Guided Toboggan Ride and Madeira Wine Tasting Tour

Wooden sleds and Madeira wine in one run. I love the mix of local sights at Mercado dos Lavradores and the simple pleasure of tasting Madeira wine at Henrique e Henrique. It’s a smart way to pack real Funchal flavor into a 4.5-hour guided outing.

One consideration: the toboggan descent brings you down on the Funchal side, so think ahead about getting back up to Monte if you want to revisit the views.

Key highlights before you ride

• Mercado dos Lavradores stop in a yellow, azulejos-fronted building designed in the 1930s by Edmundo Tavares
• Monte Toboggan ride included, a 2 km descent that takes about 10 minutes
• Hands-on toboggan control, with drivers pushing and steering from the rear and braking with rubber-soled boots
• Madeira wine tasting at Henrique e Henrique, a glass-fronted lodge with huge barrels you can actually see
• Small group size, max 8 travelers, which keeps things calmer during the ride and transitions
• Pickup options from hotels and the port, so you start without hunting for transport

The 4.5-hour loop that makes sense in Funchal

This is a half-day plan that works well when you want more than one highlight, but you don’t want your whole day tied up in logistics. The tour runs about 4 hours 30 minutes, and it keeps the pacing tight: a market stop, time around Monte, then a wine lodge tasting stop.

You’ll also like that the price includes a lot of the usual headaches. You get hotel pickup and drop-off, port pickup and drop-off, plus the toboggan ride itself. For $104.72 per person, that bundling matters because the Monte toboggan area is easy to reach with the group, and the ride is the kind of activity where a last-minute scramble can cost extra time.

One more plus: the group is capped at 8 travelers. That size tends to make it easier for your guide to give clear instructions before the slide starts, and you are less likely to feel like you are standing around with a giant crowd.

Mercado dos Lavradores: azulejos, fruit smells, and quick souvenir fuel

Your tour kicks off at Mercado dos Lavradores, one of Funchal’s best-known market stops. This is not a quiet photo stop. It’s a working market with strong scents, bright color, and a steady flow of people doing real errands.

The building is a yellow structure faced with azulejos, designed in the 1930s by Edmundo Tavares. That tile front gives it a classic Madeira look, and it also helps you orient fast. From there, you get plenty to see: stalls selling fish, exotic fruits, and local crafts.

Another detail I love here is how the entrance area draws attention. Flower sellers, dressed in traditional island costume, have colonized the market entrance. Their stalls are a common go-to if you want a small Madeira souvenir, like cut flowers, bulbs, or delicate orchid blooms.

Timing-wise, you get about 30 minutes at the market. That is long enough to wander, look, and pick up something small if you want, but not so long that you feel stuck waiting. If you go hungry, pace yourself, because market smells can be intense in the best way, especially around fruit.

Monte Toboggan at Nossa Senhora do Monte: the ride is the point

After the market, the day shifts into pure action. The toboggan experience centers around Paroquia de Nossa Senhora do Monte, the base area for the Monte run.

Here’s what you need to know about the sled itself. The toboggans are sliding wicker baskets mounted on wooden runners. The route covers about 2 km (roughly 1 mile) and takes about 10 minutes to descend. It may not sound long, but it feels fast, because it’s a public-road style descent down a street route.

The ride is built around drivers who actively manage the run. They push and steer from the rear, and they control braking using rubber-soled boots. You also sit on a cushioned seat, which helps for a smooth feel and a more comfortable hold.

The Monte Toboggan tradition is old-school but not museum-still. It’s made for real movement. People take this ride by the thousands every year, and the activity was invented as transportation in 1850. Ernest Hemingway is said to have described it as exhilarating, and that tracks with the energy you see as people get ready to go.

What to expect during the 10-minute descent (and how to enjoy it safely)

I’ll be honest, this is the part where you should listen closely. The joy of the ride comes from speed and momentum, and the driver is the key. Make sure you understand what your driver expects you to do with your hands and posture once you are seated.

Because this is a wicker basket on wooden runners and you are riding at speed on a road route, wear practical shoes. Closed footwear is the easy move, since you may need a stable footing during boarding. If you have a bag, keep it compact and secure. You do not want anything swinging into your space during the ride.

Also, embrace the fact that this is not a smooth roller coaster. The sensation is more like controlled street sledding. That’s part of the charm.

Finally, be realistic about timing. You only spend about 10 minutes sliding, but the rest of the stop is there for setup and the surrounding experience around Monte. The tour builds in time around this area, not just a quick grab-and-go ride.

Monte gardens and Funchal views after the sled

Once the toboggan run is done, the experience doesn’t vanish into thin air. You get time to enjoy the gardens and the view of Funchal from the Monte side.

This is a nice contrast if you were tense during the ride. After the speed, you can slow down, catch your breath, and take in the city from above. It’s also useful because it helps you process what you just did before you move on.

The one practical trade-off is that the ride ends down toward Funchal. That means you should think about how you will return to the higher Monte area if you want more time up there. In practical terms, a return means a taxi or a walk back up, depending on what you feel like doing after the descent.

Henrique e Henrique in Câmara de Lobos: Madeira wine tasting with big visible barrels

The final highlight is wine, and specifically Madeira wine tasting at Henrique e Henrique. This is where the tour shifts from motion to a calmer, sensory stop.

The lodge is described as glass-fronted and modern, and you can see huge barrels inside. That matters, because it turns wine tasting into something visual, not just a small sip at a counter. The space is meant to show the working side of wine, and the barrels do the talking for you.

Henrique e Henrique dates to 1850 and is known for having large vineyards and producing some of the best Madeira wines around. The company has also collected medals and awards recently for efforts meant to change Madeira wine’s reputation, pushing back against the idea that it’s only old-fashioned or stuffy.

In other words, you are not just there for a random tasting. You are at a place trying to make Madeira feel current, even if the roots go back to the 1800s.

You get about 45 minutes at this stop, and the tasting is included in the tour price. That’s a comfortable amount of time to taste, ask what you should pay attention to, and decide what you might want to buy later if you are the type who brings home bottles.

How the included pickup and small group change your day

Pickup and drop-off might sound like a convenience detail, but for this kind of tour it affects how you experience it. Getting picked up means you spend your energy on the market and the ride, not on finding the right buses or sorting out two separate rides.

This tour offers hotel pickup and drop-off and port pickup and drop-off. That gives it flexibility if you are on vacation in town or if you are starting from a cruise. You’ll also have a mobile ticket, which usually makes last-minute check-in easier once you’re already in the area.

And again, the max group size of 8 travelers is not a small detail. At the toboggan, people need clear instructions and calm timing. A smaller group helps keep that flow manageable.

Best for first-timers, couples, and anyone who likes mixing food with thrills

This is an excellent match if you want a “one ticket” day. You get a market immersion, an included Monte toboggan ride, and a Madeira wine tasting stop, all in one guided loop.

It’s also a good choice if you have never done the Monte Toboggan before. The ride is the star event, and the tour structure makes it approachable. You are not left to figure out what to wear, where to stand, or how to interpret the process. Your guide brings you through the steps, then you get to enjoy the moment.

On the other hand, if you are someone who wants a long wine stop only, or you prefer slow travel with minimal movement, the 4.5-hour window might feel busy. You are going to see the highlights, not linger for hours in one place.

Price check: what $104.72 buys you in real value

At $104.72 per person, this is not a “grab a snack and go” tour. But it can be good value if you add up what’s included.

You are paying for:

• guided stops at Mercado dos Lavradores
• an included Monte toboggan ride
• a Madeira wine tasting at Henrique e Henrique
• hotel or port pickup and drop-off

If you were to plan those pieces separately, you’d likely spend time organizing transport and ticketing, and the toboggan ride is the type of activity where timing matters. Here, the tour covers the essential pieces so you can show up and enjoy.

One more value point is group size. The tour max is 8 travelers, which often means more hands-on guidance and less waiting. That can matter when the ride is the peak moment and you want it to go smoothly.

Should you book this Madeira wine and toboggan tour?

I think you should book if you want a true Madeira mix in one half-day: local market atmosphere, one iconic Funchal adrenaline moment, and an included Madeira wine tasting at a long-running lodge.

Skip it only if the toboggan aspect is not your thing, or if you know you will want lots of free time to explore Monte on your own after the slide. The ride ends down toward Funchal, so plan for that return. If you are fine handling that, the combo is a great way to make your time in Funchal count.

FAQ

How long is the guided Toboggan ride and Madeira wine tasting tour?

It runs for approximately 4 hours 30 minutes.

Is pickup and drop-off included?

Yes. The tour offers hotel pickup and drop-off and also port pickup and drop-off.

Is the Monte toboggan ride included in the price?

Yes. The cost of the toboggan ride is included.

How many people are on the tour?

The maximum group size is 8 travelers.

Does the tour require good weather?

Yes. It requires good weather, and if it is canceled due to poor weather you will be offered a different date or a full refund.

Is free cancellation available?

Yes. You can cancel up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the start time, the amount paid will not be refunded.