Let’s go Sailing in Hawaii

Every year my wife and I celebrate our wedding anniversary by doing something crazy/special. This year, we decided to go on a boat and sail around the Hawaiian islands. Living & working in America gives us plenty of choices. Hawaii is only 5 hour flight and it costs a few hundred bucks to fly there and back.

We found Kainani Sails operated by Brian “Keao” Shaw & Iwa Hartman on AirBnB.

Kainani Sails

AirBnB is where you get to rent from real people – not hotels or larger charter businesses. We wanted this to be “personal” and special holiday and not have to rush everywhere we visit. Basically doing it at our own pace. Kainani Sails has a boat which is a fully equipped 43′ sailing yacht. It is also their home. Perfect. Let’s go!

Our sailing trip took us along this route
Our sailing trip route. Yellow icon was the start & finish. Click map for larger view.
This is us! From left clockwise: Iwa (Crew), Keao (Captain), Urszula & Ernest (me)
This is us! From left clockwise: Iwa (Crew), Keao (Captain), Urszula & Ernest (me)

What you need to know:

  • You will sail in a fully equipped 43′ sailing yacht. It has kitchen, 2 bathrooms (again don’t expect a hotel bathroom), living room, master cabin with a comfy queen size mattress and 2 smaller cabins and an engine so you can still move when the wind is down. See pictures of it here.
  • There is fresh water on board for bathrooms and drinking.
  • Captain Brian “Keao” Shaw has around 10 years of sailing experience and is USCG certified. Having grown up in Hawaii he also knows the local waters very well.  He will even turn on the motor when a whale is sited to make them aware of us – that’s caring for nature. With Iwa Hartman as his crew you are in great hands.
  • On board you will also find surfboards, snorkeling & fishing gear, a 2-person kayak, deck chairs, a small library, outdoor grill, and a 10′ tender with a 15 hp outboard known as the “Zodiac”. Your taxi shuttle to the shore.

Things to prepare before:

  • To prevent nausea and vomiting caused by motion sickness ask your GP for prevention pills. We received Transderm Scop in 10 patches (a 30 day supply). Each patch goes behind your ear and lasts for 3 days.
  • A rashguard to keep yourself from getting burnt by the sun. You will be on the boat, snorkeling, surfing etc… always in the sun. This will protect you from the UV.
  • waterproof housing for your camera. The world below is amazing. You will regret it if you do not have a camera capable of taking video or photos underwater.
  • A book or an iPad with digital books. There’s nothing like kicking back reading a book and watching the sun set or early in the peaceful morning indulging your mind.
  • You and Keao will create your meal schedule to make sure you eat healthy. Done before your trip via email.
  • A waterproof jacket. When crossing the channels between the islands the wind picks up and waves get larger. You may get splashed when sailing.
  • LED headlamp / torch. When the sun sets you will want additional / personal lighting.
  • Buy some snacks, red wine & alcohol before you board. My favorite is the Chopin Vodka, 4 times distilled and rated well in San Francisco for the last 2 years.

My favorite things to do on the boat

  • My sleeping habit changed from 3am – 8am (ahh the life of an entrepreneur software engineer) to 9:30pm sleep and 6:00am wake up as the sun rises. My body naturally went into this cycle with the sunset and sunrise rhythms. I had a ton of energy each day without a need for caffeine. I did not drink a single drink with caffeine while on board.
  • Sleeping on the stern (back of the boat) under the stars. I created a nice comfy bed and slept under the stars each night – simply amazing! Without any light pollution you could see every star possible with the naked eye. I felt like the character in Altered States tapping into evolutionary state when our ancestors used to sleep under the stars.
  • Sit at the bow (front of the boat) on deck chairs with your partner to enjoy the open seas as you sail.
  • The master cabin has 2 roof windows which open up. Sneaking in and out of the cabin via these windows felt like being a kid again.
  • Take stunning photos from all corners of the boat. Just hold on tight coz the boat does rock with the ocean and leans during full sail.

Our journey begins

Saturday (Feb 18)

  • For short trips of around a week its cheaper (with coupon) & more convenient to leave your car at the airport parking. We flew out of flew out of Oakland International so parked our car at Park ‘N Fly.

Lahaina Bay - Home for the next week! Aloha!!
Lahaina Bay – Home for the next week! Aloha!!
  • We flew Hawaiian airlines Boeing 767 into Kahului Airport on Maui (Hawaii). That’s the top part of the island. It’s best to catch a shuttle bus (which fits around 10 people) from the airport to Mala Harbor (the south side of the island in Lahaina). A 1-hr car ride. Grab the shuttle bus as soon as you walk outside the airport.
  • Captain Keao picked us up from the bay on the “Zodiac” (outboard) and took us to the fully equipped 43′ sailing yacht parked further in the Lahaina Bay.
  • Having arrived to the sail boat, we were greeted by Iwa (his crew) and helped on board. I must say this was a very friendly welcome and we felt like at home straight away. Thanks folks!
  • That afternoon we watched an amazing sunset and then star gazed. Using an iPhone app Sky Safari to identify the stars, planets & constellations was super fun… before falling asleep under the stars.
Sunset over Lanai
Sunset over Lanai

Sunday (Feb 19)

  • Early morning we set off sail to Honolua Bay. This is the west side of Maui. It was a 5 hour journey and Urszula got to sail the boat under Captain Keao’s supervision. Here’s a nice video of our sailing treck Sailing adventures in Hawaii with Kainani Sails.
  • The private residence bay was amazing. Rich in corals and surrounded by rocky cliffs with 2 beaches where about 2 dozen surfers were catching 6 foot breaks coming from the open sea along the cliff faces. So Keao and I grabbed 2 surfboards (the boat carries 3 surf boards) and we paddled to the break. We had a kick ass time while Urszula went snorkeling & underwater recording with Iwa.
  • As the sun was setting a large pod of Spinner Dolphins came into the bay. I call them Tunas because they the young ones look it. They are famous for their acrobatic displays in which they spin along their longitudinal axis as they leap through the air. Urszula and Iwa set out on a kayak to get closer to these amazing creatures Sailing adventures in Hawaii with Kainani Sails.
Spinner Dolphins playing with us in Honolua Bay
Spinner Dolphins playing with us in Honolua Bay. Click pic for larger view.

Monday (Feb 20)

  • We set out sail early towards Maunaloa on Molokai island. A secluded place that reminded me of the 1st episode of Planet of the Apes (1968) when the crew crash lands on a planet in the distant future. Nothing but beach, sand and mother nature.
Molokai
Molokai
  • Molokai is the fifth largest of the main Hawaiian Islands. It is one of the least touristy islands and very native.

Tuesday (Feb 21)

  • We departed before sun rise to beat the winds while crossing the channel. However we hit some pretty crazy winds and the seas were angry my friends. I was thinking Mavericks! This was the time I gave in and plonked motion sickness patch on and the waterproof jacket.
  • When we hit Lanai’s Au’au channel the winds settled and oceans calmed down and turned deep blue. I have never seen anything like this before.
Lanai cliff faces west facing
Lanai cliff faces west facing
  • We stayed the night in a secluded bay near these amazing rock cliff faces where Urszula came face to face with a 3 meter shark in the coral rich bay.
  • It was funny to watch those touristy charter boats come in loaded with people, they bobbed out for 30 minutes into the water and had to get back on the boat to leave again. What a rush. Did the tourists even get a chance to take in the beauty of the surroundings and underwater. While we kicked back and snorkeled at our own pace taking in everything nature had to offer.

Wednesday (Feb 22)

  • We headed into Lanai Bay and parked the boat amongst other boats. This was a big change to the secluded areas we visited earlier. A lot more populated.
Lanai bay
Lanai bay
  • Lanai is sixth-largest of the Hawaiian Islands. A privately owned island. It is also known as the Pineapple Island because of its past as an island-wide pineapple plantation. The only town is Lānaʻi City, a small settlement. Lanai has the longest stretch of coral reef in Hawaii and the beaches on this island are down right deserted.
Secluded cove near Four Seasons at Manele Bay
Secluded cove near Four Seasons at Manele Bay
Secluded cove near Four Seasons at Manele Bay
Secluded cove near Four Seasons at Manele Bay
  • I highly recommend you visit the Four Seasons Lanai at Manele Bay. A brief walk from the bay and they have great Mojitos (my favorite).
  • The beach at the base of the hotel is also amazing with fascinating tide pools, great snorkeling, red sea cliffs and a stunning cove.
Four Sesons beach at Manele Bay
Four Sesons beach at Manele Bay

Thursday (Feb 23)

  • We loved Lanai so much we set sail back to Maui later in the afternoon.
  • Stopping along the way in the middle of the ocean and jumping off the bow to hear the Whales sing under water. (see video) and to feed some crazy black fish (see video). hehehe that was fun! I think they wanted to feed on Urszula.

 

Sailing back to Maui
Sailing back to Maui
  • Sailing back to Lahaina Bay I took charge of being the Captain hehe under Keao’s training around the instrumentation and reading the sails/winds I sailed us back into Lahaina while we all enjoyed the amazing sunset.
Please call me... Captain!
Please call me… Captain!

Friday (Feb 24)

  • Early morning we hit the surf in Lahaina Bay with our surfboards. Plenty of people catching perfect waves.
Surfs up!
Surfs up!
  • Lunch time we said our goodbyes – it was tough after such an amazing week with Iwa & Keao. Not only did we have an amazing time but we also made friends. That is something we will never forget. Keao dropped us off at Lahaina bay port where the friendly folks at Enterprise car rental picked us up for the next journey in Maui.

Wow, we sailed in Hawaii

We couldn’t have asked for a better trip. Both Keao and Iwa were outstanding hosts. From looking after us with healthy food (we got some recipes), entertainment, history lessons of the sights, sailing lessons to opening up their stunning waterfront property (the 43′ sailing yacht) to us. We felt like we were at home but away from home. Urszula counted 76 Whales during our trip! I started to call this whale pollution because there were so many of the them hehe I really decompressed and disconnected from my reality and lived a life which I can only compare to what I believe our ancestors did once when they were one with nature.

Here’s a short video of our trip

Want to experience the same?

Everyone should at least one in their life sail. Especially around beautiful Hawaii.

Check out more photos here on Flickr

Here’s how to get in-touch with Keao or Iwa from Kainani Sails:

Videos you should watch:

Enjoy!
~ Ernest

Author: Ernest W. Semerda

Veryfi cofounder (#YC W17 cohort) ~ mobile automation software designed for the construction workforce. GSDfaster founder ~ be more productive. Follow me on Twitter: @ernestsemerda