W ith the afternoon off from a conference near Lisbon, I hired a guide to take me to Sintra—stronghold of the Moorish invader 1,200 years ago, center of monastic learning in the Middle Ages, pleasure garden of Portugal’s monarchy in the 19th century, and all of it spread across an upland pine forest knit together with hiking trails. It takes a guide to make sense of it all.

Just not the guide I got. Vasco (let us call him) was an affable man with a newish Mercedes and a confidence that his grand car would make up for any shortcomings in historical knowledge, English proficiency, or exertion.

“What are we going to see?” I asked, as we drove into the park.

“Is palace. His name is Pena Palace.”

“Who lives there?”

“Who was lives there,” Vasco corrected me. “Was kinks. Was kinks and quince.”

It was at this point that something amazing came into view. Looming over the forest, at the top of a stovepipe of granite, were a series of crenellated battlements and towers, with pennants fluttering. This was the fortress built by the occupying Arabs in the 9th century as a base for watching the coast and terrorizing the countryside.

“Can we get there?” I asked Vasco.

You can get there,” Vasco replied. He dropped me off at a trailhead half a kilometer from the fortress. Ten minutes later I was standing beneath the mossy archway of the castle. It is impressive what one can accomplish with nothing more than religious zeal, sophisticated military architects, and an indifference to the comfort and safety of slaves. The castle was beautiful. It was impregnable. It was also, I noted with alarm, exceedingly easy to fall off of. Its highest point was several hundred yards ahead, up a steep staircase of wobbly looking boulders that ran along the edge of a cliff.

I was in third grade when I discovered that I was scared of heights. We had season tickets to the Boston Patriots. Then one of the joke franchises of professional sports, the Pats played in a succession of borrowed stadiums. That particular year, they were playing at Harvard. My father had a system for avoiding the Boston traffic. For a couple of bucks, the owner of Buzzie’s Roast Beef, in the shadow of Charles Street station, would let us park the car for the afternoon, and we would take the Red Line the three stops into Cambridge.

There was a hitch, though. Buzzie’s was separated from the station by a rotary, with cars squealing through at 70 miles an hour. A pedestrian overpass was the only way to reach the train, and what a pedestrian overpass it was. It was low-tech, rusty, ill-maintained, and probably named after some Hibernian political hack, like everything else the city government built in Boston. Its walkway was made of an iron mesh that you could see straight through to the street below. I took one step onto the grating and dropped to my hands and knees. Until then I had thought of myself as a tough, independent eight-year-old, and I think my father thought of me that way, too. But that day, he carried me across the bridge. And although I managed to walk across under my own steam to get to our subsequent games, week after week, it took a supreme effort of self-control not to whimper.

That fear has never totally gone away. I have always been mystified by those photos you see on the covers of hiking pamphlets and trail maps, with people yukking it up as they dangle their toes off of cliff-top promontories. Driving across bridges means chanting to myself and hyperventilating. I have walked the rim of the Grand Canyon leaning like a lambda into the canyon walls. After having looked forward for months to walking the storied fortifications of Diyarbakir in eastern Turkey, I discovered that they were accessible only via a two-foot-wide, railingless staircase that ran up the side of the wall for three stories. I skipped them. I just stood on a street corner in that crime-plagued city and waited for my friends to come back.

At the Moorish castle I resolved I would not go back to Vasco and tell him I had been too chicken to climb it. I was going to make it to the castle summit even if it meant looking ridiculous. There was no rush. There were rock posts every two or three feet, and they had been standing for about 1,200 years. All I had to do was grab one in a bear hug, then lurch and grab the next one. This worked great. Slow but steady. Don’t look down. I was about halfway to the summit when I noticed a woman descending the cliffside towards me, using the same method. When we got about five feet apart we gave each other a smile of recognition—and, I have to say, mutual encouragement. I sat down on the steps just as I had knelt above the Boston rotary of 1970, and let her slide past. Then I stood up, grabbed the wall, and kept climbing.

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