I confess to being a cruising sailor who gets (almost) as much kick out of working on and puttering about my boat as I do sailing her. I do most of my own maintenance on my boat. I 'contract-out' only a few of the heavy jobs that are both unpleasant and time consuming so as to allow myself plenty of time to do the detailed work that I enjoy and that which needs my attention the most. Having had the same boat for 32 years, I have a pretty good idea of what needs to be done and by when so as to maximize the sailing season and prevent downtime when it counts.
In the off-season, I have developed a maintenance rotation and timing schedule that provides for fall winterization, boat covering and spring preparation for launch plus on-going maintenance. My in-water season commences about May 1 and ends about October 31. I have found that adhering to a couple of 'dead-lines' helps me to get the boat ready for both winter and the sailing season without any stress or particularly long days of work. Remember: this is supposed to be fun!
In eastern Canada we seldom receive significant snow-fall before mid November, so as I am generally hauled-out by November 1, I try to have my boat covered by Remembrance Day. Once the boat is out of the water the first job is to have her bottom pressure-washed. This is one of those jobs that I 'contract-out'. I have spent way too much time in rain-gear with water running down my sleeves and a deck-brush in hand to think that this is a glamorous part of yachting. Then it's on to winterizing the fresh water system, the head, holding tank and the engine. Again, I obtain professional help with the latter so as to assure myself that it is done properly. Drying the bilges is done after all of the above. Then it is on to covering the boat. For my suggestions on this topic, note the 'Winter Cover' link on the left-hand bar of this website.
Once the boat is winterized and covered, I always have a feeling of relief because I no longer have to be concerned about the weather. After I make sure that the galley, icebox and head are clean and perishables are removed, I then focus on the list of maintenance items that I have been keeping all summer. When I'm not actually sailing my boat, I find that it is amazing how quickly I forget what needs to be done. I keep a running list in the back of my log-book of the projects that really need to be addressed over the coming winter. It is the basis of what is to follow.
I have found that the temperature and weather are usually much more agreeable and conducive to completing projects on the boat the six or so weeks after haul-out than they are the six or so weeks before launch. In November and December the ground and water are usually not frozen, while they are very likely to be in March and April. Also, boatyards are virtually deserted at the end of the season so interruptions are fewer. As a result I do almost all of my interior painting and varnishing before Christmas. I find that there is often a cold front that passes through around New Years that stops work on the boat for some weeks. I find that I can heat the boat and make progress aboard (and keep my feet reasonably warm) as long as the daily highs make the freezing mark or above. I plan on doing whatever can be done in my work-shop at home in January and February when the weather is colder.
Certain jobs are permanently on my 'to-do' list. After the engine winterization and the removal of any engine components to be serviced, such jobs include bilge cleaning, especially in the area of the engine, engine paint touch-up and coating it with anti-corrosive spray. One trick that an experienced yachtsman shared with me years ago is to cover my engine with an old cloth coat. The caution is that the coat material must 'breath'. I was listing his boat and admired the condition of his obviously old engine. He gave me his 'secret'. I tried it and I have been amazed by the results. I have shown many boats in the winter, especially on mild days when the frost comes- out. The engines on these boats have been white with frost. The same day I have made a point of checking my own engine, under her coat: no frost at all is apparent. Try it, its amazing. The result is a remarkable reduction in the tendency of components of the engine to rust. And I can't help but believe that the engine benefits on the inside as much as it does on the outside. So covering the engine is the last job I do for it.
When it comes to interior painting and varnishing, I do it on a rotation. I do not attempt to do everything every year. Some high-wear areas do in fact get an annual recoating. The rest gets done sequentially as needed. I sand and prepare surfaces on the colder days when my heater can't keep up and I paint and varnish on the warmer days. Having all of this done early so that it gets to set, untouched, for a couple of months before the boat is used again makes for very durable paint and varnish surfaces. It also means that the interior is ready for the usual spring-cleaning once the warmer weather returns. Trying to paint and clean at the same time is futile.
I acknowledge that it takes a certain level of commitment and enthusiasm to get to work on maintenance projects immediately after the boat has been hauled out of the water. Many people just want to move on to other activities. But for me getting a start on what I know needs to be done shortens the winter and sustains my interest in my boat. Furthermore, if there is work to be done on sails, canvas, electronics or machinery, I make sure that the goods are taken immediately to the repair shops and I ask that they be completed by Christmas time. By doing so I have some hope of actually getting them back by April and there is less of a chance that I will have to compete for the attention of the service providers with all those who deluge them with work in the spring. Requesting completion by Christmas is important: it's a low cash-flow period for many of them so they often actually do complete the work by then so as to be paid at that time.
I know from long experience that projects other than annual cleaning and painting have to be completed by the end of March or they will start to interfere with my usual pre-launch schedule. Again, the point is to time the work so that you can proceed at your own pace given the weather and allow you to make progress without feeling pushed.
When it comes to spring preparation, the readiness to take advantage of good weather when it comes is critical. Remember to take your cues from the weather and not the calendar. I have long found that there is a weather window here around the third week of April that allows for hull painting and on-deck work that may not occur again until late May. This is where any preparation that you do in the fall can pay big dividends. It may permit you to take better advantage of the good spring weather when it comes. I delay the removal of my winter cover until the arrival of this period of good weather and I try to do everything that I can with it on the boat. But there does come a time when it is in the way and it simply has to be removed to allow work to continue.
My boat is of wood-epoxy construction and I paint the topsides myself. In the years that I do so I sand the hull (or contract it out) in the fall so that when this weather 'window' arrives I am pretty much ready to paint. It is such pro-activity that allows me to get the boat ready early in the season and to take the best advantage of it.
Many people complain of the shortness of the boating season in eastern Canada. I believe that if you take full advantage of the six months available for boating by preparing your boat for the water in advance it will not only prolong your enjoyment of your boat, but it will seemingly shorten the winter considerably too.