Definition of “Adventure” is:
1 a : an undertaking usually involving danger and unknown risks
1 b : the encountering of risks
2: an exciting or remarkable experience
3: an enterprise involving financial risk
- Marrian-Webster Dictionary
If you seek adventure, sailing, or getting a taste of what it is like getting off the grid, join us on one of the few true adventures left in Hawaii. Kainani is our home, a 43’ sailboat with 3 private cabins and 2 bathrooms; enough space to make it possible for us to share the adventure with you.
This is our Adventure Cruise, and the boat is rented per person, and sometimes the boat will include guests other than your party. For a private yacht please see our listing under "Private Yacht with Captain".
While onboard, everyone needs to understand that being on a boat means being flexible, especially with Mother Nature. All destinations and adventures are subject to weather conditions, so please be prepared and understand that the ocean is our home and an uncontrollable force. We promise to do our very best to keep everyone comfortable during the trip by finding calm and safe anchorages.
For other reviews/pictures please see our F__ B__ page Kainani-Sails
Let us tell you about Kainani, a Beneteau Oceanis 430. She is a fully equipped sailing yacht designed with comfort and safety in mind. Kainani is ready with many of the amenities of home, such as a full galley (kitchen) with refrigeration, electricity, and lots of fun things like surfboard, a kayak, small library, fishing gear, masks & snorkels, and a motorized dinghy. We aim to have people on board for 4 nights to give a chance to really get away. If you are unable to make 4 nights, let us know and perhaps we can work something out special for you.
Still reading? Great! Here’s an example of what to look forward to:
We encourage everyone to take part in sailing the yacht, to bringing in the latest catch. We encourage team spirit and appreciate your help while onboard, from keeping the vessel organized to preparing meals, and in return we do our best to make you feel at home and keep the adventure going.
Here is an idea of what a 7 day (2 night minimum) adventure may hold.
Day 1: Pick up in Kailua Kona and set sail for Kealakekua bay (Captain Cook memorial) and enjoy some of the best snorkeling in Hawaii, and perhaps swim with Hawaiian Spinner Dolphins.
Day 2. Sail down to Honomalino and small quite beach, and enjoy the views.
Day 3. Okoe Bay and enjoy getting away from the crowds as we will most likely see no one else
day 4. Set sail North for Honaunau the city of refuge a most on most peoples list while visiting Hawaii, and small anchorage with excellent snorkeling.
Day 5. Hookena, a short trip up the coast is the small quite village of Hookena where you can disembark kayak and explore the down..
Day 6: Keahou. We anchor here for one reason! To swim with Manta Rays! for the more adventurous it is a night dive (with dive lights) and you can get in the water with the gentle Giants of the sea. For most people this is a once in a life time experience.
Day Seven: Is always the worst as we are sure our guests are leaving as good friends, and we always hope to see them again soon.
About Us… Keao is the owner and captain of Kainani. He was born and raised on the Big Island of Hawaii but spent his college years in Oregon. Keao is also a United States Coast Gaurd Certified Captain. He has sailed the west coast of the United States, Mexico, and much of the South Pacific. He also has experience as a charter boat captain here in Hawaii.
We are more than happy to host you, your family, and/or your friends. Every trip is unique, with different places, different people, and different conditions. We are able to carry no more than 6 guests, so expect a personal and memorable experience. Contact us for more info, questions, or concerns.
Hope to sail with you soon! – Keao, & Kainani
*We know that this trip is not for everybody; we always try to make everyone feel at home and comfortable onboard. Please understand that all departure and arrival dates depend on the weather and sea conditions. The channels within Hawaii can be very rough. The Captain of the vessel will do everything within his power to complete the cruise within the time frame. The responsibility of the Captain beyond all others is to keep the passengers and vessel safe. With this understanding, we cannot guarantee any arrival dates or times to any location and will not be responsible for any missed fights or other arrangements. For overnight adventures, some anchorages may be slightly unsteady. Everyone must understand that this is a boat and that we are on the water, a surface that is always changing.
P.S. Smoking is allowed outside (and downwind) only.
Please contact us for information about day sails or if you are interested in sailing over the horizon to foreign lands!
My time aboard Kainani Sails was a life changing experience. It was as though I were in heaven during that time, and now that I've returned to the city, am living a mere mortal life once again.
First off, I discovered a love of sailing! This was easy to do under the guiding influence of such accomplished sailors as Keao and Iwa. They are worthy of your trust, and are truly exceptional people. Kindness, generosity, patience, depth of perception, and joy are hallmarks of their character, and I enjoyed every moment in their company.
Secondly, by sailing on Kainani, I was able to enjoy Hawaii in all its natural splendor. Swimming, snorkeling and diving in the clear refreshing ocean; watching the great humpbacks breach and listening to their song (even from inside my bunk on quiet nights!); seeing flying fish spray out from the water across the bow while sailing; observing sea turtles pop their heads up to peek at you; viewing the islands from the sea and then riding the dinghy to shore to explore them... these are just a few of the many delightful experiences to be had - besides eating the astoundingly delicious meals that Iwa manages to cook up without fail three times a day!
Finally, I enjoyed a peaceful serenity unlike anything else. The pure simplicity of sailing, being on the ocean, inhabiting its rhythms, and gazing up at the multitude of stars at night is a deeply restorative experience.
In closing: a word to the details. I had a private bunk, the sheets were soft and clean, and there was more than enough space for privacy/solitude. Although water is a precious commodity on board a boat, there are hot showers available, and plenty of fresh drinking water. The boat itself is immaculately kept. As I've already mentioned, the food is superb, and the environment is supremely easy-going and relaxed - if you desire a particular experience (ie. swim with sea turtles, go surfing or kayaking), they will make it happen for you.
I will be forever grateful for the time I spent with Iwa and Keao on Kainani Sails and highly recommend this amazing adventure.
I had a great time with Iwa and Captain Keao on our trip around the islands of Maui, Lana'i and Moloka'i!!! They both are lovely hosts. We were two guests (a young lady and I) and I don't have words to thank Iwa and Keao enough for their caring and looking after us. We had wonderful sailing adventures, sunsets, whale watching, snorkeling, fishing, swimming, hiking... - and always excellent food, good conversations and great music. I told all my friends back home in Munich that they have to spend a week on Kainani if they ever come to Hawai'i. Unforgettable! Thank you again.
Our time onboard Kainani is unquestionably the best vacation experience we had. Keao and Iwa not only showed us Hawaiian from a new perspective, but also introduced us to a different life style. This trip has put sailing life on our bucket list.
Keao and Iwa are extremely caring and accommodating hosts. Not to mention that Iwa is an excellent chef. My wife and I spent 4 nights on Kainani. There's one other guest. I think all of us felt quite at home during the entire time. As none of us has specific agenda, our daily activity consists of sailing, swimming, snorkeling, kayaking, sun bathing on the deck or on beaches, and enjoying healthy meals in good company. All of these is punctuated by occasional excitement of watching whales and dolphins, climbing coconut tree, and catching fish.
It's safe to say that we will be on Kainani next time we visit Hawaii!
When I found Kainani Sails on airbnb I thought it looked like a fun adventure and a bit of a risk considering my boyfriend and I were traveling with my 4.5 year old. It turned out to be a great adventure! The first day we saw whales and I spent about 10 minutes swimming with a sea turtle in the bay. The second day we caught a 40lb Ono (hawaiian for delicious and for good reason!) and explored Moloka'i. The third day we snorkeled and cruised around Lana'i. The fourth day we explored Lana'i and went to a beautiful beach by the four seasons resort. On the last day, as we sailed back to Lahaina a pod of about 100 dolphins swam around the boat much to the delight of my little girl and everyone on board. It was truly an incredible journey. Watching Keao climb up a tree with a machete to get us some coconuts is a memory that will stay in my mind for years to come!
The food was delicious and followed our dietary needs. There was fresh fruit and vegetables available. The guacamole was superb. Every meal was prepared by the crew and we ate together as a group. Although cleanup was also taken on by the crew, helping out on the ship felt good and was always welcome.
By far the best part of the ship, even considering the awesome adventures, was the good company of Keao, Iwa (pronounced "eeva") and Kelly. We felt like part of their sailing family from the moment we boarded. We ate every meal together, shared stories about all our journeys and they helped guide our adventures each day. Spending so much time in small quarters, who you are with makes all the difference. It really speaks a lot to the quality of their character and their laid-back, open personalities.
As far as having a kid on board, the biggest challenge was the isolation. Although everyone on board helped keep her entertained (which was greatly appreciated by us!) we were all thankful to be back on land where she could run around and play with other kids more freely.
All in all, it was an amazing trip. It was not a vacation though. It was an adventure. And like most worthwhile experiences, you need to do your work. While we managed to get in every activity we would have had to do as separate excursions, it also was a few days rocking about, limited personal space, few showers and no air conditioning. A small price to pay for being face to face with a sea turtle or surrounded by a pod of playful dolphins, something to keep in mind when considering this (website hidden) -- When Keao recommends ways to prepare for seasickness, do take his advice. He has no control over the weather and if the boat gets rocky it better to have something to help you out instead of a day lost to seasickness.
we had a wonderful time with Iwa and Keao!
loved every minute of sailing, snorkeling and spending time with our hosts!
we would love to come back!
Our family of 4 had a fantastic time on board Kainani. Keao and Iwa were great-- Keao took us to some great spots where whales and turtles could be seen up close and Iwa whipped up yummy meals and satisfied a bunch of picky eaters. Iwa is also great with kids and our five year old took to her immediately. Our time on board was nothing short of MAGICAL. When unexpected extreme wind conditions were forecasted in the middle of our trip, they very graciously helped us make alternate plans, refunded the remaining time, and even drove us an hour to our hotel.
This is a excellent way to see HAWAII! I will do this once a year, if i can. It's a perfect get away. Yes, i said perfect. From start to finish, relaxing. Food is wonderful, which is a big deal for me. The captain and his crew will become like family. There is never any pressure to do anything, unless you want to. Everyone is easy going and layed back.
Anything you wanna do is provided for you. Your day can be as long or as short as you want it to be. If you wanna just layout or do some exploring on shore. Captain and his crew are very open to whatever activities your up for that day.
Think outside the box. By the box, i mean the five star resort/hotel you my be thinking of booking. If your looking for something new and exciting to do, this is for you. Happy Sailing, everyone
This was my first time Hawaii and after this trip can't imagine a better way to see the some of it's most beautiful Islands. When I came across Kainani on Airbnb it really did seem too good to be true but it turned out to be better than I could ever have expected, so much so I decided to sail with Iwa and Keao for an additional 5 days. I met them both for the first time not long after arriving in Lahaina, both so friendly and so incredibly hospitable. They made me feel right at home on board. They were very open to teaching me the ropes on the boat, always showed such enthusiasm in any activity we took on, and prepared some pretty amazing meals throughout the entire trip. I never felt a want for anything. They always ensured the highest level of comfort possible, within their control of course, while at sea. We swam with whales, sailed with dolphins, stalked sea turtles, walked along the most amazing shore lines and beaches, explored tidal pools, snorkeled, fished for our dinner, and got to watch the sun rise and set nearly every single day. So many great memories!!! Everyone should see Hawaii with Iwa and Keao as their guides.
From the Host:
Thank you very much for your detailed description. We are truly saddened that one of you had a difficult adventure. We knew that one day we would have a guest that would be unhappy with what we have to offer, and we understand that being on a yacht can be very difficult due to close quarters. We have been doing inter-island trips now for the better part of a year, and this is the first time we have ever had anyone leave unhappy.
We feel that some of the complaints have been taken out of context and that it is only fair that we be given the opportunity to address them. First off, since the reviewer's husband was hoping to come back in a couple of days we were limited to anchorages near Lahaina that would allow enough time to pick him up if he was able to return. One of these anchorages was in Honolua Bay, a marine sanctuary where fishing is strictly prohibited. In addition, many of the places we anchor at have shore breaks which make bringing a 250lb boat ashore very difficult. For this reason we anchor within kayak and/or swimming distance.
The second point we would like to make is that we are an adventure travel service, not a luxury travel service and we feel that the price we charge reflects that. We do everything in our power to make the experience unforgettable, and we ask that guests come on board with an open mind. We also ask that guests be prepared to lend a helping hand, be it in the kitchen, on deck, or on shore. We provide the means for your adventure, but it is up to you to make the most of it.
Lastly, we are on a sailboat in the Pacific Ocean and everyone on board needs to be prepared for itinerary changes that may be dictated by the weather. After our guest found out her husband would not be returning she informed us that she would be flying out that evening. Upon our return to Lahaina we found out that the storm we had not been expecting was heading in and we needed to seek refuge in Lana'i asap. Ten minutes into searching for hotel accommodations, our guest asked to get off the boat. We did as requested and headed to Lana'i. Safety is and always should be the number one concern of everyone on the ocean. During the storm, a total of 5 boats sunk or broke loose, ran aground and were destroyed.
We admit that this type of adventure travel is not for everyone. If you are expecting the Four Seasons and Michelin-rated restaurants, this is most likely not the adventure for you.
Me and my husband have spend one week on the wonderful Kainani Sails and are now left with wonderful memories of continuous adventure and beauty from day one to day seven. If you choose Kainani Sails for your stay while in Maui this is something that you can expect:
Room: We had a chance to stay in the master bedroom and it is everything that you see in the photos. The room was very clean, had a separate bathroom/shower, enough space to store all our clothes and a very comfy bed.
Hosts: Both Keao & Iwa were fantastic. They made us feel very comfortable from day one. Throughout the whole trip they always made sure we were having a great time and were very flexible depending on what we wanted to do. The captain demonstrated extensive sailing experience by managing all weather conditions and always made us feel very safe.
Food: Delicious. Every day we had a variety of new foods that were well prepared and very tasty. Thank you for sharing some of the recipes :)
Adventure: We travelled between 3 islands: Maui, Molokai & Lanai. The hosts were very familiar with all the islands and knew all the best spots to stay at. The trip was filled with many exciting adventures. Whale watching was spectacular. I counted 76 whales on the trip. We also got a chance to swim and kayak with a fun pod of spinner dolphins that played with us for at least 30 minutes. Through the trip we also snorkelled in a variety of amazing spots and saw exciting underwater life. My husband also surfed in few locations and we got a chance to fish. Basically we saw and did everything that we wanted and more :)
So to end my review if you can imagine yourself sitting on the dock, eating delicious food, enjoying great company while watching beautiful sunsets and whales jumping on the horizon then this is definitely for you!
Thank you Kainani Sails for a memorable trip!!!