It’s a long way from Fishers Island Sound to the Diamond Head Buoy off Honolulu, Hawaii. Four young women from Connecticut are getting ready to make the leap to compete in the 51st edition of the iconic Transpacific Yacht Race.

By Lindsay Gimple


Megan and Lindsay Gimple, pictured aboard Dreamcatcher in the Marblehead to Halifax Race, are two of four young women from southeastern Connecticut joining TRADER Sailing for the 51st Transpac. © Sam Webster

It felt impossibly far, the first time I pushed off from Stonington Harbor bound for Block Island. Sixteen nautical miles is a grand ocean-crossing voyage to a gaggle of teenagers on a J/24, provisioned for the weekend with a staggering amount of tortilla chips and a questionably sufficient volume of sunscreen. Leaving the Watch Hill Passage was leaving the known, beyond the reaches of even the most adventurous Fishers Island Sound 420 sailor.

A similar feeling arises now, in my mid-twenties, pushing off towards another unknown adventure: the 51st Transpacific Yacht Race (, better known as the Transpac. The Transpac is a 2,225 nautical mile yacht race starting near Point Fermin in California and finishing at the Diamond Head Buoy off Honolulu. While it is one of the oldest offshore races in the United States, I did not know about the Transpac until I saw the movie Morning Light, which documented the training and race of a TP52 full of young sailing talent. I was twelve when I saw the film, still sailing around in Optis. I could not comprehend what it meant to race across an ocean beyond the fact that it was, without a doubt, the coolest sailing story I had seen.

Until recently, competing in the Transpac sounded unrealistic. I sailed primarily as a junior and collegiate dinghy crew before settling into a full-time job as a mechanical engineer. When the local youth sailing team, the MudRatz, announced they were putting together a campaign for the 2018 Newport Bermuda Race, I almost did not apply. The biggest boat I had sailed was that J/24, which felt insignificant in comparison to the ocean-proven Stephens & Sparkman Swan 48 Dreamcatcher. A little bubble of courage simmered in my mind and I submitted my application on the last day it was open.

That decision provided a mountain of opportunity, coupled with a mountain of boatwork. After a lengthy maintenance and training period, I raced on Dreamcatcher as a watch captain and safety officer for our class win in the Bermuda Race. I stepped into the Program Lead role for the 2019 Dreamcatcher Summer Campaign, managing the schedule and pushing through a boat refit to make it to the start line of the Marblehead to Halifax Ocean Race. With tireless effort from my co-skipper and our navigator, and unmatched persistence from the crew, our young team again made the podium in our class. Knowing what a dash of boldness could bring forth, I followed up that campaign by sending an application to The Magenta Project, an international sailing organization dedicated to advancing opportunities for women in performance sailing. I was accepted into their mentoring program and worked to expand what I thought possible in my offshore sailing.

Ready to increase my performance skill and gain more miles on the open ocean, I was in the stages of preparing a newly acquired MudRatz boat for the 2020 Newport Bermuda when the COVID-19 pandemic shut down the racing season. With the cancellation of the Bermuda Race, what would be the next chance to go offshore? If I wanted to continue expanding my experience, it made sense to pursue the Transpac the following summer. Throughout the fall I researched the race and the previous entries. Surely there would be a team looking for a young offshore sailor to join their next race. The hypothesis proved correct; TRADER Sailing was that team.

TRADER Sailing, run by retired U.S. Marine Doug Pasnik, is a team driven by camaraderie and adventure. Doug found the Andrews 70 TRADER in Southeast Asia and sailed her across the Pacific to Hawaii, where he has built a sailing outreach program for military veterans and their families. Given the beautiful sailing conditions in Oahu, they are on the water over 50 times a year. In 2019, Doug’s core crew decided they needed a new challenge, so they took on the Transpac for the first time. In preparing for the 2021 race, Doug was looking to extend opportunities to the military veteran community and younger adventurous offshore sailors to match his vision of enhancing maritime skills and developing leadership.

Doug posted an ad on the race’s crew-wanted board: “Bring me your crew – to train in Hawaii, transit the boat, and race the return.” In a burst of optimistic confidence, I sent him an email, stating that I was the skipper of a youth offshore team based in Mystic, CT, and we were looking for a boat to sail with for the race. I hit send, hoping I could convince some of my previous crew to join me if Doug responded to my inquiry. I started mentioning the Transpac to a few of the Offshore MudRatz, gauging if anyone was secretly as inspired to jump on this opportunity as I was.


Megan Gimple enjoys a sunrise in the Marblehead to Halifax Race.
© Sam Webster

From the minute I mentioned it, my sister Megan Gimple (21) was all-in. A junior at the University of Rhode Island, Megan is an original MudRat. She has rigged up with the ‘Ratz since the team was, as she puts it, “just a couple local kids who wanted to stay on the water into the fall.” Through Optis, 420s, sportboats, and offshore, Megan uses her humor and her willingness to try anything once to capitalize on the opportunities that come her way. She is the light-hearted off-watch mate passing jokes up with the morning coffee, but she is also the determined helm hunting for the best performance. She loves living in these moments and is willing to work for them by taking on the many odd jobs that propel a team towards the race. It may mean scrubbing the bilges with nothing but a toothbrush, going door-to-door seeking sponsors or proofreading press releases, but she’s on it. Megan notes, “You work hard for months and then when you do finally get to the start line you get the reward of the bliss that comes with life offshore. Being offshore is an intoxicating experience. It’s an experience unlike most things; all you have to focus on is sailing the boat and being alive.”


Annie Longo trims, somewhere between Newport and Bermuda. © Sarah Wilkinson/SWCreative

Annie Longo (23), skipper/bow-woman of the well-loved Mystic River Mudheads J/24 DZB, immediately responded with, “What can I do to help?” She is enthusiastic and always ready to contribute. After completing the Bermuda Race with Dreamcatcher, Annie took on a role as ocean advocate, sharing the story of our race and sustainable offshore practices with the wider sailing community in Southeastern Connecticut. As a UConn graduate with degrees in Political Science and Environmental Studies, Annie’s reason for wanting to go further offshore is beyond simply sailing. “Blue water sailing helps me connect to the earth, to nature, to the ocean, which is a very important part of my wellbeing,” she explains. She will share that starting offshore sailing was far from comfortable. On her first overnight sail, Annie recalls, “I was 13, I was the only girl, the only person from my yacht club, I was the youngest, and I got seasick! But I pushed through and proved to myself I could do it. Because I did, I experienced the best night sky I had ever seen with loads of shooting stars.” Annie’s persistence is a key trait, currently aiding her with both The Magenta Project and the 11th Hour Next-Gen Program as she works with her mentor Damian Foxall to bridge sustainable solutions with offshore racing.


Sarah Wilkinson steers Dreamcatcher toward Bermuda. © Sarah Wilkinson/SWCreative

Sarah Wilkinson (23), the perpetual MudHead, has a mission in life: never stop sailing. She is adamant on this, 100%. The Transpac has always been one of her dreams, so when I mentioned I may have found a ride, she immediately scheduled it into her plans. Sarah sees the excellence in the sport, not only through the many races she has sailed, but also through the lens of her camera. As a sailing photographer, she is always looking to capture the best views, but as a sailor, Sarah seeks the best opportunities. Between Bermuda Races and Block Island Race Weeks, she is currently a mentee with The Magenta Project, paired up with professional ocean racer Annie Lush. This is an apt pairing, considering that Sarah dreams of competing in The Ocean Race. For Sarah, the Transpac is another chance to step up against the best and grow her skills on the water.

With these three women locked in, I was ready when Doug responded to discuss the possibilities with TRADER Sailing. On our call, I began detailing the crew’s experiences with offshore racing, sustainability, and working hard for a goal when Doug stopped me to ask a question.

“To be clear, you four are all women?”


Lindsay Gimple trims in the Newport Bermuda Race. © Sarah Wilkinson/SWCreative

When I confirmed this was the case, Doug’s face lit up, and I knew we had found a partnership that could take us all the way to the finish line. Thinking about what he recognized on that call, Doug says, “When Lindsay approached me, I saw an incredible opportunity unfolding to meld everything I have been trying to accomplish with TRADER. I know the women will bring strong racing skills, and a thirst for adventure! I believe combining their experience with the life-experiences of our military veteran crew will make for a winning combination.”

From that point, we joined TRADER Sailing to put forward a fully realized ocean racing campaign. We have built out our social media, marketing, and sustainability plans to complement Doug’s existing maintenance and training schedules. Our on-board reporter, a U.S. Navy veteran and professional filmmaker, Justin Edelman, has documented the journey from the start. The team works virtually at this point, but the promise of spring training in Hawaii is motivating us through the seemingly endless snowstorms in the Northeast.

The starting line of the Transpac may seem impossibly far for a bunch of twenty-somethings from Fishers Island Sound, but leaving the known is what we’ve been doing from the beginning. At least for this ocean-crossing adventure, we are glad to have found a bigger boat.


How to Follow TRADER Sailing

Homeported in Honolulu, TRADER Sailing is a military outreach sailing team currently funded through donations and crew contributions. They are actively seeking sponsorship and support for the 2021 Transpac. To help TRADER Sailing provide this opportunity to the veterans and rising sailors, please visit To learn about sponsorship opportunities, contact Sponsorship Lead Neil Stewart at






Lindsay Gimple can be reached at

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