Sailing as a sport and pastime likely started when other means of propulsion came into being for commercial shipping. The steam engine, steam turbine, and diesel engine were the death knell for the famous Clipper ships that plied the oceans for trade in various commodities around the world.

Today sailing can take many forms, from bobbing around a cove or a lake on a small one man dinghy to circumnavigating the world in a sturdy ocean-ready cruiser, and plenty in between. Racing has always been a part of recreational sailing too, most famously the America’s Cup inaugural event, and the famed Bluenose winning the old Schooner races near the end of the ‘fishing under sail’ era on the US and Canadian East Coast.

Sailing requires some basic skills and knowledge, much more than hopping in a runabout and tooling around the bay. Understanding the physics of moving a boat by breeze takes training and practice. Navigation, weather awareness, storm techniques and many other skills are required when sailors venture beyond their local harbour.

Sailing can be entered into at many levels, and deciding at what level you want to jump in is the first decision you need to make. What follows is a brief simplified breakdown of the various types of sailboats you might consider.


These fall into two categories, sailing dinghies – small, 12 feet and under, single masted boats with room for one or two, generally quite stable, not necessarily fast and mainly meant for pleasant, lazy circuits of your favourite local lake or harbour. They may feature lug sails, sprit sails or perhaps even a 2 sail sloop rig in some cases.

Racing dinghies make up the other sector. These are generally powered up boats, very quick when well handled, athletic boats that require skilled agile crews to stay upright. Competitive racing fleets exist around the world, often in ‘class organizations’ where the boats are all kept strictly identical so that truly ‘the best sailor wins’. Examples start with the ubiquitous 14 foot Laser, a one-man single sail boat, to the more recent powered up ‘49ers’, two man boats with a powerful sailplan and capable of flat out planning speeds.


A step up from dinghies, these are single masted single sail boats that are big enough, usually , to have some accommodations below decks. There are more modern cat rigs today from a few manufacturers, their appeal lies in ‘the look’ and simplicity in handling.


Once you’ve graduated from dinghies, the next most popular recreational sailboat is likely the sloop rigged boat. A single mast, and usually two to three sails (Mainsail, Headsail(s) and perhaps Spinnaker) make for an efficient rig for making good way in a wide variety of wind conditions and directions. Sloops can be a small as dinghies, but today there are sloops over 200 feet long. Most typical is a boat with some accommodation somewhere between 20 and 50 feet in length capable of being sailed by as few as one or two people.

The term cruiser is intended to describe boats that are not necessarily particularly fast for their size, but more focused on creature comforts, room for lots of stores and supplies, designs deemed more ‘seakindly’ and perhaps better suited for more ambitious passages and/or living aboard for extended periods.

Sloops considered to be racers are faster, more performance oriented, will have fewer amenities below to save weight and may require crews of 6 or more to efficiently race. These are sometimes raced in ‘one design classes’ (all identical, like big dinghies) but more often rated and compared in some sort of handicapping system.

There are also boat designs labeled ‘Racer/Cruiser’ or ‘Cruiser/Racer’. These boats are designed to do either, but with more emphasis of the first type in the label.


A cutter is a single masted sailboat with two headsails often flown at the same time. The mast is further aft in the boat to maintain good characteristics and behavior.
The cutter rig is favoured by many ocean sailors for the added variety it provides in balancing the sail plan to match the conditions at sea.


The main two masted rigs you’re likely to see will be Ketches and Yawls, followed by Schooners. They are each quite different, but the ketch and the yawl can be difficult for the layman to differentiate. Both have the taller mainmast forward, with a smaller mizzen mast aft. A yawl’s mizzen sail is generally smaller than a ketch’s, primarily because the yawl’s mast is behind the rudder post closer to the stern of the boat.

Schooners have a main mast aft, with a foremast forward of that creating a very different look that many associate with the ‘good old days of sailing. Many schooners (and ketches and yawls) will likely carry double headsails like a cutter does. This makes each sail smaller and more manageable, creates more combinations for good balance. There have historically been schooners with three or more masts as well.

All the above mentioned boats use what is called a ‘fore and aft’ rig, unlike the old square rigged clippers, barques of the golden age of sail.

Today, after dinghies, entry level boats tend to be in the mid 20 to mid 40 foot range with many sailors getting out for day sails, or weekending. Some manage to get away for several weeks in a summer cruising season but seldom venture more than 100NM from home. Still others eventually girdle the globe.

The ability to choose your poison is one of the things that makes sailing such a neat activity.. you can race, you can cruise, you can pott about, you can stop and fish, you can anchor overnight in a romantic cove with your lovely, the possibilities are quite endless.

But the first step is to decide how to start.