SV Maggie May

Voyages of the SV MAGGIE MAY


This blog will follow the sailing adventures of  the sailboat Maggie May and her crew, Captain Bill Updike and First Mate Krista Schlyer. The dream of this voyage began 30 years ago. Maggie May set sail in the Chesapeake Bay in May 2020, with a plan to sail south and work around the world. A host of early setbacks–from Covid 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. 

For now, the Maggie May is bound for anywhere, as long as life allows her and her crew to roam. Find blog entries and a link to a PredictWind tracking page at the bottom and sidebar of this page.



(c)Krista_Schlyer_-07219Maggie 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 have spent the past 7 years overhauling and 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…

Holding Maggie May is Captain Bill.


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. For Bill this is a time of sabbatical, a time for learning how to live slower, in each present moment, and  where instead of working 60 hours a week at a job, he works 60 hours a week fixing things that go wrong on a boat. 


Krista has wanted to live on a sailboat since she fell down the companionway stairs of a friend’s boat in American Samoa 20 years ago. It is about freedom she thinks. 

Krista works as a freelance conservation photographer and writer and for the past 15 years she has chronicled the landscape of the US-Mexico borderlands, the Anacostia River watershed in Washington DC, the longleaf pine forests of the southeastern United States, and many more places. You can buy her books through the Book Store page and  see some of her images in her online galleries with the International League of Conservation Photographers (and even buy prints and support this voyage). 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 in 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. 


This blog will chronicle the adventures of Maggie May, Bill and Krista. We don’t know how long we will be out or where we will get to. The end of this story will be a surprise for all of us.

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





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