06/02/2026
After two seasons in Door County, Calypso is finally making her way home to Milwaukee! ⛵🎉
We had originally planned to bring her south at the beginning of May, but a colder-than-normal spring delayed launch schedules throughout the area. Yesterday was finally the day we'd been waiting for. 🙌
The day started with an early drive to Sturgeon Bay, as Angie transported Captain Don and crew: Sam, Kim, and Josh, north to meet Calypso for the journey home. We arrived expecting a mid-morning launch, but as often happens in boating, the schedule had other ideas. 😄
When we arrived, Calypso was still blocked in by several larger boats that needed to be moved first. Rather than spending hours staring at the boatyard, the crew took the opportunity to explore a little of Door County, including Fish Creek and a stop at Wilson's for one of their famous root beer floats. 🍺🍦
Back at the yard, the waiting continued, but so did the preparation. The dinghy was inflated and launched, fenders were set out, gear was organized, and the crew got everything ready for departure.
Finally, around 4:30 PM, it was Calypso's turn. 🎉
Watching a 41-foot sailboat lifted from her stands, carried across the yard, and lowered back into Lake Michigan never gets old. ⚓
After fueling up, topping off the water tanks, and making final preparations, Don, Sam, Kim, and Josh departed Sturgeon Bay around 9:00 PM for the overnight journey south. Meanwhile, Angie made the drive back to Milwaukee while the crew pointed Calypso toward her new home. 🌅
This morning brought a beautiful Lake Michigan sunrise as Calypso continued toward Milwaukee under a mix of sail and power. ⛵☀️
Once she arrives, Calypso will call South Shore Yacht Club in Milwaukee home. While she'll certainly be used for some personal adventures, she'll also serve as the classroom and floating home for several of our advanced sailing experiences, including our popular Learn to Sail Vacations, where students earn certifications while living aboard and exploring Lake Michigan.
If all goes according to plan, we're excited to have Calypso arrive at her new home later today! 🎉⛵
06/02/2026