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.


  • Si Dios Quiere
    Most people in the rural areas here don’t have air conditioning or televisions or even electricity necessarily, yet there is an energy and an air of contentment I have seen nowhere else in the world, certainly not in my own country. There are dark sides of course. There are always dark sides. To all of us and everywhere. And we have been here long enough to see some of those too. But what I take with me is laughter, generosity, self reliance, wildness, commitment, beauty, and for me a deeply inquisitive drive to better understand the nature of contentment. The world turns on this ethereal phenomenon. The Dominican Republic knows something important. 
  • A creature of flight
    They were no longer wild creatures with their own endeavors toward life. They were curios and props for a culture of beings often too obsessed with being seen to see for themselves what is right in front of them. A wild bird mutilated. A creature of flight, flightless.
  • Under Rocks and over sand
    On Bonaire’s western shore, Maggie May floats upon aquamarine glass over what is known as the Bonaire House Reef. It’s a coral reef that extends the length of the town of Kralendijk, the main city center of the island. Though this reef has been more impacted by human development and enterprise than many other areas of Bonaire’s coral community, it is still healthier than…


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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