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Private Maui Sailing Charters Kaanapali Beach, Lahaina, Hawaii"""

Bedrooms 3
Property type boat


About the property

Find Your Sea Legs & Sail Away With Us!


Maui Sailing Charters offers private sailing charters by the hour or overnight/multi-day charter experiences. Whether looking for a daytime activity or a place to stay, give us a call or email for rates and availability! 808-495-1001


Private Day-Sails $275 per hour (3 hour minimum)

Inter-Island Cruises rates per day (2 day minimum)

1-3 people $1375 per day + taxes & fees

4-6 people $1500 per day + taxes & fees

For groups of 7+ we also have a powerboat option to accommodate up to 24!

Join us for a unique adventure in Hawaii. Kainani Sails specializes in private sailing adventures and is the only sailboat offering multi-day trips based out of Lahaina, Maui. Great for couples, families, or a small group of friends- experience the Hawaiian Islands in an off-the-beaten-path type of experience. Whether you want to spend a few hours sailing, a day on the water snorkeling and sailing, or even a few nights onboard- we are happy to help make it possible for you. Our sailboat features 3 private cabins, 2 bathrooms, a full galley, and all the gear for a good time. Depending on how much time you have to spend onboard- sail amongst the islands of Maui, Molokai, Lanai- or beyond! We are here to help you make the most of this adventure, so please don't hesitate to email or call us with any questions or concerns.

More Details

Keao Brian Shaw
Member since: 2013
Speaks english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
January 31, 2018

About Keao Brian Shaw

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!

Keao Brian Shaw purchased this boat in 2011

Why Keao Brian Shaw chose Lahaina

Whales, Dolphins, Turtles, Fish, and the Ocean literally under your feet!

What makes this boat unique

A new view every day! Find the real Hawaii off the beaten path. Get your feet wet and find your sea legs!!!

Guestbook comments from the owner

What can I say?! This has been the BEST vacation of my life! Not only did I get to see and hear so many Humpback Whales, but I also discovered that I love to sail! I will never forget your kindness and generosity- and I am so glad to know you. Heres wishing you both many more beautiful adventures together!
Feb 2014
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Accommodation and Amenities for this vacation boat rental in Lahaina, Hawaii

Property Type:
  • boat
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
House Rules:
  • Max. occupancy: 6
  • Events Allowed
  • children welcome ...
  • smoking allowed ...
Location Type:
  • Beach View
  • Beachfront ...
  • Near The Ocean
  • Ocean View ...
  • Oceanfront ...
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Linens Provided
  • Towels Provided ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Kitchen ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 private marine heads (Bathrooms)
  • 3 Bedrooms, Sleeps 6
  • Master Cabin - 1 queen , Master Cabin with in-suite Bathroom. Boat sized/shaped bed.
    Aft Cabin - 1 double , Aft Cabin with Shared Bathroom. Boat sized/shaped bed.
    Aft Cabin - 1 double , Aft Cabin with Shared Bathroom. Boat sized/shaped bed.
  • 3 private cabins
  • Books
  • DVD Player
  • Games
  • Music Library
  • Stereo
  • Video Library
  • Boat
  • Deck / Patio
  • Kayak / Canoe
  • Outdoor Grill
  • Water Sports Gear
  • 2 beach chairs
  • wheelchair inaccessible
Leisure Activities:
  • beachcombing
  • boating
  • eco tourism
  • shelling
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • hiking
  • kayaking
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • surfing
  • swimming


Wonderful! 4.9/5 -
(8 traveler reviews)

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Private Maui Sailing Charters Kaanapali Beach, Lahaina, Hawaii
average rating of 4.875 based on 24 reviews

Perfect Vacation for our Family

  • 5 of 5

We are a family of 6 with kids 16, 14, 10, and 9. We spent 3 nights onboard the boat. This was the most wonderful vacation ever. From the very beginning Iwa was very responsive to my many emails. Keao was a terrific captain. He was very knowledgeable, fun, safe, and engaging. We went to Lanai, seeing multiple whales along the way. We also went to Molokai where we did a short hike. We anchored in a magical deserted cove off Maui. Keao played countless card games with the kiddos. He took us to spots where the kids could snorkel and/or leap off high cliffs into the ocean. I highly recommend Kainani Sails for anyone looking for a little adventure for their family. A couple of our kids slept on top of the boat at night under the stars. There was plenty of room for all of us. Despite the warm daytime temperatures, things cooled down nicely at night. We made all of our own meals onboard, but Keao and Iwa will do all the shopping and cooking for you if you'd like. One thing I really liked was that Keao was able to recognize right off that our kids are daredevils and always looking for excitement. He adjusted to keep them engaged. I feel he would adjust the itinerary based on the needs of the guests along with the sea state and the weather. This was a great way to see 3 Hawaiian islands in 1 trip.

  • Submitted: 8-Jan-2016
  • Stayed: December 2015
  • Source: VRBO, from HomeAway
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3 0
Thunder Bay, ON, Canada

Christmas on Kainani

  • 5 of 5

My husband, three daughters, and I just spent an amazing Christmas on board Kainani! We booked the three day sail as a surprise for our girls for Christmas and they claim that it was the best Christmas present ever.

Booking was easy and straight forward. We had no trouble getting in touch with them and everything went exactly as planned. We were a little nervous as there was storm moving through the night before we were to depart but Captain Keao knew exactly where to take us so that we could still have a great day with bad weather.

We took our own food as we have some allergies, and my only complaint was that we took food that was too easy to prepare! The kitchen facilities were great and we could have cooked gourmet if we had wanted to. The bedrooms, although small, were very comfortable and the bathrooms were perfect.

Keao did an excellent job as captain, tour guide, and card shark. He was friendly and helpful and found great activities for us every day. We visited Maui, Lanai, and Molakai in our three days; spent one night in a harbour as the weather was rough, and two nights just anchored in bays by the shore. We helped sail, swam with turtles and manta rays, snorkelled, hiked, kayaked, fished, and saw MANY whales! We also enjoyed just sitting on the deck and watching the sunset, and then playing cards after dark.

It was an excellent three days and I would highly recommend this adventure to anyone. We really feel like we saw Hawaii in a different and unique way. I'd go back in a heartbeat!

  • Submitted: 19-Feb-2015
  • Stayed: December 2014
  • Source: VRBO, from HomeAway
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3 0
St pete florida

Great trip

  • 4 of 5

Had a wonderful trip on the boat. Three nights. Captain very knowledgable and fun. Boat was comfortable for four of us. It was a bit warm at night when we travelled and aft cabins did not have fans. Saw wonderful sights and loads of creatures. Great way to see the islands. Will have to arrange drop off and pick up at launch site

  • Submitted: 7-Dec-2014
  • Stayed: November 2014
  • Source: VRBO, from HomeAway
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0 0
Portland, Oregon, USA

Fabulous Sunset Sail!

  • 5 of 5

My husband and I chose to sail with Kainani Sails because it was the only affordable private sailing option in Maui. We were not disappointed! We chose the 3-hour private sunset sail, and it was just the romantic and intimate experience we were looking for. It was perfect in every way. Hope to sail with Captain Keao again soon!

  • Submitted: 4-Dec-2014
  • Stayed: December 2014
  • Source: VRBO, from HomeAway
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Salt Lake City, UT

Incredible Experience!

  • 5 of 5

This is the best, most affordable family activity on Maui. It was so nice to have the whole boat to ourselves rather than sharing with a bunch of strangers. We booked the 4-hour morning snorkel sail. Snorkel gear was provided, as well as instruction by the crew who even jumped in with us to point out turtles, fish, eels, and even a eagle ray! The captain even let the kids take turns steering the boat. Definitely a memorable day! I recommend this unique trip to anyone headed to Maui. We want to come back to sail with the whales. You can't find a better deal for a private boat!

  • Submitted: 4-Dec-2014
  • Stayed: October 2014
  • Source: VRBO, from HomeAway
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Holden, MO USA

Best time ine HI.

  • 5 of 5

My mom's disabled, I have a nine year old and a teenager and my husband. We all had the best time with Keao and his sailboat. There was plenty of room, so everyone had their own room, and the master bedroom has it's own bath. Three bedrooms! Everything is top quality and very, very well taken care of.

As for your Captain, Kaeo will be part of our family forever. The guy has Coast Guard certification and many, many hours at sea. He's a gourmet chef and one of the most charming and amusing people I've met. He makes everything so easy, so it really is "no worries". We've managed to take that feeling home and I cannot ever thank him enough for that. We will be back.

  • Submitted: 3-Jun-2014
  • Stayed: May 2014
  • Source: VRBO, from HomeAway
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Car: not necessary

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.


Rates & Availability

Rental Rates for this vacation boat rental in Lahaina, Hawaii

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jun 12 2017 - Jun 12 2018
1 night minimum stay
Standard pricing
1 night minimum stay

Additional information about rental rates

Day Rate $275/hr Overnight Rate $1500/day. 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.

Owner's Cancellation Policy

No refunds for cancellations made after payment is made
Contact Owner