I first went to New Zealand in 2006. I was 20 years old and setting off on my first long journey away from home, bound for Brisbane, Australia, for a semester of college at the University of Queensland. The nice thing about life in the Southern Hemisphere—particularly for a college student—is that everything is backward. Which means the school season is backward as well, and classes for the semester don’t start until mid-February, at the end of the summer Down Under.

Given the extra free time, I proposed a two-week jaunt to New Zealand to the dozen or so Penn State students who were heading with me to Oz. A girl named Lindsey was the only one who said yes. We met for the first time in the Los Angeles airport and set off together across the Pacific. We spent a day acclimating in Auckland, walking around the city, heading down toward the Viaduct to see the old America’s Cup boats, learning about the coffee culture and the difference between a “flat white” and a “long black.” I quickly tired of the city, however, and the next day we hopped a flight to Wellington, the southernmost city on the North Island.

Here we started looking for opportunities on the other side of Cook Strait and found a small charter company in Picton that would rent us a 28-foot sailboat for a reasonable price. Lindsey had never sailed before, but was up for the adventure. My experience growing up on the Chesapeake sailing with my Mom and Dad was enough to convince the charter company that I was capable, so we set off on the next ferry to Picton.

The Marlboro Sounds, which mark the northern terminus of the South Island and branch off of the notorious Cook Strait, are an extraordinary cruising ground. The scenery is fabulous, the weather in summertime is fresh, and the sailing is spectacular. The real challenge in the area, as I soon discovered, is the deep water. The bottom is steep—to right up to the shore in places, which can make anchoring tricky.

The rep from Compass Charters, a very friendly woman named Crystal, met us in Picton, a small town in an idyllic spot at the head of Queen Charlotte Sound. The boat was a Herreshoff 28, a little classic cruiser, bigger than I’d expected, but still cozy for two. We motored out into the sound past some race boats and then sailed out toward Cook Strait. I felt tentative at first—this was the first time I’d ever piloted a boat without my Dad aboard—but eventually we hit our stride and had a wonderful first day. During the summer that far south, the evenings are long, and even though we didn’t leave the dock until 1800, we enjoyed three hours of daylight before finding a spot to anchor for the night.

It was a place called Tawa Bay, inside Endeavor Inlet, a tidy little hidey-hole surrounded by steep hills and green trees. There were a few other boats around, and at the time I never wondered why they were all anchored so close to shore.

We picked a spot just before dusk, and I flaked out about 60 feet of chain on the foredeck while Lindsey steered. She did a great job for someone who had never seen a tiller before. The depthsounder read “30”—a little deep, I thought, but by then it was getting dark, we seemed very close to shore, and I wanted to relax and enjoy the last of the daylight behind the hills.

I dropped the anchor and started panning out the chain, all the while wondering why it felt so heavy and why it hadn’t hit the bottom yet. Wait a sec, I thought. New Zealand. Former British colony. They use the metric system here, right? That 30 on the depthsounder meant 30 meters. More than 90 feet. Holy moly!

By then I’d let out all 180 feet of the anchor rode, which was all chain. I tried hauling the anchor up again so we could move to a shallower spot, but the electric windlass gave up the ghost almost before it started. The boat didn’t seem to be dragging, and it was getting dark, so I decided to stay put until morning.

I didn’t get much sleep that night. Now I understood why my Dad was often awake on windy nights at anchor in the Chesapeake poking his head out the hatch. As the wind swirled down from the surrounding hillsides, our boat swung back and forth on its anchor, and I kept popping up the companionway to see how far from shore we were.

Come daylight I hailed Compass Charters on the radio and informed them of the situation. Crystal said there was no manual override on the windlass, so I found some towels to wrap around my hands (there were no gloves onboard) and started heaving the anchor up, 10 feet at a time, while Lindsey took the helm and tried to keep the little boat head to wind. Needless to say, this didn’t get us very far. The boat had oversize ground tackle, which I’m sure is why we stayed put overnight, but now it was giving me a headache (not to mention a backache).

As Lindsey struggled to keep the boat straight in the gusty winds coming off the hills, I became increasingly concerned I’d get the anchor halfway up only to have the boat blow ashore before I could get the rest of it aboard. Fortunately, we had plenty of tools with us, and behind one of the settee cushions I found a big pair of bolt cutters. Just the thing for cutting away the anchor, I thought. Which is precisely what I did. I was surprised how quickly they cut through the 10mm chain, and in an instant we were free.

Not having an anchor took all the stress out of the rest of the trip. We sailed farther into Endeavor Inlet that day and found a mooring off an adventure lodge ashore. My “Lonely Planet” guidebook recommended a hiking trail up the forested hill behind the lodge, so we took the dinghy ashore to explore. The next two nights were much the same, as we found plentiful moorings (which were plentiful) instead of anchorages, and truly enjoyed ourselves. I got more confident handling the boat, Lindsey grew to love sailing, and we had a memorable charter.

Crystal greeted us back at the marina in Picton when our time was up and handed me a bill for $800 for the lost anchor and chain. She forgave me the incident, but didn’t forget two years later when I chartered the same boat with another girl, Mia, who later became my wife. Every night Crystal called us on the radio and jokingly asked if we still had our anchor. 

Illustration by Tadami Takahashi; photos by Andy Schell