Free at last, free at last! After four months of winter imprisonment in a DIY boatyard, my classic sailboat was unchained from a work bed of dirt and stone April 10 and returned to its natural element. As we motored away from Casa Rio Marina in Mayo, Md., I released a loud “Yee-hah!” and waved farewell to any who might be listening and watching.

I will not rush back any time soon, however; too much work awaits me at such yards, which may be vanishing anyway because of restrictive regulations. Painting my boat from keel to cabin top and stem to stern is a job I will not take on again by myself. In a perverse way I am relieved to admit this fact of life that is slowly overtaking me, and I’ll only take on such work again in short stages. But when it is all done, there is nothing quite as enjoyable and satisfying as a freshly painted and varnished boat. I again varnished with Pettit Flagship. Stripped exterior mahogany coamings were sealed with Epifanes Dutch Mahogany Stain and covered with 10 coats of Epifanes Wood Finish Gloss, which boasts no-sanding when instructions are followed. We shall see how this compares with real varnish.

I am, however, proud to state that after eight or nine winter haulouts in 26 years of owning this 1962 Sailmaster 22, I have never had Erewhon ready to sail as early as April. I credit this accomplishment to the mild winter and my son Eric, who lent a hand on several occasions with ugly bottom work and enjoyable topside painting. I had originally intended for boatyard pro Norman Gross to spray the boat with a one-part enamel, but environmental regs state that a boat cannot be sprayed outdoors unless the work area is enclosed. That probably would have added hundreds of dollars to a costly spray job, so I returned to the roller and brush, best done as a one-act, two-person drama on an open stage.

Fortunately, Eric has helped me before with this technique, rolling on small panels of paint as I immediately follow up fast over his head with a proper, high-quality brush to level out and feather a horizontal flow. This time around I used a deep-green monourethane from Epifanes. But such delicate work done outside in public for all to see is haunted by many curses and obstacles.

To wit: One must not start painting topsides when it is too early or too late in the day. Or when it is too hot, too sunny, too cold, too windy, too humid, too damp, too buggy, or with too much tree junk in the air or questioning weekend gawkers around to distract. This focused process must be done quickly and with no backsliding to correct an errant drip or drooping sag, to cover a minuscule paint “holiday,” or to remove a flying suicidal insect or dust mite.

This kind of exacting work attracts sidewalk superintendents who do not mean to interfere but do just that by butting in and watching behind our backs, even if they say nothing. Worse are those with unwanted or unwarranted comments with an urge to get so close to fresh paint they touch it with the bill of their caps. Next time, I’ll rig a police tape to keep them away along with posting a “NO DUST” sign on the dusty entrance road. Invariably, they ask what brand of paint I am using. I want to answer, “It’s the painter, not the paint,” but I am not that accomplished an amateur to do such boasting.

I actually rather enjoy the painting process, though not the difficult prep work with an orbital power sander and fine, detailed hand-sanding with a foam pad to remove any traces of old brush marks. Sanding too heavily may reveal old, pale white highlights that may require two coats to cover. And the first coat must be sanded for the second coat. There was a total of 88 linear feet to sand on my 22-footer, if my mathematics are accurate.

I regret to say that new brush marks are visible if you touch the hull with your nose, but the horizontal flow went well enough this time. Once the boat was in the water, however, reflections erase any mistakes and no one will get that close again except me when I scrub the waterline. After such a job is done properly, I guarantee the painter will get satisfaction.

The boat’s bottom, on the other hand, remains in stark contrast in forced negligence because it is sorely in need of a professional, tented paint blasting, even though I always use ablative paint. In the recent past, I have chosen a green Pettit Ultima, which has served me well, and the bottom gets two coats every two years or so. I received an electric power-washer last Christmas and Eric used it with some success in blasting off loose, flaking paint. Power-sanding the bottom is out of the question for me because of bad shoulders and knees. Bottom blasting would probably cost about $1,500, but in 2015 or thereabouts, when I surrender to this inevitable job, the charge may be more like $3,000, which is more than I will be worth.

A major hardware improvement this winter was the installation of a pair of Lewmar No. 6 halyard winches to replace my old and tired Merriman bronze winches, which I have turned over to Bacon’s maritime consignment shop because I cannot bear to toss them. The new polished-chrome Lewmars match my existing Lewmar sheet winches. Also this winter, my roller-furling jib purchased new at Bacon’s was washed and restitched at this traditional used equipment and sails loft in Annapolis. I purchased an old stripped tiller there last year and refinished it at home with 10 coats of Flagship varnish. My mainsail wintered at UK Sails in Annapolis for washing and general repairs.

With only my jib rigged, I motored in light morning air to my Wells Cove slip on Spa Creek in Annapolis, where my boom awaited. I cabbed it back to Casa Rio to pick up my car and attempted to fill the interior with paint cans, equipment, two stepladders, and a rescued child’s wagon with slatted wood sides. The car trunk was already filled to capacity.

I took possession of this discarded wagon a year ago and used it well. To facilitate the swift-moving, topsides painting project and keep supplies at hand and on a stable platform, I loaded it with a small, deep tray of green paint, an open can of green paint, and a can of Epifanes thinner used regularly to replenish the supply and keep the paint thin and in a flowing state of motion. Eric pulled the little red wagon behind him as I monitored the paint-mixing situation: Too much thinner and paint will run; too little and the brush will pull and paint will not flow evenly and feather to blend from the new into the old.

What pitfalls await in 2015, I dare not wonder. We shall see. For now, a new season of cruising awaits Erewhon and me.

Jack Sherwood is writer at large for Soundings.

This article originally appeared in the June 2012 issue.