Editor's note: In the fourth century B.C., Alexander the Great forged a path from Greece through the modern Middle East to Persia. It was a path of conquest that empires would follow through the ages. Traces of each can be seen today in the culture, monuments, continuing military presence and people along the route, which ended for Alexander in Babylon — modern-day Iraq. In this project, GlobalPost correspondent Theodore May sets out to see how Alexander’s influence lives on. He will be blogging about his travels at Backpacking to Babylon.

CAIRO, Egypt — It was about 9:30 on a cloudless morning in mid-October when I suddenly had the feeling I was flying.

Moments before, I had leaned over the handlebars of my creaky one-speed bike to get a look at the front brakes. That was all it took. Turning my eyes from the road for a minute, I careened into a sand bank, sailed over my handlebars, and landed square on my head, crumbling to the desert floor in a fit of laughter.

Before I set off on my six-month journey to retrace the footsteps of Alexander the Great through the Middle East, I had packed a first aid kit full of gauze, bandages, rubbing alcohol, etc. I reasoned that anyone who planned to make a living out of walking with an overstuffed backpack was likely to take a tumble or two.

Six months of walking later, I had yet to take a fall. Three days on a bike, though, and I had already taken two opportunities to express my affection for the desert floor.

Alexander the Great’s 600-mile journey through the vast and uninviting expanse of the Sahara posed a formidable logistical challenge for me. Walking as I do, the desert leg would have taken about a month and a half on foot.

So I chose to tackle the route by bike, a mode of transportation I had little familiarity with. Friends with cycling experience warned me that the journey still wouldn’t be easy. I scoffed. On a bike, I figured, I’d have the opportunity to rest and coast at the same time. Free mileage!

The two-day ride from the Mediterranean coast to Siwa Oasis seemed to confirm my theory. The wind was at my back, the road was flat, and traffic was scarce. I spent my one night in the desert cheek by jowl with a couple of old Bedouin men in the guard hut alongside a cell tower. In all, the first leg of my bike trip wasn’t all that painful.

Siwa was the purpose of Alexander’s daring journey through the desert and a particular highlight of the trip for me. After founding the coastal city of Alexandria, the Macedonian army set off for the oasis with the purpose of realizing Alexander’s dream to have the oasis’ renowned oracle name him the Pharaoh of Egypt and as a descendent of the gods.

I spent days exploring the oasis, eating the local food, visiting the ancient sites and enjoying the shade provided by the palm groves. Because it’s a nine-hour drive from Cairo, the oasis remains largely cut off from the outside world. Siwans retain a unique language and donkey taxis are still the best mode of transportation for foreigners.

This was the one time in the journey I was literally able to stand in Alexander’s footprints — during a visit to the tiny temple chamber where Alexander had his fateful audience with the oracle. Some historians argue that it was the oracle’s willingness to declare him a descendent of the gods that propelled Alexander to attempt to conquer the known world.

After several days in the oasis, my father joined me. He had been eager to accompany me on a leg of my journey, and he trained on a bike for a week or two ahead of time so that he’d be ready for the nearly 500-mile journey through the desert from Siwa to Cairo.

It was at this point that we ran into trouble. I quickly figured out that because I was drinking six liters of water a day, it would be physically impossible for me to carry enough food and water for the journey ahead. We remedied this by hiring a couple of local Siwans to accompany us in a support jeep. They’d carry water, cook and set up camp at night, while my father and I would spin the chains on our old bikes.

As my father pointed out with a laugh, this trip was made all the more authentic by the fact that we were attempting it on bikes that were around during the time of Alexander.

Our second logistical hurdle came when the Egyptian intelligence services in Siwa forbade us from biking from Siwa to Bahariya, which was the next oasis on our itinerary. After rounds of late night negotiations at the military barracks, we were granted permission to bike one day and drive the rest.

It was in Bahariya, therefore, that we launched on our final four day push to Cairo. It was also here that we learned a basic principle of biking in Egypt: the road ahead will always be uphill and the wind will always be head on. As a local desert guide would say to us later: “Why did you bike in this direction? If you go the other way, it’s all downhill and with the wind!”

How thoughtless of Alexander.

We pushed about 60 miles a day, often fighting through strong headwinds. Our bikes were in such bad condition that even the downhills felt like a grind. At nights, our guides drove us a half mile into the desert and cooked up chicken or meat, vegetables and rice. We slept in sleeping bags under the stars. Our guides took a liking to the whiskey my father had brought, polishing off the bottles before we could get a word in edgewise.

On our last day into the capital, a week and a half after leaving the Mediterranean coast, we biked through heavily industrialized areas of the desert. Trucks streamed by us as we struggled to keep our bikes on the gravel shoulder. Many drivers seemed to think it their duty to welcome us to Egypt by slowing down and honking their incessant hellos.

All I could think of as I sipped a gas station-bought Pepsi minutes after finishing the trip was how much the oracle must have meant to Alexander for him to subject his troops to weeks of life in the barren, inhospitable terrain of the Sahara.

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