Fun in Funchal: Riding Wicker Toboggans on the Island of Madeira

They’re known as sledges. Wicker toboggans mounted on wooden runners that take riders on a downhill run through the streets of Monte, a mountain village high above Funchal. It would seem to fall in the category of “why would you want to do that?” – especially when you learn that the toboggans are steered by drivers called Carreiros, whose thick rubber-soled boots serve as the only steering and braking system.

But it turns out that the sledges are quite historic, a 19th century mode of transportation that shuttled people and products between the two Madeira towns. They’re also the most popular attraction on the island and can have notoriously long waits – sometimes as long as two or three hours – if you don’t arrive early. The most scenic way to reach the toboggans is by cable car, also known for its long lines.

Riding the Funchal Cable Car

Herb and I left the ship as soon as we docked around 8 a.m. It’s about a 15-minute walk from the port along the waterfront to the Jardim do Almirante Reis, home of the cable car’s lower station. Although it doesn’t open until 9 o’clock, a line was already forming when we arrived. As we waited, I noticed a sign that explained how to buy tickets online, enabling riders to avoid the ticket office line and go directly to the cable car queue. Without missing a beat, Herb ordered our tickets on his phone, and we headed to the cars as soon as the doors opened.

The ride takes about fifteen minutes, sailing slowly over gently sloping hillsides and red-roofed houses. We shared a car with four other travelers, trading phones to help each other commemorate our journeys. As we climbed closer to Monte, a light drizzle began covering our windows, a reminder of the climatic difference between the warm and sunny Funchal and the mountain village of Monte.

Riding the Monte Sledges

The Carreiros were unloading sledge-filled trucks as we made our way to the ticket office. Dressed in traditional white shirts, white pants and navy sweaters, and wearing “straw boater” hats, they gave an official air to the scene. We bought our tickets, took our place in line and watched riders ahead of us take off down the road. It was immediately clear why the lines can stretch on for hours. These are slow-loading vehicles, taking only two or sometimes three people per toboggan. And once the ride is over, the toboggans are loaded on trucks and driven back up the hill for the next group of awaiting riders.

Soon our drivers motioned for us to board. The first thought that came to mind was how open the floral-seated wicker basket seemed. There was nothing holding us in! At first the Carreiros pulled us along with thick ropes, but soon they jumped behind the basket, placing their feet on a board that ran across the wooden runners. It wasn’t nearly as fast a ride as I’d imagined, but it was a little unnerving when we’d head downhill sideways and I’d picture the basket tipping over with me on the bottom! The other thought that kept playing in my mind was that this wasn’t an amusement park ride. These were real streets with real cars.

The toboggan zigged and zagged from one side of the street to the other as we made our way downhill. We sailed through several cross-streets and passed photographers positioned at two spots along the route. Like eager paparazzi, they jumped into the road just as our toboggan approached, capturing a photo that would become a souvenir we could purchase after the ride.

Near the end of our journey, the Carreiros slowed our toboggan and returned to the front to pull us along. We seemed to be bunched in with other sledges, almost slowing to a halt. And then suddenly, the Carreiros began running again and the people ahead of us quickly disappeared down the steepest hill of the ride. And so, very soon, did we!

The ride ended midway down the mountain, and taxis were lined up waiting to take riders back to Funchal. Taxi fare is a set price of 20 euros, and our driver explained that the high rate compared with other taxis in Funchal is due to the maintenance costs for wear and tear when driving down the mountain. He replaces his brakes every three months, he told us.

Zona Velha – Funchal’s Old Town

Rua de Santa Maria

Back by the waterfront, Herb and I headed to Funchal’s Old Town to find a few attractions I’d read about before we left home. Rua de Santa Maria is Old Town’s main street, narrow and cobblestoned and what you’d expect a place that dates from the 1400s to look like. But what makes Rua de Santa Maria different are its doors. As part of the city’s “Art of Open Doors” project, artists have transformed the street into an outdoor gallery. It was late morning, and many of the shops and restaurants hadn’t yet opened, offering a perfect time to photograph some of the doors.

Forte de São Tiago

Next, we stopped at Forte de São Tiago, a mustard-color fortress above the Zona Velha seafront. Constructed in 1614, the fortress was designed to protect the island against pirates and foreign invaders. The walls are extremely weathered, but you still get a feel for the power and protection Forte de São Tiago must have displayed.

A Secret Photo Spot

The Rua de Santa Maria ends at a church called Igreja do Socorro, built in 1768. Across the street is a small pergola with a beautiful viewpoint that looks out over the water. We were the only people there, and I wondered if we’d stumbled upon a secret photo spot!

A Tea House and A Wine Tasting

Loja do Chá Madeira

Morning was soon turning into afternoon, and we were ready for a break. We headed to a tea house I’d read about that also turned out to be a great place for lunch. Tucked away in a square behind Funchal’s Sé Cathedral, Loja do Chá Madeira sits among buildings that are awash in yellow. We entered through the tea shop and went upstairs to a cozy space with café tables and a balcony overlooking the square. Our server handed us menus and told us to ring the bell on our table when we were ready to order.

Filled with a “when in Madeira” frame of mind, we opted to try the tea served with a small bottle of the island’s famous Madeira wine. “Try the tea first and then add a little wine…and see what you think!” our server recommended. This was definitely a first, but then, so was the wicker toboggan ride.

Our verdict: the tea was delicious, with and without the wine!

D’Oliverias Madeira Wine

After leaving the tea house, we passed an interesting-looking shop that offered wine tastings. Run by five generations of the Oliverias family since 1820, D’Oliverias Madeira Wine is a beautiful space filled with a floor-to-ceiling selection of Madeira wines. These are not table wines, our friendly server explained, and should be matched with foods. Dry and medium dry Madeira wines are served before meals, she told us, and sweet and medium sweet wines are for after dinner.

Our favorite was the sweet after dinner wine, which may have had something to do with the oh-so tasty chocolate honey cake that we were given to pair it with! We bought a small bottle to bring home for our family’s Thanksgiving dinner, which was beginning to take on an international theme, with wine from Tenerife and now this after-dinner treat.

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Clouds were starting to settle over the bright azure sky as we headed back to the port. Late afternoon shadows danced over tiled sidewalks, as if to tell us it was time to move on. Madeira was the final stop of the trip – our 45th anniversary celebration – and I couldn’t help smile to think we had ended our travels with something that would have made our younger selves proud:

Tossing our fears to the wind and jumping in a wicker toboggan to sail down the streets of a place we’d never been before.