Have you ever wondered what it would be like to slide down busy city streets in a wicker basket?

You probably answered “No,” but you can do just that on a Funchal toboggan run. When I first heard about this local activity, I thought it sounded too crazy to be true. But it is very true and very crazy. If you’re in Funchal, Madeira, it’s a must-do activity. Here’s what you need to know.

1. Getting There

The Funchal toboggan run is located at the very top of the town in an area called Monte. Sure, you can take a bus or hire a taxi to get there, but there is a much more exciting option: cable car. A quick 15-minute trip will cost you just a couple of bucks and take you to the top of the town. But only buy a one-way ticket. You’ll be sliding your way back downhill. When you get to the top, simply take a right and walk down the road a block or two.

2. What to Expect

You’ll quickly find what you’re looking for—a long line of men of all ages propped up alongside giant wicker baskets and wearing straw hats and winter-like boots. If you arrive at the same time as a tour bus full of people, you may need to wait in a queue for the next available toboggan. But fear not…the line moves quickly. A seemingly endless supply of toboggan “drivers” appear on command from behind bushes and buildings. You’ll quickly be seated in a sled, and the man operating the ticket booth will snap a few shots before you head out on your journey. Don’t these fine gentlemen look thrilled at their lot in life?

3. Payment

You’ll pay a pretty penny for the privilege of being pushed downhill in a basket. The cost is 25 Euros for one person or 30 Euros for two people. The man taking the payment simply couldn’t comprehend how I was passing up on the deal for the extra passenger. At the time, I was the last person in line. There was, literally, no one else to ride with me…the people in the background of the picture arrived later. Truth be told, I didn’t want to ride with a stranger anyway.

Be sure to have cash on hand. The man at the booth may have the ability to take credit cards, but it’s not a guaranty. I never dreamed the ride would cost so much, and I was short 10 Euros. The credit card machine wouldn’t connect to the Internet, so the man called down to someone at the end of the line to ask if I could pay there. Unfortunately he failed to tell me drivers. They were not pleased when they realized I hadn’t paid in advance. And the man at the end of the line worked for another company altogether. He was less than pleased to accommodate the request to use his machine. Lesson learned…

4. The Ride

Before you know it, your toboggan is sliding through the back streets of Monte gently gliding downhill along well-oiled streets. For the most part, the drivers push the basket from behind, chatting to each other over your shoulders. The toboggan moves at a fairly quick clip, and the special boots they wear act as brakes to help slow the basket around corners or busy crossroads. Your adventure takes you through active streets and intersections. Occasionally, there may be a need for your toboggan to stop for cars. From time to time, the drivers take a bit of a breather. They shift to the front of the basket, where there are two longs strings they can use to pull it along.

I didn’t time it. but the trip lasts about 10 minutes overall. And while that may seem like a short trip for the price you paid, it is a once-in-a-lifetime activity. How often can you say you took part in a Funchal toboggan run after all?

As you wind your way through twisting roads, seemingly random men pop out from the side streets to snap your picture. But there is nothing random about it. Through the magic of WiFi, your snaps are instantaneously sent to a central point to be collated into a cute keepsake album you can purchase for 10 Euros at the end of your ride. It comes with a few historical images and anecdotes and two or the pictures from your special ride. It’s worth the money if only to prove you actually rode through busy city streets in a basket.

When your ride is over…it’s just over. One minute you’re sliding through the streets, and the next minute you’re not. Frankly, I was having a blast and could have sat in that basket for another hour. I had a blast. At the end of the ride, you’ll find yourself at a small market with a handful of kiosks selling all types of local trinkets. There is also a place where you can grab a quick bit if you’ve got a hankering for something to eat.

5. Getting the Rest of the Way Back

So there’s something you should know about the Funchal toboggan run that no one seemed to mention to me…it only takes you part of the way downhill. It’s way to far to walk back to the cable cars, so you have to find another way back to central Funchal. Most people are part of a tour group, so they have a bus waiting for them. You other options include public bus or taxi. Both of which are easy to catch.

I opted to walk. And everyone looked at me like I was crazy. I don’t know that very many—or any—other people take that option. It only took about 45 minutes to reach the bottom of the hill, but the roads were steeply inclined so it was often awkward. I don’t recommend it for everyone.

The Funchal toboggan ride is just one of the many fun things to do in Funchal, Madeira. In fact, Funchal is one of my most favorite cruise ports ever, and I’ve cruised a lot. What other things do you enjoy doing in Funchal? Share them with the Wanderlust Wayfarer Facebook group.

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