Hawaiian Island Sailing Adventure
You sent a message to this owner.
- Minimum stay:1 night
- Pets considered:Yes
- Wheel chair accessible:No
Private Homes boat description
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, 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 contact us and we can arrange for that.
While on board, 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 at least 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 on board, 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 adventure may hold (2 night minimum).
Day one: welcome to Lahaina, Maui (the valley isle). If you’ve never been to Lahaina, now is the time! With crystal clear blue waters and sun 360 days a year, there is no better place to start. Upon your arrival, we’ll take your luggage out to the boat, make a quick stop at a nearby grocery store to pick up any last items, and go for a swim.
Day two: in the morning, we’ll make an exciting sail to the “friendly isle” of Moloka’i. Once anchored, we’ll have lunch on board and spend the afternoon exploring the beach.
Day three: we’ll sail up the channel to Honolua bay on Maui, a renowned surf spot and a wildlife sanctuary where the snorkeling is gorgeous and the honu (Hawaiian sea turtles) are abundant.
Day four: the next day, we set sail downwind to lana’i, where we will know what it is like to sail among giants and anchor among sea cliffs.
Day five: after some shoreline exploring, we’ll have a lazy motor sail down the backside of Lana’i where the cliffs drop into the deep blue and the fishing picks up.
Day six: we sail back up to Maui in the evening and watch the sunset while remembering the good times from the past week.
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, Iwa & Kainani
*we know that this trip is not for everybody; we always try to make everyone feel at home and comfortable on board. 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!
- Vacation Rental
- Lunch - Included In Price
- Dinner - Included In Price
- Catering Available
- Breakfast - Included In Price
- Children Welcome
- Events Allowed
- Pets Considered
Bedrooms: 3 Bedrooms, Sleeps 6, Beds for 6
- 3 private cabins
Bathrooms: 2 Bathrooms
- 2 private heads (Bathrooms)
Kitchen & Dining
- Pantry Items
- Dishes & Utensils
- Linens Provided
- Towels Provided
- Video Library
- DVD Player
- Music Library
- Deck / Patio
- Water Sports Gear
- Kayak / Canoe
- Tourist Attractions
- Sports & Activities
- Away From It All
Location & View
- Beach View
- Deepsea Fishing
- Scuba Diving Or Snorkeling
- Eco Tourism
- Whale Watching
- Wildlife Viewing
- Sight Seeing
ReviewsWrite a review
From the moment we first made reservations, we were greeted with professionalism and hospitality. Perfectly located and great hosts that do everything to make your stay perfect. It doesn't matter how active you want to be, the hosts will accommodate your wishes. The food is delicious and Plenty of it. Overall I can't say enough about the hosts that made our first sailing experience perfect. We snorkelled, hiked sea cliffs, kayaked, swam, saw dolphins, turtles, visited two other islands, drank from coconuts, and learned alot about sailing.We met as strangers and left as friends. Two young beautiful people that make you feel very welcome. I highly recommend this company for your vacation.
- Guest Barb F.
- Date of stay 09/14/13
- Review Submitted 09/28/13
Recommended for: Families with teenagers, adventure seekers, sightseeing, romantic getaway, families with young children, age 55+, girls getaway.
Owner response: Mahalo for joining us! We enjoyed the company, the conversation, and the adventures... Hope to sail with you again soon!
Family luxury adventure
Family luxury adventure
Our choice as a family to sail the Hawaiian Islands for a week on Kainani Sails is a vacation adventure our family will never forget. Thanks to the competence and confidence of Captain Kaeo we safely and comfortably explored the rarely visited or seen coastal stretches of Maui, Molokai, and Lanai. Although the voyage was truly an adventure as we explored pristine reefs, beaches and lagoons, we were also able to enjoy our trip in relative luxury aboard this beautiful yacht. And although the vessel’s accommodations made for a very comfortable and relaxing trip, it was the friendly and accommodating personality of Kaeo that made our trip so incredible and ultimately memorable. If you’re looking for a novel way to relax and “get off the grid”, while also including an element of adventure and autonomy, a sailing trip on Kainani Sails could be the perfect choice for you. Kaeo was very willing to discuss the sailing options before committing to the trip, as well as expectations, needs, addressing concerns, etc., so if you’re interested at all in this type of vacation adventure I’d recommend giving him a call or sending an email.
- Guest Jim (Redding, CA)
- Date of stay 08/05/13
- Review Submitted 08/28/13
Recommended for: Tourists without a car, families with teenagers, adventure seekers, sightseeing, romantic getaway, girls getaway.
|Dates||Nightly||Wknd Night||Weekend||Weekly||Monthly *||Event|
1 night min stay
Additional information about rental rates
All trips are subject to weather and sea conditions.
We require a 50% non-refundable deposit upon booking. The rest can be paid by cash, credit, or PayPal upon arrival.
Additional Fees and Taxes:
Adventure Cruise(Shared Yacht) is $300* per person; per night
Private Yacht is $1050* per night for up to 6 people
*If paying via PayPal or Credit Card, additional fees may apply.
Always make sure to call the number on the listing to confirm payment details.
Only pay using credit card, PayPal, check or direct bank transfer. NEVER pay by cash or instant money transfer services such as Western Union or MoneyGram. Learn more
Don't forget your vacation protection! Get protected now
Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection, Carefree Rental Guarantee, and Damage Protection so you can truly relax.
Year Purchased: 2010
About the owner: Our easy going Captain, Brian 'Keao' Shaw, was born and raised on the Big Island of Hawaii. As a USCG certified captain with a sailing endorsement, he is prepared to put your comfort and safety first. He has knowledge of the local waters in Hawaii and the open waters of the Pacific, with extensive sailing experience from the West coast of the United States and Mexico, to the South Pacific. While not sailing, he enjoys fishing, diving, surfing, exploring remote areas, soccer, photography, and traveling. With his experience in and out of the water he will help you find your sea legs in no time!
Why the Owner Chose Private Homes:
Whales, Dolphins, Turtles, Fish, and the Ocean at your door step!
The Unique Benefits at this Boat:
A new view every day! Find the real Hawaii off the beaten path. Get your feet wet and find your sea legs!!!
- Primary: 8087387987
Links to more information:
Hawaiian green sea turtle
sailing into the sunset!!!
Enjoy a romantic sunset aboard a private sailing yacht
Kayaking with Dolphins
one of two matching aft cabins
sailing with dolphins playing on the bow
swim with a hawaiian sea turtle
secluded beach on Lanai
A view of Kainani through a sea cave on the backside of Lanai
Join us for an adventure where you get get your toes wet and find your sea legs!
Some great Kayaking
Whales visit Dec.-April be on the look out!
abundant marine life!
Hawaiian Spinner Dolphins
Master Cabin with private bathroom
Be quick with the camera!
swimming pool just off the bow!
catch a fish!
honolua bay maui... jump right off the boat into a marine preserve!
Sailing outside of Lahaina... catching the trade winds on our sails!
A double rainbow over the West Maui Mountains
There have been visitors to this page since
the counter was last reset in .
This listing was first published here in 2013.
Date last modified - Thursday, November 21, 2013