I recently wrote about people expressing interest in getting into sailing (Read: Is Sailing Hard?). That involved how to identify the various ways to learn the ropes, so to speak, and gain skill and confidence on the water. There are sailing schools, associations, clubs, as well as meeting other sailors who are also learning how to sail or have more experience and can assist you in many ways. It is a sport with lifetime potential, and I think all of us in the industry will do anything to help new people join the ranks of our sailing community.

At some point it becomes the right time to purchase one’s own boat and take things up a notch by becoming a boat owner. Trust me, you can sail dozens of times on other people’s boats, even ocean passages that take weeks at sea. But until you are the captain of your own boat, it isn’t the same as when it is all on you. The intense personal satisfaction of making landfall on one’s own boat is unlike most other life experiences. The pride, confidence, and overall pleasure is almost beyond words. You make the decisions (even if it seems a collective crew effort), you have overall responsibility for safe and successful navigation to reach port, and you are ultimately responsible to manage the weather and other conditions for which you have little control.

This is true for a week offshore to an island or an afternoon across the bay. The added responsibility as owner/operator makes all the difference. If you enjoy the role and choose to remain a captain throughout your boating life, that unique and satisfying mindset will stay with you forever. There are a variety of different types of sailboats for sale on the market at any one time, here are several sailboat types for you to consider:


1. Center Cockpit: Sailboats with the cockpit well forward of the transom, somewhat midships. This allows more accommodations below decks, usually in the form of a large master stateroom. An aft cabin offers outstanding privacy from the rest of the boat, and owners find the location can be more luxurious and spacious than a traditional V-berth cabin in the bow.

The center cockpit offers increased crew protection at sea, as people are off the water as opposed to an aft cockpit. The layout also provides great access to the ship’s engine room, located under the cockpit and accessed from either passage under the deck, with a galley often on one side.

For living aboard and extended cruising, the center cockpit sailboat is very popular.

2. Cruiser: A generic and popular category of sailboat. It generally refers to those sailboats that have accommodations below deck and enough displacement to be self-sufficient for extended periods. For sailors who like to live aboard as they travel and experience the world, it is the sailboat category of choice.

3. Cutter: A sailboat with a single mast and at least two headsails. The configuration breaks up the overall sail area of the large headsail found on a sloop and provides the ability to fly two smaller headsails at sea. This allows the crew to adjust one or both of the smaller headsails to fit the sailing conditions. On a boat sailing offshore, the cutter offers greater flexibility than a sailboat with just one headsail.

4. Daysailer: Any sailboat that is intended to go out sailing for a limited time, such as the day or afternoon. Daysailers do not need the complex comfort systems and living area of other sailboats, although larger daysailers of late include below-deck living space for the occasional overnight and weekend use.

For new sailors just learning the ropes, as well as older sailors who are done with the demands of managing big cruising boats, the daysailer is the perfect choice to enjoy and extend one’s time on the water.

5. Deck Saloon: A sailboat with the saloon raised up close to the level of the cockpit. This layout offers much better visibility of the surrounding world for those inside the boat, usually with large windows to bring in light and offer a view of the world.

Many modern designs offer this layout in their larger models, as it gives sailors a connection to the outside world, one of the attractions that draws sailors to trawlers. In wet and cold weather, it is an ideal way to enjoy the journey, while warm and dry inside the boat. And when it is a rainy day at anchor, no one needs to feel stuck inside a dark sailboat interior.

6. Ketch: A sailboat with two masts, which splits the overall sail plan into numerous smaller sails, allowing easier adjustments for a short-handed crew. This arrangement is less popular than it once was, mainly due to the introduction of modern sail handling systems and powered winches. But the ketch still offers advantages to the traditional sailor who wants all the control of sail management without relying on systems.

7. Motorsailer: A sailboat that has a large diesel engine as auxiliary power, much larger, in fact, than is required to simply get in and out of one’s slip. A true motorsailer has sufficient horsepower and fuel tankage to travel long distances under power. A passagemaking motorsailer can use both propulsion sources quite effectively, able to cross an ocean under power alone, or downwind in the trade winds using both engine and sails, which contributes to high daily runs with great fuel economy.

Often maligned as being neither a good powerboat nor a good sailboat, the motorsailer concept could eventually prove the ultimate passagemaking solution if its evolution continues to develop the concept.

This is particularly the case as running under power eliminates the need for towed generators, solar arrays, and other means of generating electricity under way. The vessel already has all the electricity it needs to run the many appliances and systems of the modern large cruising boat.

8. Pilothouse: A sailboat that incorporates the deck saloon with an inside helm for ideal crew protection beyond what is possible from a dodger. This can be considered the best solution for running a sailboat in all weather, as the helm is protected from the elements and the crew can stand watch without being cold and wet. It is also synonymous with sailboats of the motorsailer category. If one expects to motor for significant periods, having a pilothouse is simply the standard for comfort and utility that cannot be offered with a traditional cockpit.

9. Racing Sailboat: Boats built for performance at the expense of other considerations. Depending on the level of racing that forms the basis of the design spiral, a racing sailboat can be a tricked-out shell with only one purpose, to be sailed by an athletic and aggressive crew. Or it can be an otherwise capable cruising boat with design modifications to provide a higher level of competitive performance. It can also be a large sailing platform that requires numerous crew to handle the many systems and controls to get the most out of the design. The best of these boats can sail around the world at incredible speeds in record times.

As one would expect, all-out racers are a terrible choice for relaxed pleasure boating. Yet many race boats that are not as extreme can make very competent cruising boats, offering speed and long daily runs with a degree of comfort.

10. Sailing Catamaran: A sailboat with two hulls, the catamaran has been one of the most dynamic additions and success stories in recreational boating. The modern sailing catamaran offers outstanding stability, comfort, and space. It is especially attractive to new boaters who do not come into sailing with ingrained preferences from learning to sail on monohulls.

Catamarans have much to offer people who like shallow draft (some can be beached quite easily), easy and relaxed sailing in most conditions, and expansive room afloat for living aboard. In addition to sailing without heeling, the visual space on catamarans is particularly appreciated when sailing in warmer waters where crew prefer open air living.

The number of catamaran builders has increased in recent years, and there are dozens of product lines to choose from.

11. Sloop: A sailboat with a single mast and a headsail flown from the bow. The majority of sailboats today are sloops and its variations, but all share one headsail flown at a time as well as a large mainsail.

The sloop rig dates back centuries and remains today’s most efficient sailing rig. Its simplicity of sail and rigging allows a sloop to sail close to the wind. For most sailing, whether day sailing, racing, or cruising, the sloop is preferred for its speed, efficiency, and simplicity.


Some sailboat builders, like Tartan Yachts, have combined features for the sailors that want to go fast, but also be comfortable while cruising. The Tartan 365, seen below, is considered a 'performance cruiser' thanks to its speedy performance while also featuring a spacious saloon and cabins.

tartan 365 cruising sailboat 


Lots of Choices

It is not surprising there are numerous choices when it is time to buy your boat. Walk the docks of any boat show and you see big and small sailboats with one hull, two hulls, even three hulls. Banners, floating tents, flags, and music thread throughout the show docks, along with throngs of people, from experienced captains and crew to inexperienced people also looking to see what is out there.

Unfortunately, the placement of boats in a boat show does not necessarily showcase boats grouped by size or purpose, as maximizing available dock space is often a challenge to show organizers. Even so, some effort is usually made to make it easier to navigate so you can find boats of a certain kind that may be of interest, especially if you have done your homework before the show.


Not Your Father’s Daysailers

For example, if one is specifically looking at daysailers, or day cruisers, these boats may be spread over land and water. Thankfully, the show program usually lists them by location or slip number.

In days gone by, some lovely large yachts fit into this category, and they were used to only go out for an afternoon sail, everyone dressed in their nautical finest.

Today, most daysailers are sailed by a small crew, perhaps just you, but still less than six people. Men and women of all ages sail these simple boats around a protected body of water. Daysailers were once considered the smallest and simplest category of sailboat, not very expensive, and they offered little in the way of varnished brightwork and fancy details and fittings. There was not usually even a tiny cuddly cabin to go below to use a head or pull out some sandwiches and drinks from a cooler kept below.

Examples of these boats range from the ever-popular Flying Dutchman and small sailboats one finds at a lake, to more modern and aggressive foiling boats like the speedy Moth.

(Below: Example of a Flying Dutchman.)

example of flying dutchman sailboat

(Foiling boats were all the rage and can achieve significant speeds that are thrilling and test the skill and balance of the people sailing them.) Over the years, daysailers have had every possible rig and sail combination, whatever it took to allow one to three people to enjoy time on the water with some degree of control.

But daysailers got a little bigger, nicer in fit and finish, and many are now considered ideal for serious sailing, yet still over a short distance and still with just the basics. They range from cool little catboats manufactured by many builders to classics like the Herreshoff 12.5. There are others that loosely fit into a “traditional” group, such as the Stuart Knockabouts.

(Below: Example of a daysailer.)

example of daysailer

The most popular daysailers now are a healthy mix of technology, simplicity, and ease of handling that makes them a joy to sail and own. Tartan’s 26-foot Fantail is a stellar example, as are the Colgate 26, Catalina 22, Hunter 22, Montgomery 17, and the First line from Beneteau. One can go out for a day and just have fun, with lunch at anchor. No need for air conditioning, bunks, or comfortable living below decks (if there even is a cabin). These boats demand little from their owners in terms of maintenance, certainly much less than the more complex cruising sailboats in the typical anchorage.

The lucky sailors among us remember the wonderfully simple feeling of pulling up the anchor by hand or dropping the mooring, raising the small mainsail, sheeting in the jib, and finding the groove to make the sailboat slice through the water with such balance that it only takes a couple of fingers on the tiller. The simplicity of the daysailer can be very satisfying to one’s outlook on life. This contrasts to our experiences on the cruising sailboat, when the stove won’t light, tools come out, and time is spent fixing things that would be better spent under sail.

Pure sailing versus the ongoing ownership struggles of a boat with complex systems. I’m all for that.

The daysailer category expanded into the luxury market, with the introduction of decidedly upscale sailboats aimed at a higher echelon sailing audience. These folks have the budget and desire for taste, style, and performance in a sailboat for an afternoon on the water and perhaps an overnighter on occasion.

For years, the beautiful lines and finish of the Carl Schumacher-designed Alerion 28 were almost unique in the daysailer group. That is until Sparkman & Stevens, Bruce King, and other top-shelf designers were commissioned to draw their interpretation of a luxury performance day sailboat. High quality builders, such as Hinckley and Morris, introduced exquisitely designed and built boats that glistened with teak decks and dozens of layers of varnished brightwork. Forget traditional sailboats for yachtsmen wearing ascots and straw hats. These boats are carbon and epoxy and Kevlar, have carbon fiber masts, the latest systems, self-tacking jibs, deep spade rudders and keels, and slippery shapes that are simply breathtaking to watch under sail.

The popular Morris 36 was joined by its larger 42 and 52 sisterships, with just enough accommodation to serve for overnight and weekends afloat. Hinckley introduced its Daysailer 42, and the DS42 still turns heads wherever she goes.

If you ever see a Friendship 40 from Friendship Yachts in New Zealand, it is quite stunning. And Chris Hood’s Hood 32 makes the definitive statement of sailing romance and beauty against the backdrop of a charming anchorage sunset.

(Below: The Friendship Yachts 40.)

Friendship Yachts 40 Sailboat


A Racer for Today’s Sailor

When a builder sets out to produce a new model destined to spend most of its life on a racecourse, the transition from daysailer to racer is a blur. The J/70 is such a boat, and while the Soling is focused on racing, it has been used as a daysailer and trainer for years.

The attributes that make for a successful daysailer may also make it competitive in a race, especially if the reduced weight and minimal creature comforts gain speed and handling advantage on the water. When there are enough boats produced to create a one-design class, then it is simply a matter of time before a new boat is considered a racer.

To be clear, true racing sailboats are not like daysailers in any way, as they are engineered to withstand the stress of pounding and leaping through waves while being the lightest weight possible, accomplished through superior engineering with modern materials. Hard core racing sailboats trade everything for speed and outstanding maneuverability. They don’t come with cushions, comfortable interiors, or any systems that add weight at the expense of performance. Visit any dock during a race weekend in a sailing town or club, and you will see that today’s racing fleet share little to the gentlemen sailboat racers of past generations.

Perhaps even more telling is that racing sailboats require more crew to sail competitively, up to six experienced people for a J/105. There are many lines to adjust the sail plan, from changing the shape of the rig to modifying the angles of the running rigging to the sails. One needs these extra crew to manage these controls. A daysailer is a piece of cake by comparison.

Where J/24s once ruled, today’s amazing racing designs look fast even tied to the dock. The Dehler 30, Mini 650s, Class 40s, Farr 40s, and X-Yachts are purpose-built racing machines that stand apart from the middle of the road racers. The Jeanneau Sun Fast 3600 strikes a balance between the extreme, all-out racing boats and other popular choices, such as the Harbor 20 and Etchells.

(Below: The Dehler 30.)

Dehler 30 sailboat 

If you examine the racing that happens well offshore, you will see the ultimate in sailing performance. These are rocket ships designed to cross open oceans, throwing huge rooster tail wakes because they are so fast. They have almost nothing in common with “normal” sailboats.

One difference between racing sailboats and their cruising counterparts can be seen in the sail inventory. Racing sails have a unique purpose, and they are not expected to last as long as cruising sails. With a significant portion of time racing up wind, sail shape is critical compared to the typical downwind sailing of the cruising sailboat, where sail shape is far less important. And while cruising sails are expected to last up to 10 years, racing sails may last one season or less, depending on the sailing conditions and one’s pursuit of performance perfection.

If one is attracted to the racing scene, attending a regatta or race series where there are many boats of different designs will be way more instructive than anything I might say here. This is especially the case if you break the ice and explain to some skippers and crew about your interest. You might be on a racing sailboat before you have a chance to say no.

If that is agreeable, you will never look back, and your path to your passion is all but assured.


A Cruising We Will Go

Again, what would seem an obvious distinction between a dedicated racing machine and one that is intended for cruising is as blurred as the move from daysailer to racer. This should not come as a surprise, however, given there is a broad category of sailboats that are considered racer/cruisers. These are boats with performance characteristics that allow them to successfully compete, but a boat that also has comfortable accommodations and does not require as many crew.

Unlike the austere interior of a sailboat racer (where one might be lucky to sleep on a sail bag), a racer/cruiser often makes a very suitable cruiser. This is particularly true for those who prefer to travel light, or for racers who also want to cruise with family. And it is just the ticket for a sailor who can’t stand the idea of going slow. Circumnavigate on a J/boat? You bet!

When one gets into the realm of cruising boats, I think it is fair to say the majority of sailboats today more or less fit into the cruising category, for several reasons. The evolution of the sport gravitated to purely recreational boating, no matter how the boat may be otherwise used. That means nights spent at anchor or in town, in a marina or on a downtown bulkhead, which often become the highlight of being on the boat. Meeting new people, seeing the local sites, and eating locally can become more compelling than sailing to get there.

I am not suggesting that sailing today means the destination is now more important than the journey, but rather the experiences after arriving are often totally spontaneous, and create memories and friendships never anticipated. One might say that is true of travel in general, although there is a camaraderie among the sailing community that one will not find railroading across Europe or driving around the national park system.

A cruising sailboat usually has enough displacement and length to handle more than simple accommodations with only space for a toothbrush. Today’s contemporary modern interior style is a wonderful complement to the traditional teak interiors common for the last 50 years. Both can easily serve as a comfortable home for as long as we choose to be aboard…even full time.

(Below: Inside the Hanse 460.)

interior of the hanse 460 sailboat 

I want to make a distinction here that I am discussing cruising sailboats that are used on coastal and inland waterways. Boat builders know that most sailors never intend to go offshore or make major passages. So, when they build their product lines, they may design and build the boats to be certified for offshore classification, but they stop short of finishing them for bluewater sailing. They build the boats to the point where they are within 80 percent of being ready for going offshore or around the world. There may be provision for a life raft in the cockpit, for example, but they do not fit a life raft locker as part of the standard build specs. The same is true for interior fittings and details that one will need to add to go offshore.

Cruising sailboats vary tremendously in size, shape, and number of hulls. And to add to the above comment about the standard production boat not ready to leave, there will be an additional investment in things one needs to go cruising. Many are essential, some required, all appreciated.

The cruising essentials include a dinghy and outboard, the tools of the trade (including binoculars for all crew), lots of fenders of different shapes and sizes, extra lines, a wide range of sail inventory, and cookware that includes everything from a colander to kitchen knives. Music players of some kind, television, Internet, logbooks, a full complement of navigation and communications equipment (plotter, radios, AIS, GPS, radar, charts), and the list goes on.

Spares for the systems and engine, from light bulbs to engine belts. Medical kits and first aid supplies. Dive mask and gear. Beefed up anchoring gear, and an extra anchor and rode are considered necessary. Let’s not forget the exterior canvas, which can include a dodger, bimini, perhaps an awning.

The complete list includes everything you need (or might need) to be totally self-sufficient. Initially this can seem intimidating, but it is also very satisfying…and addicting. One quickly learns that being self-sufficient has so many benefits in one’s life. Being able to live comfortably at anchor anywhere is a simple life pleasure that one must experience to understand. (I once anchored outside of Seattle in my wood ketch a thousand years ago, and it started to snow. The hushed sounds of the anchorage around me, while I was snug and cozy inside my wood boat with a toasty fire in my small fireplace, was grand and indescribable. No world problem could shake my serenity. I had everything I could need right aboard my naturally insulated home. It is a treasured memory.)

(Below: Youtuber @SailingGear2777 reviews 12 essential items to bring with you cruising on a sailboat.)


Stop With the Spreadsheets

When I looked at what else was on the internet about the different types of sailboats, I was surprised to see all the blogs and articles talking about how many different types of keels and hull shapes there are. What’s going on here? You are looking for a boat to go sailing, not documenting the history of the sport through the ages.

I am sorry but I don’t get such a sophomoric approach to this subject.

Sure, if you want to tuck into shallow waters for a few days, perhaps into the mangroves where there is plenty of protection from running seas in deeper water, fine. Or if you want to be closer to the shore to take your dog for a walk on the beach, no problem. Choose a boat with a centerboard or lifting keel, or a multihull, which will allow you to anchor in very skinny water. Enjoy…possibly along with the mosquitoes and flies.

Everything I’ve talked about applies to most every boat shape. Monohull, sailing catamaran, trimaran, they all fit this discussion.

The other issue these “experts” felt important to address is the boat’s sailing rig. One mast, two masts, single headsail, multiple headsails (cutter, Solent, etc), and how one must find the rig that best fits their needs.

Sorry, folks, but again, try not to get bogged down in such academic gobbledegook. Your broker will help sort out the good, the bad, and the ugly as it relates to anything that he or she shows you. There is no one rig that is best. You are not going offshore for weeks on end, so your search for a cruising boat doesn’t mean you need to adopt a NASA engineering worksheet full of equations and calculations.

Go to a free lecture or paid seminar at a boat show on selecting the right boat. Usually given by sailing couples living the dream who are willing to share their experience, they can present a most resounding argument for what works for them. After a couple of hours of lecture and Q&A, you’ll come away convinced that such-and-such a boat is ideal for you. Its hull shape is proven, others have done some amazing voyages, and you are now convinced its sailing rig is the best you will ever find. I’ve seen this countless times.

Then you go to lunch in the show food tent and happen to share a table with an interesting couple taking a break from tent duty. You learn that they just completed a circumnavigation several months ago and are helping work the builder’s booth at the show.

As they answer your questions, you learn they had a wonderful, totally uneventful world cruise on their center cockpit sloop, which leaves you totally confused. The boat they went around the world in is the opposite of what you’ve just convinced yourself you had to have for your summer vacations.

This is such a common occurrence I find it kind of funny, because it really messes with peoples’ heads…but in a good way. The experience really grounds them before they go off chasing something that isn’t anywhere near as critical as they convinced themselves it is.

When Sir Robin Knox Johnston sailed solo around the world in the first race of its kind, he chose Suhaili, a 32-foot Atkin-designed ketch. Among the dozens of potential boat designs to undertake a voyage that many believed at the time was impossible, he chose the wood ketch he already owned. Simple. He just took his own boat, as it was the only boat he could afford.

Keep in mind very few of us will ever sail out of sight of land, let alone around the world by ourselves without stopping. Of course, there are lots of differences between boat shapes, rigs, and such, but it is easy to get information overload. We tend to overthink all of this, and it is not hard to do.

As every combination of keel, hull, and rig has its pros and cons, one can be talked into one or the other, depending on what day it is. Personally, I would rank a dedicated chart table higher on my list.

That is why I feel working with a good broker is critical. He or she will sway you away from ideas and choices that might work great if you are rich, but otherwise complicate your list of requirements and keep you from making progress, perhaps highlighting you prefer shopping more than going cruising. You can enjoy sailboat cruising on many kinds of boats. It almost doesn’t really matter if it fits your basic needs. Most will do just fine.

This is especially true with multihulls. Catamarans are all the rage these days, and to a lesser extent, the elusive cruising trimaran. The days of the negative stigma associated with multihulls have gone the way of the Greek fishermen’s hat. (Those wisened old salts who wore them and freely offered their opinions have mostly passed on by now. Their opinions, mostly hearsay from the early days of pioneering multihull development, are no longer relevant on any level.)

(Below: The Excess 11 is a great option for owners wanting a sailing catamaran.)

excess sailing catamaran 

But the Greek Fisherman’s hat remains a metaphor to me about obsolete sentiments every bit as useful today as Hal Roth’s tirade 50 years ago of the stupidity of having electricity on a sailboat.

Whatever your plan is to buy a boat to go sailing, don’t get bogged down in search of the perfect boat. It probably doesn’t exist. If you want to simply go sailing for the day, there are lots of choices, and you do not need to spend a fortune. Just get the blue one. (If it turns out to be a Flying Scot, good for you.)

If racing seems like it will get your blood flowing and it is a fine way to feed your competitive nature while detaching from the pressures of a busy life, that will prove thrilling in so many ways. You will become a much better all-around sailor, and you will make lifelong friends with whom you will likely sail against for years to come, even though you tell everyone you are just “cruising.”

But if the horizon beckons, and the thought of watching dolphins leap in your bow wave as you sail up the coast or visit historic places along with friends on their boats as part of an organized cruise, go for it. Have a great time.

I guarantee you will have stories that beat any tale from anyone who spends their time on the golf course. The great stories of sailors everywhere, whether you believe them or not, are always worth telling and retelling year after year.

Sailing is a passion of a life well lived.


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