Boundless Kauai

Sometimes the especially amazing experiences are the ones that I struggle to find the words to describe. My last week in Hawaii was one of these experiences. In the last seven days leading up to my one-way return flight to the mainland, I sailed to and from Kauai with the best friends imaginable. For a week we lived at sea adrift in the ocean. We sailed to the island of Kauai alongside dolphins, beneath shooting stars, and atop bio-luminescence.  For seven days and seven nights, home was where we anchored.

Boundless Kauai

I very quickly fell in love with sailing once I moved to Hawaii. Being on a sailboat in the middle of the ocean is freeing. It allows for a special camaraderie with the people around you and necessitates contentment with simple living. During our week at sea, our largest concerns were maintaining Boundlessa 37 foot Bavaria yacht – preparing delicious food, basking in the sun, catching waves, playing games, listening to music, and appreciating the great company. Sailing is the simple life.

Boundless Kauai

Nonetheless, sailing is not for the faint of heart. The channel crossing to and from Kauai is approximately 24 hours each way. Although my stomach is strong (and Dramamine and ginger is my best friend), I am not immune to seasickness. Luckily, we experienced amazing weather – especially on the return trip which is often known for its punishing wind and swell.


For five nights, we anchored in Hanalei bay – enjoying countless sunsets and sunrises with light reflecting on Kauai’s stunning mountains. Mid-way through our trip, we departed Hanalei Bay first thing in the morning to sail up the NaPali Coast – the oldest, and therefore the most intricate shoreline of Hawaii’s main islands.

Boundless Kauai
Sailing alongside the world-famous NaPali coast

Boundless Kauai

I love sailing for the places a boat can take you. We stepped foot on beaches that few others have had the joy to visit – the beaches of Honopū Valley. To reach them, we jumped off Boundless a couple hundred yards from shore and swam to a beach with all the ocean’s current and the crashing waves.

The current was a welcome force in swimming towards land, however the swim several hundred yards back to the moving target of a sailboat from shore was harrowing. We swam beneath the most powerful shorebreak I’d yet experienced against the strongest current, finally flopping aboard the boat to regain our breath and for our muscles to stop firing. (Thanks for the encouragement, friends!)

Boundless Kauai
Honopū Valley Natural Arch
The long stretch of beach on the left is known as Kalalau, accessible to many who have hiked in by foot. We jumped off the sailboat and swam to the beaches pictured to the right, separated by a beautiful overhanging arch in the ocean cliffs.

For the remainder of our trip, we enjoyed Boundless jam-sessions complete with a banjo, guitar, ukulele, egg shaker, and beautiful voices. We did a town-run to resupply and purchase food for the journey home, enjoyed sunset surfing and a bonfire on the beach, and pulled off a most-epic outing to the St. Regis where we put on our sailboat best, enjoyed some fancy cocktails and faked it til we maked it all the way to the pool and hottub.

On the morning that we pulled up our anchor and set out for the return sail home, we were once again escorted by Hanalei Bay’s dolphins who wished us farewell.

Two days ago, I finished reading a most wonderful book called You are a Badass and it discussed the marvelous experiences that await you and your life if you will them. Had someone told me three years ago when I moved to Hawaii that I would meet the kindest, most fun-loving bunch of dreamers and sail on our friend Kevin’s sailboat to and from Kauai for six nights and seven days, I would have been floored. This trip was an undeniable and beautiful reminder of the bliss that is to be experienced and is deserved by each one of us. Some food for thought compiled by the wonderful Jen Sincero:

“The big question is whether you are going to be able to say a hearty yes to your adventure.” – Joseph Campbell

“When you are grateful, fear disappears and abundance appears.” – Anthony Robbins

“I worked for a menial’s hire/Only to learn, dismayed/That any wage I asked of Life/Life would have willingly paid.” – Anonymous

Boundless Kauai

Wishing the Boundless crew well as they are currently off sailing in New Caledonia! ❤ Until the next adventure, friends!

Hayley Sarah Blog

Boundless Kauai




One thought on “Boundless Kauai

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s