Toboggan Ride & Madeira Wine Tasting Tour

A wooden sled ride in Madeira is hard to beat. This 4-hour tour strings together three of the island’s most memorable scenes, starting with the Monte Toboggan run and ending with Madeira fortified wine. You get a small-group feel (up to 8 people) and hotel or port pickup, so you are not hunting buses or sorting directions.

I especially like that the toboggan experience is built for speed and comfort: a wicker basket on wooden runners, cushioned seating, and drivers who push, steer, and brake with rubber-soled boots. The main market stop is also a standout, with the Mercado dos Lavradores in its yellow, azulejo-faced building, designed in the 1930s by Edmundo Tavares. One drawback to consider: the pacing and which stops get full time can vary, so keep your day flexible in case timing gets tight.

Key takeaways

• 2 km toboggan ride from Monte to Funchal, typically around 10 minutes of sliding
• Mercado dos Lavradores in a yellow azulejo building, with flower stalls at the entrance
• Câmara de Lobos for poncha, whitewashed streets, and a sense of place tied to monk seals
• Henrique e Henrique wine lodge, dating to 1850, with barrel-heavy tasting inside
• Small group (max 8) plus hotel or port pickup and drop-off for smoother logistics

Monte Toboggan: the 2 km ride you feel in your stomach

The Monte Toboggan is the headline because it is simple and intense. The ride uses a wicker basket mounted on wooden runners, sliding down a roughly 2 km descent from Monte toward Funchal in about 10 minutes.

Comfort is part of the design. You sit in a cushioned seat, and your toboggan driver controls the journey by pushing and steering from the rear. The braking is done using rubber-soled boots, which keeps things manageable, but still leaves plenty of that classic “we are actually moving” excitement.

This is also one of those Madeira traditions that makes more sense once you see it in action. Tobogganing was invented as a form of transportation back in 1850, and it is still running as a working, public-day experience, not just a museum stunt. Ernest Hemingway even described it as exhilarating, and I get why: it feels fast because it is on a real downhill route with real people around.

The practical side matters here. Wear shoes with grip, and keep your phone secure. There is a lot of motion, even if the ride stays controlled, and you want your hands free to steady yourself during turns.

Mercado dos Lavradores: azulejos, flowers, and the fish hall test

After pickup, you start with 45 minutes at the Farmers’ Market in Funchal, the Mercado dos Lavradores. The building alone is worth your attention: a yellow structure faced with azulejos, designed in the 1930s by Edmundo Tavares.

At the entrance, you will see flower sellers wearing traditional island costume. Their stalls can be tempting because the prices tend to be competitive, and you will find everything from cut flowers to bulbs and potted plants. Even if you do not plan to buy, the color and variety make the market feel alive right away.

Then comes the fish hall, which is where some people either love it or feel a bit queasy. The displays can look intense, with fish shown close up, including species with sharp features and big, stare-worthy eyes. If that is not your style, you do not have to spend much time there.

The better strategy is to head for the upper floor for fruit and vegetable displays. This is where you get more pleasant browsing and a lot of seasonal produce. You can also pick up small, gift-sized items that reflect the island’s food culture without turning your trip into a shopping expedition.

One timing note. Your market time is short, so if you want photographs, do a quick sweep first, then linger where your eye lands. If you care about shopping (flowers, bulbs, small craft items), decide early so you do not lose time to wandering.

Câmara de Lobos: monk seals, Churchill paint vibes, and poncha

Next up is Câmara de Lobos, a fishing village that feels like it has been doing the same job for generations. You spend about 1 hour here, and it usually hits the sweet spot between sightseeing and real atmosphere.

The village name is tied to monk seals, which frequent the harbor. That link adds an extra layer to what you see, especially as you notice how the harbor and stony shoreline shape the whole place. You get whitewashed houses, small shops, and a bar where you can taste poncha, a local drink that fits the village mood.

Câmara de Lobos also has a connection that many people recognize. Winston Churchill chose the village to paint in 1949, and you will feel that “artist town” energy as you walk around.

The harbor area is where the colors show up. Expect colorful fishing boats and a waterfront packed with small details. Even if you are not a big history person, the way the town holds onto its working identity makes it easy to enjoy.

A practical point: this stop is meant to be walked, not power-browsed. Wear comfortable shoes. You will likely spend some time on uneven ground, and you will want to move at a relaxed pace to catch the character without rushing.

Monte scenic views on the way up: use it for photos and orientation

Before or alongside the toboggan portion, you get 45 minutes of scenic viewing around Monte. On Madeira, “views” are rarely one-size-fits-all. The road curves, the air changes, and the angles can shift quickly, so this time is useful for building your bearings.

I like this section because it helps you understand what you are about to do. Once you have seen the slope and the way Monte sits above Funchal, the toboggan route stops feeling mysterious and starts feeling logical.

If you want photos, aim for quick snapshots first, then decide if you want to pause longer. You do not want to lose your timing for the ride itself, especially in a small-group schedule.

If the group is tighter than expected, keep an eye on your guide’s signals. In a tour with timed stops, standing still too long at the wrong moment can push everything else back.

Henrique e Henrique wine tasting: Madeira fortified wine in context

Wine tasting is part of what makes this tour more than just a fun ride. You visit the Henrique e Henrique wine lodge, and the company story matters because it connects the tasting to the island’s scale.

The lodge dates to 1850 and has some of the largest vineyards on the island, with a reputation for producing some of the best Madeira wines. What you will notice right away is the setting: there are huge barrels inside a modern, glass-fronted lodge, so you get both heritage and a clean, organized tasting space.

Madeira fortified wine is different from regular table wine because it is made to be more resilient and expressive over time. In plain terms, it tends to taste richer, with flavors that can feel warm, nutty, or caramel-like depending on the style and how it is served.

Your guide should frame what you are tasting, even if the explanation level varies by person. Still, you can get a lot out of it by asking a simple question: what style is this, and what should I pay attention to first? That turns a tasting from “sip and move on” into a quick education you can remember later.

One thing to keep in mind: tasting is included, but food and drinks are not. If you get hungry after the market and the ride, you might want to plan an easy meal afterward. This is a tour where your appetite might catch up with you fast.

Pickup, timing, and group size: how to make the day run smoothly

This tour is set up for convenience, which is a big part of why it can be worth the price. Pickup is offered from multiple areas, including Funchal, Câmara de Lobos, Caniço, Estreito da Calheta, and Ponta do Sol, and drop-off happens in those same zones.

Pickup is typically at your hotel reception where possible, or outside the main entrance if you are not in a hotel. The company also notes that you should check your email or WhatsApp the day before for more precise pickup times and locations, so do not treat the initial time as the final word.

A key detail I appreciate is the “drivers will wait no longer than 5 minutes” rule. That is short, so be ready. Step outside early, and have your tour confirmation info handy.

The group is small, limited to 8 participants, which helps with the toboggan logistics and keeps the day from feeling like a cattle call. It can also mean small delays spread faster. If you arrive late or the group has trouble finding the pickup point, it can ripple through the schedule.

One caution worth stating: if anything runs behind (vehicle issues happen in real life, not just on paper), some stops might be reduced. I recommend you do not stack a strict commitment right after the tour. Give yourself breathing room, especially for the same-day evening plans.

Price and value: what $117 really buys

At $117 per person for a 4-hour outing, this is not the cheapest thing on the island. But you are not just paying for one activity.

Here is what is included:

• Hotel and port pickup and drop-off
• Professional guide and driver/guide
• Toboggan ride
• Madeira wine tasting

That combination matters because it removes most of the “hidden time costs.” You do not need to figure out transport to Monte, you do not need to coordinate a tasting stop, and you do not need to manage the market and fishing village connections on your own.

What is not included:

• Food and drinks
• Entrance at Cabo Girão (2 euros per person)

That Cabo Girão line can matter if your tour route includes the stop. I would budget the entry fee in case it shows up on your day. If you are not interested in viewpoints or skywalk-style platforms, you can still enjoy the rest of the itinerary, but it is better to be prepared.

Value also depends on your “priority list.” If you want the toboggan ride, market color, a fishing village break, and wine tasting all in one half-day, this price starts to make sense. If you only care about one or two of those, you might save money by booking fewer components separately.

When your guide pace changes: what to watch for

One of the most important lessons for any timed tour is understanding that the day can shift. In this case, the itinerary has fixed blocks, but reality can compress them.

If the guide spends less time on the market, you might see fewer stalls or have less time to browse. If the driver has to adjust for delays, you might also end up with less time at one of the scenic or village stops.

You can protect yourself with two simple habits. First, keep your own “must-do” list short, like toboggan, wine tasting, and one of the two town stops. Second, stay flexible with photo time. If you sprint for photos and miss a regroup point, you will lose time you cannot buy back.

Who should book, and who should skip

This is a good fit if you want a mix of action and culture without long travel days. The Monte Toboggan is the core for many people, and the added stops give you story and local texture beyond the ride itself.

You are also likely to enjoy it if you like food-focused places. The Mercado dos Lavradores brings fish, fruit, flowers, and crafts into one short visit, and Câmara de Lobos keeps it grounded with a working harbor feel. The wine lodge adds a different kind of local taste, with Madeira fortified wine in a barrel-filled setting.

It is not a fit for everyone. The tour is listed as not suitable for wheelchair users, so if mobility is a concern, you will want to look for another option that matches your needs better.

It is also a decent match for couples and solo travelers who want a guide to handle navigation. If you are a group of friends who prefer private pacing, you might prefer a more tailored tour, since small-group timing can feel tight.

Should you book this Madeira Toboggan and wine tasting?

If your top priority is doing the Monte Toboggan in a guided, low-stress way, this is a solid choice. The ride itself is the star, and you get it paired with a real market stop, a fishing village break, and Henrique e Henrique Madeira wine tasting.

I would consider skipping or at least adjusting expectations if you need a very strict timetable or a lot of structured commentary at every stop. On a tour like this, your enjoyment comes from the main experiences, and smaller details depend on how the day runs.

If you can keep your afternoon open and you are happy with a compact itinerary, book it. If you only want the market or only want wine, spend your time choosing a narrower option and keep the rest of the day free for beaches and self-guided wandering.

FAQ

How long is the Toboggan Ride & Madeira Wine Tasting Tour?

The tour lasts 4 hours.

What is the price per person?

The price is $117 per person.

Is the Monte Toboggan ride included?

Yes. The cost of the toboggan ride is included.

Does the tour include hotel pickup and drop-off?

Yes. Hotel pickup and drop-off are included, and port pickup and drop-off are included too.

What stops are included in the itinerary?

You visit the Mercado dos Lavradores in Funchal (45 minutes), Câmara de Lobos (wine tasting and sightseeing, 1 hour), and Monte (scenic views on the way, 45 minutes), with drop-offs in the listed areas.

Which languages does the guide speak?

The live tour guide speaks English and Portuguese.

Is this tour suitable for wheelchair users?

No. It is listed as not suitable for wheelchair users.

Is Cabo Girão entrance included in the price?

No. Entrance at Cabo Girão (2 euros per person) is not included.

How many people are in the group?

It is a small group, limited to 8 participants.

Is there free cancellation?

Yes. Free cancellation is available up to 24 hours in advance for a full refund.