Author: Kate Ammatuna, Editor: Chris Szepessy, republished with permission from WindCheck Magazine, October 2026
She was probably hip height at the time, and we must have been in Newport for her to hear about the race. I swear Maddie was born part mermaid/part gypsy in her soul. When she fell in love with sailing at a young age, I knew I wasn’t losing her to the ocean; rather allowing this water loving creature to be where she thrives.
Elle (younger by 2.5 years) eagerly followed Maddie’s lead into sailing, and soon enough I had two daughters who were striving to sail competitively. Fast forward a few years, Maddie causally mentioned to our friend, Ben Johnston, that she really wanted to find a way to get involved in the Newport Bermuda Race. He gave her the phone number of James Phyfe, owner of Digger, a J/44 out of our yacht club who had done the race several times.
She called him up, set up a meeting and brought her sailing resumé to the table. My husband and I sat there while we watched our then 14-year-old daughter tell James about her goals and confidently answer all the questions he asked. He offered her a spot on the Ida Lewis Distance Race that summer to see how she liked being offshore for an overnight race to test the waters. A few months later, I was a nervous wreck, checking Yellow Brick every 5 minutes as Maddie and the rest of the Digger crew raced in some pretty intense conditions. I couldn’t believe I allowed my first born to go race out in the ocean, in the dark, in the wind, on a boat where I only (barely) knew one other adult.
Our sailing friends assured us that this was simply the start of something wonderful for Maddie and while it was normal to worry, I should know she was having the time of her life. I don’t think I slept an ounce that night. When I picked her up the next day, it felt like it had been a year. I will never forget the beam of her smile, and her exclaiming, “Mom, that was amazing! I can’t wait to do it again.”
Although she’s obscured in this photo of James Phyfe’s J/44 Digger at the start of the 2026 Newport Bermuda Race, Maddie Ammatuna was among several youth sailors aboard. Maddie’s younger sister Elle joined the crew for the return journey to Rhode Island. © Allen Clark/PhotoBoat.com
She called him up, set up a meeting and brought her sailing resumé to the table. My husband and I sat there while we watched our then 14-year-old daughter tell James about her goals and confidently answer all the questions he asked. He offered her a spot on the Ida Lewis Distance Race that summer to see how she liked being offshore for an overnight race to test the waters. A few months later, I was a nervous wreck, checking Yellow Brick every 5 minutes as Maddie and the rest of the Digger crew raced in some pretty intense conditions. I couldn’t believe I allowed my first born to go race out in the ocean, in the dark, in the wind, on a boat where I only (barely) knew one other adult.
Our sailing friends assured us that this was simply the start of something wonderful for Maddie and while it was normal to worry, I should know she was having the time of her life. I don’t think I slept an ounce that night. When I picked her up the next day, it felt like it had been a year. I will never forget the beam of her smile, and her exclaiming, “Mom, that was amazing! I can’t wait to do it again.”
That evening, we went to the awards ceremony at the Ida Lewis Yacht Club and I heard nothing but praises regarding Maddie’s work ethic, knowledge, and overall attitude. Ten months later, I was putting her on a plane to Bermuda to complete her first delivery. I wasn’t nervous about her spending a few days on land, celebrating her 16th birthday with some sailing friends, because I knew she could navigate on her own. The moment they left the dock to sail over 600 miles back to Rhode Island, I was again glued to her location. Again, I was questioning my parenting choices and again, my sailing friends told me she was just fine. Five days after they left the Royal Bermuda Yacht Club, we were greeting her back in Warwick and the beaming smile that came from the Ida race was even brighter. This is her love and in world characterized by chaos and uncertainty, sailing provides her with a sense of tranquility.
Maddie has been earning her way on to boats, networking as if she was a CEO of a Fortune 500 company and working to show that she wants more and will do whatever it takes. When James announced he was doing the 2026 Newport Bermuda Race and asked Maddie if she wanted a spot, I don’t know who was more excited – Maddie or us. Witnessing your child reap the rewards of their own hard work is an unparalleled experience as parents. She earned it by putting herself out there, but I can’t help but think of that little blonde-haired girl looking up at me and declaring her mission statement. She should be proud of herself.
Dropping her off in Warwick on Friday, June 19 stirred a variety of emotions, but I’ve learned to put my feelings aside to support what my children want. There was not an ounce of hesitation in her eyes and she instantly got to work, doing the final prep before the boat pushed off for Newport. We then made our way via boat down to Newport and watched the start of the race. As they made their way past Fort Adams and out of the bay, I saw tears rolling down Elle’s face. She was scared for her sister. This time, it was me providing the comfort (albeit, holding back my own tears) and reminding Elle, “This is her dream. We are here to watch it happen.”
Oh, and by the way, Elle was flying down to Bermuda to complete the delivery of Digger back to Warwick. She had completed the 2025 Ida race and I somehow graduated to sleeping and only checking YB maybe twice in the middle of the night…funny how I was comforted by the fact Maddie was on the boat with her! Thanks to YB, I was able to *stalk* the location of Digger as they made their way to Bermuda. I slept, but was constantly checking the app to ensure forward movement. Three days later, we flew down, greeting the crew of Digger at the RBYC on June 23(with Dark n’ Stormies in hand, of course). We had a fantastic week of family time and before I knew it, we were walking back down the dock to send Elle off on her first Atlantic voyage – cue the mom emotions again as I watched my younger daughter hopping on board like it was the most normal thing for a teenage girl to do.
I received a few updates from James as they made their way back over the next few days, eventually waking up to a phone call around 4am from Elle saying, “Umm, hey, are you coming to pick me up?” Apparently, I was sound asleep and missed her text an hour earlier letting me know they made it back to the dock. She figured I was wide awake, but I guess after your kids have put you through this a few times, you eventually start to sleep again. And now Elle is hoping for the 2028 Newport Bermuda Race, and I’m hoping these girls keep pursing their passions no matter how many sleepless nights that means for me.
Although she’s obscured in this photo of James Phyfe’s J/44 Digger at the start of the 2026 Newport Bermuda Race, Maddie Ammatuna was among several youth sailors aboard. Maddie’s younger sister Elle joined the crew for the return journey to Rhode Island. © Allen Clark/PhotoBoat.com
It can be tough when you are not “born” into sailing, but through my children, I have learned that the community of sailing is one of the most welcoming in all the sports we have been involved with. I’ve watched each of them hop on boats full of adults who have been sailing longer than I have been alive and come back to land feeling as if they are part of the family. One of the greatest joys of parenting has been watching my daughters earn these amazing opportunities because of their work ethic, knowledge, and passion to learn how to improve because the reality is, that is what has gotten them this far, with some of the most humble and gracious sailors around. ■
Kate Ammatuna is President of the Greenwich Bay Sailing Association (gbsa.info), an organization with a mission “to introduce young children to the sport of sailing through an education in marine safety and seamanship while conducting our classes in a nurturing and enthusiastic atmosphere that will foster their passion for sailing and the environment.”