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Self-Guided Walking Holidays in Madeira: 8-Day Adventure

8 days | Moderate | 5.00
From $1,420 ()
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Madeira isn’t called the floating garden for nothing. On this self-guided walking holiday in Madeira, you’ll hike dramatic volcanic ridgelines, wander through lush laurel forests, and follow historic levadas carved into the mountainsides. One day you’re standing on Pico Ruivo, the island’s highest peak—the next you’re tracing coastal paths above the Atlantic. With luggage transfers, handpicked hotels, and a digital travel pack all arranged, this is Madeira hiking made easy. All that’s left is to step onto the trail and let Madeira unfold beneath your feet.

Adventure Highlights

  • Madeira’s greatest hits: Summit Pico Ruivo from Pico de Ariero, follow scenic levadas, and hike coastal cliffs and volcanic ridges in one seamless itinerary
  • UNESCO-listed wonders: Discover one of the world’s last surviving subtropical laurel forests found almost nowhere else on Earth
  • Travel light, hike free: With luggage transfers and pre-arranged stays, you’ll only carry a daypack while exploring the island
Duration
8 days
Season
Year-round
Group size
Up to 20 people
Accommodation
Standard, Comfort: Comfy 2-star to 4-star hotels with double occupancy
Difficulty
Moderate: Good fitness required, hiking up to 17.5 km (10.9 mi) & 3-7 hours per day, with up to 900 m (2,953 ft) of elevation gain
What's included
Lodging, most meals, transfers as described in the itinerary, and more

The adventure, day by day

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.

Day 1: Arrival in Santa Cruz or Machico
Funchal on Madeira island

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

Day 2: Ponta de São Lourenço
Ponta de Sao Lourenco

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

Day 3: The Mimosas Levada and the northern coastal path
Levada in Madeira

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

Day 4: Porto da Cruz to Levada do Furado and Ribeiro Frio
Levada do furado Madeira

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

Day 5: Pico do Arieiro to Pico Ruivo
Pico Ruivo peak in Madeira

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

Day 6: Encumeada and the Levada do Norte
Laurisilva forest in Madeira

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

Day 7: Boca da Corrida to Curral das Freiras
Pico Grande hiking path

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

Day 8: Departure
Funchal airport

After breakfast and check-out, transfer to Funchal Airport (about 30 minutes) for your onward flight.

Meals: Breakfast

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What others say about this adventure

5.00 (3 reviews)
B
Bernard Everaere

Excellent organization that we have already experienced several times with pleasure, in France and in Europe.

R
Rebecca Evans

If you’re looking for fresh air, adrenaline, and wonderful encounters… (and beautiful scenery 😉 …) you’re definitely in the right place!!

B
Bertrand Decoux

Thank you to the whole team, very professional! Excellent service before and during our stay. We recommend it!

5.00(3 reviews)
B
Bernard Everaere

Excellent organization that we have already experienced several times with pleasure, in France and in Europe.

R
Rebecca Evans

If you’re looking for fresh air, adrenaline, and wonderful encounters… (and beautiful scenery 😉 …) you’re definitely in the right place!!

B
Bertrand Decoux

Thank you to the whole team, very professional! Excellent service before and during our stay. We recommend it!

Things to know

  • Included:

      • 8-day self-guided walking holidays in Madeira
      • Accommodation for 7 nights in 2, 3, and 4-star hotels (double occupancy rooms)
      • 7 breakfasts and 3 dinners, as in the itinerary
      • Transfers during the tour, as described in the itinerary
      • Luggage transfers
      • Digital travel package

    Add-ons (pricing shown at checkout):

      • Single occupancy room
      • Printed travel package
      • Extra hotel nights in Funchal with breakfast included — available at an additional fee, let us know at checkout
      • Extra airport transfers — available at an additional fee, let us know at checkout

    Not included:

      • Travel and flights to and from Madeira
      • Lunches and 4 dinners
      • Drinks
      • Entrance fees to tourist attractions
      • Access fees to certain hiking trails (between €4,50 and €10,50)
      • Printed travel documents
      • Tourist taxes
      • Anything not mentioned in the “Included” section above
      • Insurance — recommended, available to add at checkout

    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:

      • Day 2 — PR8, Vereda da Ponta de São Lourenço
      • Day 4 — PR10, Levada do Furado
      • Day 5 — PR1, Vereda do Areeiro–Pico Ruivo (or PR1.2, Vereda do Pico Ruivo, if starting from Queimadas)
      • Day 6 — PR17, Caminho do Pináculo e Folhadal (Levada Nova)

    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:

      • Hiking boots/shoes — waterproof, sturdy molded sole, deep tread and ideally well broken in
      • Hiking socks — one pair for every day or two days of the trip (hiking/sport specific padded socks, no cotton please)
      • Sun hat — wide brimmed hat or baseball cap/bandana combo
      • Warm hat & gloves — lightweight beanie and light-to-mid weight fleece or wool gloves
      • Hiking shirts — non-cotton, breathable short sleeve and/or long sleeve shirts
      • Warm top — mid-weight sweater or pullover of wicking material such as merino wool, fleece or polypropylene
      • Insulating jacket — down-fill or synthetic-fill insulated “puffy” jacket or warm, heavy weight fleece jacket
      • Hiking pants & shorts — nylon pants and shorts, zip-offs or leggings
      • Base layer/long underwear — 1 pair of wicking tops and bottoms that are lightweight to midweight, synthetic wicking materials such as polyester, polypropylene, merino wool, etc.
      • Rain gear — waterproof jacket and pants or high-quality poncho, breathable fabric such as Gore-Tex® or coated nylon (for the pants look for side zippers that will easily allow pulling them over footwear)
      • Casual clothing & footwear – comfortable clothes and shoes to wear in the evening after activities.

    Gear:

      • Backpack — a 30–45 liter sized comfortable pack with a waterproof cover for use day-to-day while hiking
      • Personal luggage — small duffel bag, rolling suitcase or backpack
      • Hydration system — 2+ liters capacity, either water bottles or bladder/hose system and an additional water bottle
      • Trekking poles — telescopic/adjustable poles to help reduce the impact on joints and support hikers in steep and/or rocky terrain (strongly recommended)
      • Headlamp — preferably with an L.E.D. bulb that works with AA or AAA batteries
      • Picnic/lunch kit — knife, plate or bowl, box with closeable lid, utensils, etc.
      • Phone, charger, power bank
      • Waterproof travel case or pouch — used to keep important documents (i.e. passport, health/travel insurance, etc.) & phone safe from weather/water
      • Sunglasses, sunscreen, & lip balm
      • First aid kit
      • Personal toilet paper kit — toilet paper, wet wipes, sanitizer & sealable plastic bag(s) for carrying out used paper/wipes
      • Toiletries
      • Contact lenses & glasses
      • Prescription medication — with emergency back-up supply
      • Cash in local currency

    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:

      • Medications — brands of choice; all medications should be prescribed or approved by a doctor prior to use
      • Prescription drugs — any required prescriptions with backup doses (kept in carry-on luggage)
      • Epinephrine — multiple doses recommended if severe allergies are present, with doctor prescription
      • Pain relief — ibuprofen, aspirin, non-aspirin (e.g., Tylenol)
      • Antihistamine — diphenhydramine (e.g., Benadryl)
      • Non-drowsy allergy relief — loratadine (e.g., Claritin)
      • Antacid/heartburn relief — bismuth (e.g., Pepto-Bismol), antacid tablets
      • Anti-diarrheal — loperamide hydrochloride (e.g., Imodium)
      • Cold/flu medicine
      • Electrolyte replacement/drink mix
      • Creams — antibiotic ointment, anti-itch (hydrocortisone), arnica
      • Eye problems: dry/itchy — eye drops
      • Feminine hygiene — tampons, pads
      • Wound care — assorted bandages, antiseptic swabs
      • Blister kit
      • Sun protection — sunscreen, SPF lip balm
      • Various items — athletic tape/“KT tape,” nail clippers, tweezers, small bottle of hand sanitizer, sewing kit (for clothing/button repairs), disposable surgical gloves (1–2 pairs)

    Optional items:

      • Face masks — 2–3 recommended
      • Travel power adapter — electric power voltage in Portugal is 230 V / 50 Hz and the plugs are type F and C
      • Support braces — joint braces if currently needed or from past injuries (e.g., knee, ankle, elbow)
      • Sleep mask & ear plugs
      • Bug repellent
      • Quick drying towel or bandana(s)
      • Swimsuit

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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:

      • accommodation
      • most meals
      • transfers during the tour
      • luggage transfers

    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

      • Due to safety reasons, it takes a minimum of 2 people for these self-guided walking holidays in Madeira to operate. Solo hikers are not allowed to join.The maximum group size is set at 20 participants.
      • The cost per person decreases as the group grows, so it’s the perfect opportunity to hike with friends and family!

    Self-guided walking holidays in Madeira can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the self-guided walking holidays in Madeira on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    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.

  • Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    • If canceled within 48 hours of booking, a full refund will be issued.
    • If canceled 90 or more days before departure, a 70% refund of the total trip price will be issued.
    • If canceled within 89 days of departure, no refund will be issued.
    • Booking fees are non-refundable after a 48 hours grace period.
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