The Challenges of Skippering a Bigger Sailboat

From Sailing a Sunfish to a 33-Foot Sloop: What a Difference 20 Feet Makes

Fifty-year-old Annapolitan JC Johns has had his hands on a sailboat tiller most of his life. Johns grew up helping his father crew the family’s 39-foot Westerly Sealord.

“I guess I learned how to sail by osmosis. Seems like we were always headed out somewhere along the Texas coast. When I moved to Annapolis, I ‘inherited’ my grandmother’s Sunfish. That became a weekend passion: pack some provisions and head out onto the Severn. There is not a lot of room, but it’s a lot of fun,” says Johns.

jc sailing
JC and Ellie at the helm of their new, bigger sailboat. Photos by Craig Ligibel

A growing family wanting more creature comforts necessitated a fleet upgrade.

“I figured if I wanted to bring my family and friends along on a Chesapeake sailing adventure, I needed a boat more suited to Bay cruising.”

Checklist items included a roomy cockpit, a head with a shower, enough sleeping room to accommodate two adults and a gaggle of teenage girls, a sail plan that was easy to singlehand, and just enough bells and whistles to make any voyage safe and enjoyable.

“I know JC has always wanted a bigger boat where he could share his love of sailing with me and the girls,” his wife of 25 years, Jessica, said.

“We started thinking about an upgrade after my mother passed away last year,” JC said. “I got to thinking that life is short. If you want something and can afford it, go for it. The sailing gods must have been smiling on us because we found just what we were looking for at a price we could afford just around the bend from our house on Chase Creek. It’s a big commitment. Jessica and I made a pact that if we took care of some things around the house, we’d put our toe in the big boat market and see what surfaced.”

daughter sailing
Ellie at the helm, keeping a keen eye out while sailing on the Chesapeake Bay.

The couple paid around $70,000 for the nine-year-old Beneteau Oceanis Clipper 343.

“She was in pristine condition. I don’t think the stove had ever been turned on. Todd Taylor did the survey work. The seller’s broker, Deanna Sansbury, was very easy to work with.”

In preparation for skippering a bigger boat, JC took the ASA 101 and 103 courses at Annapolis Sailing School. He says, “The instructors were terrific. They assessed my abilities, listened to my objectives, and designed a sail-and-learn program that evened out the rough spots in my sailing resume and taught me the basics of big-boat sailing.”

JC says his wife loves the water but admits that she “probably will be happiest at anchor enjoying the sunset and listening to some tunes.” Cruising plans include the obligatory overnight in St. Michaels as well as four or five overnights up and down the Bay.”

Graduating from a Sunfish with a single sail measuring 75 square feet controlled by a single sheet to a more complex Beneteau with more than 500 square feet of sails and six lines leading into the cockpit is not an easy transition.

“That first sail was a little intimidating,” recalls JC. “There’s a lot that can go wrong with a rookie at the helm. A sailor buddy of mine told me that ‘bigger is better.’ After a day on the water, I believe him. The Beneteau is a forgiving boat that makes it easy to sail with minimal crew. If you get into trouble, just let the lines run loose until you figure out your next move. It’s a lot different from crewing on somebody else’s boat. When you first take the wheel of your own boat, things get serious, and I get a little nervous.”

For JC’s first time skippering his new boat, appropriately named, La Dolce Vita (the sweet life), he opted to recruit a veteran cruising sailor (yours truly) to pass along some boat-handling wisdom as we headed out into the Severn one brisk day last fall.

JC had a good knowledge of seamanship from his coursework and previous time on the water. I was along as ballast and an advisor. JC’s 11-year-old daughter Ellie came along as crew. Throughout the sail, she proved herself more than capable at steering the nearly five-ton displacement craft as well as handling mooring duties and helping set the sails.

Jc and craig new sailboat
JC and Craig sailed the new 33-foot sloop out the Severn River to the Chesapeake before the wind calmed. 

JC looked on with pride as Ellie took the wheel and steered the boat perfectly through our first official tack.” She’s a natural,” I shouted over the flap of the sails.” Just wait until she wants to put the rail down and start banging through the waves.”

Ellie shot me a grin, more than content to soak in the sun.

Our early afternoon sail was uneventful. We were the only sailboat on the river. As we worked our way to the big waters, we faced fluky winds that always seemed to be on our nose. By the time we poked out into the Bay, the wind had died down considerably, and we had mastered the cluster of lines running aft through a half dozen sail brakes.

Pretty soon the sun was setting, and we headed home, Ellie looking very salty as she steered the boat gently with her foot on the spokes of the wheel. JC and Ellie executed a textbook approach to the mooring ball. Before we knew it, we were headed back to the dock in JC’s Whaler.

“So how was it?” I asked the newly christened skipper.

“Success on the Severn,” he replied with a grin. “Not that much different than the Sunfish: same points of sail, same principles apply, but a whole lot more boat to push through the water. Next time we’ll get into some wind and see how she goes. As Captain Ron said, ’If anything’s gonna happen, it’s gonna happen out there.’”

“Dad did great, “chimed in Ellie. “We make a pretty good crew. I think anchoring out will be fun. All we need is some popcorn and some good movies.”

Note: The survey JC commissioned prior to purchasing the Beneteau turned up a few little things that needed attention during the winter. High on the list was reconfiguring the bimini to install a plexiglass window to permit the helmsman to see the sails while underway. Other to-dos included a serviceable dinghy, new bottom, a painter that floats, a pickup pendant for ease of mooring, and a remote sensor for battery and bilge alarms. “And perhaps a refresh of the cushions to make my wife happy,” JC said with a smile.

A couple of tips from Old Salt Ligibel included labeling all lines leading into the cockpit; developing a pre- and post-checklist, and making sure to complete a safety briefing before casting off. My best piece of advice: don’t let a schedule dictate your day on the water. Go with the flow. Be mindful of the weather. Sometimes the best voyage is one that keeps you in port. Don’t go out if you feel the least bit uncomfortable. In a race between a cruising sailboat and a summer squall, the weather will always prevail.

~By Craig Ligibel

Find cruising stories.