Travel Junkies

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!

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