By Mackenzie & Josh Dajani
Issue #57 January/February 2026
For many, the dream of sailing off into the sunset feels like a distant fantasy—something reserved for retirement or the ultra-wealthy. But for us, the idea took hold in our mid-20s, and we weren’t willing to wait decades to see if it was right.
The Spark
Growing up around boats and sharing a deep love for the ocean, we always knew we wanted to live near the water. But with beachfront real estate priced sky-high and our home base in Alexandria, Virginia (far from any ocean), the traditional path didn’t seem viable. Then, while on a family vacation, we took a catamaran day charter in Saint John, USVI. That experience flipped a switch—people were out there cruising before retirement. If others could do it, why not us? We realized that if we waited until our golden years, we might regret not trying it sooner, when youth and time were still on our side.
Making It Work
As young professionals—or DINKs (double income, no kids)—the challenge wasn’t just dreaming about the lifestyle, but making it sustainable. Being a mental health therapist, I (Mackenzie) saw an opportunity when COVID normalized telehealth. I built a direct sales business that gave us additional remote income. Josh worked in management consulting, a field that already allowed him to work from anywhere. The possibility of earning from the water began to take shape.
Planning and Sacrifices
Without a set plan but with determination, we started saving aggressively. We:
- Drove old cars paid for in cash. Neither of our vehicles even had an aux cord!
- Lived well below our means, never upgrading homes as our salaries grew
- Saved every bonus, and we vacationed using points
- Shopped at Aldi and found creative ways to cut expenses
- Still prioritized saying “yes” to fun experiences
Gaining Skills and Confidence
We knew that to truly make this work, we needed experience. After countless hours watching sailing YouTube channels, we took an ASA 101 course in Annapolis. That only fueled our passion further. And for our fifth wedding anniversary, we took a Sailing Virgins course (ASA103/104) in the BVIs, where we spent a week aboard a monohull, getting a real taste of sailing (minus the boat and engine maintenance).
Returning home, we got serious—crunching numbers and considering our options:
- Quit jobs, Work as deckhands in the Caribbean for experience (but not on our own boat).
- Quit jobs, sell everything, buy a sailboat in cash, and live off savings until it runs out.
- Work remotely, rent out our condo, finance a boat to make telework feasible, and log hours toward a captain’s license eventually.
