Toboggan Ride & Madeira Wine Tasting Tour

The interesting bit here is the mix. You get the speed, the craft, and the local flavor, all in one half day: a Monte toboggan ride that drops from Monte to Funchal, plus Madeira fortified wine, plus two very different stops in town. I especially love the Monte Toboggan mechanics, with the driver steering and braking, and I like how the food and wine pull you into real daily life. One heads up: the order and timing can swing a bit, so you should be ready for a shorter market moment if the day runs tight.

In a good run, the guide makes the difference. When Ruben is on your day, the vibe stays fun and the info lands in a way that actually helps you enjoy the stops more. The one drawback to plan around is communication and pacing, since not every departure matches the level of explanation you might expect, and one person I heard from got little support during the wine tasting.

Key things I’d circle before you book

• Monte Toboggan ride: a cushioned wicker basket on wooden runners, about a 2 km descent in roughly 10 minutes
• Mercado dos Lavradores: a yellow building with azulejos, designed in the 1930s by Edmundo Tavares
• Câmara de Lobos: a photogenic fishing village tied to monk seals and a real poncha bar scene
• Henrique e Henrique tasting: a glass-fronted wine lodge dating from 1850, with huge barrels and major vineyard scale
• Small group: limited to 8 people, with hotel and port pickup in parts of Funchal and nearby towns

From hotel pickup to Monte, how the 4 hours flow

This is a tight, four-hour format, with pickup built in. You meet your driver at your hotel reception when possible, or you wait outside the main entrance if you are not in a standard hotel setup. Pickups cover areas including Funchal, Câmara de Lobos, Caniço, Ponta do Sol, and Estreito da Calheta, and drop-off returns you to the same regions.

The pacing works best if you treat it like a sprint through Madeira, not a slow walk. You have a fixed block for the main market in Funchal, then you move to Câmara de Lobos for wine and sightseeing, and you finish around Monte for the ride and the best views on the way down. You will be on and off vehicles a few times, but it is straightforward.

Two practical tips help your day feel smoother. First, be ready right at the pickup time. The driver waits no longer than five minutes after the scheduled pickup. Second, wear shoes you can grip in crowds and on uneven market floors, because the market and the village both have areas where standing and turning quickly makes sense.

Also, keep in mind that this tour is a small-group experience. With a max of eight people, you should get closer to the guide than on big bus tours, but you still have to stick to the group schedule. That is why I say timing matters: the ride is the star, so everything else tends to flex around it.

Mercado dos Lavradores: azulejos, cut flowers, and fish you might blink at

The stop in Funchal is at Mercado dos Lavradores, the main market in a yellow building faced with azulejos and designed in the 1930s by Edmundo Tavares. Even before you reach the stalls, you see the island side of Madeira. Flowers sellers in traditional island costume take over the entrance area, with cut flowers and bulbs on offer, including orchid blooms that can tempt you into carrying a souvenir.

If you like color, this is your place. You can walk the edges of the stalls and still see the whole rhythm of the market: people browsing, seasonal produce, and that constant mix of smells that says you are not in a tourist-only shopping area.

The fish hall is the part that can catch people off guard. It can feel intense, with scabbard fish that show sharp teeth and large staring eyes. If you are squeamish, you do not need to linger there. I suggest moving quickly through the fish area and then heading upstairs.

On the upper floor, the mood softens. You get more pleasant sights and fragrances, with lavish displays of seasonal fruits and vegetables. This is where the market shifts from raw, salty seafood energy to a more market-fresh shopping experience. It is also where you can buy small, food-like gifts for later, if you want something easy to carry.

This is a 45-minute stop, so do not plan to shop like you have an hour of browsing budget. Instead, think of it as a sensory stop: see the place, pick one thing you genuinely want, then move on before the group pulls away.

Câmara de Lobos: poncha, monk seals, and the village Winston painted

Next comes Câmara de Lobos, one of Madeira’s most atmospheric fishing villages. The name comes from monk seals that frequent the harbor, which adds a neat layer to the setting. It is easy to see why this village draws painters and photographers, because the center stays very human scale: whitewashed houses, small shops, and a bar where you can taste poncha.

Poncha is a local drink, and the bar setup here makes it feel like part of village life, not a staged tasting. If you want to try it, this is the point in the tour where you can take your time and let the village rhythm land.

The waterfront itself is another highlight. The stony beach has colorful beached fishing boats, and the colors make the whole stretch feel lively even when the fishing day is quiet. If you like art history, there is a fun connection too: Winston Churchill chose Câmara de Lobos for painting in 1949.

One thing to remember is that this is not a museum stop. You are walking through a real working village. That means you will see everyday movement, not just curated sights. It is a good change of pace after the market, because it turns food and supply into scenery and stories.

You also have about an hour here for wine tasting and sightseeing, so if you want photos, take them early. The light can shift, and you do not want to spend all your best photo time later while the group is ready to move.

Henrique e Henrique Madeira wine tasting: fortified wine in a winery from 1850

If Madeira wine is your interest, you will get a real winery moment here at Henrique e Henrique. The lodge is modern in presentation but dates from 1850, with huge barrels inside a glass-fronted setting. It is also described as owning the largest vineyards on the island and producing some of the best Madeira wines around.

What you can expect from a tasting like this is less about a formal lesson and more about a guided introduction to Madeira fortified wine. Madeira fortification has a different logic than many table wines, and that shows up in the flavors. You will likely get a short explanation of what makes Madeira distinctive, then a chance to taste and compare how it feels in your glass.

The value of this stop is that it ties Madeira wine to place. You are not tasting wine in a generic tasting room far from everything else. You are tasting it while you are already experiencing the coastal village feel of Câmara de Lobos and the market culture that surrounds food and daily life.

Still, I will be honest: the quality of support during the tasting can depend on the guide’s style. One person I heard from said the tasting felt more independent than guided. So if you care a lot about understanding what you are tasting, ask questions early, and keep your curiosity active. Guides can answer best when you prompt them directly.

If you want a small plan, taste one item slowly first, then ask what to look for in the next pour. That keeps the tasting from feeling like a rushed checklist.

Monte Tobogganing on wooden runners: speed, safety, and how braking works

Now for the part people talk about. Monte Toboggan is a ride on a wicker basket mounted on wooden runners. The descent is about 2 km, roughly a one mile drop, and it takes around 10 minutes. The key detail is that it is fast, and it is public road level.

The ride is made by thousands every year, and Ernest Hemingway once described the experience as exhilarating. You feel why when you see the track come down from Monte toward Funchal.

The mechanics are simple, but they are the whole thrill. You sit in a cushioned seat. The driver rides at the rear, pushing and steering. Braking is done using rubber-soled boots, controlled at the runner contact points. In other words, you are not on rails with a modern braking system. You are on wood and the driver’s skill.

That is also why your body language matters. Hold on the way your driver suggests. Stay balanced. Keep your hands and feet where you are told. If you tense up too much, you can make the ride feel harsher than it needs to be. I think calm helps, and the cushioned seat gives you a little forgiveness on the jostle.

It was invented as a form of transportation in 1850, so the ride is not just a modern amusement idea. You are doing a recreated transport method that turned into a tradition. That adds meaning even if you are mainly there for the speed.

One more practical note: the scenic views on the way to Monte are part of the overall experience, and they are also where you get the context for why the descent feels so dramatic. If your day feels rushed, at least look up and take in the view once before the ride starts.

Price and what you actually get for $117

At $117 per person for a 4-hour tour, you are paying for a bundle. The cost covers the toboggan ride itself, hotel pickup and drop-off, port pickup and drop-off, a professional guide, and the Madeira wine tasting. That is a lot of built-in value because you are not just buying a single activity. You are also covering transport and two distinct cultural stops.

Where the value can change is in how consistently the day runs according to plan. One person had a strong ride experience but felt the rest of the tour ran short, with the market portion left out and the day ending earlier than expected. Another person ran into timing trouble at a market-related component and had a long wait after a transport issue, which cut the tour short.

I cannot control those variables. What you can control is your expectation-setting. Treat the Monte toboggan as the main event, and treat the market and village moments as important bonuses that are worth your attention. If you go in with that mindset, the day still feels like it delivers what matters most.

Also, note what is not included: food and drinks, plus an entrance fee at Cabo Girão listed as 2 euros per person. If your day includes that viewpoint stop, bring small cash or card readiness.

Who this suits best, and who should skip it

This tour is best for people who want a classic Madeira mix: market color, a village atmosphere, fortified wine, and an old-school speed ride. You will probably enjoy it most if you like experiences where the guide nudges the story but you still do your own exploring with a plan.

It is a small group limited to 8 participants, so you avoid the chaos of big bus tours. That matters in a place like the market, where crowd flow makes a difference.

One clear limitation: it is not suitable for wheelchair users. The toboggan itself and the movement through market and village areas make it hard to adapt.

If you want heavy, continuous commentary every step, you might want to manage expectations. Some guides may deliver more info than others, and the pace of a short tour can reduce how much you hear. The fix is simple: ask direct questions when you are listening, and you will likely get better answers.

Should you book this tour?

I think you should book it if Monte tobogganing is on your Madeira must-do list and you want a curated day that also includes wine tasting and two strong cultural stops. The $117 price feels fair when you count the included ride, pickup, guide time, and wine tasting in one half day.

Skip it or at least reconsider if you are the type who hates any schedule pressure, because this is a four-hour sprint. If you are sensitive to time changes, build in a little extra buffer on your travel day plans and keep your expectations grounded: the toboggan ride is the anchor, and everything else is part of the bonus package.

If you get Ruben, you are likely in for a genuinely fun guide style that helps the day feel lively instead of rushed.

FAQ

How long is the Toboggan Ride and Madeira Wine Tasting tour?

The total duration is 4 hours.

Where do you get picked up?

Pickup is available from Caniço, Estreito da Calheta, Ponta do Sol, Funchal, and Câmara de Lobos, where possible meeting is at hotel reception. If your accommodation is not a hotel, you wait outside the main entrance.

What does the tour include?

It includes hotel pickup and drop-off, professional guide, the toboggan ride, Madeira wine tasting, and driver/guide. Port pickup and drop-off are also included.

Is food included?

No. Food and drinks are not included.

How much is the Cabo Girão entrance fee?

The entrance at Cabo Girão is listed as 2 euros per person, and it is not included.

What languages are available?

The live tour guide is available in English and Portuguese.

Is the tour suitable for wheelchair users?

No, the tour is not suitable for wheelchair users.

Can I cancel for a full refund?

Yes. You can cancel up to 24 hours in advance for a full refund.

How long will the driver wait at pickup?

Drivers will wait no longer than 5 minutes after the scheduled pickup time.