SV Maggie May


WELCOME to the sailing adventures of SV Maggie May and crew, Captain Bill Updike and First Mate Krista Schlyer. SV Maggie May set sail in the Chesapeake Bay in May 2020, with a plan to sail south and then westward all around the world. A host of early setbacks–from Covid to contractors to squirrels–put the idea of a circumnavigation on a distant hold (see early blog entries) and demanded the crew reevaluate their goals, and even the idea of goals. What began as one dream has been hammered by the capricious Fates into 1000, and now the Maggie May is bound for who knows where.


  • Off Soundings
    I think about that moment when our depth sounder goes from 290 feet to – – -. That’s somewhere beyond 300 feet, how much beyond is practically irrelevant. This passage the depth will fall to almost 10,000 feet. The sounder will read – – -, off soundings.
  • Boiling, Guadeloupe
    About midway down the western edge of Guadeloupe there is a small bay where the town of Bouillante nestles within the foothills of towering green peaks. Here most of the population speaks French, the air smells strongly of sulfur, and every day, for most of the daylight hours and long into the night, the community gathers in water that pours first out of the…
  • The Beginning
    I woke this morning at first light and climbed the four steep companionway stairs into the cockpit. I have climbed these stairs 1000 times in the past 18 months. The boat interior was dark but the sun, still below the mountains to the east, cast a pale light on the clouds in the western sky. Presently it began to rain, a light sprinkle only,…


Maggie May is a 39 foot Westerly Sealord sailboat built in 1986 in England. When we bought her in 2013 her name was Vilkas. Apparently this means ‘werewolf’ in Lithuanian, an omen we overlooked initially. We spent 7 years overhauling, caretaking and sweet-talking the werewolf. A job that will never end. But  she returns our love with a comfortable place to live and she’s happy sailing in 15-20 knots, and capable of moving along in 5. She’s heavy but quick for her girth, plucky and determined. We renamed her Maggie May after our Corgi/Dachund mix dog who died a few years before we bought Vilkas. This is the original Maggie May…

CAPTAIN BILL dreamed of living on a sailboat when he was a little spud growing up near Lake Michigan. He’s spent much of the past 15 years working in the sustainability field in Washington DC, so living in limited space, with limited water, food and energy is the perfect living lab for learning how to thrive in an environment of natural scarcity. Energy efficiency, solar, wind, waste reduction and water conservation have been as integral as rigging, sails and engines in the preparation for this voyage. We’ll be blogging about sustainability along the way.

For Bill this is a time of sabbatical, a time for learning how to live slower and smaller, but also so much larger in the space of each present moment. Instead of working 60 hours a week at a job, he works 60 hours a week fixing things that go wrong and appreciating things that go right on a boat. 

FIRST MATE KRISTA has worked as a freelance conservation photographer and writer and for the past 15 years, chronicling landscapes of grief and beauty along the US-Mexico borderlands, and the Anacostia River in Washington DC.

The allure of this sailing adventure, in addition to fulfilling a lifelong dream, was to spend some time honing the craft of photography and writing, learning Spanish and ukulele, and reading poetry and all the books she can squeeze on the boat. Mostly, it is a time to see all the loveliness there is to see, and find some healing from the work of documenting the ongoing degradation of the natural world. 

Follow along on the adventures through our Maggie May tracking page and through the Maggie May blog posts in the sidebar.

Support this Blog and Journey

My plan was always to do a free blog to share the journeys of Maggie May and any cool, interesting and important things we might find along the way. Even with all the setbacks we’ve had, I want this to be a free blog. But if you are enjoying the story, and have some funds to support this journey and ongoing storytelling, you can help us continue on this path. Thanks!


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