Escape The Winter Blues In Madeira

Madeira is one of those mysterious, magical places that you’d think more people would have heard about. A territory of Portugal in the Atlantic Ocean, Madeira lies roughly 600 miles southwest of the mainland, and about 320 miles due west of Morocco. It’s not only closer to the United States compared to more well-known island destinations like Hawaii, Santorini, or Ibiza, but also cheaper, while still boasting stunning scenery, incredible cultural experiences, world-class wine, and a few unique surprises you can’t find anywhere else. The underrated island is easily accessible with weekly direct flights departing from JFK in New York. After a quick eight-hour hop across the Atlantic, Madeira’s numerous treasures will be yours to behold.

East Madeira: Mountains, Sunrises, And Strange Forests

Flights to Madeira will land in Funchal, the capital and largest city. Its location in eastern Madeira makes for a convenient place to base trips into this half of the island. Book a room for a few nights at the illustrious Castanheiro Boutique Hotel, whose radiant, inviting modern corridors include a lively bar, a gym, a relaxing spa, and a lovely rooftop infinity pool with a 360-degree perspective of the city and enclosing elevation. Take some time to explore Funchal proper, whose weathered, historic streets open up to spirited nightlife once the sun sets. Whatever your plans are for the evening, be sure to end up at Vila do Peixe for dinner, biting into a juicy, seasoned steak with an attractive view of the bay. Funchal is also a terrific place to visit for the holidays. Famous for its animated citywide party on New Year’s, you’ll be dazzled as the enveloping sky is suddenly lit ablaze with a kaleidoscopic array of vivid fireworks at midnight.

Once you’ve beaten the jet lag—or perhaps if it’s kept you up all night—start your day with a memorable sunrise boat tour with the Happy Hour Crew. Enjoy the included breakfast as you watch the darkness receding slowly from the horizon, revealing the silhouettes of hilly topography taking form as the soft reds of the sun peek above the water. Although it’s easy to be distracted by the image of Funchal at daybreak, remember to keep an eye on the water! Dolphins are sometimes visible greeting the new day alongside boats in the harbor, so don’t miss a chance to take in the morning sights with some aquatic friends.

Fully awake and back on land, head slightly east and grab a hearty lunch at one of the outside tables of the Restaurant Inn & Art, taking in the pleasing sea breeze and the swells of the Atlantic from the lofty balcony. Afterward, head north, straight into the heart of the mountains enveloping Funchal. Madeira’s dramatic scenery—less rolling ridges and more an abrupt series of cliffs—frequently allows for truly breathtaking perspectives of the island and the ocean. After climbing up and around some curves and gaining some height, pull over at Terreiro da Luta and take in the picturesque sight of Funchal behind you from a bird’ s-eye view.

Continue ascending, noticing the trees beginning to disappear, until you arrive at the fresh air and wide-open spaces of Pico do Arieiro. Far from the bustle of Funchal, admire these quiet mountains that comprise the interior of Madeira and take a picture of the idyllic mist that often can be found accenting the colorful, jagged range. If the allure of the trail is too much to resist, put on some decent hiking boots and embark towards Pico Ruivo, the tallest point in Madeira, allowing yourself to be astonished by the constant visual onslaught of gorgeous, rugged peaks along the way.

You might have noticed that the surrounding woods on the way to Pico do Arieiro have a strange, ethereal quality to them. There is much more to this laurel forest, known locally as the Laurissilva, than it seems at first glance. As laurel forests are nearly all but extinct globally, the Laurissilva is one of the rarest biomes in the world. Madeira’s Laurissilva, doubling as a UNESCO World Heritage Site, is also the largest of those remaining.

The forest, whose small, gentle leaves, seductive emerald hues, and hazy ambiance appear like something out of a dream, has plenty of winding paths inviting you to get lost within. Find entrances at Poiso or Ribeiro Frio, and as you marvel at the sensational greenery, you might wonder what the little river of water in the impeccably constructed stone vessel rushing by your feet is. This is one of Madeira’s ubiquitous “levadas,” miniature aqueducts built over the centuries to transport water from the island’s wetter and more elevated north to the drier, more populated southern half. If you take the trail at Ribeiro Frio to the mesmerizing vista at the end at Levada dos Balcões, you might notice fellow hikers standing with outstretched palms filled with seed as if waiting for something. The local birds, known for their friendly disposition, are known to flutter into visitors’ hands for a free meal. Try it yourself—grab a handful of seeds from the forest floor and wait for a hungry feathered friend to perch on your fingers for an unforgettable photo opportunity.

Continue north past the Laurissilva to the town of Santana on the island’s northern shore, finding the adorable Casas de Santana once you arrive. The triangular huts, constructed initially from abundant nearby trees and cereal crops, have thatched roofs that allow efficient drainage and interiors that effectively regulate temperature. With their bright, eye-popping red, white, and blue color scheme, the Casas are iconic of Madeira and a testament to local ingenuity. If you haven’t entirely satiated your outdoors fix, swap out stunning mountains for spectacular beaches at Ponta de São Lourenço on Madeira’s eastern terminus, where beautiful juxtapositions of serene water and isolated islands are frequently found on the quiet paths. There’s no better chaser to a day of hiking and exercise than an invigorating outdoor yoga class led by local teacher Emilie Mangoni (@emiliemangoni_yoga on Instagram), whose thoughtful breathwork, eclectic sound toys, and creative vinyasa flows will leave your body feeling just right after hours of exploring on your feet.

Finally, cap off your adventure in the east with a glass of robust, authentic Madeiran rum from Engenhos do Norte in Porto da Cruz. Considering the island was once one of the foremost sugarcane exporters in the world, the former factory-turned-distillery continues this legacy, doubling as a museum with its charming, old-fashioned buildings and intriguing collection of 19th-century machinery perfect for strolling with a drink in hand.