Sailing on “Cay of Sea”

Severn River Sailing by Ruth Bailey
Severn River Sailing

I have started a small sketchbook, dedicated to our sailing adventures this season. The sketches are done quickly, attempting to capture the feel of the moment more than striving to be accurate. I start each sketch with pencil, and move to a permanent sepia pen after I have planned out the sketch. The pencil lines are erased, and later, I can come back in and augment the sketch with watercolor.

We enjoy going to the annual rendezvous of owners of “Watkins” sailboats, of which ours is the 27′ model. The rendezvous usually takes place at a marina in the southern part of the Chesapeake Bay, 80 – 90 miles from our home port, since most of the attendees are from the Norfolk area.

But before we set out for nine days on the boat at the beginning of the season, we like to take an overnight close to home to find out what supplies and equipment we took off the boat for the winter and have forgotten to put back on. This is our “shakedown cruise,” and yes, we found out that our bed pillows for the boat had migrated to the guest bed during the winter, and my husband’s float coat, a jacket with a built-in life-preserver, had been worn home last fall and was still in the hall closet.

The Shakedown Cruise
May 9, 2014 – The Shakedown Cruise, the first sailboat cruise of the season


Lots of boats on the bay; Packing for the cruise
Lots of boats on the bay; Packing for the cruise
"Don't make me look fat"
“Don’t make me look fat”
Ruth Bailey watercolor
Fishing for stripers, going through Knapps Narrows & finding sun
Ruth Bailey watercolor
Relaxing after dropping the hook & a little music
Ruth Bailey Watercolor
Larval shrimp littered the boat; each pole had an osprey nest; and, no wind going home


























Ruth Bailey is an artist who sails with her husband, Rick, throughout the Chesapeake Bay on Cay of Sea, a Watkins 27 coastal cruiser.  You can read more of her blog posts and see her art on her website, Ruth Bailey Art. They both post on the blog, Middle Bay Sailing






Ruth Bailey is a Chesapeake Bay artist featuring watercolor. She sails with her husband, Rick. You can see more of her work on her website,

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