One sees this question every now and then on the Internet these days, and it baffles seasoned sailors who have never really considered it seriously. Most always asked by people who have little experience with what the sport of sailing is all about, sailors find it a strange question as it is an activity that is as diverse as most any leisure activity anywhere.

It is true that at its most basic level, sailing can be pursued by most people with a small, low maintenance sailboat and limited budget. A 13-foot Sunfish, for example, is very simple and low tech and quite heavy at 120 lbs. It has been a popular sailing choice since it came out in 1953, given it can be found in the thousands around the country. One can find these daysailers hidden in the shadows of many lakefront homes and resorts, and they were instrumental in introducing young people to how wind can power a small boat, however rudimentary. A quick glance to any of the boating websites out there can give you many options for sailboats for sale at reasonable prices.

inexpensive sailboat for sale

There are many small daysailers of different designs out there, such as the Optimist dinghy, Laser, and Hobie. They offer minimal controls, have nothing approaching comfortable seating, but their sailing performance is enough to provide an afternoon of enjoyment when the sun is out on a perfect summer day. Small daysailers make their mark among thousands of childhood memories.

Most small daysailers are basically wash-and-wear watercraft, and it takes very little effort or money to maintain the boats from season to season, beyond a thorough washing and polish of the fiberglass. Small daysailers constructed in wood take a little extra care, with maybe a bit of paint and a touch of varnish from time to time. But the wood or aluminum masts and all of the rigging can be reused without much care for quite a long time.

If you are considering buying a daysailor, this type of boat with minimal upkeep can making sailing a cheap hobby for beginners or anyone that wants to step into the recreation. There are nearly 2,000 sailboats available for sale on today's brokerage market and approximately 25% are $30,000 or less.

At some point, however, one reaches a tipping point of sorts as the boat, the sailor’s skills, and the sailing dreams get bigger. Complexity goes up with boat size, and it is no longer as practical to store the boat behind some trees or pulled onto a makeshift cradle platform for the offseason. The boat now must remain in the water in a slip or on a mooring or stored in a purpose-built storage rack without its masts. The simplest daysailers can reach lengths up to 20 feet or so, but “bigger” boats can also begin at 20 feet. John Guzzwell sailed around the world on his 20-foot Trekka.

Trekka sailboat 

As boats go up in size, they also typically begin having some level of accommodations down below. A bunk to sleep on, a bathroom of some kind, sail storage, and a galley to cook the most basic meal or make coffee. And above this size the boats stop being “cheap” hobbies because they have more things that work together to make them sail faster and more efficiently, have some form of auxiliary power, and they require more experience and training to get them to sail well.

There are hundreds of these smaller “real” sailboats out there that continue to feed one’s blossoming sailing hobby. One can get by with seasonal cleaning and detailing, but now there are winches to clean and grease, there may be some kind of engine, and everything on the boat has a purpose. To anchor out for an evening or weekend, which is well beyond the capabilities of the original small daysailer, these boats carry anchors attached to chain and nylon rope to secure the boat to the bottom.

Using anchoring as an illustration of the size and complexity factors, it is not hard to understand that as boat size increases, so does the size and weight of the needed anchor to properly secure the boat. While maybe still manageable by athletic young people to lift and move, the anchor is soon even heavier, with longer chain, and becomes more of a challenge to physically wrestle without mechanical assistance. This comes in the form of an anchor windlass, which is another piece of equipment that is expensive and requires greasing and maintenance.

windlass and anchor on sailboat 

The job to keep the boat shipshape and looking good—and working well— becomes lists of tasks that take time. And, as many sailors at that point are building their careers, paying others to perform these maintenance services makes sense. Having a boatyard sand and paint the bottom with anti-fouling coatings, becomes expensive. The paint alone costs hundreds of dollars per gallon.

To offset this increase in costs, one now has a sailboat that has far more ability than the daysailer, and one can take family and friends out for longer periods and travel farther. This is where one may evolve into a cruising sailor. At this point, it is no longer simply a hobby. It can easily go on to become one of life’s great passions, as it opens up the world to a life of travel and meeting new people and cultures. Seeing the world from the deck of a sailboat is incredibly romantic, given that it continues to draw in men and women attracted by the lure of the natural world and cultures beyond their known experience.

There is a well-known estimate floating around the cruising world that one should expect to spend 10 to 20 percent of the boat’s value in yearly maintenance costs. For full-time cruisers that may seem a lot more than what they spend, but then again it is worth considering. One needs to pay for a slip, insurance, a yearly haul out and all sorts of “normal” maintenance.

(Below: Once you're ready to step into a slightly larger sailboat, the Hanse Yachts 315 offers easay sailing at a reasonable price point.)

hanse 315 sailboat 

These normal tasks include new bottom paint (with extensive preparation), new zincs, engine oil/filter changes, new belts or hoses, upgrade worn lines and other gear, varnishing brightwork, and there always seems to be equipment that breaks or wears out. Or perhaps is found necessary to continue one’s cruising. A new radio, autopilot, dodger canvas and acrylic windows in the cockpit, maybe a new windlass motor or primary winch upgrade. These are not strictly considered maintenance items but are on the wishlist every sailor maintains for when it is time to haul the boat and spend money getting the boat up to desired level of capability or condition.

None of the above is ever cheap and can easily meet or exceed that 10-20 percent estimate over a period of years, if not each year.

Another sailing pursuit that can take one’s simple hobby in new directions is when one discovers that sailboat racing is its own raison d’être. Sailboat racing is an amazing sport that captivates those who are drawn into it. Racing has never been much of a spectator sport, but that doesn’t matter to those out racing on any given day. The thrill of sailing at the edge of performance while beating other sailors just as intent to reach the next mark first, is hard to describe.

Dedicated sailboat racers spend insane amounts of money getting the most performance out of their boats, which are often purpose-built speed machines that demand experienced crew to get the most out of the design. Racing boats also need perfectly designed and constructed sails to maintain their full speed potential. It is common for skippers to buy a new set of sails before a major regatta. This is a very expensive proposition that costs well in excess of five figures and takes sailboat racing to an entirely new level as an expensive pursuit. Racing can be far and away more expensive than cruising on island time looking for the next perfect beach.

So, while some websites on the Internet may claim sailing is a cheap hobby, it is an incomplete and one-sided discussion unless one is specifically talking about entry-level sailing. Once the budding sailor has the epiphany of that first sunrise offshore, arriving at a new destination that is exotic and exciting, or wins a trophy for a race well sailed, it is no longer a casual, “cheap” hobby that requires only the most basic financial investment to enjoy.

And most sailors would not have it any other way. It keeps the sport exclusive for those dedicated souls who find being on the water is the only way to live.


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