How to Escape Your Day Job Option Number 1: Sail Around The World

My favorite television show when I was a kid was Gilligan’s Island. I thought the castaways were the luckiest people in the world to live in such a beautiful place. Ever since then, I had dreamed of sailing off across the horizon and making landfall at a tropical island paradise.

When I finally had a chance to buy a small sailboat as an adult, I jumped at it. But before buying I figured it would probably be smart to learn how to sail first. So, Kerri and I took sailing lessons from an ASA certified sailing school on the Columbia River. We had a lot of fun sailing the school’s boats, and afterwards, we purchased a used San Juan 21 sailboat. It was a great little boat and we had a lot of fun sailing her. Then Kerri became pregnant with Sydney and we decided we should buy a bigger and “safer” boat, commonly referred to as 3-footitus. So, we bought a 26 foot Westerly Centaur. A classic English built twin keeled sailboat that had crossed oceans.

At that time I was reading a lot of books by Hal Roth and other sailors who had sailed around the world. I had also stumbled upon many websites of cruisers that were in the process of sailing around the world and were writing online log entries about their experiences. It all looked like a great adventure and I wished we could be out there doing what they were doing. Kerri and I discussed doing such a cruise, but Kerri has a small problem that would prevent her from ever crossing oceans. She gets seriously seasick! But there was also the option of crossing oceans with a different crew and Kerri could meet me at the next port. It sounded good, but was probably not a very practical solution. The other downside to sailing around the world is that it can take a lot of money to buy an ocean worthy boat and then a lot more money to equip the boat with all of the latest gadgets and systems to make cruising and living aboard a sailboat as safe and comfortable as possible. Many people have sailed around the world on small basic boats, including a Westerly Centaur just like what we owned. But, that would be uncomfortable and cramped. Many people had sailed around the World on shoestring budgets, but that did not sound like a lot of fun. Sailing around the world is a good option for some people, but it was not going to work for us. So, sailing around the world was out!


Dreamer. Photographer. Sailing addict. World traveler. I left my desk job in Portland, Oregon to travel the world...


  1. Desmond says

    We already lost the house! I would have to agree with the list. My wife and I just moved to Florida from Montana, for me it was to get closer to sailboats; my wife sunshine and no snow.

    My life long dream has been to travel the world. When a roommate of mine told me that an ordinary person could afford a sailboat a light bulb went off in my head. “This is it! I can travel the world by sailboat.” It felt as if the universe had opened my mind and filled it with answer to my questions. I figured I would buy a sailboat and it would become my home. I could take my home wherever I dreamed. It was perfect! Since that moment I’ve flown to California taken ASA 101-104. Then I found my wife, kicked out my roommates, got married, sold the house, sold almost every earthly possession and moved to Florida.

    Your list, points out there is so much to be concerned with when thinking on water rather than land. Did I bring enough water, food, spare parts, should I go through the Suez Canal or around Africa? Do we have the skill needed?

    After a while I lost sight of what I and my wife really wanted to do most, and that was to travel around the world…

    I have been pushing around in my mind the idea of an alternative path to go around the world rather than sailing. One day, I was searching for some trivial information on sailboats (like I always do) and I happened upon your article “How to Escape Your Day Job Option Number 1: Sail Around The World” and I believe you have the right answer! We have taken your advice to become “permanent tourist…” We already are doing this in Florida. We pay our monthly rent and its gone but we aren’t there traveling. The same money could be spent in France or Turkey.

    I’m still a sailboat addict! Its in me bones and someday I will sail around the world, just not yet. Right now, I’m taking one for the team since we both want to see the world sooner than later. We still have a few things to work out but reading your blog really helps. Thx!

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