Sailing is a sport that a competent and knowledgeable skipper on a well-prepared boat can enjoy immensely all alone. But let's face it, there is something especially rewarding and fun about being able to share our passion with others. We enjoy teaching others how to sail, passing on the values and traditions that form the basis of the seafaring community and simply having friends aboard to talk to.

But which friends on which outing? For that, you have to consider the length and type of trip and the two qualities you most want – ideally, in balance – in your crew: companionship and teamwork. After all, a crew that is perfectly suitable for a weekend jaunt to a port 15 miles away may be useless, and even dangerous, on a voyage across the ocean or on race day. And some excellent sailing or racing crewmembers are simply not fun to be around on a pleasure trip.

JIM HAYNIEFirst mate Aaron Clark clips in for a rough night watch in the Atlantic off Nags Head, North Carolina.

There are three kinds of friends to take sailing. I think of "the crew" as the people who contribute in a significant way to the sailing of the boat. They enable the skipper – that would be me – to take longer trips, sail more aggressively and safely encounter harsher conditions than would be prudent alone. "Guests" designates people who really do not sail or operate the boat but are present mainly for companionship. And, of course, there is what some call "the admiral" or "my crew."

In my case, "my crew" can best be described as "a hundred and some-odd pounds of unpredictably moving ballast that complains." She loves to be on my boat, a 1988, 37-foot Hunter Legend I christened Serene Zelda, for up to four hours at a time, doesn't mind rough conditions or the boat heeling, loves to fish and even likes toughing out a storm now and then. But she has no interest in learning the names of the "ropes," as she calls them, refuses to learn how to operate the engine and is annoyed when asked to move so a lazarette may be opened or a jib sheet adjusted.

To her mind, arriving late for a nice meal in the restaurant at the destination port is far more disastrous than the potential damage caused by the grounding that delayed us. Still – and I know many other skippers, both male and female, can identify with this – even though sailing with "my crew" is far more trouble and a bit more dangerous than sailing alone, there's nothing I love more than when my beloved agrees to go out with me.

Often, guests who come on a sailing trip are similar to "my crew" in that they neither know what to do nor care to learn but are simply along for the ride. These folks help to meet the companionship purpose of the crew. Sure, we let them steer some and occasionally ask them to pull a line, but they cannot be depended upon for the boat's care. If the boat is well set up for single-handing, guests are fine for day sails or for short trips, but that's about it.

So why bother with guests who aren't useful as crew, add to the inherent risk of the sport and can sometimes cause problems? Because a good trip is made extra special and memorable by having a crew that really enjoys each other's company. And, on the flip side, a potentially great sailing adventure can turn catastrophic if crewmembers don't get along. The unhappiest moments I have ever encountered on a boat occurred because of personality conflicts among some of my hand-chosen crewmembers. I knew them all well, and I liked them all very much in different settings. I had also sailed with them all quite a bit and felt comfortable with their skills and knowledge levels. But socially they were not a good mix, something I did not realize until they – we – had to spend five long days together.

GETTING ALONG

Crewmembers need to respect each other, trust each other and depend upon each other. They must be able to enjoy each other's company, share good conversation and, yes, tolerate each other's annoying habits. They do not need to become bosom buddies, but it certainly helps if they genuinely like each other on some level. But I do try to mix it up. If all the members of the crew are from the same office, they invariably wind up "talking shop." Who needs that?

JIM HAYNIEThe three-person watch works well. Aaron is at the helm, Tom, being fresh, is lookout, and the author took the photo on his way back from a chart entry.

Having folks from different occupations, cultures, educational levels, social circles and ages, and who bring other interests beyond sailing, adds a special level of enjoyment to those 14-hour periods of 6-knot winds that barely move the boat – just enough to forgo firing up "ole Bessie" but leaving nothing for the crew to do except sit and watch the scenery. True, it doesn't matter how interesting folks are to talk to when a squall line comes through or when everyone is in a mad scramble to avoid being run down by the container ship that just made a surprise turn directly for your boat. But those moments usually last for short periods of a long trip, so good company does add a lot. The teenager who crews with five guys in their mid-50s will please refrain from playing rap music loudly on the stereo, and I hope the old men will also find something better to talk about than golf and gout.

Lastly, regardless of their relationships on land, all hands must willingly and punctually obey commands of the skipper or other officer in charge. Aboard a sailboat, it's not uncommon for a young person, a clerk or a truck driver to have authority over, respectively, her elder, his supervisor or a wealthy CEO. What matters is that the crew and the guests get along and function well together.

SAILING ABILITY AND KNOWLEDGE

Truth be told, I have solo sailed Serene Zelda far more than I have sailed with adequate crew. I often do simple day sails but have also made several longer trips alone, and lots more with only guests or "my crew" aboard. Most of these trips are in the busy Chesapeake Bay, so they are limited in range by how long I can stay truly alert and physically able to manage the boat. The trip from my homeport in Irvington, Virginia, to Hampton near the mouth of the bay is my favorite, and generally the 70 miles take 10 to 14 hours. To go farther, however, I need to either get into truly open ocean water out of major transport sea lanes so I can sleep, or at least have one other competent sailor aboard. Simply going out for a day sail and returning to my homeport has never fulfilled my image of myself as a seaman (or frigate captain, explorer, pirate, etc.). I look forward each year to at least one voyage that includes several consecutive days of sailing with no stops. Such excursions, which demand a full crew, a formal watch schedule and a lot of preparation, allow us to be (at least pretend to be) self-reliant sailors even if a potential safe harbor is always within 150 miles. In the process, we relish going through storms, we get to struggle through mishaps and gear failures, we see Mother Nature from the closest viewpoint and we generally forge long friendships.