During all the years I have been sailing, especially as a small-boat sailor, one question invariably comes up. And depending on where the discussion takes place, possible answers are all over the board from well-meaning people accustomed to traditional answers to this classic question.

With social media and the general free-for-all of everything now published, printed, texted, emailed, and discussed on the dock and at boat shows, it seems to be as popular as ever.

Just how large a sailboat can one person sail single handed?

A 40-foot sailboat is the maximum size for one person to be able to single-handedly control safely. It can be successfully argued up or down a couple of feet, based on the experience and abilities of the sailor. This has been proven by a great many accomplished people.

Many sailors have done amazing voyages in boats well under this length, and others have made serious cruises on boats that are considerably larger. But a word of caution is in order. To focus only on length overshadows other important criteria. Other factors figure heavily in determining the suitability of a big sailboat for single-handed operation.

I am not talking about racing around the world by professional sailors, or across oceans to some destination hundreds (or thousands) of miles away. Rather, I am talking about an average sailor, man or woman, of average stature and physical condition, who has experience and chooses to sail alone. It may be a temporary lifestyle situation, or some other factor that sets the solo requirement for a boat that is to be safely sailed on a regular basis.

(Below: Youtuber Captain Christa sailing her 31-foot boat by herself.)

Another often overlooked kind of solo sailor is one whose spouse or partner cannot meaningfully contribute to operation of the boat. They may be disabled in some way that keeps them from taking part in the activity. Or they may be completely uninterested or inexperienced in sailing, or both, and they come along for the travel and adventure experience. I suspect this may be a larger part of the sailing community than many of us will admit. But if the boat can be out sailing under the control of the short-handed sailor, everyone is happy, and they get to explore new places and see the world together.

There has never been a size unanimously accepted for sailing voyages in the past. Even a brief look back at sailboat cruising shows that size is not universally important. John Guzzwell sailed around the world in his 19-foot Trekka, Tanya Aebi circled the globe in her Taylor 26 (the Canadian version of the Contessa 26), and Frank Casper cruised extensively on his 30-foot Elsie. On the other end of the spectrum is Bill Pinkey on his Valiant 47 circumnavigation, and, of course, who could forget Alain Colas crossing the Atlantic on his 236-foot, four-masted Club Mediterranee?

Mark Schrader sailed around all five capes on his Valiant 40, as did Jeanne Socrates more recently on her 38-foot Najad. Robin Lee Graham went around most of the world on his 24-foot Dove, and 16-year-old Laura Dekker made the record books on her 40-foot Guppy.

So, it should be clear that overall size is just a number, and not the only factor. Keep in mind that many of these voyages, particularly ones going after a record of some kind, did not involve regularly getting in and out of slips and marinas. And for others, it is just common sense that many small boats were chosen for financial reasons (and perhaps it was the boat they already had).

(Below: Solo-Sailor Jeanne Socrates on S/V Nereida arrives in Victoria Harbor.)

 Jeanne Socrates on her sailboat

When we look at many of these examples, I acknowledge that having a boat with only sitting headroom in the saloon is certainly doable, if not all that comfortable for full-time living. Small boats are inherently slower (forget the notion of 200-mile days), and simply don’t provide the quality of living experience many of us expect in the 21st Century.

Even as I write this, though, I know there are people quietly living aboard a 20-foot Pacific Seacraft Flicka or some other munchkin cruiser. I know, I was once one of them.

I have always enjoyed the simplicity and tuck-into-anywhere versatility of a small cruising boat. While I never harbored the dream of sailing to Hawaii like John Letcher in his 20-foot Island Girl, I did fantasize about living the good life in a sailboat under 26 feet. Those were the days. Every inch needed to serve double duty, interior furniture regularly transformed for other purposes: a galley, chart table, and liquor cabinet all in one. In my mind somehow it all worked.

But I was young and immortal.

Again, we are talking about an average man or woman, without Olympic-level physical ability, who is simply looking for a boat to enjoy cruising or perhaps live aboard. People like you and me, who may be young or old, and possess some sailing experience. A Catalina 30 or Southern Cross 28 is quite a comfy home for the right person, fully capable of extended coastal cruising. A well-appointed 36-footer may be the height of luxury for others.

There are many examples of boats out there with only a single person aboard. But as these sailboats get larger, so does their volume and weight, and the required equipment and deck gear gets more expensive and complex to handle the increased loads. At some point the relatively complicated systems to ease the chores of sail handling and close quarter maneuvering include electric or hydraulic winches, furling gear, windlasses, autopilots, and electronics. These systems are generally very reliable, if not foolproof, and require regular maintenance and occasional service.

Big boats also need lots of electric power for these systems and general house service, so it is not uncommon to run a generator much of the time under way when sailing. In recent years, new forms of power generation are out there, including more efficient diesel generators. And there are more choices for water, wind, and solar power generation as well.

The original 64-foot Kiwi Spirit II, sailed solo by 80-year-old Stanley Paris, proved too much boat for the aging sailor, as its systems were too complex and required continuous work to keep operational. His next KSII was only 53 feet overall but, while it was easier to handle, still too proved too much. The reality is that big boats are rarely, if ever, simple boats. And simple is good when it comes to solo sailing.

(Below: Stanley Paris on board Kiwi Spirit II.)

stanley paris on his sailboat

That being said, Jimmy Cornell, author of World Cruising Routes and founder of those popular ocean crossing rallies, gave a slideshow of today’s current cruising scene, based on data collected as host of his many events. The size of cruising sailboats has steadily increased over the years, mainly because current designs and systems fit the needs of many cruising couples and others. In his most recent survey, presented at the start of the Covid pandemic, he showed that the average size of cruising yachts cruising around the world (but not necessarily going around the world), is just over 43 feet. Most of these boats are sailed by couples. Yachts checking into Tahiti now average 45.2 feet. So, it seems that for extended world cruising with two or more crew, larger sailboats are mainstream, whether monohull or catamaran.

I am a member of the Ocean Cruising Club, and the biannual publication shares the adventures of members who are out cruising. The trend for most of these people, again mostly couples and those cruising with friends, is to be on larger boats than one would have expected some years ago. To read stories from people cruising on 54-foot yachts is common. The few solo cruisers who publish are in much smaller boats, often well under 30 feet.

There is an often-repeated “rule” that single sailors should not expect to handle a sail larger than 300 to 400 square feet. I don’t know where this came from, but it seems to be a universal belief. And there is also the conclusion that interior comfort can be sacrificed if the reduced boat size makes it easier to handle. As far as I am concerned, neither is the case these days.

While the complexity of systems on a large sailboat (50 to 60+ feet) may be intimidating for the average sailor, systems sized for a 40-foot or smaller sailboat are not, and often include some form of manual assist or backup. Electric winches on a 40-foot sailboat are really nice to have and are nothing compared to the monsters one finds on large sailboats. I sailed to Bermuda on an 83-foot sailboat with hydraulic winches, and they were impressive. And huge.

I spoke to Jonathan Bartlett, who runs the Annapolis loft for North Sails. North Sails is a big player in today’s sailing world, with over 70 lofts around the world. Jonathan’s years of experience certainly qualify him to speak with authority.

He never mentioned the 300 to 400-square-foot argument. His more immediate concern was the importance of a single person being able to get a big boat in and out of a slip. Even with a bow thruster, one often must be at the bow to fend off a piling or another boat, and if you are alone, who is driving at the helm? There may also be windage issues. And if one’s boat proves too difficult (ie., scary) to move in and out of the slip without drama, how often will he or she be inclined to even go out???

Jonathan said that, in his opinion, the largest boat size to be considered for a single sailor is 40 feet. And he feels that is more than enough boat for most everyone. Today’s boat designs offer as much interior volume and accommodations in 40 feet as the 45-footers of the 1990s. That is more than enough room for a single sailor, even for living aboard. Anything above 40 feet is just too much…living space, overall volume, and effort.

On the flip side, he added that the decks of small boats are often difficult to move around without stepping on tracks, cars, lines, and all sorts of other obstacles.

“A boat’s deck layout is really important for a single sailor,” he said. “Great footing is critical, and there should be fewer tracks to walk on, or having to walk between shrouds when moving around the boat.

(Below: The 348 from Hanse Yachts gives you the ability to control the entire Helmsman system from the cockpit.)

hanse 348 sailing yacht 

“How a boat is set up is way more important that the size of the sails.”

Jonathan pointed out that many of today’s sailboats are intentionally made to be easy to sail, with furling mainsails and smaller headsails. “Compared to the mid-1990s, we are getting away from large genoas, replacing them with larger mainsails. These mainsails are captive, easily reefed, and under complete control with full battens.”

He went on to say that smaller headsails are easier to trim, and for the solo sailor, why it is also vital that sail trim duties take place at the helm in the cockpit, so the single sailor can do it all from one place without a lot of moving around. The days of working at the mast are over.

“Look at the French designers and builders,” he went on. “They get it. The Jeanneau and Beneteau lines, for example, are all about very simple-to-sail controls, sails are easy to put up and take down, and the boats are very sailor friendly. That is what gets people to go sailing, because it is easy and fun.”

Big, powerful mainsails have mostly replaced large headsails, and short-footed headsails are easy to manage. Bartlett pointed out that the J/105 is a good example of a boat that is easy to sail. When it is easy to trim the main and jib from the helm, it is simple…and makes people want to go sailing.

(Below: The J/105 from builder J-Boats.)

JBoats sailboats

To further the simplicity argument, he suggested that, instead of the traditional spinnaker or Code Zero for light air, a gennaker in a sock is a better fit for the single sailor and probably the way to go. The gennaker is a free-flying asymmetric spinnaker that does not require a spinnaker pole and is flown from the bow. It is easy to control and can even be used when the boat is steered by an autopilot. It is easy to put up and take down, and one can drive the boat downwind in full control.

“Our sport pushes bigger boats than is usually called for,” he added. “And some builders consider their boats suitable to be single-handed, even when they probably aren’t. Hallberg-Rassy and Hylas come to mind.”

Two boats that he mentioned in our conversation as good examples of nice sail plans and controls are the Harbor 20 daysailer and the Outbound 44. I know the Harbor 20 fleet is a popular one-design at the Annapolis Yacht Club, as it epitomizes a sail plan that is so easy to sail, easily managed by one person. And he thinks the Outbound has a great deck layout and overall consideration for sail handling by a short-handed crew. While it is on the bigger side of the 40-foot mark, especially now as it is replaced by the Outbound 46, he feels the builder continues to work to make it fit the needs of the solo sailor. But at 46 feet, it can be a challenge to dock in close quarters.

Another line he feels hits the mark are the newer, 39 to 40-foot Jeanneau and Beneteau boats. They are also very simple and easy to sail from the helm. This makes people want to go out sailing again and again. The lack of drama is a lot more important than many realize.

The Tartan line of sailboats from Seattle Yachts now come with the Cruise Control Rig (CCR), designed to make sailing easier and put the controls back in the cockpit where they belong. Self-tacking jibs and furling boom mainsails go a long way to make life easier, safer, and more fun.

As far as sails go, Jonathan said the solo sailor should look at sails that are lighter and have lower stretch qualities. Traditional Dacron sails are heavy and “stretchier,” whereas new composite sails offer light weight and are flatter in shape that won’t easily stretch. Heavy Dacron sails are also harder to trim and tack.

If one is outfitting a boat for solo sailing, composite sails are the way to go.

I have long been told that a larger boat is easier to handle at sea, as the motion is more settled. I think that is true, especially when compared to a 28-footer bouncing around in choppy seas. Up to a point (and that 40-foot mark) a boat’s motion can be more comfortable, under way, at anchor, or at the dock. That is especially true if one minimizes weight at both ends of the boat. Small boats tend to hobbyhorse when sailing because it is difficult to keep the ends light.

On a bigger boat from a good designer, the boat’s motion is not only easier to live with but is decidedly faster through the water. Daily runs are possible that can not be achieved in smaller hulls.

Another consideration is space. Small boats compromise space in every respect. For a single person (and the sailor who cruises with a non-sailing spouse), accommodations on a 40-footer are more than enough, and there is still space for increased fuel and water tankage for longer range and self-sufficiency. Being able to motor a long distance is no longer a luxury in many cruising areas and having sufficient water supply lessens the requirements for a watermaker.

Additional space also means one can carry more batteries, and the components of other systems, and proper access to them. It is imperative to have good access for a happy ship.

As I already mentioned, having a way to generate electricity while sailing is vital, to power all the systems, electronics, and autopilot. This gets harder to fit inside a small boat and represents a real challenge. Access is usually also compromised in the process of fitting it all in.

I am not pushing that everyone buy a big boat, but I know from past experience that when sailing a smaller boat, under 36 feet for sure, even more so under 30 feet, there is a greater chance of tripping as one moves about. It is almost unavoidable, as there is just so much under foot. Cars and tracks, running rigging, trim, shrouds, items secured to lifelines, and those hideous wire jacklines that some idiot came up with that roll when stepped on, causing many a sailor to lose their balance. On a larger boat, deck space is often less cluttered, and provides more sure footing, even as we eliminate the need to go work at the mast or foredeck in the first place.

(Below: A young Bill Parlatore in 1977 putting baggywrinkle in the rigging of my wood, gaff-rigged Tahiti ketch.)

bill parlatore on his sailboat 

And staying on the boat is a top priority no matter what size boat you sail. For anyone sailing alone, the use of strong, non-stretch webbing jacklines is highly recommended. Being attached to the boat is critical for personal safety. If set up properly, wearing a harness and staying clipped onto the boat as one moves around the deck is neither inconvenient nor difficult. It is also the only way to have two hands free with any degree of security. The alternative of not being attached to the boat is unthinkable, as there are no good ways to get back aboard if one goes over the side.

I once asked Dodge Morgan about his man overboard contingency, if any. He gave a presentation of his around the world trip on the 60-foot American Promise at a Safety at Sea seminar in Annapolis. American Promise was a heavy, yet fast sailboat designed by Ted Hood, specifically to sail nonstop around the world as quickly as possible. It did so in record time, cutting the previous record in half.

When I asked Dodge about what provision he made for falling overboard, he said that any overboard rescue device he might have for that situation was just “a sick joke” in his mind. Once you go overboard when sailing alone offshore, the game is over.

Every effort should be made to make it safe to move about the boat when sailing and to stay aboard. This is important no matter what size boat you sail.

While I have many fond memories of sailing small boats and making coffee in the early morning at anchor on a swinging stove by the companionway, now I am older, wiser, and no longer immortal. So, offsetting any flexibility and balance issues, I have more wisdom and budget to pursue what makes sense now.

If I went looking for sailboat to continue sailing by myself, I suspect I would be looking for a boat that does everything I want, and is close to, if not dead on, that 40-foot mark. I might start looking at 36 feet, but I expect my interest in creature comforts would dictate a larger platform. The idea of a separate shower is appealing to me now, as are the many spaces and lockers that allow me to put things in proper places where I can get to them easily without fumbling through lockers. The main anchor on the boat would be big, but not as overwhelming as one finds on larger boats.

I also think my comfort level in a roomy interior would make a world of difference as I relax at anchor these days. I’m no longer interested in transformer-style accommodations. I relish the idea of easily stepping into a dinghy or water taxi from the stern, which is a much higher priority than it might have been years ago. A proper chart table and saloon are also well worth the price of admission, as well as plenty of opening hatches to let in the breeze.

And for the solo sailor with a “guest” aboard, it is much the same. They should be able to handle the boat by themselves and accept that the second person really only contributes to the enjoyment of the accommodations, and perhaps reading the cruising guide, leaving the physical aspects of sailing to the sailor.

There is no reason why a single person should have to give up much of anything with today’s modern sailboat, and they should get the smallest big boat that works for them, all the way up to 40 feet, plus or minus a foot or two.

The right boat will provide a great platform for adventure, without the drama, anxiety, and emotion of trying to handle too much, or suffering from too small a cruiser that forces us into camping mode at the stage in life where we should be enjoying the fruits of a successful life.

See you on the water.