10 Must-Do’s for a Most Epic Sailing Trip!

Last week I embarked on my first open-water multi-day sailing trip. It was all things incredible! It turns out that a couple days spent on the open ocean basking in the sun, snorkeling, fishing, and learning more about the sport of sailing refreshes and invigorates the soul!


It is no secret that my blog has been lacking in new posts these last few months – not because I haven’t had plenty to write about this spring – but because of a lack of creative motivation and inspiration to string words together in the way that I am often, easily able to do! I figured that I could either sit down and force out uninspired, lackluster blogs, or accept my lull in motivation and take a blogging-hiatus. In yoga we are taught that where we are in our poses, mindset, and life is okay – that it is where we are meant to be. And so I decided to accept my lack of motivation and creativity to generate weekly posts and decided instead to enjoy my time spent developing relationships with friends, practicing yoga, surfing ocean waves, and most recently, embarking on a first, spontaneous, inter-island sailing trip with friends on the Kamanakai.


On Wednesday of last week, Clay and I packed up and prepared to embark on our first overnight sailing trip! We boarded a flight to Lanai with our friend Kevin, where we met up with Captain Wayne and the Kamanakai Crew – Amanda, Amy, and Becca – to sail to Honolua Bay, Maui before returning home to the windward side of Oahu. Two days and two nights on a sailboat and not quite knowing what to expect, I am happy to say that my first inter-island sailing trip was a great success!


Blue skies soared above us and dolphins danced below the bow. We enjoyed a deep-water swim stop, a sunset hike, and big sea waves. We managed to catch both a Mahi Mahi and an Ono within a matter of minutes – perfect for a 4th of July weekend BBQ! We enjoyed amazing views of the Cliffs of Molokai lit up by the morning sun, swam with the biggest sea turtle I have yet to see, and enjoyed the camaraderie of being on a 34 ft craft with 6 people for two days.


With high hopes to embark on more sailing trips in the future, here are the 10 Must-Do’s of sailing that I quickly learned upon my two days with the Kamanakai crew!

10) Overpack Provisions

While on a boat, a run to the market is no easy feat! Be generous in your packing of provisions – it’s rare to wish you had less! (This applies to both food and beverage!)

9) Bring your snorkel gear!

In trying to pack light, I wasn’t sure if my snorkel gear was a waste of space. As it turns out, it is definitely not! Bring your snorkel gear so you will be prepared if the opportunity arises to snorkel at your evening’s destination or somewhere along the way!


8) One Pot Meals

Simplicity goes a long way on a sailboat as you often cook in a cubby-hole of a kitchen. When it came our turn to cook dinner, Clay, Kevin, and I cooked up a one pot Mexican quinoa dish (recipe courtesy of Ashley!). It was a great success.  You can find it here!

7) Make your sandwiches the night before

For a long day of sailing, do whatever you can to minimize tasks needing to be performed below-deck. For the Kamanakai crew, this meant an assembly line of sandwich-making to to prepare for the long day of sailing ahead! (On day two we sailed from Honolua Bay, Maui, to Kaneohe Bay, Oahu – covering 55+ miles!) Pre-made sandwiches were crucial to the well-being and success of our crew!


6) Bring your sleeping bag and sleep beneath the stars

My favorite place to sleep on a sailboat is on the deck. Away from city lights, the stars are spectacular. And you enjoy a fresh, all-night breeze that you don’t get below-deck!

5) Sail with the sun

I’m a sucker for sunrises – and a sunrise as seen from a sailboat in the middle of the ocean is tough to beat! Sleep with the stars and rise with the sun.


4) Pack your fishing rod and reel

Sailing trips are an opportune time for fishing! And you might become the favorite on board if you catch that evening’s meal! Our crew caught a Mahi Mahi and an Ono within minutes of each other. Well done, Clay and Kevin. They were delish!



Feelings of sea sickness were not absent from our grand adventure! Thanks to one of our crew members, Becca, I learned that ginger water can go a long way. (But try to avoid looking at it as you drink – chunks of brown ginger in your drinking water can cause the exact act you are trying to prevent!)

2) Swim break fun!

When in calm, slow-moving waters, hop in for a dip! (As long as Captain knows :P) Turns out, Wayne had the best back-dive on deck!


1) ALWAYS wear your bathing-suit!

With day two of our sailing trip being the day to cover some serious miles, I opted to remain in my ExOficcio quick-drying undergarments for the day. With the wind at 20+ knots and wanting some sun protection, I planned to keep warm and avoid sunburns by sailing in my long-sleeve sun-shirt and shorts. All was well until I realized that going below deck to use the head instantaneously brought about feelings of sea sickness. Swimsuit bottoms would have been preferred as I resorted to hanging my bum off the ladder on the back of the boat to relieve myself and utilize the great outdoors. At least I was able to keep my breakfast! 😛



Our two day and two night sailing trip was the epitome of a Hawaiian adventure, and a perfect one at that. As it turns out, I love the open ocean and the adventure of sailing. Thanks, Wayne, and the Kamanakai crew. I cannot wait for more!






2 thoughts on “10 Must-Do’s for a Most Epic Sailing Trip!

  1. Beautifulness, Hayley! I’m so glad you & Clay received such a stellar opportunity. It sounds like it was perfection! ♥


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