Lahaina, Hawaii

Hawaii Sailing Adventure

with Brian S.

1 review

Brian S.

We'll start our adventure in Lahaina, a small town with crystal clear water, views of Molokai and Lanai. We'll then head up the coast to Honolua Bay, a renowned surf break and popular snorkel spot. Otherwise we head west to the Island of Molokai, also known as the “Friendly Isle.” With a population of approximately 8,000 people, expect to go “off the grid” for a few days. Enjoy kayaking, beach combing, and stargazing at its best! We'll also snorkel below sea cliffs and swim with dolphins!

Let me tell you about my sailboat, Kainani. Kainani is a 43' Beneteau. She is a fully equipped sailing yacht designed with comfort and safety in mind. Kainani is ready for adventure with 3 private cabins (bedrooms), 2 heads(bathrooms) with hot water showers, a full galley(kitchen), and lots of fun things like surfboards, a kayak, small library, fishing gear, masks & snorkels. We aim to have guests stay for at least 6 nights and 7 days. If you can not make all the days, let us know and perhaps we can work something out special for you.

Meals, water, fuel, safety equipment, USCG certified captain. Kayak, fishing, surfing, snorkeling (mask and snorkel provided), private rooms (couples will be given the master cabin w/private shower and bathrooms). If you’re not interested in staying a full week, want to explore a certain part of the Hawaiian Islands, or just want to stay aboard the boat in one location, let me know! I'm flexible.

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per person
for 7 days

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Brian S.

I was born and raised on the Big Island of Hawaii. As a USCG certified captain with a sailing endorsement, I am prepared to put your comfort and safety first. I have 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, I enjoy fishing, diving, surfing, exploring remote areas, soccer, photography, and traveling. With my experience in and out of the water I will help you find your sea legs in no time! Full profile

1 Review


I went to Maui in search of an adventure. I am a nature lover and a diver so I was really excited when I lucked out and booked a cabin on a 43' sailboat. Captain Brian and first mate Iwa were warm and welcoming as we set sail to Molokai'i and Lanai for a ten day adventure. The view of Maui from the water is spectacular. Everyday was a paradise cruise, we viewed countless humpbacks breaching, dolphins spinning around the boat, dramatic cliffsides and the most incredible snorkel spots imaginable. I particularly loved being in the water so it was great that fins and masks were available on board. I will never forget all the life under the sea, sea turtles, eels, octopus, whales and all the abundance of tropical fish!! My warmest memories are from the crew, the dinners of fresh caught fish and precious local expertise were the delight of the trip and really create a unique trip to remember. I would recommend them to those with an adventurous spirit. if you want to learn the ropes or just sun on the deck or check out some super marine life, call up Brian and Iwa, I have no doubt they'll take good care of you and make sure you get what you came for. Aloha!!

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