Never before in my life did I dream that I would take a wicker basket toboggan ride down the steep streets of an island town. It never crossed my mind that perhaps someone might have a full-time job building woven sleds with greased up rudders for the sole purpose of hurtling oneself down an incline, or that men (dressed all in white) could make a career out of using their rubber-soled shoes to steer and brake such a unique style of transportation.

I promise I’m not making this up.

There are certain types of travel activities that make me exceptionally happy: offbeat and inexpensive ones that I would probably never find anywhere else in the world.

But let me backtrack for just a moment.

My day spent wandering around Funchal, the main hub of civilization in Madeira, started off relatively normal. I downloaded a self-guided walking tour and checked out some unique features of the small city and its special history. After a brief respite midday, I decided that a cable car ride would be an excellent break from the miles and miles of walking I had done since my arrival in Portugal five days prior. The “cars” were big and roomy – I thought I would be looped in with another group given my solo status, but I was able to get my very own.

And oh, what a glorious ride! The ocean created the perfect backdrop, with the orange-roofed houses dotting the ever-sloping hill. There was just enough green to perfect the views as I rode in contented silence for at least 10 minutes.

After arriving at the very top, there were a few options on how to get back down. Quite a few travelers opt to ride the cable car on a return trip. Some hail a taxi and make their way back to their respective lodgings. And a few, myself included, decide to take the infamous wicker sleds. This is a rather well-known activity for those traveling to Maderia – the website boasts that 30 km/hr (18 mph) speeds are guaranteed! Apparently it began in the early 19th century as a legit form of transportation to get from the top (Monte) to Funchal proper.

I lined up in the queue and began searching for viable partners. It was 10 euro more expensive to ride by myself, and I thought it would be fun to experience this with some other human beings. I saddled up to two lovely ladies from the UK and asked if I could go down with them.

“Of course, luv.”

Everything happened so quickly. Two runners (men dressed in white) started dragging us along to pick up speed.

And then we were off.

Sitting so close to the road felt like I was practically scooting downhill on my butt. There were some tight turns and few cattywampus sideways slides that added a whole new layer of fun. I enjoyed listening to the delightful laughter of my UK companions as well as watching the sled in front of us, the runners expertly using their shoe soles to make the ride a success.

All too soon, the ride had come to an end. I thanked all parties involved and began the rather long trek back to my Airbnb.

No regrets, I thought. Traveling is about trying new things and taking a few chances.

Today I did both.