Winds up to 22 knots, a reef that wasn’t there, and the quiet thrill of doing something you once thought was too much — our second crossing of Lake Michigan was equal parts challenge and growth. This is the story of how our comfort zone expanded, one gust at a time.
A Sister, a Regatta, and the Sea
We planned for a quiet overnight on the boat — just us, the marina, and an early start the next morning. What we got instead was a noisy festival, a last-minute hotel room, a flamenco dancer, and one of the best sails of the season. My sister joined us for her first-ever monohull sail , and I was at the helm to bring us back in — this time with spectators watching from our neighboring slip! (No pressure, right?) Spoiler: I nailed it. But not without a few nerves.
Second Time’s the Charm: A Smooth Sail and My Redemption at the Helm
After a rough first landing on our season opener, I was more than ready for a second shot. This time, everything clicked — calm winds, smooth sailing, and determination at the helm. I learned that docking isn’t about power; it’s about patience, timing, and a few well-placed nudges. And just like that, I found my redemption… and a rhythm I can’t wait to keep building on.
First Sail of the Season: Cold Winds, New Sails, and a Humbling Return
We kicked off our 2025 sailing season with crisp weather, new sails, and a few rusty edges. From the thrill of unzipping a surprise sail upgrade to the humbling moment of botching our return to the slip, this outing had a little bit of everything. First sails are never perfect, but they’re always unforgettable.
Monohulls vs Catamarans: Which is Right for You?
Having viewed endless hours of YouTube videos on sailing monohulls and catamarans, we have often wondered how monohulls compare to catamarans. Now that we have spent time on both, we can answer that question for ourselves! Through our experiences, and a fair bit of research, we've come to appreciate the unique characteristics of each. There's …
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More Than Money: Why Our Liveaboard Dream Still Matters
These days, it's hard to ignore the news about the economy. When we hear about the stock market being unpredictable and the future of Social Security feeling uncertain, it can make anyone think twice about their long-term plans, especially big ones like our dream of retiring onto a sailboat. Living here in Iowa, Kent and I have been paying attention, knowing that our goal of trading our landlocked life for the freedom of the ocean has financial implications.
Maritime Literature: Practical Wisdom from ‘Sailing a Serious Ocean’
Kent and I have been exploring maritime literature focused on sea disasters, finding value in John Kretschmer's book, "Sailing a Serious Ocean." You'd think listening to tales of tempestuous seas and near-catastrophic events would send us running for the nearest landlocked cabin. Instead, we feel a strange sense of calm! The author combines engaging storytelling with practical seamanship lessons. And we're motivated to learn because adventure without a solid grounding in safety is a risk we're not willing to take.
Embarking on Season Three with SailTime Chicago
Kent and I are excited to return for our third sailing season with SailTime Chicago aboard Red Sky, our Jeanneau Sun Odyssey 349. We've enjoyed memorable moments, from hosting family during events like the Chicago Air and Water Show to crossing Lake Michigan. We're eager for more adventures and updates in 2025!
Our Grand Traverse Bay Adventure
Just six months after completing sailing school, we took the plunge and chartered our first sailboat in beautiful Grand Traverse Bay, Michigan. This maiden voyage - our first time without an instructor - was a true test of our skills and a fantastic adventure filled with challenges and triumphs. It solidified our love for sailing and taught us valuable lessons about teamwork, living in the moment, and the magic of the Great Lakes.
Evans’ North Atlantic Crossing
In June 2023, Jade and Brett Evans, of Expedition Evans, along with their crew (2 pups and a guest), chronicle their 18-day voyage across the North Atlantic Ocean. This incredible series provides a peek into their life at sea, posting daily videos of their passage from Bermuda to the Azores off the coast of Portugal.
