How Do I Choose A Sailboat?


Last Updated by

Daniel Wade

May 12, 2020


Before the 1960s, boatbuilders constructed sailboats one-at-a-time to suit a customer’s specific needs.  They built the vast majority of recreational craft out of wood using skills passed down through generations.  Boat designers and boat builders had extensive sailing experience, so they often knew how to guide a project to suit a buyer’s desires. By the middle of the 20th century, something big happened.  Engineers pioneered fiberglass boat construction which allowed factories to mass-produce standardized sailboats.  Hundreds of models from dozens of manufacturers soon flooded the market.

These days, many excellent used sailboats go up for sale every day.  The majority are fiberglass boats, but some wooden designs pop up occasionally.  Most of these boats are quite affordable but there’s so many to choose.  Before buying a sailboat it’s essential to consider several factors to ensure it fits your plans.  You wouldn’t want a dinghy for long offshore passages, nor would you appreciate a 55-foot schooner for an afternoon on the lake.  In this article, we’ll go over what you need to consider before choosing a sailboat.


Table of contents for this article

What to Consider Before Choosing a Sailboat

You can’t just pick any old sailboat for any old passage.  Without careful consideration, you could end up with a boat that’s unfit for your sailing goals.  Worse yet, you could be stuck with a boat that’s too big to handle.  Luckily there’s plenty of information available on virtually every kind of sailboat ever sold.  But before we dive into the specifics, ask yourself a few questions.

Where do I plan to use my boat?

A deep, heavy, and lumbering offshore cruiser isn’t necessary for short regattas around San Francisco Bay.  It’s essential to be realistic about your sailing goals.  While it’s nice to dream about weeks at sea, it’s usually not wise to purchase a blue water sailboat unless you honestly intend to use it offshore.  That being said, the opposite is also true.  Unless you’re a highly experienced sailor, it’s best to pick a large and hardy boat if you intend to sail offshore.  For coastal cruising or occasional overnight trips, a pocket-cruiser or day-sailor is a better choice.

Where can I afford to store my boat?

If you own fifty acres of land near Galveston, you probably won’t need to worry about storage.  In reality, most people can’t keep a large boat on their property.  Marina and dry-storage fees increase with every foot of length, which makes a smaller boat more economical.  For occasional sailors, a tailorable cruiser is a great choice.

How long do I plan on staying aboard?

Many people spend multiple days on their boats.  Sailboats over 20-feet in length usually have cabins with amenities, and many include full showers and kitchens.  Thousands of people live aboard their sailboats full-time and enjoy the many freedoms that come with it.  For a liveaboard, you’ll want a cabin with at least 6-feet of headroom.  Oh, and bathroom facilities are a must.  If you have no interest in sleeping aboard, you can sacrifice cabin space for lower mooring fees and upkeep costs.

How many crew members will I take along?

Cabin space is imperative for extended voyages with other people.  While you might be okay with sleeping in a pipe-berth above the stove, your guests might not be.  Fortunately, you don’t need a crew to operate some sailboats.  Many boats are single-handers, which are easy to sail without an extra hand.  Before you buy, be sure to determine how you want to crew your vessel.  If it’s just you aboard, don’t buy a massive sailboat with complicated rigging.  You don’t want to buy a boat only to discover that you can’t use it.

Sailboat Size

The size of a sailboat can play a significant part in its capabilities.  It’s pretty easy to narrow down the appropriate dimensions for your boat.  If you want a cabin with living space, you’ll usually need to go above 20-feet in length.  However, sailboats like the West Wight Potter 19 and the Cal 20 offer comfortable cabins.  For standing headroom, you’ll generally need to search for boats 25-foot in length or longer.  If you plan on taking extended blue water voyages, you’ll need to be especially careful when choosing a sailboat size.  If the boat is too big, it’ll be difficult (or impossible) to handle alone.  If it’s too small, it’ll be uncomfortable or hazardous.  For single-handed offshore passages, boats between 26 and 35-feet are often sufficient.

As with any rule, there’s always an exception.  Pacific SeaCraft once produced a remarkable 20-foot offshore cruiser called the Flicka 20.  This heavy-displacement sailboat fit on a trailer and often made long blue water passages with ease.  Its small cabin featured a full berth, shower, kitchen, and sitting area.  It was one of the tiniest ‘real’ offshore cruisers ever, and it’s an excellent choice for minimalist sailors.

Hull and Keel Type

There’s a wide variety of sailboat hull shapes to choose from, but it’s not all for looks.  Slight variations in hull shape and displacement cause considerable differences in handling.  Traditional sailboats often feature a long, heavy, and deep keel called a full keel or displacement hull.  Also known as a ballast keel, these boats are a great choice for heavy seas and long offshore passages. Their deep, heavy keels offer excellent stability and increase motion comfort.  While displacement hulls are a proven option for offshore sailing, their weight can make them cumbersome to store and operate in shallow water.  Another excellent long keel option is called the fin keel.  Fin keels are usually narrower and lighter, resulting in nimble handling characteristics.  These vessels are fast, light, and can hold their own on long voyages.

However, long-keel sailboats usually draw several feet below the waterline, which can make shallow waters impassable.  This is where a bilge keel truly shines.  Unlike full and fin keels, bilge keels are off-center on the port and starboard side.  With multiple keels, you can navigate shallow water and remain stable when heeling.  Bilge keels offer superior motion comfort to fin keels but typically fall short of traditional designs.  A bilge keel is an excellent design for the typical cruiser.  If you don’t spend much time in the ocean, a centerboard may be the best design for you.  A centerboard is a fin keel that you can remove, allowing passage in very shallow water.  You’ll still need to watch out for your rudder, but centerboard boats are great for lakes, reefs, and rivers.  What these cruisers lack in offshore capability they make up for in versatility.  Island hopping boats such as sharpies use centerboards to allow easy beaching.

Another less common form of shallow-draft sailboat uses leeboards.  This classic Dutch design features retractable hinged fins mounted to each side of the hull, providing the same features as a centerboard.  Only one board is in lowered at a time and switched during tacking.  Leeboards were once ubiquitous on smaller workboats in Europe, and you occasionally run into them on unique cruisers.  Many people consider leeboards to be awkward, but some traditionalists prefer the design.  Island hoppers benefit from leeboards, as the lack of a centerboard trunk increases cabin space.

You can read more about keel types, here on Life of Sailing.

Hull Material

Fiberglass boats satisfy the majority of boat owners.  These vessels are durable, long-lasting, and relatively easy to maintain.  Most foreign tourist ports provide access to glass and resin, so on-the-go repairs aren’t usually a nightmare.  For some, fiberglass doesn’t cut it.  Working with the material often requires sanding which produces toxic dust, and fiberglass epoxy can be particularly noxious.  Wooden boats are an excellent choice for a traditional sailor, and you can even build one yourself.  There are many types of wooden sailboats, but you can expect to pay more upfront for all of them.  Well-built wooden boats last for a century or more, and upkeep is usually non-toxic and straightforward.  A wooden sailboat can be extremely rewarding to its caring steward, but they require specialized tools and meticulous care to function.

When it comes to hull material, there’s no right or wrong answer.  Whether you choose fiberglass, wood, steel, aluminum, or even ferro-cement is a matter of preference.  For the majority of sailors, a simple fiberglass boat will perform brilliantly.


It’s a good idea to consider the popularity of a sailboat before choosing.  Common sailboats have lots of user data available on sailing forums, so you can get an idea of how it handles.  Online resources help you figure out what issues are common with your boat, and what upgrades fellow sailors recommend.  The more popular the vessel is, the more resources exist.  

You’ll often find 1960s and 1970s-era sailboats from big names like Catalina, O’day, Contessa, Cal, and Pearson.  These are all great boats, and they each have large online communities.  When choosing a sailboat, do some brand research.  If you can’t find much information about the boat, it may be best to investigate it yourself.  Just remember to choose the sailboat that best fits your needs.

How Do I Choose A Sailboat?

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