This Madeira trekking holiday takes you across volcanic ridges, lush levadas, and coastal cliffs over 8 days and 6 hiking stages. You’ll walk through terraced farmland, laurel forests, and historic mountain paths, summit Pico Ruivo, and descend into dramatic valleys before finishing in Funchal. Luggage transfers, hotel stays, and route navigation are arranged in advance, giving you complete flexibility while keeping logistics effortless.
Arrive at Funchal Airport and transfer to the seaside town of Machico, the first settlement founded on Madeira when Portuguese explorers landed here in 1419. After checking into your hotel, take time to wander the waterfront promenade, relax on the beach, or enjoy your first dinner overlooking the Atlantic as you settle into island life before the hiking begins.
Accommodation: Hotel in Machico
Meals: Dinner
Today you hike along the easternmost tip of Madeira, a rugged volcanic peninsula where steep cliffs plunge into the Atlantic. The landscape here is strikingly different from the rest of the island, with windswept hills, colorful basalt formations, and expansive ocean views in every direction. After the hike, transfer to the seaside village of Porto da Cruz, where you can relax by the coast or swim in natural basalt pools.
Hiking: 8 km (5 mi), 3.5–4 hours
Elevation: ±500 m (±1,640 ft)
Accommodation: Hotel in Porto da Cruz
Meals: Breakfast
Today you follow historic levada trails that once served as vital connections between Madeira’s villages. Walking along the Mimosas Levada, you pass terraced farmland, small agricultural shelters, and lush vegetation as the path winds through quiet valleys and rural communities. Along the way, you gain insight into traditional island life and the irrigation systems that shaped Madeira’s landscape.
Two hiking options are available today.
Hiking (short): 11.7 km (7.3 mi), 3-4 hours, +50 m / -210 m (+165 ft / -690 ft)
Hiking (long): 17.5 km (10.9 mi), 5-6 hours, +500 m / -565 m (+1,640 ft / -1,854 ft)
Accommodation: Hotel in Porto da Cruz
Meals: Breakfast
Today’s hike follows one of the most beautiful levada routes in eastern Madeira. Starting from Porto da Cruz, you climb through terraced gardens and farmland before reaching Portela and joining the famous Levada do Furado. The trail gradually narrows as it crosses deep ravines and dense forest, revealing spectacular views of the island’s central peaks. Near Ribeiro Frio, you can visit the famous Balcões viewpoint for a breathtaking panorama over Madeira’s dramatic valleys.
Two hiking options are available today.
Hiking (short): 14 km (8.7 mi), 4 hours, +190 m / -10 m (+623 ft / -33 ft)
Hiking (long): 17 km (10.6 mi), 6.5 hours, +790 m / -45 m (+2,592 ft / -148 ft)
Accommodation: Hotel in São Roque da Faial
Meals: Breakfast, dinner
This morning you transfer into Madeira’s dramatic central mountains for one of the island’s most iconic hikes. Starting from Pico do Arieiro (1,818 m / 5,965 ft), you traverse spectacular ridgelines and narrow paths carved into volcanic rock, with deep valleys on both sides. After reaching Pico Ruivo, the island’s highest summit, you descend to Achada de Teixeira before transferring to Santana, a village known for its traditional triangular houses.
Hiking: 8.2 km (5.1 mi), 4.5 hours, +550 m / -700 m (+1,805 ft / -2,297 ft)
Hiking (alternative): 13 km (8.1 mi), 5 hours, +900 m / -300 m (+2,953 ft / -984 ft)
Accommodation: Hotel in Santana
Meals: Breakfast, dinner
Today’s route follows one of Madeira’s most spectacular ridge traverses. The trail alternates between steep climbs and descents while offering sweeping views toward both the northern and southern coasts. Walking through wild landscapes dotted with heather and basalt formations, you gradually descend toward Encumeada Pass, surrounded by lush forest and dramatic mountain scenery.
Hiking: 13.5 km (8.9 mi), 6–7 hours, +900 m / -1,480 m (+2,952 ft / -4,855 ft)
Hiking (alternative): 4–10 km (2.5–6.2 mi), 3–4 hours, ±250 m (±820 ft)
Accommodation: Hotel in Encumeada
Meals: Breakfast, dinner
Today you hike along sections of the historic Camino Real da Encumeada, once used by landowners traveling between villages. The trail winds across mountain ridges with spectacular views over the Valley of the Nuns and surrounding peaks. Along the way you may spot endemic flora and bird species unique to Madeira.
You can also choose to climb Pico Grande for an additional challenge before descending into the Curral das Freiras valley. After the hike, transfer to Funchal for your final evening on the island.
Hiking: 11.9 km (7.4 mi), 4–4.5 hours, +200 m / -800 m (+656 ft / -2,625 ft)
Hiking (optional Pico Grande summit extension): +2.3 km (+1.4 mi), about +2 hours, ±350 m (±1,150 ft)
Accommodation: Hotel in Funchal
Meals: Breakfast
After breakfast, transfer to Funchal Airport for your onward journey. If you have time before your flight, consider enjoying a final walk through the historic streets of Funchal or visiting the city’s famous botanical gardens.
Meals: Breakfast
Included:
Add-ons (available to add at checkout):
Not included:
To fully enjoy these Madeira walking holidays, it’s recommended to have a reasonably good level of fitness and prior hiking experience.
You should be comfortable hiking up to 17.5 km (10.9 mi) & 3–7 hours per day with up to 900 m (2,950 ft) ascent, and significant descents up to 1,480 m (4,855 ft). Some sections follow levadas with drops beside the trail.
If you can handle full-day hikes with sustained elevation changes, you’re well suited for this trip.
Want to see what else is there in the area? Discover more Portugal walking and hiking adventures here!
The following items are required for these self-guided walking holidays in Madeira unless otherwise noted. When packing, think layered clothing systems that work together and can be easily added or removed.
Avoid cotton or cycling-specific clothing. Synthetic fabrics dry quickly and perform well in active conditions. Merino wool is also an excellent option—it dries fast, is comfortable to wear, and naturally resists odors even after extended use.
Clothing:
Gear:
First aid kit suggestions:
Carrying a basic personal first aid kit is strongly advised, as unforeseen situations may arise during travel. Access to medications and first aid supplies can be limited in certain destinations, making it essential to bring necessary prescription and over-the-counter items. Travel plans, vaccinations, and medication use should be reviewed with a healthcare provider in advance to ensure a safe and smooth journey.
Here’s a basic list of what’s generally a good personal travel first aid kit:
Optional items:
Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining these self-guided walking holidays in Madeira, we take care of:
Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!
Digital travel package includes documents available in English, French, and German, sent by email, and provides access to a smartphone travel application for navigating hikes and accessing local maps (available in English only). It also contains the list of booked accommodations, and all the detailed information needed for a successful trip. If desired, a printed version of the travel package can be provided for an additional fee; it will be ready and available at the first accommodation of the itinerary, including maps, a topo guide, and a travel folder—you can add this at checkout.
As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.
Yes. Luggage transfers between accommodations are included in this trip. Your bags are transported by vehicle to the next hotel, so you only need to carry a daypack with essentials like water, snacks, and personal items during your hikes.
Group sizes and pricing
Self-guided walking holidays in Madeira can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The price for these self-guided walking holidays in Madeira is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
The starting point of your self-guided walking holidays in Madeira is Funchal. To get there, most people fly into Madeira Cristiano Ronaldo International Airport (FNC). An airport transfer (1 per group) is included to reach Funchal.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.