About Me

My name is Derek Hillen and my first experiences sailing were as a boy with my Dad in southern California on his 24 foot wooden folkboat, “Happy Daze.” As an airline pilot he had irregular days off and many times would yank me out of school to go sailing just off the coast for a morning or afternoon.

Skipping school to go sailing made a big favorable impression on my mind and I really looked forward to these outings. However, just as I was getting old enough to understand a little about boats, around 8 years old, my Dad sold Happy Daze and moved on to another hobby. But the seed of the experience lay dormant within me for years. I knew I loved the ocean, I loved boats but that is about all I knew.

In college I was given a box of dusty old sailing books from a friend of my Dad’s, a fellow by the name of Chuck Chester, now departed. I think he was cleaning out his garage and had always dreamed the dream of sailing distant seas to mysterious isles. Sadly, he never made it. These books by the early immortals of sailing, like the Hiscocks, the Pardeys, Tristan Jones and the great Bernard Moitissier, were the warm rain that caused that dry dormant seed in my little brain to sprout and grow.

I was totally intrigued that people would actually, could actually, step onto a yacht and sail from California, for example, all the way to Australia. You can do that? The thought turned the ocean into a big highway and I only needed a small boat like my new heroes had, not an aircraft carrier to do it. Well, I wanted to do that but first I had to finish college, get a job and save some money like everyone else.

After graduating from McGill University in Montreal, I moved to Asia full time. I traveled around the region extensively and spent six years in Taipei, Taiwan learning Mandarin Chinese. After that, I moved to Sapporo, Japan to study Japanese martial arts and the language as well. I put up with the snow and the beatings for three years and decided, although I didn’t have enough money to buy my boat, I wanted to learn about boats. So a good friend and I, Rick Cline, bought motorcycles in California and rode them up to Alaska. We actually left the day the LA riots began.

On a boat just like this

I went to Kodiak Island, home of the world’s largest bears, to work on a fishing boat for the summer. Rick went to find fame and fortune in Homer, AK. For me, Kodiak was a great experience and I crewed on Jim Pearson’s boat, Dawn Mist, salmon seining in Uganik Bay.

It turns out, however, one of my latent and hitherto unknown abilities was that of scaring all the fish away. We didn’t catch much and I left Alaska at the end of the season broke – but I still had my bike.

My buddy, Rick, by the way is still in Alaska, married with two adorable children and living in Homer, 18 years on! I didn’t want a winter in Alaska so I rode my motorcycle down to Costa Rica, sold it to a rich farmer and flew out to Taiwan to get a job.

While looking for a job in Taipei as an English teacher (again) I turned up at a local brokerage firm for an interview. Due to a case of mistaken identity, they hired me to be a stock broker and trained me for two and a half years.

I was then lured away by UBS and sent to New York. Yep, weird but all true. What makes it even stranger is that I never studied finance in school and failed pretty much all the math courses that came my way.

New York, wow! Bright lights, big city. That was cool. It was also right on the water and now was my chance to learn to sail. Yep, I still didn’t know how to do that but I finally had a real job and water. I took some courses from Colgate and ASA and read every book I could get my hands on. Then I started looking for a boat. I didn’t know how to sail but I bought the boat anyway: a 1981 model Cape Dory 33 in 1996 for $45,000, named “Galileo.” This turned out to be a very good choice.

Over the next two years I spent a lot of money and time fixing her up. She was set up to be a day sailor and I had to replace just about everything on board and install new systems, such as radar, a Monitor wind vane, a roller furler, propane, a stove, hot water, etc. That was a learning experience. When I wasn’t working on her or paying people to work on her I sailed on Long Island Sound every chance I could get. I even took random days off work just to go sailing. Nothing matched the feeling of being out on the water during the week having the whole Sound to myself. Nothing matches the feeling of just being out on the water, period.

Galileo sailing down the Florida Keys

On holidays, I would singlehand her up through the Sound to Block Island, Martha’s Vineyard or Nantucket. This gave me valuable experience. Finally, the big day came and I quit my real job in May, 1998. I pulled my boss into a meeting room and the conversation went like this:

Me:       “I need to talk to you about something.”

Boss:   “Damn. I had a feeling. You’re leaving, aren’t you?”

Me:        Nodding my head.

Boss (shouting):    “Tell me it isn’t Goldman Sachs! You’re not going to Goldman, are you!?”

Me:       “No. I am going to sail around the world.”

Colleagues were blown away when I came out of that room and told them. I got two different reactions, which I found curious. The first was “What! Wow! Right on! Good on ya.” And the second was, “Really? I could never do that. That’s not safe. It’s crazy.” It was surprising to see which reaction people responded with. Those whom I thought would be all for the idea often could only come up with excuses of why they wouldn’t do it and others I had thought wouldn’t get the enterprise were actually the most for it. People, you never can tell, I decided.

Selling my Ikea furniture, quitting my lousy apartment and moving on board Galileo was one of the happiest days of my life. I was now a full time liveaboard! Now I could devote myself all day every day to getting Galileo ready for our big trip. The plan was to sail to Sydney, Australia for the 2000 New Year celebrations (remember, this was 1998). I was going solo because, basically, all my friends worked! It was either that or sit on the dock for the rest of my life. Yolo. I was going, no matter what.

My Dad flew out to join me for the first part. We left Connecticut, where I kept the boat, early October and sailed south. He stayed with me until we reached Annapolis but had to go home because a bear was terrorizing my Mother who was staying at home alone on our farm.

The bear would come up to house at night, stand up and peer in the windows at her fogging the glass while she was alone reading in the living room. Honestly, I don’t know what the big deal was.

After my Dad flew home, I was a singlehander again and took Galileo through the Chesapeake and down the Intracoastal Waterway – the long ditch, to Beaufort, NC. From there I did a four day offshore passage, my first, to Florida. More on the trip, including the NW Caribbean part onward to Guatemala, I will write up in the Galileo logs.

Nordkapp, Norway. Arctic Ocean.

I had to leave Galileo for hurricane season 1999 and didn’t want to just hang around for six months in the rainforest on a river swatting mosquitoes. So, I flew back to California, bought an old Goldwing motorcycle and rode it across to the US to New York. I put her on a KLM flight to Amsterdam and spent six months living the dream on the bike.

I rode solo again because, see, all my friends still had boring jobs. I went to 18 different countries and rode 18,000 miles in Europe. I rode the farthest north you can go, Nordkapp, Norway and stuck my hand into the Arctic Ocean. I rode the farthest south you can go, Gibraltar, and stuck my hand into the Mediterranean. And I rode everywhere in between. It was awesome.

By and by, it was time to get back to Galileo and go cruising again. Man, life was great. As I passed through New York I met up with friends who were still working. Through their evil influence I agreed to be interviewed by a few banks to see what the landscape was like.

This was right before the tech bubble blew up and they were desperate for people who knew anything about Asia, or tech. Well, that was me. Long story short, I ended up going BACK to UBS WITH A PROMOTION AND A RAISE! Neither of which I would have had if I had stayed put like a good boy and kept my nose to the grindstone. Galileo would have to wait.

UBS sent me back to Taiwan and the first week there I met my future wife, Ariel. She was from the Bronx and was in the middle of completing her three year MBA program which required a year abroad to learn a language. Lucky for me she chose Mandarin and Taiwan.

Lucky for me I already knew my way around Mandarin and Taiwan and was able to impress her a little, I guess. Anyway, we spent three years in Taipei which included her moving to Singapore for six months for her internship with Citibank and then back to the US to complete her degree (which I am still paying off, by the way!). We married in 2001. I quit UBS again, for the final time, I swear, March 2002 because we had another boat and another adventure waiting.

Gettin’ Hitched

The rest of our story continues on the logs here.