“Wanna sail?” Finding sailing crew is a never-ending search. Here’s why.

Cruising a mid-sized sailboat is like driving a small city bus without breaks on roads without curbs. One person can do it but that’s tough, especially if there’s no automation. It requires extreme concentration and physical stamina as well as skill, and you can still  really bang-up the boat. Most captains would rather find crew than risk it, but that’s often not much easier. 

Gene Miller, a tall, lanky economist who looks more like the Marlboro man than a Washington, D.C. analyst, is  fine with tough, but after semi-retiring from traveling the world to jump-start economies after natural disasters — from Haiti to New Orleans — he also wanted some fun.

A few years ago, Gene bought a yellow-hulled CC-35 racing boat, called Stinger, once renowned in the Annapolis area for being a sleek runner. The brass plaques that testify to her three wins in the Annapolis-to-Bermuda race are still screwed into her teak cabin wall. That was in the 1980s. Now, the plaques are time-tarnished and barely readable. The only automatic equipment on this boat is the GPS navigation.

Gene Miller
Gene Miller

That makes sailing Stinger solo a lot like bronco riding. Gene braces his feet in a solid position with knees controlling the helm (a huge steering wheel) and a line (what sailors call rope) to the jib (the front sail) in each hand for tacking (turning the boat).

His knees are pressed against the wheel spokes as he guides the boat across the wind. When the off-white, front sail whips across the top of the cabin to the other side of the boat, Gene releases one line, wraps the other around a winch and pulls as hard as he can with both hands creating a low “tthzzzzzz” sound as the winch spins as fast as he can make it. The entire boat rocks to an opposite tilt. The main sail snaps into place with a loud “THWAAP!”

He was out on this day for a pleasure cruise and luckily didn’t have to worry too much about the main sail as long as he kept the boat close to the wind, allowing him to focus on filling the jib with the available breeze.

Gene’s wife, Kristen, is below in the cabin. “I love her. We have a lot in common. But,” he says lowering his voice so Kristen doesn’t hear, “she’s not a boat person.” That’s when Kristen pops her head out the cabin hatch and asks brightly, “Anybody need a beer?”

Gene decided he needed to find crew.

Stinger, sailboat owned by Gene Miller
Gene Miller’s sailboat, “Singer” (yellow hull) awaiting crew

Finding Crew

Stories are told of men being shanghaied in the 1700 & 1800s at Chesapeake Bay area taverns  and waking up to find themselves conscripted on a waterman’s boat for the oyster season. Getting crew is an age-old problem. In modern days, captains usually start by asking friends.

“My circle of friends at that time were not sailors,” says Steve Wukina, who sails out of the Annapolis area. None wanted to sail as much as he did. He got tired of asking and sold his boat. Steve now crews on other people’s boats.

sailing on the Chesapeake Bay
A typical busy weekend day sailing on the Chesapeake Bay at the mouth of the Severn River by Annapolis

Jim Ritter keeps a 30-foot sloop in Deale, Maryland, about a 20 minute drive south of Annapolis. Once he’d gone through his friends, he tried co-workers. “For the last 10 years the only crew I could get were the guys in my office and I wore them out,” he said.

To give you an idea of how intense the problem is: nearly half of all sailboats registered with the Maryland Department of Natural Resources are in Anne Arundel County, which includes Annapolis, along the Chesapeake Bay’s Western Shore. That’s why Annapolis bills itself as “America’s Sailing Capital.”

The City of Baltimore and Baltimore County combined are nearly three times as big, but have half as many boats, according to the DNR.

Boats in Maryland 2015
Boats registered in Maryland for 2015 (Courtesy Maryland Department of Natural Resources)


Captains carefully guard their lists of potential crew and rarely share if asked. “If you need five people on a boat,” says Michael Jewell, “you need 20 people on your list.” Michael has been sailing for 12 years and owns a 40-foot Oday sailboat called Moon Bounce. “Even then,” he says, “you have trouble because people have commitments.”

Deale, Maryland, marina
Marinas in the Deale, Maryland, area attract Washington, DC boat owners and a couple marinas have more than 500 slips, making them the size of a small town. Anne Arundel County has about 10,000 boat slips.

Michael was seeking crew at a Listing Party in Eastport, an historic neighborhood on an Annapolis peninsula surrounded by water and marinas. A listing party is similar to a lawn cocktail party but skippers walk through the crowd looking for likely crew.

Some are looking for racing crew and will ask for weight, height and experience to see if you fit their needs. Others want to simply cruise around the Bay and need people to keep their boat from bumping into things when necessary, maybe pull a line or two when told.

The Chesapeake Bay boating magazine Spin Sheet hosts listing parties on a regular basis. Everyone gets a name tag, either “With a Boat” or “Looking for Boat.” Names in red are for those who want to race sailboats. Blue names bring together the calmer cruising boats. Then, to make it flow better, everyone gets a plastic cup for beer or a rum drink provided by Spin Sheet as a courtesy.

Before the party, there’s a panel discussion for potential crew on what the job requires: what kind of clothes to wear (quick-dry sports clothes & no black-sole shoes), how to respond (“Skippers won’t ask you to go out unless they’re really extending an offer, but that doesn’t mean it’s a date!”), how to behave on the boat (“If you bring beer, bring enough to share”).

Spin Sheet crew listing party
Crew listing party at Annapolis Maritime Museum hosted by Spin Sheet magazine. Here’s the 2015 party dates & locations.

Various marinas host similar parties, usually in the Spring. For a time, listing parties were a prime source of crew, but attendance has been dying down for several years. One boat owner said he’d met people with experience at these type of crew parties, but “I wouldn’t want them on my boat.”

Experienced sailors told me that I could simply walk to the end of a pier on a summer weekend and introduce myself. That’s all it takes to get on a boat, they said. “No friggin’ way,” I thought. What person who owns an expensive boat would want me — a stranger — to crew with them. I tried it at my neighborhood pier on the Severn River. I was new in the ‘hood, didn’t know anyone and had very little experience, but figured it was safer for me close to home. Sure enough. I was invited on a boat.

Gene tried advertising for crew in the classified section of a boating magazine, another traditional way of getting crew, especially for longer sails or transporting boats to the ocean or Gulf of Mexico. “I got a lot of really weird calls,” he said. “I had to figure a way to weed out people.” After two years of starts and stops on finding crew by the traditional means, Gene decided to try the Internet.

Sailing Hits on Social Media

Skippers, like Gene, are always looking for a new, better or different way to connect with people who can help get the boat in and out of the slip. Experience is good, but ‘trainable’ will do quite well.

They went online.

Until the past couple years, the Internet had been used mainly as a posting board – to issue notices, advertise events, or search for crew. Yacht Clubs and Annapolis-area neighborhoods have websites where members can post their crew needs. It was similar to the pin-up board at a small town grocery store.

Then came social networking. That’s changed everything.

Gene, wearing his traditional starched, buttoned-down long-sleeved shirt, comfortably worn blue jeans and scruffy raw-hide leather boat-shoes, speaks thoughtfully in a measured voice, with the stub of a lit cigarette waiving in one hand as he punctuates his point when explaining how he set out to learn about social networking. “Why not narrow myself to a group with similar passions and skill sets?” asked Gene.

Gene Miller sailing on Stinger
Gene Miller on Stinger

He came across Meetup.com and started his own group on a February day, the “Washington-Annapolis Sailing Meetup Group.” Three months later, nearly 80 people were signed up.

The social networking website, Meetup, connects people who organize stuff with people who want to do stuff. The organizers pay between $12 and $17 a month to find people in their geographical area for anything ranging from parents’ groups to software development circles. It has almost 17 million members and has been signing up between 15,000 and 20,000 people every day.


Jon Jones’ crew used to be his wife and kids, but the kids grew up and his wife travels a lot. “I got tired of sailing by myself, so I started actively seeking crew.” Jon sailed “Wind Orchid,” a Catalina 350 sloop, out of Deale.

Jon also went online, but not through his own group, he connected with the online version of the Baltimore-Annapolis Sailing Club, started in 2008, which also has a MeetUp.com site.

Jon Jones sailing Wind Orchid
Jon Jones sailing Wind Orchid

He sends out an email crew call for a Wednesday night race. At the beginning of the summer, response was lukewarm. “We were short one person, but we had four and that is enough to handle things.”

Jones now maintains a crew list with anywhere from 20 to 50 people on it and has a waiting list of people who want to crew weekends on his boat. An overflow crowd shows up on Maintenance Day; spend a Saturday doing chores on the boat and you’re moved up the wait-list.

Despite their success, the search continues. Both Gene and Jon joined the Annapolis Sailors Club on Meetup.com. It was started by two women, both sailboat owners, who got tired of driving to Baltimore to crew on other boats when they live in the “Sailing Capitol of the World.”

The ASC group began in April 2012. By the end of May the group had reached 100 members and got a note from Meetup.com congratulating them on the unusually quick growth. Two years later, they’re holding steady at a little more than 200 sailors.

The Internet’s Downside

Social media comes with its own challenges.

“(Captains) used to size up crew eyeball-to-eyeball,” said Kristen Berry, co-director of J World Annapolis, a sailing school, “but in the Facebook era we’ve lost that important element”

In other words, you never really know what kind of person is really going to show up. Crew members have claimed they’re experienced sailors when they really mean that they’ve sailed many times but not necessarily done much more on the boat than break-out the appetizers and drinks. These skipper are not providing free cruises, they’re looking for crew.

When asked about the types of people he’s found through social networking, Jon hints at stories he could tell. He’s since moved to Texas with his wife and boat, keeping his email list going and expanding it whenever possible. Jon writes in an email that he has made many wonderful friends in the last few years “since we opened up Wind Orchid to our crew method.”

Stinger Gets a Crew

Gene finally put together a crew, using his social media network, and decided to host an afternoon training sail from his dock just off of the Annapolis harbor. I was waiting with him as his crew arrived. He was nervous. The only person he’d met in person was the First Mate (basically, the back-up skipper). He wanted a strong First Mate with experience so he could keep an eye on the other crew members.

A woman on the upper side of middle-aged walked down the dock dressed for a boat party in stylish white pants and a big bag slung over one arm, while the other hand held a leash leading a small, white dog wearing a bright yellow life jacket with a handle and happily wagging its tail. Here was the First Mate.

Gene wasn’t expecting this and stared in disbelief as she boarded the boat. He’d met her at a sailing class where she’d been an instructor on “What Not to Wear & Bring” on a sailboat. She was wearing the same sort of outfit that she’d warned against. Gene decided on the diplomatic route and said, simply, he hadn’t expected a dog. The First Mate said she couldn’t leave her dog at home.

Pulling himself together, Gene asked her to help him get the boat ready by hooking a new sail on the mast rings while he pulled it up the rigging. Setting the dog aside on the boat, the First Mate climbed on top of the cabin to grab the mast. But she couldn’t hook the sail to the eyelets. Each attempt raised Gene’s stress level. If she couldn’t do this, he thought, what else can’t she do?

Gene pulled her aside and asked her to leave his boat. He said he wasn’t comfortable with her as a First Mate. She walked down the pier toward her car, tears forming in her eyes as she towed the dog behind.

It’s not a guaranteed fit.

A few minutes later, the rest of the crew came bouncing down the pier — two men and a woman, international economists from the World Bank headquarters in Washington, DC. None of them had sailed before but they followed directions. The new main went up easily, lines were tossed off the pier and the boat didn’t slam into the pilings on the way out of the slip. Stinger went into the Chesapeake Bay under sail.

Stinger did a lot of unplanned circles that day as each of the crew got a chance at the wheel, confusing many of the other captains on the bay who couldn’t tell which direction she was trying to go. “We’re training here,” Gene shouted apologetically as the other boats scattered out the way.

“We’re racing,” yelled back a captain on a sleek, newer sailing yacht that was skimming by on an extreme tilt.

Sailboat race on the Chesapeake Bay
Sailboat race on the Chesapeake Bay

Gene’s crew froze in astonishment, including me, eyes locked on the splendor of the other boat gliding by only a couple feet away, within touching distance from Stinger, creating white caps that slapped against our historic racing boat. It showed us what sailing can be; the thrill of riding the edge in a 10-15 knot wind.

Predicted bad weather never materialized. Mrs. Gene supplied jokes, snacks and beverages while Gene told sailing stories. He finally had a crew that pulled lines, held the wheel while he took a break, and experienced the inner-joy of sailing along with him.

Realizing this, Gene grinned and squinted toward the horizon, silently enjoying the wind of a sailboat cutting across the Annapolis harbor entrance.


crew on the sailboat, Stinger
Gene Miller steers Stinger with a different crew later in the summer found through a MeetUp group, the Annapolis Sailors Club.

How to find sailing crew

Cynthia Reuter

Cynthia is a former radio reporter, turned TV producer, who started covering local politics in Missouri, then state politics, then national politics in Washington, DC. Writing about the Chesapeake Bay region is a breath of fresh-air.

Cynthia Reuter has 13 posts and counting. See all posts by Cynthia Reuter

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