The Maiden Voyage Pt. 1 | Planning Stage
- Nick McReynolds
- Jun 13
- 3 min read
Updated: Jun 15
Since I was a kid, I’ve dreamed of sailing from one country to another—no captain, just me and the open sea.
Back in high school, with absolutely zero sailing experience, I found a guy on Facebook planning a voyage from Galveston to London. He said I could join him and his wife. I was all in. But just before the trip, his wife got sick and the plan fell apart. Still, the idea lodged itself in my brain and never let go.
Years passed. Then, seemingly out of nowhere, the idea resurfaced—and this time, it became an obsession. I couldn’t stop thinking about it.
My dad and I have a long history of big adventures. We’ve gone spelunking in Costa Rica (with my mom and brother, too), taken four-wheelers through the Grand Canyon, and recently partied at Oktoberfest in Munich. So, when this sailing idea reignited, I knew exactly who to call.
I shot him a text:“I got our next badass trip for next summer.”
He replied with a talking head emoji and a simple:“I’m listening.”
Then I laid it out:“Double-handed sail from Florida to the Bahamas.”I explained that “double-handed” meant it’d just be the two of us onboard.
He responded cautiously:“We don’t know how to sail!”
To which I replied:“Why would we? We haven’t done it yet.”
His final message:“True… but… we don’t know how to sail.”
That exchange happened on April 18, 2022.
Learning to Sail
It took a while, and our plans shifted more than once, but by early 2024, we were both signed up, separately, for sailing courses. My dad knocked out ASA 101 and 103 over a long weekend in Indiana. I started with ASA 101 in Texas and later completed 103 and 104.
My course began before his. The material wasn’t difficult to understand, but there was a lot of it, and the instructors were intense—hardcore racing guys who had no patience for beginners. We spent half the day in the classroom and half on the lake. Two people quit after the first day. It wasn’t exactly “fun,” but I knew I wanted this badly enough to push through.
My dad’s class, by contrast, was smooth sailing. He loved his time on the water in Indiana.
The courses gave us a solid foundation, just enough confidence to believe we could actually pull this off. At that point, we tried to rent a boat in Texas to test our new skills together. Problem was, no one wanted to hand over a sailboat to a couple of rookies with fresh certifications. We finally found someone willing to rent us a 15-foot dinghy basically a bathtub compared to the 35- to 40-foot cruiser we hoped to take on the big trip. Worse, there was almost no wind that day. We barely moved. Not much of a test run.
Still, we didn’t let that stop us.
The Plan Comes Together
We began calling charter companies, trying to find someone willing to rent us a real boat and further attempt a international crossing. Crossing international borders without a captain turned out to be a major obstacle. Eventually, we revised our plan: Instead of Florida to the Bahamas, we’d sail the British Virgin Islands. It wasn’t technically a country-to-country trip but it was still adventurous, and possible without owning our own boat.
Although it still wasn't easy to find someone to let a duo with a limited skillset takeout their boat. They always encouraged us to find a captain to join the excursion but that was not the plan.
We finally found a company that agreed to rent us a boat, on one condition: we’d need to spend the first day with a captain. If he approved of our skills, the boat was ours.
The boat was beautiful a 34’ Jeanneau, monohull, three berths, a wide open cabin, a cramped nav station, a dining table you had to climb over when opened, and a pump gravity toilet. But we loved it. And it became our gateway to exploring the 50+ islands that make up the sailing capital of the world.
Countdown to Departure
The boat was just the beginning. We still had to get fishing licenses, register the vessel, stock provisions, plan our water intake, and map a float plan accounting for tides, wind, currents, and potential anchor spots—not to mention research all the incredible things to do in the area.
After a year of training, planning, researching, and obsessing over every detail of sailing, it was finally time to board my flight to the Virgin Islands.
A childhood dream was about to become real.
