learning the hard way

Teacher gets schooled during sailboat delivery

Whether you’re showing an old friend how to sail or training your own novice sailing crew, on-the-water training sessions require careful planning and preparation.

When my friend Stefan Wessel purchased his first sailboat, an Ericson 27 named Whisper, we decided I’d teach him to sail during the 50-mile trip to his home port in Newport, R.I.

It seemed like a good idea at the time.

The adventure begins

I had three students in all: Stefan, his wife Claudia, and another guy named Pete. In calm conditions, three students and one instructor would have been fine, but in 19-knot winds and a long fetch … not so much. I raised the sail while Stefan steered. Lucky for me, I enjoy the rough stuff.

Heading out of Avery Point in Groton, Conn., we entered Fishers Island Sound and encountered a strong east wind. Stefan had wanted to learn to tack, so we tacked. But tacking through the obstacle-laden sound was like tacking through a pinball machine, and we fought hard to keep some easterly progress.

My biggest blunder

While acquainting myself with the chart, I had Stefan hold a tack for too long and too close to shore. Whisper sailed onto a rock plateau in about 4 feet of water. The wind spun the boat around as it bounced in the waves.

We let out and hauled in the sails to pirouette with help from the east backwind. One wave picked up the bow, and the stern lowered to bounce the rudder. After the crew moved to the boat’s low side, we had good heel with wind abeam, and when a good wave came we sailed off.

We opened the bilge cover and checked the bilge. No water was coming in, but we kept rechecking anyway.

Trying to re-establish the crew’s confidence, I explained that the keel was strong and assured them that we had not whacked the fiberglass. I offered to check the keel and rudder for damage in port.

It hadn’t helped that Whisper had no depth finder, and I suggested that Stefan install a through-hull transducer as far forward as possible.

If I had compared the longitude reading on the GPS with the chart, I would have quickly noticed the dangerous location, which was well marked. From that point on, I used this positioning technique and found it especially useful in the dark.

Engine trouble

After securing a snapped jib halyard and loose track block with short pieces of line, we sailed through the rest of the sound without any problems. Tacking through the well-marked Watch Hill Passage would have been difficult, so we started the engine, rolled up the jib and motored through the channel with a few other boats.

The engine stopped running about 15 minutes out of the channel. We were heading into the wind, so we unfurled and kept sailing.

We later started the engine a few times and opened the gas cap in case the vent line was blocked, but the engine quit again after 15 or 20 minutes.

Stefan changed the fuel filter. Although the fuel looked good, he noticed that it was being depleted from the filter and needed time to refill. His diagnosis helped us decide when and how to use the engine.

After much tacking, we arrived in Point Judith around 2100. We were prepared to sail through the breakwater, but the engine started. We dropped the sails, motored into the well-lit harbor and picked up a mooring. A helpful bartender called a Newport cab service to take us home for a good night’s sleep.

Stefan and I returned the next morning to move the boat the rest of the way home. We motored out of the channel into some pretty big waves. The engine stopped again, so we unrolled the jib, and I went on deck to raise the main.

A few hours into Narragansett Bay the wind died. The engine wouldn’t run, so we rigged the dinghy to act like a little towboat.

We gassed up the dinghy’s 3.5-horsepower engine and motored into Newport at about 4.5 knots. I sat on the rail, holding down the bow of the dinghy with my foot. We kept the mainsail up just in case. I think Whisper rides better with a sail raised anyhow.

When we reached Portsmouth, we took down the sail, tied it up and moved the dinghy back to the stern. If Whisper’s engine quit again, I could start the dinghy and push us into the slip.

Fortunately, the engine fired up and we motored into the marina. Stefan placed the boat into the slip perfectly. Whisper was home.

Lessons learned

You need at least two instructors or experienced crew when teaching first-time students or cruising for more than an afternoon. One instructor can train a student on the helm while another teaches the new deck man how to hoist the sails. On a longer trip, one instructor can train and the other can navigate—or maybe even rest a little.

If you’re training someone aboard a newly purchased boat, you need to check for basic equipment such as anchors and a boat hook. Consider making a checklist to help you remember the essentials.

Expect new boaters to get seasick while pounding through 4- to 6-foot waves. Seasickness can affect someone’s ability to read a chart or small-screen GPS. Ginger candy can be helpful; I plan to put some in my sea bag. Resistance to seasickness is another good reason to bring along a broken-in crew member.