Membership - American Sail Training Association

It's What You Make of It
by Heather Flanagan

"The greatest part about living and working on a tall ship is what you learn about yourself. You learn to deal with people and personalities you never dreamed of having to encounter on a daily basis. You learn your strengths and weaknesses. You learn what your breaking point is."

A new friend of mine said to me on the last day of the Tall Ships® Nova Scotia event, “I never realized something so tiring, dirty, and difficult would be so addicting.” I have found that many people who try out tall ship sailing share the same sentiment, myself included.

Tall ship sailing isn’t fun and games; it is what you make of it. I am not going to lie and say that it is easy, because it isn’t. The days are long, the nights are short, and the daily projects can be frustrating. Those that decide to be tall ship sailors don’t go into it because the pay is that great either. Tall ship sailing is difficult because there is no experience required. Everything a trainee does is on the job training. Sail theory is learned and almost immediately put into practice. You pick up most of the theory as you go along. On Picton Castle, Captain Moreland would often ask “So, are you confused yet?” We’d obviously nod yes and he’d reply “Good. Sailing a traditionally rigged vessel isn’t easy. If it were, everybody would be doing it.”

Tall ship sailing is tough. Your calloused and splinter ridden hands will quickly attest to that. Those who stick with it really have their hearts in it. There were dozens of times when I wondered what I was doing on a ship. I did not really need to be awake at 2 am.  I could be at home in my warm, cozy, and still bed. I didn’t have to go 90 feet in the air to teach a new trainee how to stow a royal sail.  I could be at home folding sheets. I didn’t have to hand wash 26 plate settings.  At home we have a dishwasher.

Then I saw several shooting stars, the Milky Way, and the constellation, Scorpio. The dolphins started swimming alongside the ship and whales were seen in the distance. In port, the crew and trainees were treated like celebrities. I saw the most beautiful sunrises and sunsets. I met dozen of crew members from other tall ships from around the globe, toured their ships, and went to their receptions. I worked every second to help the ship get to her next destination. It is an amazing feeling to give your all and then give a little more.  It is the feeling of love, dedication, and reward.

Sailing on a tall ship has been one of the most exciting adventures of my life thus far. I started last summer onboard the Continental Sloop Providence as an intern. I chose the internship, even though I knew nothing about sailing, because I didn’t want to spend my summer working in a coffee shop. That summer was one of the most stressful, yet most rewarding, summers in my 17 years of life.

Aside from the few knots I vaguely remembered from Girl Scouts, I knew nothing pertaining to sailing. I felt useless. I was sea sick at least once a week and to this day I feel bad for those who were witness. I was petrified to go on the head rig and even more fearful to go aloft. I was woken up at peculiar hours to work. My showers were limited and my clothes remained dirty. I lived with ten strangers, I worked with ten strangers, and I ate with ten strangers. We did everything together. I remember saying to one of those strangers, “I can’t wait to go home, I am never doing this again!”.

He and I are really great friends now. Those peculiar hours in the night that I was woken up became apart of my normal sleeping habits. I would be the first to volunteer to go on the head rig and I started to warm up to being aloft. I laugh at the statement “I am never doing this again.” I have to thank all of the Providence crew, they were great. Each one took his or her time and mentored me. I learned knots, navigation, setting courses, and cooking on a ship. I even learned about the generator and engine.

I helped teach students from the Bronx about sailing, some of them had never even been to a beach. Everyday they were excited. They were the greatest group of teenagers I had ever had the pleasure to work with. I actually knew enough by the middle of my internship to be a mentor to them.  I no longer felt like an outcast among the more experienced and professional crew. And then, my internship was over.


When I moved into my small dorm room at college,  I met my two roommates and listened to their gripes about the small room that was to be shared between three people. I thought it was great. I had a bed, a dresser, and a desk…all to myself. On the Providence, I only had a bunk. I mourned the loss of my ship life and my ship board family. I had become accustomed to my early morning wake ups and starts to the working day, although I never missed cleaning the heads. I missed setting sails and teaching our cadets about tall ships. I am incredibly thankful for my friends in the sailing world because I could chat with them about knots, rigging knives, and the best foul weather gear. My roommates were a little less than thrilled to discuss the numerous wonderful benefits of pine tar. My life consisted of checking the billet bank on the Tall Ships America website weekly and then daily. That was when I found the TALL SHIPS CHALLENGE® internship, the most fun job anyone could get.

After getting the internship,  I discovered that I would be sailing onboard the Picton Castle to the four ports in the TALL SHIPS CHALLENGE® race series. Picton Castle was first on the list of ships I wanted to sail on so this experience was the greatest surprise of all. I did a little to prepare for the ship by reading up on her and making frequent visits to her website, the best you can do to prepare is pack smartly. No book can really prepare a person for what he or she will experience. The tall ship experience is different for everyone.

Some people try sailing to find something and some people sign on with no expectations. I only had three desires, learn new things, meet new people, and go to amazing places. I know that those aren’t too exciting, but I knew that I wouldn’t be disappointed.

I got exactly what I wanted. I learned to sail a 300 ton, three-masted barque. I traveled to places I had never been and I met the greatest people.

This summer, my family grew by two dozen. The people I sailed with started out as strangers, then co-workers, then friends, and essentially they all became family. We were a very diverse group of people when we stepped off of the ship and into the real world wearing our best, yet still tar and paint stained, clothing. Quite often we had to remind each other that we are in the real world and had to watch out for cars. We’d crowd restaurants and loudly exchange stories about each other. We’d listen to stories of injuries we sustained, disastrous yet hilarious mistakes we made, and how much we though we were going to dislike one another. In time, we learned nearly everyone’s life stories.

Just like any family, we’d get each other angry. We’d frustrate each other and make fun of each other. However, by the time the sun was setting, moods were improved and disputes were settled. We were each other’s therapists. A ship is no place for bottled anger or hidden emotions because those feelings are toxic to ship life. We’d express our feelings, sometimes tactfully and sometimes not so well, but grudges were never held.

Whenever I was asked by someone on the ship why I enjoy sailing, I would point to the after dinner scene. It was nice seeing some people relaxing on deck reading books and exchanging card games. We’d laugh about the day’s events and star gaze. Sometimes we’d sleep under the stars, I always did unless there was foul weather in the midst. We’d have dance parties on deck. I’d sit and wonder what my “normal” shore life would be like if I had never sailed and I could not imagine doing anything else.

The greatest part about living and working on a tall ship is what you learn about yourself. You learn to deal with people and personalities you never dreamed of having to encounter on a daily basis. You learn your strengths and weaknesses. You learn what your breaking point is. I learned that I had several, but after two seasons on a tall ship, I have found I can deal with more difficulties than I had ever imagined I could. I learned a little bit about what I want to do with my life. I want my history studies to focus on maritime history and I also want to teach in the inner city, specifically in the Bronx. I saw how happy those cadets were to be on the ship. I know I can’t bring all of my students to ships but I can bring ship life, stories, and photos to them and hope that the same curiosity that sparked in me will spark a call for adventure for them.

Tall Ships America • 221 3rd St., Bldg. 2, Ste. 101• Newport, RI 02840 USA • (401) 846-1775 • asta@tallshipsamerica.org