... More 

Helpful?
Thank Hank S
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Awe. Thanks Hank!! You and your gang were tons of fun and Maddie is simply adorable!! How can you resist her charm and desire to move here!! I think she may win you all over!! Let me know how we can assist in your "relocation"!! So looking forward to sailing with you all again!! CaptIn Elayne, Eric and Heidi!! More 

1 review
Reviewed 12 March 2017 via mobile

Captain Elaine was great, and our sail trip was one of the absolute favorite things we've done our two weeks on the island. We arrived hungry and enjoyed sushi, fruit, cheese and crackers while we sailed north along the island. The captain gave us some simple lessons in sailing and we had a stunning sunset to cap it off. My... More 

Helpful?
Thank Jennifer B
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Thanks for sailing with us!! We had so much fun out there with you guys!! Come visit us again next time you all get together for some adventure!! Happy Sailing!! More 

Okoboji, Iowa
2 reviews
Reviewed 28 February 2017 via mobile

Ok this experience was superb. Excellent equipment, Captain Elayne and Eric were awesome instructors, great training, fun to be around. Booked second day with them two days later.

Helpful?
Thank rebeyou
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Well.....you and Jill are awesome students!!! We had a lot of fun out there practicing maneuvers, teaching some new ones, laughing and harnessing the breezes that decided to visit us........ from EVERY direction!! Give Murph a HUMUNGOUS HUG from me when you take your 104 test and remember...... heaving to is a maneuver.....not something we do overboard!!! Bow through irons....backwind... More 

Wilsall, Montana
Level Contributor
12 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 26 February 2017

There is nothing like seeing the sunset over the ocean. Being on a sail boat is the way to go. No motor noise! Captain Elayne was introduced to my husband and myself by friends(msjday1) who invited us to join them on this sunset cruise, April of 2016. We are boaters and feel comfortable on the water, but it has been... More 

Helpful?
Thank cmshrstock
Elayne W, Manager at Hawaii Island Sailing, responded to this review

We had tons of fun with you too!! Thanks a Brazillion for the fish recipe!! We use it all the time...I mean....all the time!! Looking forward to hanging out with you guys on your next visit!!! Let's catch enough fish to fill the freezer!!! See ya soon!! Happy Sailing!! Elayne and the gang More 

Las Vegas, Nevada
Level Contributor
152 reviews
64 attraction reviews
common_n_attraction_reviews_1bd8 94 helpful votes
Reviewed 15 January 2017

Although Captain Elayne was not able to make our booking, Captain Eric filled in with Cassidy and they were great. We appreciated their sailing skills and friendly company. Despite the whales sleeping in that morning, we had fun just being on the sailboat out on the beautiful water. One of us felt a little seasick and they suggested she steer... More 

Helpful?
Thank CapricornSister
Elayne W, Manager at Hawaii Island Sailing, responded to this review

Thank you for your review!! Even though Captain Elayne was too sick to sail that day the entire crew at Hawaii Island Sailing are hooked on sailing!! Eric and Cassidy had a wonderful time sharing the beautiful ocean and their sailing skills with you!! We look forward To sailing with you again soon!! Happy Sailing!!! More 

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