Kailoa Passages

Kailoa is a sailing vessel traveling down the east coast to the Bahamas.

sunrise over the atlantic ocean

Onward to Annapolis, It’s the Middle, June 22nd to June 25th , 2025

“Challenges are romanticized.
We’re conditioned to think they’re heroic. Short-lived epic. Instagramable.
But most real challenges aren’t like that.
Sure, the beginning, scary. The finale is dramatic.
But the hardest part, the part that actually changes you?
It’s the middle.
The mundane, day-after-day slog. The monotony. The lonely grind.
That long, drawn-out struggle where you want to quit, not because it’s impossible, but because it’s unglamorous
and boring.
All challenges – all hard things – reward you”.
Nikki Henderson @nikkihendersonsailing

With Rob’s help, we departed Beaufort on Saturday, June 21, for a 350 NM, two-night sail from Beaufort, NC, to Annapolis, MD. Under conditions of high heat and no wind, we motored almost the entire way. Thank goodness, Scott found a way to replace the blower, part of our engine system. The sea was calm, and numerous dolphins accompanied us along our route. We could also make out schools of fish from the ripples in the water.

The first night of the passage was quiet and uneventful. Boring! Nikki Henderson’s Instagram post on challenges hit home. “It’s the middle. The mundane, day-after-day slog. The monotony. The lonely grind.”

Reflecting on the last year, there is a significant amount of work that goes on behind the scenes to maintain a sailboat. The “To Do” list is endless. Being at sea can be a drudgery of pain, discomfort, frustration, fatigue, and boredom, along with breakdowns, mistakes, and mishaps that are a challenge.

Countless hours at night, mechanical issues, or sailing through a driving rainstorm, it’s a grind. There is always something that presents a daily challenge. Our mooring line was sucked into the bow thruster before we left Marblehead. Our beloved dog died on board Kailoa 2 weeks into the trip. Being stuck, waiting for favorable weather windows. Exposure to extreme weather… heat, cold, wind, and rain. Running aground on an unmarked shoal. Opening the out haul by accident while rounding Cape Hatteras at 2 AM, OOPs. Adding black rubber burn marks to Kailoa’s top sides while pulling off the dock in St Augustine in high wind. The black eye that Kim received when her face intersected the floor. Then there is pulling the dinghy engine start cord 100 times when she acts up. Sleepless nights during 1000s of NM night passages. Missing family and friends.

We rounded Diamond Shoals off Cape Hatteras around 8 PM that night. The winds picked up, and Scott enjoyed a few hours of sailing during the midnight shift with the code zero and one reef in the main, until we couldn’t maintain our course. With the start of Kim’s watch (3 AM to 6 AM), we furled in the sails. Kailoa’s speed slowed in the strong current as it rounded Cape Henry lighthouse the next day. We have a diesel capacity of approximately 70 gallons, but we were using fuel at a rate of 1.3 gallons per hour. With more than half our fuel gone, we won’t make it to Annapolis, especially
with no wind in the forecast. We decided to pull into Hampton, VA, to refuel around 4 PM. This added several hours to a long trip, but it was necessary.

The waters of the Chesapeake Bay were flat, causing biting flies to follow along. To fight boredom, we all swatted between watches and turned it into a game to see who had the best aim. Points were only given if a body was actually found. This camaraderie is the essence of sailing, the shared experiences that bring us together. The completely calm waters let us see the slightest movement, schools of fish, and Cownose rays, which were easy to spot because they tend to stay near the water’s surface. On long trips, you look for anything to keep yourself entertained.

As night fell, ship traffic increased, and we relied on our AIS and radar to preventpotential collisions with vessels and channel markers. Rob’s laser focus was sharp as he took on more than his share of the watch that night, working diligently to ensure everyone’s safety. The Chesapeake Bay, with its peaceful yet challenging waters, proved to be both a test of resilience and a reminder of nature’s beauty.

On the morning of June 24, we arrived in Annapolis just before noon after being at sea for over 54 hours. Celebrating a birthday at sea can feel lonely, but it wasn’t long before Kim received well wishes via text, social media, and calls from Natalie and Shannon. Scott cooked his famous egg sandwich to make the day special. A heat dome had settled over the entire East Coast, causing dangerously high temperatures. Scott booked an Airbnb for a couple of nights to escape the heat and arranged dinner at the Chart House. Kim’s college roommate, Irene, managed to break away to meet us. What
a treat! The comfort of air conditioning and a delicious meal with friends was even more meaningful because of the challenge of the passage. “All challenges – all hard things – reward you”.

A crew change-out took place on the 25th, with Rob’s departure back to Marblehead. THANK YOU, ROB!

All for now, Kailoa Signing Off.

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