From Desk to Deck: TotalBoat Employee Lindsay Races the Great Chesapeake Bay Schooner Race

Boats racing on open water photo by Deadrise Marine Photography

Here at TotalBoat, we love highlighting the incredible restoration projects and high-seas adventures shared by our talented ambassadors. But this week, we’re switching gears to shine a spotlight on one of our very own team members, Lindsay, who recently embraced the adventurous passion of the boating world by participating in the legendary Great Chesapeake Bay Schooner Race (GCBSR).

The history of schooner racing on the Chesapeake Bay is rooted in the historic trade rivalry between Baltimore, Maryland, and Norfolk/Portsmouth, Virginia. Historically, the fastest sailing vessels that delivered goods and people earned the best price for their cargo by beating slower schooners into port. The modern GCBSR was born in 1988 when Captain Lane Briggs of the Tugantine Norfolk Rebel (which is the world’s only sail-powered schooner-rigged tugboat) challenged Pride of Baltimore II to a race from Baltimore to Norfolk. This race revives that intense historic rivalry between schooners, captains, and cities on the Bay. Lindsay’s experience this year was described as exciting, terrifying, and an adventure to say the least. Read on to hear about her thrilling journey aboard the schooner Libertate!

Photos taken by Deadrise Marine Photography

Deadrise Marine Photography boats on water

Lindsay's Experience Racing to Save the Bay

We sat down with Lindsay to discuss her exciting journey, the challenges she faced, and how this type of experience connects back to the TotalBoat mission.

How did you get involved with the Great Chesapeake Bay Schooner Race, and what inspired you to take part this year?

I was first introduced to the GCBSR in 2020 while crewing on the AJ Meerwald, New Jersey's official tall ship, but unfortunately, the race was canceled due to the pandemic. The following summer, I worked on the junk rigged schooner Summer Wind in Baltimore. Shortly after that, a former crewmate linked me up with TotalBoat! Being part of the TotalBoat team has allowed me to stay connected to the marine world and has deepened my love for all things nautical. This year, in 2025, I reached out to the GCBSR organizers to see if any captains needed an extra deckhand. To my great fortune, Captain Paul Carrol invited me aboard the Libertate, which is also a junk rigged schooner.

You mentioned the weather was both beautiful and intense — can you describe what it was like out on the water during those shifts?

During the day, everyone was in awe of the beautiful weather. The steady blowing northwind and sunny sky made for quick-paced sailing. We were hitting the boat's top speed, 7–8 knots. By night, things were certainly more intense; the winds were stronger than they had been in a very long time, blowing 18 knots with gusts reaching 20–28 knots. The perfect conditions allowed some of the larger, heavier boats that usually lose due to insufficient wind to perform well; for instance, the Norfolk Rebel placed for the first time in all 36 years of the race.

What was it like being part of the crew during the night portion of the race when the winds picked up? Any memorable moments or challenges?

I definitely have a newfound appreciation for safety gear, wool socks, and non-skid surfaces! When the boat keeled further than anticipated and my boots were filled with the brackish waters of the Chesapeake, I had to find my stamina. I stayed up until dawn assisting the captain. We faced several challenges, including an extremely low battery, a broken prop, a soggy dinner in the galley, and a torn jib sail, but none of these stopped us! Coming in 3rd place is an incredible achievement!

What did that moment feel like when you crossed the finish line?

To be honest, it was exciting, but the adventure didn't stop there, and I almost didn’t notice when we crossed the finish line. I finally felt a true sense of achievement watching Paul Carrol and his father, Peter Carrol, accept the award in Norfolk, Virginia. Peter, the original captain of Libertate, is 90 years old, making him the oldest person to have participated in the race. We came in 3rd place!

As someone who works at TotalBoat, how does your love of sailing and experiences like this influence your work or connection to the boating community?

On the days when boating means 90% sanding and painting, I will remember this trip. It’s a powerful reminder of why so much hard work is put into these finely crafted vessels. The immense beauty of nature and the adrenaline of the voyage are worth all of the time and energy spent.

Racing to Save the Bay: TotalBoat Products Fuel Your Next Schooner Adventure

Lindsay’s thrilling third-place finish in the GCBSR demonstrates that our team truly embodies the adventurous passion of the boating world. We know that maintaining the integrity of these classic schooners, and any vessel, requires dedication and effort. Notably, the Great Chesapeake Bay Schooner Race is proud to say that they are “Racing to Save the Bay!” because all net proceeds from the race are donated to support youth education and other efforts aimed at saving the Chesapeake.

Whether you are restoring a classic boat or just getting ready for your next quick sail, we understand that sometimes the hard work involves sanding and painting. That's why TotalBoat is committed to providing the highest quality goods, from Epoxy Resins and Wet Edge Topside Paint to Gleam Marine Spar Varnish, to ensure your boat is ready for whatever adventure awaits.