Cloudy Day: a home for when the world turns gray

Cloudy Day, then still named "Cara Mia", on a linear mooring in Bellingham,
WA, September 2021. Mainsail not present as it had recently been shredded in a
violent storm.

Cloudy Day is a 1971 Challenger 32 masthead-sloop sailboat (which, because counting is overrated, is actually about 33ft length overall). At a glance, here’s how I currently have her outfitted:

Okay, now for storytime…

Cloudy Day is actually my second sailboat, though the first was only briefly in my care: I learned to sail in spring/early summer 2021 on an unnamed-so-far-as-I-understood-things 1978 Clark San Juan 28. Realizing the boat wasn’t quite the one I wanted to invest tons of time or effort into (particularly, the electric motor refit I wanted to do), I parted with that SJ28 and purchased Cloudy Day.

I purchased Cloudy Day in Bellingham, WA in August of 2021 for about $10,000 USD1 in a Craigslist deal. At the time, she went by the name “Cara Mia”, evidently Italian for “My Beloved”. After day-sailing her around Bellingham Bay and surrounding waters through the rest of the 2021 season, she spent the winter first in Blaine Harbor, and then later in Squalicum Harbor back in Bellingham, largely unused while I tended to other matters in life.

The following summer (2022), I hauled the boat out for a rather extensive electrical refit and a repowering of the auxiliary drivetrain, which I intend to retroactively document here in the near future, replacing the Yanmar 3GM30F diesel engine (I hate fossil fuels and fossil fuels hate us all) with a 10kW 48V electric motor and a 280AH LiFePO4 battery bank (48V, 16s). While doing that work (and plenty more as it came up), I realized that for the first time in my life, I had a space that was completely mine, and a space I could make as cozy (or as rugged) as I wanted, with nobody to answer to but the sea. I never intended to be a liveaboard: indeed, when I bought the boat, I explicitly was looking for something “good enough for weekend or summer-holiday-week getaways, maybe with some company sometimes” and not much more. But alas, I decided that either the upcoming fall, or the following spring, I’d move aboard. Long logistics-heavy story short, I wound up finding winter moorage in Friday Harbor, WA for October 2022 to April 2023, and moved aboard full-time in late October - leaks in the ceiling (from deck fittings) and all. It was around this time that she was rechristened “Cloudy Day Real Estate”2, later shortened to simply “Cloudy Day” for practicality purposes.

For personal life reasons, the winter of 2022-23 was relatively quiet as far as boat projects went: I finally worked on replacing the saloon ceiling / deck core, which had rotted away due to water intrusion and caused deck flex once removed, I worked on the interior plumbing (including installation of a composting toilet and replacing the old electric water pumps with foot pumps in the head and galley), and finally installed solar panels.

Here, friends, is where I pause this page for a moment (as of March of 2023). This summer I’ll be sailing Cloudy Day around to some remote and quiet places and finally getting a proper taste of the full-time liveaboard cruiser life, and I’ll try to find some time in that process to come back here and fill in more of the history of this boat, and break out some sub-pages for individual projects undertaken :)


  1. Which in $CURRENT_DAY dollars is calculatable here 

  2. A pun if there ever was one: I’m a fan of the band Sunny Day Real Estate, an emo band from the 90s here in the PNW, where it’s exceptionally cloudy most of the year. The name also has a second meaning, alluded to in the title of this page: when all else goes to shit in the world, there’s always the option of hopping aboard Cloudy Day and setting sail to other, possibly greener, pastures.