When we bought her she was named Box Bee. The first owner was a pilot and when he filled in his expenses he had to tick box B in order to claim exemption from...something (can't remember what). Over the years he made enough money to buy a boat, and hence the name. Funny and original, but not our story, so we looked around for another idea.
Rewind a bit. Our Sadler 29 was called Magewind, which is the name of a magical wind in the Earthsea books of Ursula le Guin - favourites of mine for many years. The name was given to the Sadler by her previous owner, Rod Usher, who before Magewind had owned another boat with an Earthsea-derived name, Lookfar. After Rod sold us Magewind he bought a Nauticat 33 and called it Tenar.
Anyway I got out my well-thumbed Earthsea trilogy and started reading out every possible name. None of them was quite right - until we got to Kalessin. This seemed to be a name that was fairly easy to spell and pronounce, a key advantage for a yacht name. Kalessin is the eldest dragon, incredibly wise, capable of long flights and on one occasion carrying two protagonists home from the land of death.
"Its head, the colour of iron, stained as with red rust at nostril and eye socket and jowl, hung facing him, almost over him. … It did not move. It might have been crouching there for hours, or for years, or for centuries. It was carven of iron, shaped from rock -- but the eyes, the eyes he dared not look into, the eyes like oil coiling on water, like yellow smoke behind glass, the opaque profound, and yellow eyes watched Arren."
The Farthest Shore, Ursula K le Guin
There is one other yacht called Kalessin that we know of, and it seems she is UK "Part 1" registered, as is our yacht. Because yachts on the Part 1 registry have to have a unique name, we ended up with Kalessin of Orwell.
The drawing is by Sergio M. Banchero, but since I found it on a Rumanian website using Cyrillic characters, I can't tell you any more.
The name is best known for a Norwegian "black metal band" (it says here) called Keep of Kalessin. You can listen to their music on their website but I really wouldn't recommend it. They must get very sore throats.
We toyed for a long time with the idea of a dragon decal on the side of the yacht but in the end felt we didn't need it. I'm not sure if Kalessin of Orwell is still a dragon to us, but it still seems like the right name.
Of course, it's said to be bad luck to rename a boat. Fortunately for us we used Vigor's Interdenominational Boat De-Naming Ceremony, and we hope that we have pacified any interested gods.
I do not care what comes after;
I have seen the dragons on the winds of morning...
- Ursula K. LeGuin (A Wizard of Earthsea)