Hawaii Sailing Adventures
Hawaii Sailing Adventures
5
Scuba & SnorkellingBoat ToursPrivate Tours
About
Hawaii Sailing Adventures offers luxury boat and yacht charters around Maui, Kaanapali, Kauai, Niihau, Lanai, Molokai, Honolulu, Waikiki, Oahu, Kaneohe Bay, The Big Island and the "unknown" islands of Hawaii. Visit Napali Coast, Kaanapali & Kohala Coast, whale watch, snorkel and more. We're proud to offer the "only catamaran sailboats available for private vacation charter in all of the Hawaiian Islands" Just your family and friends: Lagoon 42, Fountaine Pajot 46, Sunreef 62 catamarans. Contact our team to talk further about boat charters and private sailboat & catamaran trips for your Hawaiian vacation! Accepting booking in these areas: Maui, Lanai, Kauai, Molokai, Oahu, Honolulu, Big Island! Beneteau 39, 42, 43, 50, Nautor Swan 46 (new to fleet - Kauai) Beneteau Oceanis 41 monohulls.
Molokai, Hawaii
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Hawaii Sailing Adventures
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Travelers talk about
(2 reviews)
(8 reviews)
(2 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles12 reviews
Excellent
11
Very good
1
Average
0
Poor
0
Terrible
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Sarah Sabay
Seattle, WA2 contributions
5.0 of 5 bubbles
Jan 2024 • Family
We had the most memorable family sailing trip on the Blaze II. Weather and water conditions were perfect, and it was obvious that Capt Kim and Capt Taylor truly cared about our making this the best experience for our family of 12. Within the first 2 hours on the water, the kids counted more than 40 whale sightings, which included mama whales and calves, lots of tail and fin slapping, and a couple of breaches. Snorkeling conditions weren’t great, but we had plenty to do: the kids loved jumping off the boat, the raft with a pool in the middle, kayaks, and fishing for Ono. This trip was a reschedule because we were originally booked when the Lahaina fires occurred, but Jerry and everyone on his team were communicative and flexible with arranging new dates. This was a bit of a splurge for us, they only do private charters, but worth every penny because all 12 of us agree that this day of sailing was the highlight of our vacation.
Written January 30, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

joeZ
New York City, NY18 contributions
5.0 of 5 bubbles
Aug 2022
Spent two days onboard with Capt Whitney in Maui. My family and I had a great time and we able to get to some beautiful spots to snorkel and swim with turtles. Able to get away from the large groups and have a whole area to ourselves.

The whole experience was top notch from the time i first found the company till leaving the boat. There was constant communication with office and as we got closer starting to speak with the Capt and crew to plan sights and meals.

Our Captain was Whitney who exudes the Hawaii outdoor spirit. From the time we got on the boat she made us all feel welcome and safe. On top of being a great captain she is an outstanding chef. Her Poke and Chicken dishes were some of the best during our entire vacation. My daughter is still talking about her teryikaki chicken!

If your thinking of an excursion you should seriously consider this company
Written September 12, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Jess_123456
Symi, Greece2 contributions
5.0 of 5 bubbles
Jul 2023 • Family
Jerry took us on the sunset cruise and it was absolutely fantastic! He has an excellent knowledge of the city and he made us feel extremely welcome and comfortable as soon as we got on the boat. There was 12 of us and he provided food and drinks too. I couldn’t recommend this enough! Thank you Jerry!
Written July 28, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

txsooner2
Fort Worth, TX60 contributions
5.0 of 5 bubbles
Aug 2022 • Family
Look no further for private charter! Our group of 8 had a fantastic trip. Jerry was always responsive during the booking process. We sailed with Whitney and Greg and did a full day from Lahaina to Honolua Bay. We chose time of 11-7 to see sunset on way back into Lahaina. Snorkeled at Honolua Bay then enjoyed awesome meal prepared by Whitney and Greg. Highly recommend!!!!
Written October 3, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

BobT-VB
Virginia Beach, VA51 contributions
5.0 of 5 bubbles
Apr 2019 • Couples
Amazing just isn’t enough to describe our sail with Kim and her crew! Beyond amazing is close - but words just can’t do justice for our best vacation experience ever!
Thank you so much!!! From our first getting on your remarkable boat, to sleeping under the stars, the stunning landscapes, snorkeling, diving, great food, rainbows, private coves with no one in sight and new friendships you guys made the trip more than we could ever expect. Our up close and personal visits with the dolphins and whales are memories we will cherish for our lifetimes!
Jerry and Captain Kim were very accommodating and customized our trip just for us and our schedule. I had to stretch the budget to make it work but the money spent was the very best we've ever spent on a vacation!!! If you can't afford it - find a way to make it work - it's worth double the price! Swavek and Carol were a great crew!!
Jerry and Captain Kim are a small operation and I had concerns sending them a deposit. Just know they are real people and are trustworthy and reliable!
Please feel free to have anyone wanting references on you or the boat contact me anytime. We love you guys!!!
We are a family of seven. This was our annual trip and the best ever!
Written April 18, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you so much for the kind words Bob. I am sure glad you had such a good time on your sailboat charter to Maui and Lanai. Jerry
Written April 18, 2019
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Hannah P
1 contribution
5.0 of 5 bubbles
May 2019 • Family
We are a family of five visiting Hawaii for the first time, and looking for a unique experience to celebrate Dad’s 50th birthday. We didn’t want anything with a crowded tour group; but were looking for something with more of a local, intimate, laidback feel. This experience with Hawaii Sailing Adventures was more than what we could’ve asked for!!

Our trip was to and from Kaneohe Bay from 7:00 - 10:00 am, aboard a Beneteau Oceanis 393 with Capt. Mike and Hana. Including breakfast and taxes for five adults, everything came to $759.69 USD ($1,055.42 CAD) at the time. This trip was excellent value considering how clean and spacious the boat was, and how we were able to experience the sand bar without anyone else around.

Mike and Hana were both very welcoming, and ensured that our journey was safe and enjoyable. The timing of our trip was perfect in terms of being at the Kaneohe Sand Bar while it was low tide, and because we were able to swim, take photos, and snorkel before the larger tour groups arrived. The ride to the sandbar was filled with gorgeous views of the mountains and ocean, and Mike and Hana were awesome tour guides, and gave us great information about the area. Jerry was quick at responding to emails, great at answering any questions we had, and overall made planning this trip a breeze. If you’re looking for an experience that is tailored to exactly what you’re looking for, and off the beaten path of large groups, look no further!

(I had originally posted this review on Yelp)
Written May 7, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you Hannah, Next time I want to take you on a sailing vacation on one of our catamarans to Maui, Lanai and Molokai ! Aloha, Jerry
Written May 7, 2019
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

surlej
Zug, Switzerland1 contribution
5.0 of 5 bubbles
Dec 2018 • Family
We - a family with 2 teenager boys - spent 6 days sailing between the beautiful islands of Hawaii. It has been a wonderful trip! Swavek is a great captain, VERY helpful, VERY responsible and he is taking great care that everyone is alright and happy! He knows his way around, has good suggestions where to go and what to do and was also very open to our ideas and thoughts! Sam, also very friendly and helpful, completed the crew. To plan the trip in advance we had great help from Jerry. He has great knowledge and is highly reliable! Thank you guys!
Written April 20, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

BobT-VB
Virginia Beach, VA51 contributions
5.0 of 5 bubbles
Apr 2019 • Family
Amazing just isn’t enough to describe our sail with Kim and her crew! Beyond amazing is close - but words just can’t do justice for our best vacation experience ever!
Thank you so much!!! From our first getting on your remarkable boat, to sleeping under the stars, the stunning landscapes, snorkeling, diving, great food, rainbows, private coves with no one in sight and new friendships you guys made the trip more than we could ever expect. Our up close and personal visits with the dolphins and whales are memories we will cherish for our lifetimes!
Jerry and Captain Kim were very accommodating and customized our trip just for us and our schedule. I had to stretch the budget to make it work but the money spent was the very best we've ever spent on a vacation!!! If you can't afford it - find a way to make it work - it's worth double the price! Swavek and Carol were a great crew!!
Jerry and Captain Kim are a small operation and I had concerns sending them a deposit. Just know they are real people and are trustworthy and reliable!
Please feel free to have anyone wanting references on you or the boat contact me anytime. We love you guys!!!
We are a family of seven. This was our annual trip and the best ever!
Written April 16, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Bob L
2 contributions
5.0 of 5 bubbles
Aug 2018 • Family
Spent three amazing days and two nights with Captain Jerry and his crew on the north shore of O'ahu. I highly recommend a trip with Hawaii Sailing Adventures - you will love every minute of it.
Written February 1, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Melinda K
6 contributions
5.0 of 5 bubbles
Aug 2018 • Family
My family and I went on a week sailing adventure on O'ahu with Capt Jerry this last August and it was the best vacation we have ever had. The boat was clean and well stocked (food was amazing), Capt Jerry and crew were wonderful and so very educational and fun to hang out with. The whole process from booking to home was seamless and what vacations of a lifetime are all about. My father and teenage kids all had an equally great time, and still talk about going back next year. We saw things that most people never get to experience, from sea life, to culture, to landscapes. The boat was so fun and stocked with all the needed gear to play and have fun no matter what location we dropped anchor. If you want an amazing personalized sailing adventure book with Capt Jerry and Hawaiian Sailing Adventures!
Written January 28, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Hawaii Sailing Adventures - All You Need to Know BEFORE You Go (2024)

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