Private airport transfer to Funchal, the bustling city that hosts the majority of the island's population., Take time to explore or catch up on some rest. Tonight is a group briefing with your guide.

Our massive island traverse begins today! We begin our series of day hikes across this mountainous Portuguese island with a somewhat mellow classic: the northern coastline hike to Porto de Cruz. Beginning in town and following the famous levada system- channels where water runs, unobstructed and carried by gravity throughout the island. These waterways are actually World Heritage sites and are reknown throughout the world as the Levadas da Madeira. This vast network is celebrated worldwide for its engineering success and was originally developed to irrigate the sugar cane that made the island famous as the world’s second biggest producer of sugar in the 15th century. But today; we’ll use these waterways as our initial guides. Walking along them, we gradually climb in a northwestern direction around the slopes of the valley. Finally, we reach the cliffside and a jaw-dropping view that makes the long journey worth it. Turning left and following the north coastline, it's a very gradual trail for nearly 7 miles as we undulate along the cliffside, making our way eventually, into the town of Porto de Cruz on the north side of the island. We'll enjoy a nice walk around this quaint seaside town before transferring to nearby Santo Da Serra to our hotel. Tonight we rest as tomorrow we head inland and the intensity begins to increase.

Today we walk from the hotel in Santo da Serra to Levada da Serra do Faial, ultimately reaching the Levada do Furado. The walk from here is pretty impressive as we navigate our way through multiple tunnels carved through the rocky mountainside. We will encounter numerous waterfalls and small ponds and our trail is almost constantly shaded by the bold canopy of this lush sub tropical forest (Laurisilva).
The Laurisiva of Madeira is an outstanding relic of laurel forest that was previously widespread through Europe. Madeira possesses the largest living area of this type of Laurel Forest. It hosts a unique array of plants and animals (mainly birds) including endemic species such as the Madeiran Long Toed Pigeon.

At the 3,000 foot high Levada do Furado we will take another trail that will lead us to up to Poiso (4,580 feet)- our final destination. From here we transfer back to our hotel in Santo da Serra.

Get ready for one of the most challenging, but also most rewarding, treks of the island traverse. This morning we pick up where we left off at Poiso. From here we climb up almost 1,500ft to Pico Areiro, one of the highest peaks on the island. From here we take in immense views over the valley of Ribeira do Cidrão, which flows into Ribeira dos Socorridos at Curral das Freiras. Scan over the Paul da Serra plateau, part of the western mountain massif of the island. After a brief stop to celebrate these views, we continue to Pico Ruivo - the highest mountain of the island. Our adventure from peak to peak will lead us through a hole in the mountain wall, several tunnels, along steep mountain escarpments and up arduous stairways. All the while, the clouds swarm through, changing the weather frequently. These are all great distractions from our final push, a challenging ascent of about 40 minutes to 1 hour, finally bringing us to our cloud-kissed mountain hut atop Pico Ruivo- the highest point on the island! Tonight we dine with our own private cook in this cozy mountain lodge, celebrating the day's achievements.

After breakfast, we undertake a descent down to Levada do Caldeirão Verde, which will allow us an opportunity to enjoy crossing two types of ecosystems that are part of the Natura 2000 Network: the Central Mountain Massif and the Laurisilva forest. Along the Levada do Caldeirão Verde we will enjoy views of the São Jorge Valley and the north coast of the island. Here we relax after a big elevation loss. We finish at Pico das Pedras at almost 3,000ft; just past the Casa das Queimadas.
Casa das Queimadas is a shelter built early in the 20th century and was primarily used by those who worked in the area or who were passing through. It is constructed with the famous traditional thatched roof and is linked to the construction of the Caldeirão Verde levada, featuring typical architecture of the Santana village. Our day ends today in the seaside valley of lush Sao Vicente.

Morning shuttle from Sao Vicente to the trailhead at Encumeada. Beginning at Levada do Norte, the second longest of the island, we start by crossing 2 long tunnels ( around 1 km each) . At some point, however, we will stop following the levada to take a trail that leads us up to the area known as the Pinnacle. This is a big climb with lots of stairs. The reward, however, is real with stunning panoramic views over the valley with Pico Ruivo and Pico do Areeiro as the backdrop. Here we sit in awe, eating our lunch, realizing how far we have come and the amazing extent of our accomplishment. We're not finished yet, though. We continue along the Laurisilva forest until we reach Casa do Caramujo. Immersed in the indigenous forest, Casa do Caramujo is an abandoned house in the mountains, used in the past as a vacation house by wealthy families. Nearby you can also find a winter pond. From Casa do Caramujo we climb up an engaging path that unfolds revealing panoramic views, making for a very complete day. Our hike ends at the Estanquinhos trailhead. Tonight we stay in the seaside village of Jardim do Mar- our base for the final two nights of our adventure in Madeira.

Today’s walk is splendid with total immersion in the Madeira countryside- it is a hidden gem that is often overlooked by hikers. The day starts with an ambitious descent down to sea level. The more popular mode of getting to the ocean is by using the Achadas de Cruz cable car system- Europe's steepest cable car! We will stick to the trail, enjoying the peace and quiet of our massive descent to the incredibly unique fishing village of Faja da Quebrada Nova. This small parish was once home to a small population who tended to their livestock and agriculture. This area is very much off the beaten path isolated by tall mountain cliffs and, until recently, only accessible by boat. After poking around this secluded part of the island, we continue hiking along the coast for a few miles. Next, we ascend up and along the Vereda de Tristao to a viewpoint where we have magnificent views of the sea cliffs, close to Santa village. From here we walk through Santa village, and descend along an old paved path to reach Porto Moniz. Congratulations you have officially completed your cross-island traverse! From Porto Moniz we transfer back to our base at Jardim do Mar for a celebratory final dinner at the famed Joe's Bar.

Morning transfer to Funchal for your return flight home. Book flights for after 2pm to allow for transfer time.