VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More
Maui Sailing Charters offers private sailing charters by the hour or overnight/multi-day charter experiences. Whether looking for an activity or a place to stay, give us a call for rates and availability! 808-495-1001
Rates: Private Day-Sails $250 per hour (3hr minimum) Shared Adventures: $400 per night (5nt minimum) Inter-Island Cruises $1200 per night (3nt minimum)
Aloha! Definition of “adventure” is: Ad-ven-ture: noun 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
Adventure cruise: 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.
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. 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!
Multi-Day Private Jan 1 - Dec 31, 2015 3 night min stay
My Standard Rate 1 night min stay
Rates are based on 1 guests; add $400 per night, per additional guest
Additional information about rental rates
Shared yacht charters are offered at a rate of $400 per person, per night. Private charters start at $250 per hour for the entire yacht. An additional 3% Permit Fee along with 4.166% GE Tax is added on to all payments. If paying with a credit card or Homeaway Payment, an additional 3% transaction service fee will be added on to all transactions.All trips are subject to weather and sea conditions.
Cancelled bookings will not receive a refund.
Travel with confidence
Pay with an approved method (credit card, check, or bank transfer) to protect your payment up to $1,000. Before making a payment always call the owner at the number listed on our website, and never use instant money transfer services such as Western Union and MoneyGram.
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.
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations.
Ensure you're prepared in case of accidental damage.
Set sail on a private yacht in Hawaii. Enjoy a unique experience of exploring the island by the sea. Snorkel with a Hawaiian Sea Turtle, watch dolphins play at the bow, sail under natural sea cliffs, play on exquisite white sand beaches, and relax in the shade.
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!!!