Portugal: Madeira Island

You arrive in Lisbon, where our team welcomes you and transfers you to your hotel in the heart of the city. After a rest, take a stroll near the hotel to catch your breath with your first sunset over a city painted with traditional alleyways. In the evening we gather for a briefing with the rest of the group and a quick overview of the days ahead.

A full day exploring the Portuguese capital. We start in Belém to visit the historic Torre de Belém and the majestic Jerónimos Monastery, with an obligatory stop to taste the original Pastel de Nata from its famous bakery. In the afternoon we ride the famous yellow Tram 28 through the winding alleys of Alfama, Lisbon's oldest quarter. We end the day with an evening of soulful Fado music in one of the district's local restaurants.

A short flight takes us from Lisbon to Madeira, landing at Cristiano Ronaldo International Airport overlooking the Atlantic. From there we head to Funchal, the island's capital, and wander its old town, the Zona Velha, with its narrow lanes and doors painted as works of art. A free evening to recover and prepare for the coming days of walking across the island's mountains.

The Madeira crossing begins on the outskirts of Machico on the east coast. We climb gradually along the old levada channels into the UNESCO-listed Laurissilva forests — a laurel forest more than 20 million years old. We reach the peaceful mountain village of Ribeiro Frio with its old trout farm, and stop at the Miradouro dos Balcões viewpoint for a stunning look at the island's central peaks.

Summit day. We take a high mountain path along a narrow ridge past the peaks of Pico do Areeiro before it stretches on to Pico Ruivo, Madeira's highest summit at 1,862 m. The trail weaves between clouds and sharp volcanic peaks, with glimpses of the island's north and south coasts at the same moment. Tonight we sleep in the mountain refuge near the summit, ready to watch the sunset over a sea of clouds.

We watch the sunrise over Pico Ruivo, then begin the long descent across the island's central peaks towards the famous Encumeada Pass, the meeting point of the island's eastern and western mountain ranges. From the Encumeada viewpoint, in clear moments, you can see the north and south coasts at once — a rare sight that sums up the beauty of this leg of the journey.

The most magical day. We cross the high Paul da Serra plateau to the legendary Fanal forest, one of the world's oldest laurel forests, its twisted moss-covered trees more than 600 years old. When the fog plays among the gnarled trees, the scene turns surreal. We descend gradually towards the north coast, arriving at the quiet seaside village of Seixal.

The final stage of the crossing. We walk along the rugged north coast past dramatic Atlantic scenery to Ribeira da Janela, known for its rock stacks rising just offshore. We end the crossing with a swim in the natural pools of Porto Moniz — volcanic pools formed by cooled lava on the coast — to celebrate crossing the whole of Madeira.

After one last Madeiran breakfast, the team transfers you to the airport for the journey home. You leave carrying memories of an island and a capital: Lisbon's historic alleys, the proud summit of Pico Ruivo, and Madeira's twisted forests that resemble nowhere else on Earth.