Our Goal: To obtain our Captain's Licenses, to retire onto a sailboat, to sail the Bahamas and possibly beyond, for at least a year, maybe more.
What We're Working on in 2025:
- Swapping helm duties to build confidence
- Sailing in less-than-optimal conditions
- Getting more comfortable having guests aboard
- Making connections with other sailors
- Anchoring everything in joy, not perfection
The plan (in retrospect):
2025
May
First Sail of the Season on Red Sky! That crisp day in May marked the return of routines, fresh sails, and big lessons at the helm — building confidence one tack at a time.
June
Our second crossing of Lake Michigan! From Chicago to New Buffalo, we were under reefed sails, steady winds, and building gusts — topping out at 22 knots, our highest yet! It pushed our limits in the best way: not with fear, but with growing steadiness.
2024
October
Received our TWIC Credentials
The Transportation Worker Identification Credential unlocks commercial waterways and serious ambition — a formal step toward professional seamanship.
BVI Catamaran Charter Trip
We chartered – and learned how to sail – a catamaran in a weeklong trip to the BVI! Learning to sail and host guests in paradise built confidence for doing this lifestyle together.
July
First Crossing of Lake Michigan
Our inaugural journey across open water showed us what cruising full coastlines feels like.
May
Radio License & Red Sky Check Sail
Kent upgraded his radio license to Amateur General! His upgraded radio skills and a successful check sail locked in our ability to sail independently on Lake Michigan.
February
Signed on with SailTime Chicago again!
Have plans to spend time on Lake Michigan sailing a 34 ft Beneteau Oceanis, Red Sky!
What We Accomplished
2024 was full of small wins that quietly added up.
We crossed Lake Michigan for the first time — a multi-leg trip that gave us our first real taste of passage-making. We chartered a catamaran in the BVI, learned new systems, hosted guests, and saw what life at sea might actually feel like. We earned our TWIC credentials, Kent upgraded his radio license, and we signed on for another season with SailTime Chicago.
These steps are building toward something bigger: the skills and the confidence we’ll need to live aboard someday.
2023
August
Seasonal Sailing with SailTime Chicago
Late in the season, we joined SailTime Chicago where we had access to a 31 ft Beneteau Oceanis, Sister Sail. For a handful of weekends at the tail-end of the summer, we sailed on Lake Michigan. The consistent weekend sails aboard Sister Sail gave us rhythm and real freedom on the water.
July
First Bareboat Charter, Traverse City
Four days with only us in command confirmed we could lead a cruise on our own. Spent 4 days on the water on a 32 ft Marlow-Hunter, Dark Horse. Our first charter experience was a success 😊
February
Offshore Sailing School -Tampa, FL
Eight immersive days on a 48-ft Jeanneau anchored our training in real sea life — docking, provisioning, living aboard.
Sailing School Adventure – Part 1
Sailing School Adventure – Part 2
Sailing School Adventure – Part 3
What We Accomplished
We kicked things off with a deep dive — literally — spending eight days learning to sail with Offshore Sailing School in Tampa Bay. First, we day-sailed. Then, we moved aboard a 48-ft Jeanneau and lived the rhythm of life at sea: docking, anchoring, provisioning, maneuvering, and learning to trust ourselves. It was immersive, exhausting, and unforgettable — and it gave us our foundation.
This summer, we booked our first bareboat charter out of Traverse City. Four days on Dark Horse, a 32-ft Marlow-Hunter, taught us what it feels like to be the ones in charge. No instructors, no checklists handed down. Just us, and the water. It was a test run — and a thrilling one.
Then in August, we joined SailTime Chicago — a quiet but decisive step. It gave us consistent access to Sister Sail, a 35-ft Beneteau Oceanis, and our first taste of routine sailing on Lake Michigan. The season was short, but it changed everything. It confirmed what we suspected: we wanted more of this.
2023 was about building confidence, taking calculated risks, and choosing to begin. The experiences we had that year still shape the way we sail today.
2022
Spring & Summer – Sailing at Lake MacBride
Becca earned Lightweather Helmsman ranking while Kent upgraded his radio license. Each training moment brought us closer to sailboat independence.
What We Accomplished
Summer of 2022, we kept sailing locally at Lake MacBride — and Becca officially earned her Lightweather Helmsman rating through the University of Iowa Sailing Club. It was small-boat sailing, but it taught us the language, the muscle memory, and the joy of harnessing wind and water.
Kent earned his Amateur Radio License, planting seeds for the kind of seamanship that looks ahead — toward offshore communications and safety systems. In small ways, we were starting to imagine how this might all grow into something bigger.
2021
Joined University of Iowa Sailing Club
Learning to sail on 14-ft FJs taught us how to sail and love the challenge.
What We Accomplished
This year we got on the water for real.
We joined the University of Iowa Sailing Club and started learning to sail on 14-foot FJs — light and fast.
2021 taught us that this wasn’t just a passing interest. Sailing challenged us, energized us, and gave us something to build toward. It stuck.
2020
It all started in 2020 — the year we fell in love with sailing from our couch.
Stuck at home during the early pandemic, we found ourselves binge-watching YouTube sailing channels. First came Sailing GBU and Gone with the Wynns, then Sailing Ruby Rose and Acorn to Arabella, and so many more. Their stories — building boats, crossing oceans, learning as they went — felt like portals to a different kind of life.
Those videos planted the idea that maybe, someday, this could be us.
Early YouTube favorites: Acorn to Arabella, Bums on a Boat, Expedition Evans, Gone With the Wynns, Sailing Good, Bad, and Ugly, Sailing Ruby Rose, The Art of Boat Building, Tips from a Shipwright, Tom Cunliffe, and Zoffinger.
SAIL & SAVOR BLOG 