Sailing Changed the Way We Do Summer

Kent and Becca sitting in the cockpit, smiling, with the lake and chicago in the background.

Our summers used to mean road trips, trout streams, and backyard weekends. Now, every other weekend, we grab our go-basket, hop in the car, and head for Lake Michigan. Sailing has brought a new rhythm to our lives — one that’s part adventure, part ritual, and totally worth the laundry piling up.

Crossings: Lakes and Thresholds

Red Sky on the dock in New Buffalo, sun setting in the background.

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 

Kent and Becca sitting behind the wheels of a double-helm sailboat.

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

the sunlight glimmering on the water in Lake Michigan, buildings on the horizon.

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.

Monohulls vs Catamarans: Which is Right for You?

People partying on the deck of a large boat

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 …

More Than Money: Why Our Liveaboard Dream Still Matters

Two sailboats on wavy water, under a cloudless sky

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.