About

More Life, Less Work – My Story

I’m writing this article sitting on my sailboat. We’re anchored off the island of Bequia (pronounced Beckway). Bequia is part of the country of St. Vincent and the Grenadines. We started splitting time between working and sailing the Caribbean in 2009 (it is now April 2023). We’ve been living this lifestyle now for 14 years.

What is the lifestyle?

We sail our boat for six months during the Caribbean “dry” season (winter – December to June). We return home during hurricane season. When we’re home, I work a contract job through an employment agency for roughly six months. We’re able make and save the money we need to spend another winter in the Caribbean. It’s an awesome way to live!

How did I get started?

When we went started our sailing journey in November 2009, we originally thought we’d go sailing year around until we depleted our cruising money. Then we’d sell the boat, and go back to working again.

Things didn’t work out quite like we’d originally planned. Other sailors suggested a better plan might be spending summers at home. The insurance companies dictate your where you can sail during the summer months. That is due to the hurricane risk. It also rains a lot! The new plan was to go home during the hurricane season and return the following sailing season.

The company I’d quit in November 2009 had tons of work, and they’d been asking me to help them. We put together the idea to return home with the possibility of working. We went home so that I could take another contract job.

I worked for six months during the 2010 hurricane season, and we returned to the boat again in November 2010. This started my six-month life schedule followed by a six-month work schedule. I’ve been able to work when needed and sail when I wanted by working contract jobs.

Do I have any regrets?

Only one: I wish I’d started this life/work approach sooner!!

Hi, I’m Gary……..please join me on this journey!
Hi, I’m Gary……..please join me on this journey!