Spread appeared in Explore Magazine

It was a familiar sensation. The feeling of complete surrender, the incessant giggling, and the particular sound that skating over pavement makes. It wasn’t until my toboggan reached the bottom of the five-kilometer hill that I remembered why. I had recreated my favorite childhood pastime (to the detriment of my mother’s nerves): riding a skateboard while being towed by a friend on a bicycle.

With knees unscathed and a view that is unequivocally extraordinary, the experience of riding a toboggan vastly better.

From Top…

Looking up from the gorgeous seafront of Funchal, you can see the cable cars floating along the hillside nearly 800 meters overhead. This is where your adventure begins in earnest. The 10-minute cable car ride offers an incredible panorama of the island and vistas of beautiful homes that dot the lush canopy.  Once you arrive at the top, it’s a short walk to the toboggans – plus it’s impossible to miss the guys dressed in white with straw hats and wicker sleds.

Dating back to the 1850s, these two-seater sleds that glide on wooden runners were the primary means of downhill public transportation in Funchal. Today the Monte Sledge continues to operate with the added thrill of having to share the road with cars. Not to worry, though, they are expertly driven by two men in rubber-soled boots that act as human brakes.

The drivers, better known as “carreiros,” take their passengers from the steps of the Nossa Senhora do Monte Church downhill to Livramento, a suburb of Funchal, sometimes reaching speeds of 40 kilometers per hour.

To Bottom

I was filled with excitement and anticipation when it became my turn to sit in the toboggan. In preparation for my trip, I came across somewhat of an urban legend that claims that Ernest Hemingway rode the toboggan and said it the most exhilarating experience of his life. As the wicker creaked under my body, I thought, well if it was good enough for Hemingway, it is good enough for me.

And then we were off.

This mode of transport is unconventional to say the least. As we zipped downhill my carreiros drove from behind controlling our basket through a combination of leaning and pushing, while at times using their thick rubber soled shoes to brake or speed up the by pulling on the ropes. For quite some time we bounced from side to side as we maneuvered tight turns along the city’s walls. Then the enormity of the view would serve as serenity breaks as we built momentum for the next descent or thrilling corner. Throughout the ride there was one constant and that was the silly smile on my face. It truly made me feel like a kid on a skateboard again.

Riding a toboggan synonymous with Funchal, yet there’s more to explore and experience in Funchal’s green countryside. If you’re looking for a wonderful glass of wine, a home for architectural wonders, or lush gardens to stroll, you’re certain to find it here. This is an ideal destination is filled with exhilarating experiences beyond zooming downhill in a wicker basket.

Not to be Missed

Before heading downhill on your toboggan adventure, climb the 250 steps to Our Lady of Monte Church. Built on the foundations of a primitive 15th century chapel, this church is the most important pilgrimage site in Madeira. Our Lady of Monte is adorned with elegant chandeliers, a statue of the saint revered since the days when the island was first settled, beautiful pieces of gold and silver crafted in the 17th and 18th centuries and the tomb of Charles I of Habsburg, the last emperor of Austria, who went into exile in Madeira in 1921. If your visit happens to land on the patron saint’s feast day (Aug. 15), you’ll no doubt revel in elaborate processions and lively celebrations throughout town.