Our chief navigator is having difficulties locating the portage trail, which, he says, will take us straight up a steep ridge to a chain of lakes and obscure paths that eventually will lead to the Steel River, a rarely paddled southern Ontario waterway.

With compass and GPS in hand, Cliff plots our position on the topographic map. A few minutes pass before he sheepishly raises his head. "We're right here," he mutters, stabbing a blue spot on the map with his index finger. "We somehow overshot the portage by about a half-mile. Damn, this is embarrassing. Me, the author of a book on backcountry navigation!"

"Not a problem," Gary says, turning around into a stiffening headwind.

We are four friends, each captaining our own canoe, on day one of an eight-day jaunt on the Steel River Circle Route. Cliff is Cliff Jacobson, 66, author of the aforementioned Basic Essentials of Map and Compass and 11 other canoeing titles, as well as a recipient of the American Canoe Association's Legends of Paddling award. Gary is Gary McGuffin, 47, who with his wife Joanie has taken the mantle of Canada's canoeist laureate from the late Bill Mason. Between Jacobson and the McGuffins, they have authored some of the top-selling books of the genre. If there are such things as canoeing celebrities, I'm paddling with them.

A few months earlier, Cliff invited Gary, registered Adirondack guide Jim Mandle and me on what he called "a last hurrah," on "an all-time favorite canoe trip of mine." It would be his eighth trip around the 80-mile loop. Although the three of us had scant knowledge of the Steel Circle Route, a voyage Cliff first tackled in 1976, we immediately accepted our buddy's invitation. If this route was one of Cliff's all-time favorites, it had to be pretty sweet, right?

Cliff is pissed. Partly because we failed to notice the sign, but more so because there is a portage sign.

At 5-foot-6 and 129 pounds after a big meal, with graying, dark brown hair, and hazel eyes magnified by thick bi focal glasses, Cliffy could easily pass for Woody Allen's younger brother. But instead of wrinkled tweed and corduroy, our high-strung, outspoken guy is garbed in olive-green wool pants held up by bright red suspenders, a red-and-black plaid wool shirt, wide-brimmed Tilley hat, and knee-high Chota mukluks. By contrast, easygoing Gary is paddling in front of the pack, with leading man good looks—perfect hair and teeth, dressed from head-to-toe in the latest action wear and outfitted with the best outdoor and camera gear, most of it gratis from the manufacturer (and some for which he's paid handsomely to promote).

Naturally, it's Gary, with his acute photographer's eyes, who spots the gap we're looking for. "That must be it," he says, pointing toward a thin break in the phalanx of trees. "How did we miss it?"

How, indeed? Drawing closer, we see that a two-foot-square metal portage sign marks the trail bearing the silhouette of a stooped-over chap with a canoe over his head. If that weren't enough, a cluster of fluorescent survey ribbons flaps in the wind nearby, not to mention a regulation-sized highway STOP sign nailed to the neighboring tree.