Catherine Tobin, 100 Days In Her Own Words

Navigating the Dream: Lessons and Confessions of a Pirate Centurion

by Catherine Tobin

I am a Centurion. I spent the majority of my time racing or cruising in Annapolis and Baltimore, but also raced in the Annapolis to Newport, the Rolex Middle Sea Race, did an ocean delivery and boated in places such as Miami and New Hampshire and also took a few SUP lessons.

So why did I do it? I've always thought that sailing has a certain Je ne sais quoi, and my happiest life moment outside of giving birth to my son, was spending a vacation in the BVI with the UVA sailing team.

Unlike many sailors, I didn't grow up sailing. It wasn't until I was at UVA that I learned to sail. After UVA, I participated in some community sailing while living in Boston, but didn't get into big boat racing until I finished law school and my ex-husband and I joined Fishing Bay Yacht Club in Deltaville and started racing on big boats.

I left my husband in November of 2013 and moved to Alexandria. While our divorce was fairly amicable, divorce is emotionally challenging and was compounded in many ways by me moving by myself to Alexandria, VA to be closer to friends and have greater future career prospects. I started going to therapy and was told I should work on the hobbies I enjoyed. Sailing was one of those hobbies. In the summer of 2014, I fell in love with a sailor who had a boat in Annapolis. While he ended up breaking my heart, I also fell in love with Annapolis. By the end of the summer I was regularly racing on a J-105 and occasionally on an Albacore.

When I was making my New Year's Resolutions at the end of the year, I felt that I was a Jack of all Trades and a Master of none. Sailing was something that I wanted to Master and I thought the challenge of 100 days on the water would really help me improve my sailing skills while providing emotional catharsis.

I decided I wanted to focus my sailing efforts. For racing, I wanted to continue to improve as J-105 bowman and start racing offshore. I also decided to join Chesapeake Boat Club as I wanted to be able to take people cruising as a way to help me make new friends doing something I love and to teach my son how to sail.

I had no idea I would learn so much as a result of this challenge, but I am so happy that I did. Here are some of my lessons:


  • Remain Calm in all situations-A lesson from the Rolex Middle Sea Race

Mayday! Mayday! Mayday! Sailing vessel DU4 launched a distress call called over the VHF. DU4 and the vessel I was on, the Australian 50 footer Bella Sassy were off the coast of Malta participating in the Rolex Middle Sea Race. It was October 23rd and day 6 of the 606 mile counterclockwise race from Malta around Sicily and then back to Malta. While the first few days were slow, we were now experiencing near gale force winds along with large swells. For the next several hours, we heard all of the radio communications between DU4 and the AMF Operations Centre trying to get assistance to the yacht whose crew member sustained a life-threatening head injury and the boat had maneuverability and power failures. Eventually, the largest Offshore Patrol Vessel, P61, made way to the area and conducted a medical evacuation. It was a tense few hours for us as we sailed through tough conditions and finally arrived back in Malta in the wee hours of the morning. In large part, we were able to finish the race in tough conditions because we remained calm in a tough situation.

  • Always have safety equipment & know where it is and how to use it- lessons from the Chesapeake Boat Club J32's

First Aid

It was blowing about 20 knots and myself and another member of the Chesapeake Boat club took out a group of friends on a J32. I was helming the boat and doing fine, but gave the helm to the other member who then gave the helm away again when I needed help lighting the stove. Soon, we accidently gybed and a racer friend got hit in the head with the boom and blood was gushing everywhere. We quickly found the first aid kit and cleaned everything up, motored back and she went and got stitches. I'm very thankful I knew where the first aid kit was and that it was stocked and this is one of the first things I ask for when I am on a new boat.

Swimming Safety

Another night a friend and I anchored by the Thomas Point lighthouse and had dinner. We decided to go for a swim to the lighthouse. Darkness quickly fell and the tide and current became problematic. My friend asked me to leave and go get the boat and he said he would float. I finally made it back to the boat and lit flares and was able to find my friend with the assistance of the coast guard. I won't be swimming at dusk again.

  • Know where you can go and where you can't go

My son Dalton is 5 and has a fascination with knots. He and I took out a H20 by ourselves and when we came in, I realized there were knots in the lines I needed to put the boat away. I focused on untying them, but in the process, we managed to run aground. Thankfully, we were not on the shore and were able to get towed out quickly. However, this experience has made me incredibly conscious of depth and where I am going as well as situations that could distract me.

  • Relationships

Relationships on the water come in all flavors. I believe that everyone should be treated with respect when sailing or sharing a boat. While I always try and assume positive intent in everyone I meet until proven otherwise, especially as a female I try and be careful. Another female friend of mine and I had to make a hasty departure off of a boat we were staying on during the Newport boat show. While I knew other people that had sailed with the male sailor who owned the boat we were staying on, we had a few situations arise that weren't appropriate. The lesson here is to take more precautions as it relates to personal safety and get out when you don't feel safe.

I've also realized that I can't date someone who doesn't share my passion for the water. After a dating hiatus, I recently went on a first date. While this man had many good qualities, he couldn't get over why I would want to be "uncomfortable" and sail when I could be comfortable and powerboat. No thank you.

I've also watched the marriages and relationships of many people around me who sail fall apart because their partner doesn't like to sail or isn't supportive of the sailors desire to spend time on the water. And, while for the second summer in a row, I have been emotionally hurt by a sailor, I know that I'll eventually find the right person for me who also shares my passion for the water.

  • Never Stop Improving

While I've known how to sail for about 10 years, I want to continue to improve my skills and become more competent. I learned so much about sailing this summer, and want to continue my journey.