Back story

I didn't grow up planning to live on a boat, nor did I ever dream of owning a sailboat. I grew up on a Caribbean Island called Puerto Rico where the water was a part of daily life. My whole family loves power boats, I'm the odd one out.

When I was very young, my family had a 13 foot Dell Quay Dory (looks very similar to a 13 foot Boston Whaler) and we would go out on it every weekend. We would tie up to a reef islands and explore the mangrove or snorkel in the corals.

Then when I was a young teenager, we upgraded to a 23 foot Four Winns. This was a huge upgrade since now we had a cabin and could sleep anchored out instead of returning to shore before sunset. This is when I decided that I wanted a boat when I was older so that I could sleep out as much as possible. 

When I was 13 years old, I learned to windsurf rather quickly. The concepts of how to harness the wind to move me came naturally and I was covering great distances in no time! While I was never formally taught the finer points of sailing at this time, basic concepts just made sense to me. I knew I could hit my fastest speed on a beam reach, running was slow, and you could never go directly into the wind. I would play with the dagger board and explore new reefs that I had never visited with my family before! This opened a whole new world to me and I loved the wonders that could be discovered at the next reef over. Some reefs had higher sea urchin populations, others had more starfish or conch shells. Every reef was a new adventure waiting to be discovered and observed. 

When I got a bit older, my parents got me a kayak and the windsurfing came to an end. I would paddle around the reefs and explore, just as I did with the windsurfer, but the shallower draft allowed me to get further into the reefs without fear of grounding. Once again, I was enthralled with the new places that I could go; albeit at a much slower pace.

Being very pale, my skin would burn in a matter of minutes under the strong tropical sun. I would wear a long sleeve rash guard to protect my arms, along with gloves and a hat; but my legs would always burn up! I decided to cover my legs with a bed sheet which led to my rebirth of sailing. 


In the mornings, I was in charge of taking our dog to land for her to do her business. Instead of going to the land of the reef we were on (top map), I would paddle out to the reefs on the horizon (bottom map).


In the early hours there was no wind and the swell was very minimal. By the time we made it to the reefs and she was finished running around, the sea breeze had picked up and we would return to the boat. 

I found that the sheet I carried for my legs could be tied to my paddle and raised in the shape of a square rigger! I would sail back to the boat from the horizon in the morning and enjoyed every moment of it. I experimented with different ways of tying the sheet to the paddle to sail on various points of sail. Being how the kayak had no keel, I was never able to do more than a beam reach. I pretty much paddled upwind and sailed back to the boat.

In the past, my sister would run the jet ski next to me while I sailed to estimate my speed. My top speed on the windsurfer was 45mph, and only 18mph on the kayak. While it was considerably slower than windsurfing, it was still much faster than paddling back!

As I grew up, I still looked forward to my weekends on the water! We would visit the same few reefs but what we would find there was always different. I had planned to live in Puerto Rico when I was older, somewhere out in the country where I could still go out on the water every weekend; but then the political situation on the island changed and we left.

We moved to Maryland when I was in college and stopped going out on the water. Once I went to dental school in Baltimore, MD, I began making choices about how I wanted to live once I graduated.

I knew I wanted a boat that I could sleep on so I could once again experience the waves rocking me to sleep. Many of my classmates were buying houses and I began to look at where I could live after I graduated. This ended very abruptly when I saw the price tags on these houses! If I bought one of these homes, I wouldn't even be able to afford a dinghy! 

I was experiencing a dilemma. I wanted to have a boat, but couldn't figure out how to afford one while paying for a house. The solution was simple: No house! At first I thought this was ludicrous. I didn't think that people lived on boats! I looked around the internet and came to find that living aboard was actually a thing! This opened up a whole world of opportunity.

I gave it some thought and decided that I didn't want a power boat because I couldn't relax while thinking about the fuel costs to operate a motor yacht. The choice was simple, I would live in a sailboat!

Then it struck me that I had no idea how to sail a sailboat! When you steer a windsurfer, you tip the mast fore and aft. To steer the kayak, I would put my foot in the water to create drag on the side I wanted to turn towards. Sailboats looked awfully complicated with all the ropes running everywhere! This is when I began my studies into the art of sailing.

Any free time I had between studying for dental school was spent reading about sailing and combing yachtworld for a potential cruising home. I read forums and stories, watched videos on YouTube and absorbed as much information as I could get my hands on. This went on for 4 years while never actually touching the water. 

Once I graduated, I took an "introductory" weekend class on sailing to finally put all the theory I had collected to use. Luckily it all came together for me and I was completely hooked! That weekend I sailed a 23 foot Sonar around the Baltimore Inner Harbor for 2 days. My third time sailing was when I brought my 45 foot Morgan back to Baltimore (luckily that also worked out well).

I bought Wisdom with the plans to take her across the oceans, she just needed some work first! She had a noisy diesel engine that I hated and was in need of a major refit. The sum of these situations is what has led me to become the sailor I am now. I'm always looking for a better way to do things and wondering why things are done the way they are. 

Since I did not grow up sailing, everything on a sailboat is new to me and I question the purpose and function of it all. This leads me to develop a deeper understanding for how and why things are done on a sailboat. Curiosity and the desire to learn have driven me to become the person I am today and will continue to shape me into who I will be in the future.