By Airwaves Senior Writer Taylor Penwell
US Virgin Islander Teddy Nicolosi is one of the top names in junior sailing of his generation. The St. Thomas resident had an outstanding Optimist career and has since been taking on other classes by storm. Nicolosi is currently a junior at the Antilles School on St. Thomas and was part of their team that won the Baker National Team Race Championship last year. In addition to high school sailing, Nicolosi is actively competiting in the Club 420, 29er and Nacra 15 classes. He took the time out of his busy schedule to answer questions for Sail1Design Airwaves readers.
Please tell the readers and me a bit more about yourself Teddy.
I am a junior at the Antilles High School on the US Virgin Island of St. Thomas. I enjoy watching and playing sports, hanging out with my friends, and of course sailing. I currently sail the Nacra 15, Club 420, and sail on the Antilles High School Sailing Team.
Where are you from Teddy?
I was born in Chicago, Illinois, and lived there until the age of 7 when our family moved to St. Thomas. I have lived here in St. Thomas ever since.
Where did start sailing?
I first started sailing at the St. Thomas Yacht Club.
What age did you start sailing?
I first started sailing when I was 9, and when I was 11 I began sailing competitively.
What drew you to racing?
The curiosity of how it works and the idea of doing a competitive sport on the water drew me to racing.
You had a very successful optimist career, tell us about your top finishes and successes.
My best finishes in the Opti class started at the end of the summer of 2014. This was when I won my first big regatta, the New England Championship. The following regatta was the Opti Midwinters located in New Orleans, Louisiana, and I won that regatta too. Then at the end of 2014, I won the Orange Bowl Regatta in Miami. In the spring of 2015, I finished second overall at the South American Championship. Later in that summer, I finished 2nd overall in the North American Championship. In my last regatta of my optimist career, I took 7th place at the Optimist World Championship in Poland.
What do you attribute your success in the optimist class to?
Many things led to my success in the optimist class. The most significant attribution to my success was practice. During my opti career, I sailed around 4-5 days at first with the coach Santiago Galan and later the coach Augustin Resano. I also participated in many international regattas and gained experience quickly. After two years of intense practice and many regattas, I was able to reach the top of my fleet and win regattas.
How often do you train?
Now, I train about 3-5 days a week.
The Virgin Islands has produced some amazing sailors in junior sailing, what type of things do you think separate sailors from there compared to other places?
The Virgin Islands has produced some amazing sailors because of its junior sailing program and the amazing weather we get. Many of the best sailors from St. Thomas began in the optimist with the junior sailing program at the Yacht Club. Their really good coaches helped the sailors get off to a great start in their sailing careers. Another advantage the Virgin Islands has, is the weather. We can sail year round and rarely miss a day of sailing because it is almost never too light or too windy.
Now that you’ve aged out of the optimist, what boats are you sailing?
At first I sailed high school sailing with Antilles, some Club 420, which are basically the same as high school except with trapezes and spinnakers, and the 29er, which is a fast and high performance boat. Now, I still sail the same boats except that I sail the Nacra 15, an even faster boat, instead of the 29er.
What your top finishes were in all the boats you’ve sailed in?
In the Club 420, I’ve gotten 12th at Orange Bowl in 2015 and 7th in 2017, both with fleets of about 100. I was 10th in both the Hyannis Regatta in 2016 and the Buzzards Bay Regatta in 2016. I have also won a few smaller regattas in the Midwest and in St. Thomas. In the 29er I finished 8th at New England’s in 2016 and 7th at Orange Bowl in 2016. Our high school sailing team won the Baker (team race) National Championship and finished 6 in the Mallory (fleet race) National Championship. In the Nacra 15 I’ve gotten 4th in two regattas this past fall/winter with about 15-20 boats and won a small regatta two weekends ago with 4 boats in Port Charlotte.
How has the transition from a single-handed boat to double handed boats been like?
The transition was not very easy. At first I found it kind of annoying sailing with other people. Even if you sail your best and they make a mistake, then you do worse than what you could have done. It also stinks when you are the one that makes a mistake because then you feel bad for causing your teammate to do worse than what they could have been doing. Another challenge with double-handed boats is finding your teammate. Even if you were to sail with the best sailor in the world, you would still need time to get used to sailing with them and figuring out what jobs are whose on the boat before you could perform your full potential. The other problem with teammates is finding one. For example in my 29er career, I believe I ended up sailing with 10 or more different crews in a time span of a year and a half. This made it extremely difficult to perform at my full potential because I was always still getting used to sailing with my new crew. Although, now I do not mind it as much. For the past 6 months I have been mainly just sailing with my younger sister Mia, instead of switching around crews.
What are some of the characteristics you look for in crew members?
The most important characteristic, in my opinion, for a crew, is their determination and desire to learn more and become better sailors. I like crews that ask questions, even if they think they are dumb questions, because this shows that they are interested in learning how to become a better sailor. I also like crews that are athletic, because after all it is a sport, and being naturally athletic and strong makes a huge difference.
Your high school, Antilles won the National Championship last year. Tell us a bit about that experience.
Winning the High School National Championship was one of the best experiences in my life. I remember we were winning the regatta, but not by much going into the last race, so the race still mattered and there was a lot of pressure. We were all very anxious to win, but scared to loose. Luckily for us, right after the start, the race committee saw lightning, canceled the race and sent us in ending the regatta. I still remember that feeling of joy and accomplishment when our team found out that racing was done and we won. We sailed in celebrating. Still to this today I cannot believe that we won Nationals and when I think of it it reminds me of how far we have come and how great of sailors we are.
You’ve been sailing on the 29er circuit for a while now. How has that experience been and what have been some of your highlights so far?
My 29er career has had its ups and downs. I’ve had a few alright finishes, but never amazing ones. One of my main problems was finding a crew that I could sail with for awhile. In the end I found it frustrating and wanted to start fresh in a new high performance and fast boat, the Nacra 15.
What are your goals moving forward with sailing? Are you planning on doing an Olympic campaign or attending a college sailing program in the United States?
Moving forward I plan on attending Yale University with my older sister Grace Ann and sailing on their amazing college sailing team. Right now Mia and I are trying to qualify for the junior Olympics in the Nacra 15. It’s hard to tell if I’ll make an Olympic campaign, but if the Nacra 15 goes well, I can try to qualify for the Olympics in the Nacra 17 (a bigger, faster, and more advanced version of the Nacra 15).
What drives you to keep getting on the water and competing?
What motivates me to practice and compete is the love I have for the sport. I love the water, traveling, and meeting new people that comes with sailing. I also love the feeling of winning which I assume everyone does, and I am willing to do what it takes to achieve that, which is getting as many hours as possible on the water.
When you’re not sailing, what other things do you enjoy doing?
I enjoy other sports like basketball and football. When I was younger and during my optimist career I played basketball as well as sailing. Now I don’t play anymore, but I still love to play pick up games of basketball and football with my friends. I also like watching TV, boating, and hanging out with my friends.