
I’ve always prided myself on being open to new destinations. I have a genuine curiosity for the world and, when the opportunity to visit Madeira came up, I jumped at the chance to discover a place I knew next to nothing about. I thought I’d be going to a lovely island, perhaps a little remote, but not necessarily anything extraordinary.
What I found, however, was heaven.
The allure of Madeira isn’t just in its stunning landscapes, breathtaking views, or even its remarkable food (though all of these are certainly worth mentioning). No, what truly makes Madeira so enchanting is its unique charm. The island feels untouched, as though it exists in a realm apart from the ordinary world, where time slows and nature hums in a quiet symphony. Its narrow streets, lush greenery, and warm, welcoming locals make it feel like something out of a dream.
But now, as I sit here reflecting on my experience back home, I am caught in a dilemma: how do I talk about Madeira without perhaps contributing to the loss of what makes it so special? Tourism is a double-edged sword, and as much as I want to share my experience with others, part of me wants to keep this gem to myself. There’s a risk, you see. The more people that visit, the more the island’s unique charm could be dulled by commercialization, overdevelopment, and the inevitable wear and tear that tourism brings. It’s something I’ve seen happen in so many other beautiful destinations around the world.
Madeira is a place that deserves to be preserved, where its beauty and authenticity must be cherished rather than exploited. The island feels like an intimate secret—a place that is still in touch with its roots, yet on the verge of being discovered by the masses. As much as I want others to experience it, part of me hesitates, because I don’t want to be the one responsible for diminishing the very thing that made me fall in love with it.
That said, there is a reason I feel compelled to share my experience. Madeira truly is one of the most wonderful places I’ve ever visited. From the wild coastline that plunges into the ocean to the peaceful levada walks through forests that look as though they belong in fairy tales, it’s an island that leaves an indelible mark. But as much as I want to promote it, I am torn between spreading the word and guarding its solitude. So, if you do decide to visit, let it be with the same respect and admiration that I have for this enchanting island. Its charm is a treasure worth preserving.
A Short History of Madeira’s Highlights

The Levadas:One of the most iconic features of Madeira are its levadas—irrigation channels that were originally built to carry water from the island’s lush mountains to the arid farming regions below. Dating back to the 16th century, these aqueducts were an engineering marvel of their time, cutting through rocky terrain and often clinging to steep mountainsides. Today, many of these levadas have been turned into scenic hiking trails, offering visitors a chance to explore the island’s wild beauty in a truly unique way. As you walk along these paths, it’s easy to marvel at the ingenuity of those who built them, and the way they’ve become a symbol of Madeira’s deep connection to nature and sustainability.
Hillside Agriculture: Madeira’s steep hillsides are both a challenge and a gift for its agriculture. The island’s farming history is defined by its terraces—known locally as poios—which have been carved into the hillsides over centuries. These terraces are used to grow a variety of crops, including sugarcane, bananas, and the island’s famous vines. The arduous process of farming in such a challenging landscape has led to a culture of resilience and ingenuity among the island’s farmers, who have managed to turn these tough conditions into a productive agricultural landscape. The unique microclimates across the island allow for the cultivation of a diverse array of produce, and many of the traditional farming techniques are still in use today.
Our tour and dinner at Razão Concept (Socalco Nature). The wine made here is incredible!
The Wine Industry: Madeira wine is an integral part of the island’s heritage. Produced on the steep slopes of the island’s volcanic soil, this fortified wine has been crafted since the 15th century and was famously discovered by early Portuguese explorers. Its distinctive taste comes from the unique aging process that involves heating the wine and allowing it to oxidize. The island’s wine industry flourished over the centuries, becoming a prized export, and it remains a key part of the island’s identity today. The wine is not just a drink; it is a symbol of Madeira’s resilience, its historic global connections, and its ongoing dedication to quality craftsmanship.
Tourism, A Double-Edged Sword: While tourism has been a boon for the island’s economy, it is also slowly beginning to erode some of the very qualities that make Madeira so special. The island is increasingly being marketed as a must-visit destination, leading to the development of more hotels, restaurants, and tourist attractions. While this has brought more jobs and prosperity, it has also introduced the kind of mass tourism that threatens to overcrowd the island’s natural spaces. Small villages and quiet areas are becoming more crowded, and the delicate balance between preserving tradition and embracing modernization is being tested. As the island becomes more popular, the charm that first drew me in—the serenity, the authenticity—feels at risk of being lost to commercialization. It’s a sad reality that many hidden gems face, and Madeira is no exception. If we’re not careful, tourism could ultimately spoil the very thing that makes the island so appealing in the first place.
History of the Madeira Toboggan Ride:
The tradition began in the 1850s, in the capital city of Funchal. At that time, the only way to travel down the steep hillsides of the island was on foot or by carriage, which was often a slow and difficult process due to the island's rugged terrain. However, enterprising locals began using wooden sledges as a faster and more efficient means of descent. These sledges, or "cestas," were designed with runners and made from wicker and wood, resembling a type of toboggan. They were used by residents to navigate the hilly roads from the mountainous areas down to Funchal, particularly in the area of Monte, a village located high above the city.
The toboggans were traditionally pulled by teams of men known as "carreiros." These carreiros would guide the sledges down the winding roads, steering them with ropes, often wearing traditional white clothing and straw hats. The process was not only practical but also became an iconic part of life on the island. As tourism began to grow, the toboggan rides quickly caught the attention of visitors seeking a thrilling and authentic way to explore Madeira's famous hills.
Today, toboggan rides are a popular attraction for tourists in Funchal. Visitors can take a ride from the hilltop village of Monte, descending through the picturesque streets and enjoying panoramic views of the city and the Atlantic Ocean. While modern toboggans are now built with more safety features, the spirit of the original tradition remains intact.
These toboggan rides are a unique and cherished piece of Madeira's history, combining local ingenuity, cultural pride, and the island's natural beauty. However, as with many traditional attractions, there is a concern about the balance between preserving the heritage of the toboggan ride and ensuring the safety of both riders and carreiros in the face of increasing tourism.
Our Resort Stays
Photos of our first resort stay: September 14-18: Savoy Saccharum Hotel
What an amazing stay!!! I loved everything about this hotel, especially its proximity to the ocean and town of Calheta!
Our hotel stay September 18-20: Sé Boutique Hotel
This was located perfectly, but the rooftop bar I was excited to see fell completely short and was not safe at all. Rooms were older but comfortable. It was very unique and I'm sure was a great price point for being in a wonderful area of Funchal
My Itinerary:
Friday, September 13: 12215 depart Calgary Airport, 1804 land in Toronto and overnight in Toronto
Saturday, September 14: Arrive Toronto Pearson Airport, flight departs at 2315. This was a very long day!
In my research I found that Madeira had one of the most difficult airport landings to maneuver in the world, rated in the top 5. I had a window sea and was ready for action! The winds were not terrible and my view was a dark one coming in during the night. We landed with only a mere few side to side sways and finally a bump. YouTube proved me wrong and I would live to see Madeira!

Sunday, September 15: Breakfast at the hotel Free in the morning , 1200 Lunch Box to go (Hotel Reception) , 1330 Whale and Dolphin Watching with On Tales
1800 Pick-up to Dinner at Razão Concept (Socalco Nature)
Monday, September 16: Breakfast at the hotel Dress Code: Comfortable clothes and shoes, windbreaker, rain and sun protection 0930 Pick-up to Levada/Walk dos Prazeres and Picnic with Madeira Adventure Kingdom 1800 Pick-up Dinner at Quinta das Vinhas Madeira
Tuesday, September 17 : Breakfast at the hotel. 0900 Pick up at Hotel for Full Day Jeep Tour Northwest Side with Brave Landers, Fanal Forest, 1230 Lunch at Quinta do Barbusano, 1830 Dinner at Alambique Restaurant
Wednesday, September 18: Breakfast at the hotel, 0800 Check-out the Hotel Pick-up to tour (Ribeira Brava, Cabo Girão e Câmara de Lobos) & East Side , 1300 Lunch at Quinta do Furão1800 Pick-up to visit the Meliá Madeira Mare Hotel and Dinner
Thursday, September 19: Breakfast at the hotel. 0900 Cable Car Ride to Monte and Wicker Toboggan Sledge with Guide. 100 Food and Cultural Tour with Food on Foot, Free time, 1800 Pick-up to Dinner at Nini Design Center Restaurant: Sadly I missed this dinner as I fell very ill.
Friday, September 20: 04:20 am Pick-up to Airport and fly back home. Flight departs, landing in Toronto. 1440 Flight departs for Calgary, arrives at 1700
Grab my bags and drive another 3 hours home!
Here are photos of everything we did on our itinerary! I do not have one favorite thing that sticks out, rather the entire trip was memorable. Such charm and simplicity, I will definitely return one day.
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