Today we’d like to introduce you to Marianna Fleischman and Jack Benson. They and their team shared their story with us below:
Jack bought the boat in 2017. It is a 1978 Van de Stadt (designer) Agulhas 45 (model), named for the cape in South Africa near to where it was originally built. After shopping around with a modest budget, looking for a blue water-capable boat he could grow into, Jack settled on this one. A family friend has its sister ship in Scotland and has always spoken highly of its build quality, performance, and safety.
A few months after the purchase, he moved the boat from southern Maryland to its current home in Canton, Baltimore. It was in Canton, just down the street at the local West Marine, where Jack met Marianna by chance one Friday afternoon.
Marianna had started sailing recently after purchasing her boat, a San Juan 24, which she was also keeping in Baltimore. We started dating officially after a few months of friendship, and sailing was and is a huge part of our life together. We’ve completed many races in the bay, offshore deliveries, and a handful of offshore races (together and separately) in the years since, growing our skills and confidence.
We were forced to take a brief hiatus from boat life when Marianna took a new job in Pennsylvania and moved to a landlocked town outside of Philadelphia. Jack continues to spend most of his time in Baltimore, where his job opportunity is greatest, and we make the “medium-distance” arrangement work for us.
We married on the boat in 2023, with a beautiful ceremony in Annapolis in November. Immediately after, we set our sights on refocusing our efforts on preparing the boat for what had always been the dream: Bluewater cruising and a transatlantic voyage.
We’ve redoubled our efforts in the last several months, and we are already making great progress in installing new systems and enacting upgrades and improvements. We have also started live-streaming our projects on Twitch to share our story with anyone who wants to tune in. Our goal is to set sail in the spring of 2026, sailing from Baltimore, Maryland, to Baltimore, Ireland.
Can you talk to us about the challenges and lessons you’ve learned along the way? Looking back, would you say it’s been easy or smooth in retrospect?
Small defeats are common with boat work and can feel like death by a thousand papercuts.
Not having the right tools, unexpected difficulty with projects, fear of failure, cost, etc. There are lots of pitfalls. Having a boat is not cheap, and preparing it to be self-sustaining for long voyages only adds more complexity. There is doubt in our abilities and our resolve to take this goal on.
There is also the doubt that creeps in when putting yourself out there on the internet to share your boat life. We worry about being entertaining, engaging, and creative and balancing that with a desire to share our story authentically and in a way that doesn’t distract us from our goals.
In terms of your work and the industry, what are some changes you expect to see over the next five to ten years?
Regarding sailing, we predict that competitive high-end racing will be less attainable due to the pace of technical development, putting peak-performance boats beyond the reach of most people.
The shift toward boats designed for single- or double-handing will likely continue, with companies designing new cruising or racer-cruisers for couples or solo sailors. As the current generation of sailors begins aging out, there will be an abundance of affordable boats on the market, and we hope that will grow the sport as a whole.
We hope to see the sport diversify, with more women becoming involved, inspired by the likes of Cole Brauer and the crew of Maiden. We also hope to pave the way for sailing live-streaming! The YouTube sailing community is vast yet saturated with highly-produced, sanitized versions of sailing. It can be difficult, if not impossible, to make your mark in that arena.
We hope by live-streaming, we can fill a niche of those seeking approachable and very genuine representations of boat life… including lots of boat work and sometimes little sailing! We expect this genre to grow.
We would love for you to join us aboard and follow along on any of our social media platforms. You can find us below:
Contact Info:
- Website: Twitch.tv/sailingwithbernard
- Instagram: @Sailingwithbernard
- Youtube: http://youtube.com/@sailingwithbernard
Image Credits
Devon Rowland Photography
