Toboggan thrill in the mountains. This half-day tour strings together Monte, a fast downhill sled run, and Madeira’s most dramatic valley scenery into a tight 4 hours. I like that you’re guided with real local context, and the big sights come in a sensible order, helped by guides like Tony and Lucy who keep things moving and explain what you’re seeing.

You’ll get two highlights that are hard to fake: the 2-kilometer Livramento toboggan and the secluded Curral das Freiras (Nuns Valley), with its lava-rock setting and 16th-century pirate story. The only real drawback to plan around is timing and weather: if it’s rainy, the toboggan setup can change, and you may face a small added cost depending on how many people share a basket.

Key points at a glance

• Early arrival to beat the queue: the first stop is Monte so you can get on the sleds sooner
• A real taste of the island: included liquor tasting in the valley (plus optional chestnut cake)
• Big viewpoints without a full day: Eira do Serrado’s 1,094 m overlook plus Pico dos Barcelos
• History with a viewpoint: Monte’s church includes the tomb of Emperor Charles I of Austria
• Small-group feel: multiple pick-up options and a mini-bus setup often keep things friendly

Monte plus Toboggan: a very Madeira kind of half-day

Madeira can feel like you’re always heading uphill. That’s exactly why this tour works. You start in Funchal, then swing up into Monte, where the day turns from sightseeing into something physical and fun: the old toboggan down Livramento. It’s the kind of experience you can’t reproduce on your own with a rental car and a map.

What I like most is the balance. You get adrenaline first, then you slow down for viewpoints and the valley. You’re not just collecting stops. You’re seeing how the island’s geography shapes everyday life here: steep roads, tunnels, and those high lookouts that locals and visitors rely on.

It also helps that the tour leans on guides who clearly enjoy the work. Names like Tony, Daniel, Lucy, and Sandra show up again and again in feedback, and the common thread is good timekeeping plus humor that makes the history land better than a textbook.

The plan is about 4 hours, so you won’t end up exhausted or stuck for an entire day. The tradeoff is you need to be ready for a “pack it in” pace. Each stop is focused, not sprawling.

Pickup and timing: how you avoid the worst of it

This tour is built around one practical idea: start early and get the sled ride done before the crowd peaks. That’s why Monte is the first big activity. The toboggan line can swell later in the morning, and the easiest way to dodge it is exactly what this route does—arrive with the schedule advantage.

If you’re staying in Funchal hotels, your pickup is usually straightforward from the many listed options around the city. If you’re coming from Santa Cruz, there may be an extra pickup cost (listed as €10 per person). Caniço and Garajau are noted as having no additional pickup cost.

If you’re on a cruise, you don’t head to the cruise terminal meeting point for this shared-style pickup approach. Instead, the meeting point is around the Cristiano Ronaldo Museum area, roughly 8 minutes from the ship. That matters if you’re trying to minimize walking at the start of the day.

One more timing detail that affects your day: pick-ups for Santa Cruz, Caniço, and Câmara de Lobos are noted as earlier than Funchal. So if you hate early alarms, this is where you want to check your exact pickup time and plan breakfast accordingly.

And yes—bring a jacket and water. Mountain weather can shift fast, especially when you’re moving between sea-level Funchal and higher viewpoints.

Monte’s church stop and Emperor Charles I’s tomb

Monte isn’t just a launchpad for the toboggans. It’s one of Madeira’s historic tourist anchors, with a compact center that’s easy to explore in a short visit.

A key stop is the church where you can see the tomb of Emperor Charles I of Austria. This is the kind of detail that gives the day a “wait, what?” moment. You’re in a Portuguese setting, surrounded by Madeira’s greenery and stone roads, but the history reaches into Central Europe.

In a short tour format, this stop matters because it gives you context for why Monte became important as a destination in the first place. It also helps break up the rhythm between riding the bus and hopping into the toboggan line.

If you enjoy a bit of history but don’t want a museum day, this is a sweet spot. You’ll get the essential story and then move on—no lingering, no sitting through long explanations.

The 2-kilometer Livramento toboggan ride: fun, old-school, and well run

This is the headline act. The tour includes the toboggan (basket-sledge) ride down the old road of Livramento, a 2-kilometer downhill run. The bus meets you at the bottom, then the men (carreiros) load the sleds onto a truck for the next cycle.

That detail matters for two reasons:

1. You’re not just hopping on a ride. You’re seeing a living system that’s been running for years.
2. The “old transport” feeling is real, not staged.

How to think about safety and comfort

The ride is exciting, and it’s normal to feel a little thrill when the cart picks up speed. The bigger point is that guides handling your group approach safety the old-fashioned way: clear instructions, careful control, and keeping you aware of what’s happening.

In feedback, people repeatedly praised how guides made passengers feel comfortable and handled timing well. That early-arrival strategy also reduces the stress factor—less queueing means you spend less time getting nervous and more time enjoying the ride.

Weather and the number of riders

One important practical note: on a rainy day, the toboggan arrangement can change. If you have three people in one basket, the data notes that they may not go down in rain. If a third person has to be handled differently, there can be an additional €10 cost. Also, if you book as a single rider, there may be an extra €10 charge because singles can take up two places when pairing isn’t possible.

If you’re traveling as a couple or small group, it’s usually simpler. Still, it’s worth checking the day-of conditions in your own planning, because wet roads can affect how rides run.

A small souvenir angle

At the bottom of the run, there are souvenir photos available, with pricing mentioned as €10 in some reports. If you’re the type who likes a keepsake, this is an easy add-on right after the ride.

Eira do Serrado: a high viewpoint that makes everything click

After the toboggan, the tour climbs to Eira do Serrado, a viewpoint at 1,094 meters above sea level. This is one of the best moments of the day because it gives you a “connect the dots” view of Madeira’s structure.

You’ll see across to major parts of the island from a high vantage point. The scenery around this area is also part of the experience: chestnut trees and eucalyptus plants show up in the area, and you’re close enough to feel how the island’s vegetation changes with altitude.

What makes this stop especially useful is the way it sets up the next segment. Once you see the scale from Eira do Serrado, Curral das Freiras (Nuns Valley) isn’t just a name—it starts to look like the isolated bowl of terrain it actually is.

You’ll likely get some free time here, which is good because it lets you do the practical stuff: take photos, step away from the group for a minute, and catch your breath before the valley.

Curral das Freiras (Nuns Valley): lava rock, pirate history, and liquor tasting

Now for the part that surprises people. Curral das Freiras, often called the Nuns Valley, is surrounded by lava rock and sits apart from the rest of the island. It takes its name from a group of nuns who once inhabited the valley after fleeing pirate attacks during the 16th century.

There’s also an important clarification that helps avoid confusion: there is no convent here in the modern sense. The tour notes that you’ll see a nun house rather than a convent.

What you do on the ground

This is a guided visit with a meaningful chunk of time on-site. The day’s pace slows just enough that you can actually enjoy the view and the feel of the place, not just pass by it.

The tour includes a liquor tasting in the valley village. The tasting is described as traditional liquors made locally, and it’s included in the price. This is where you get to try something that’s more personal than buying a bottle later at a souvenir shop.

Food is part of the culture here too, but it’s not automatically included. You can try traditional chestnut cake and pastries in the area, but the cost for those is separate.

One optional add-on: the 200-year-old nun’s house has an entrance fee of €1 if you choose to visit. If you like short history moments, it’s a low-cost way to deepen the story.

Why this stop works for value

It’s easy to underestimate how much value you’re getting from this part of the day. The included tasting makes the stop feel “complete,” not like just another viewpoint. And because Curral das Freiras is visually distinctive—isolated, rocky, steep—your photos look like you went somewhere more remote than you actually did.

In feedback, people also described the area as having shops and a restaurant, so you’re not stuck without options if you want something sweet after the tasting.

Pico dos Barcelos: the quick final panorama before you head back

On the way back toward Funchal, the tour stops at Pico dos Barcelos, another viewpoint at 355 meters. This is more compact than Eira do Serrado, but it’s a nice “last look” at Madeira before you descend into the city.

Photo stops here can be quick, but the payoff is that you get different angles of the coast and settlements. Think of it as a final correction to your mental map: the island doesn’t look the same from every height.

This segment also helps the tour feel well paced. After the intensity of the toboggan and the slower valley experience, you get a lighter touch stop that doesn’t drain your energy.

Guides make the difference: what you should look for in your host

One of the strongest signals in the feedback is that the guide/driver isn’t just a dispatcher. People consistently praised guides like Tony (noted for humor and bilingual help), Daniel, Lucy, and Sandra for being attentive and organized.

Here’s what that means for you practically:

• You’ll spend less time wondering what’s next because the timing is managed.
• You’ll get explanations that connect the dots between geography, history, and daily life.
• You’ll likely feel more confident during the toboggan, since safety instructions are clear and the ride is handled well.

If you’re choosing a half-day activity and you care about getting real local context without adding time, the guide component is a big part of the value.

Price and value: does $47 make sense for what’s included?

At about $47 per person for a 4-hour outing, the price looks reasonable once you break down what’s actually covered.

You’re not only paying for transportation and viewpoints. The tour includes:

• Hotel pickup and drop-off
• A guided tour
• The toboggan ride
• Free liquor tasting in Nuns Valley
• For cruise guests: pickup from the meeting point near the Cristiano Ronaldo Museum

That cocktail of inclusions is what turns the day into more than a basic bus sightseeing loop. The toboggan alone is the kind of activity that would cost extra elsewhere, and adding the tasting means you leave with something memorable that goes beyond photos.

Costs to consider on top:

• Cakes/snacks and coffee/tea are not included.
• The nun’s house entrance is €1 if you want it.
• Rain-related changes can lead to a possible €10 extra cost depending on how many riders share a basket.
• Pickup costs for certain Santa Cruz hotels can add €10 per person.

So the best value is for groups traveling together in a way that matches the toboggan basket setup. Couples and small groups usually find fewer extra charges.

Who should book this Monte and Nuns Valley tour

This is a great fit if you want:

• A classic Madeira experience that feels old-school and fun
• Strong scenic payoff in half a day
• More than just viewpoints, including the tomb stop and included tasting
• A guide who keeps things organized and makes the history understandable

It might be less ideal if:

• You hate early starts, because pickup can be earlier for certain areas and the tour works best when you reach Monte early
• You travel with a larger group and worry about rain affecting the basket arrangement

Families can be comfortable with the pacing since it’s 4 hours, and feedback included positive notes about children enjoying the day. Just be ready for stairs, uneven terrain around viewpoints, and the general mountain-walk reality.

Should you book this Monte plus Toboggan tour?

Yes, if you’re the type who wants your Madeira day to feel like Madeira. The toboggan ride plus Nuns Valley pairing is exactly the kind of contrast that makes the island memorable—adrenaline, then isolation and quiet beauty.

Book it if your schedule allows you to handle an early pickup and you’re okay with a tight itinerary. It’s a smart value choice because the core experiences are included, not optional add-ons.

If rain is in your forecast and you’re traveling with exactly how many people you’ll share baskets with, check conditions and be flexible. The tour’s structure is designed to reduce stress, but weather can still change how the ride runs.

FAQ

Is the toboggan ride included in the price?

Yes. The guided tour includes the toboggan ride, plus hotel pickup and drop-off.

Where is the tour pickup for cruise ship guests?

Cruise guests meet at the Cristiano Ronaldo Museum area. The notes say this is about 8 minutes from the ship, and pickup from the cruise terminal itself isn’t offered for this shared-tours approach.

Is there an actual convent in Nuns Valley?

The tour notes that there is no convent in Curral das Freiras. You’ll find a nun house, not a convent.

Do I need to pay extra in the Nuns Valley?

Liquor tasting is included. Chestnut cake and pastries are not included, and the 200-year-old nun’s house has an entrance fee of €1 if you want to visit.

What should I bring for the day?

Bring water and a jacket.

What happens if it rains?

On rainy days, the toboggan ride setup can change. The notes say baskets of three do not go down in rain, and a third person may need to pay an additional €10 depending on the situation.