Some Days Will Make You Question Everything
Community
Mar 29, 2026
From Working on Tugs and Barges to Buying a Sailboat
Meet Alfred. He had spent his entire life around the water but had never actually sailed. That changed in college when a sailing video popped up on YouTube while he was hanging out at a friend’s house. It was there on his couch that he decided he wanted to cruise. Not long after, he left school, took a job working on tugs and barges, and spent the next five years saving everything he could with one goal in mind: buying a boat and starting a life on the water.
Eventually, the long work trips and trying to cruise during time off started to take a toll. So he made a plan: save money, prepare the boat, and leave for the Bahamas in the fall of 2024.
A Reminder That Nothing in Life Is Certain
Then life reminded him just how uncertain things can be. After a close friend passed away in October of that year, he knew it was time. With that reality weighing on his mind, he quit his job and began sailing south from New York. After his first real offshore passage and spending nearly four days at sea from New York to Norfolk he knew he was capable of much bigger adventures.
Cruising Isn’t Always Smooth
Cruising isn’t always smooth, though. While sailing through the Bahamas, his engine gave out completely. He spent six weeks sailing around the islands before eventually returning to the United States without an engine. Moments like that can be stressful, especially when problems stack up one after another. But there’s something incredibly rewarding about pushing through those challenges.
When you finally fix the thing that’s been giving you hell… when you improve something on the boat that once seemed impossible… the struggle starts to shine through on the other side.
What's Next?
Looking ahead, one big goal stands out: sailing the boat all the way to Panama, where generations of his family once lived along the Canal Zone. Beyond that, he prefers to keep his goals simple. As long as the journey is still fun, the next adventure will always appear.
His Advice?
Alfred's advice to anyone dreaming about this life is simple: don’t expect every day to feel magical. There will be days that make you question everything. When that happens, slow down. Stay somewhere for a while. Get to know the locals, recharge, and let the place remind you why you started.
Eventually, you’ll be ready to go on another adventure!
