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.
Your adventure begins with arrival at Funchal Airport, where you’ll transfer to the seaside village of Santa Cruz or Machico—Madeira’s first Portuguese settlement, founded in 1419. Check into your hotel and spend the rest of the day settling in: stroll the waterfront promenade, relax on the beach, or simply ease into island life before the hiking begins tomorrow.
Accommodation: Hotel in Santa Cruz or Machico
Today’s hike takes you to Madeira’s easternmost tip, a wild, wind-scoured volcanic peninsula where dramatic basalt cliffs plunge into the Atlantic and gulls breed by the hundreds. It’s a landscape unlike anywhere else on the island, with a chance to take a dip along the way. After the hike, transfer to the seaside village of Porto da Cruz, where you can cool off in the natural “basalt swimming pool” carved into the coastline.
Hiking: 8 km (5 mi), 3.5 to 4.5 hours, +/-500 m (+/-1,640 ft)
Meals: Breakfast
Accommodation: Hotel in Porto da Cruz or B&B
Between the Caniçal tunnel and the village of Maroços lies the Mimosas Levada, an irrigation canal once used to carry grapes for winemaking between Porto da Cruz and Machico. You’ll follow this level path along the levada, surrounded by mimosas that bloom year-round, passing “palheiros” (small agricultural shelters) scattered across “poios” (mountainside terraces) before reaching the more populated village of Maroços, its levada banks bordered by flowers.
Hiking: 17.5 km (10.9 mi), 6 to 7 hours, +500 m/-550 m (+1,640 ft/-1,805 ft)
Alternative (shorter route): After a short transfer to Maroços, follow the easy levada before climbing to Boca do Risco pass and the northern coast balconies. From here, a scenic path, partly secured with handrails, leads to Portela. Descend to Porto da Cruz—a small village at the foot of Pena de Águia, the “Eagle’s Peak”—by bus or on foot.
Hiking: 11.7 km (7.3 mi), 3.5 to 4 hours, +/-300 m (+/-985 ft)
Meals: Breakfast
Accommodation: Hotel in Porto da Cruz or B&B
From Porto da Cruz, you’ll climb toward Portela at 600 m (1,969 ft)—or skip the ascent with an optional taxi transfer (not included, about €20). From there, the trail follows the scenic Levada do Furado east, narrowing through deep ravines with the island’s high peaks on the horizon. Near Ribeiro Frio, detour to the Balcões viewpoint for sweeping views before a short transfer to your hotel in São Roque da Faial.
Hiking: 17.5 km (10.9 mi), about 7.5 hours, +900 m/-150 m (+2,953 ft/-490 ft)—or 13 km (8.1 mi), about 4.5 hours, +400 m/-150 m (+1,310 ft/-490 ft) without the Portela climb
Alternative (if the path to Ribeiro Frio is closed): The route heads south after Lamaceiros along the Levada da Serra to Quatro Estradas, with the option to continue on to Águas Mansas.
Hiking: 14.5 km (9 mi), about 6 hours, +150 m (+490 ft)
Meals: Breakfast, dinner
Accommodation: 2-star hotel in São Roque da Faial
After breakfast, transfer into the island’s dramatic central mountains for one of Madeira’s most spectacular hikes. From Pico do Arieiro (1,818 m/5,965 ft), the trail—now a one-way route, reopened in 2026 after a two-year closure—skirts narrow ridgelines and rock tunnels to Pico Ruivo (1,862 m/6,109 ft), the island’s highest peak. Descend to Achada da Teixeira, then transfer to Santana, home to the island’s fairy-tale triangular houses.
Hiking: 8.2 km (5.1 mi), 4 to 4.5 hours, +550 m/-700 m (+1,805 ft/-2,297 ft)
Alternative (if the Pico do Arieiro–Achada da Teixeira trail is closed): The hike instead starts from Queimadas Park, climbing Pico Ruivo before descending to Achada da Teixeira.
Hiking: 13 km (8.1 mi), 5 to 5.5 hours, +900 m/-300 m (+2,953 ft/-984 ft)
Meals: Breakfast, dinner
Accommodation: 2-star hotel in Santana
Transfer from Santana to Encumeada (about 50 minutes), where a lush, round-trip levada walk awaits. The path is lined with hydrangeas, agapanthus, lilies, and azaleas, threading through the São Vicente valley via a handful of tunnels—including one leading to Folhadal, a natural amphitheater cloaked in native laurel forest. Waterfalls cascade between rock pools along the way, and the Levada do Norte eventually climbs back up to Encumeada pass, where your hotel awaits just below the trailhead.
Hiking: 10 km (6.2 mi), 3 to 4 hours, +/-250 m (+/-820 ft)
Meals: Breakfast, dinner
Accommodation: 2-star hotel in Encumeada; half-board
Today’s hike follows the historic Camino Real da Encumeada, a former royal road, past Passo de Ares, Pico do Serradinho, and Boca do Cerro. Enjoy panoramic views over Curral das Freiras, Funchal, and Paul da Serra, with a chance to spot endemic species like the Madeiran mahogany, kinglet, and kestrel. From Relvinha, a long switchback descent leads into the Curral das Freiras valley—the Valley of the Nuns—where you’ll transfer to Funchal for your final evening.
Hiking: 11.9 km (7.4 mi), 4 to 4.5 hours, +200 m/-800 m (+656 ft/-2,625 ft)
Optional (Pico Grande summit): From Relvinha, take on a slightly technical climb of Pico Grande—one of Madeira’s ten highest peaks—before rejoining the main descent into Curral das Freiras.
Hiking: +2.3 km (+1.4 mi), about 2 extra hours, +/-350 m (+/-1,150 ft)
Meals: Breakfast
Accommodation: hotel in Funchal; B&B
After breakfast and check-out, transfer to Funchal Airport (about 30 minutes) for your onward flight.
Meals: Breakfast
Included:
Add-ons (pricing shown at checkout):
Not included:
Should you need to make any changes to your booking after confirmation, please be aware that a €50 administrative fee applies to each modification.
Please note that occasionally, the itinerary needs adjusting—usually due to logistics like fully booked accommodations, trail closures, or bad weather. Any changes are always made with your safety and comfort in mind.
Accommodation can shift too, though rarely, depending on availability. If an alternate accommodation is used for a given night, it’ll always be in the same star range as advertised.
To join this self-guided walking tour in Madeira, great fitness and some prior hiking experience are recommended.
The most you’ll hike in a day is up to 17.5 km (10.9 mi), over 3 to 7.5 hours, with up to 900 m (2,953 ft) of elevation gain and up to 800 m (2,625 ft) of elevation loss—or more if you add the optional Pico Grande summit on day 7.
Some sections follow levadas with drops alongside the trail, so this route isn’t recommended for those uneasy with heights. Since luggage is transferred between hotels, you’ll only need to carry a daypack each day.
Want to see what else is there in the area? Discover more Portugal walking and hiking adventures here!
Yes—since 2025, several of Madeira’s most popular trails require a paid time slot booked in advance through the official Simplifica website (between €4.50 and €10.50 per person). The trails affected on this itinerary are:
Book as early as possible, especially for day 5: the Pico do Arieiro–Pico Ruivo trail reopened in 2026 after a two-year closure and now runs as a one-way route with limited daily capacity.
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:
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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.