Walking the Islands of Madeira | May 2026
Volcanic, wild, diverse — Madeira is a heaven for walkers. On this small-group adventure, we experience the most beautiful routes on this Portuguese island, from gentle strolls along flower-lined levadas (centuries-old waterways) and spectacular coastal footpaths to more demanding forays among the jagged ridges and peaks of the mountainous interior. There’s also time to relax by the sea in Machico village, see waves crash close to shore in Porto Moniz and discover the historic importance of Funchal, an old trade hub for sugar and wine.
Deposit + Single Supplement + Inclusions and Highlights + Daily Mileage + Map
This remains a public trip for our vendor, so please know that reservations are open to the Greater World; if this trip appeals to you, grab your spot while you can! Ilse is going on this trip as a paying client and hopes that you'll consider joining her! Like with her usual private group trips, she'll handle all the logistics for you, except air, so you can just relax into the excitement of having this spectacular experience to look forward to!
Non-Refundable Deposit: $895
Single Supplement (very limited supply!): $878
Highlights
Walk through the botanical paradise of Madeira, taking the most scenic trails on the island
Stroll alongside flower-lined levadas with stunning views over the Atlantic
Marvel at spectacular mountain scenery, including Pico Ruivo, the island’s highest peak
Watch sunrise from Pico Arieiro, one of the highest mountains on the island
Uncover the cultural side of Madeira with an exploration of the capital, Funchal
Hike through the mystical Fanal Forest, where twisted trees create a fairytale setting
Key Information
Accommodation: 5 Superior nights (hotels), 2 Classic nights (hotels)
Five days walking; one free day
Group normally 5 to 16, plus leader. Minimum age: 18
Altitude maximum: 6,109ft (1,862m); average: 2,460ft (750m)
Not suitable for vertigo sufferers
Transport by private minivan
We may need to amend the itinerary depending on local weather conditions, which can change quickly
Countries visited: Portugal
What's Included
All breakfasts and three dinners
All accommodation
All transport and listed activities
Tour leader throughout
Arrival and departure transfers for everyone
What's Not Included
Travel insurance
Single accommodation (available on request)
Visas or vaccinations
5 Days of Walking & Trekking Pace: Moderate: 3mph-4mph (5kph-6kph)
Terrain: Low altitude; some rough terrain – good paths with some steep ascents
Day 2: 8 km / 5 miles
Day 3: 12 km / 7.5 miles
Day 4: 12 km / 7.5 miles
Day 5: 11 km / 6.8 miles
Day 7: 9 km / 5.6 miles
Saturday may 16
Start Machico
We start at our hotel in Machico, which overlooks the beach of Machico Bay. There will be a welcome briefing in the evening, in which we can discuss the adventures to come and you can ask any questions you may have.
Alternatively, if you’d like to settle into the adventure, ask Ilse about booking an extra night or two before the trip begins.
Machico: Hotel Dom Pedro (nights 1-2)
Sunday May 17
Walk to the easternmost point of the island, Ponta de São Lourenço, a rocky peninsula with ocean views for miles
Today we walk the classic route along the Ponta de São Lourenço. Although challenging in parts, this path takes us through fantastic scenery as we admire wallflowers, stalwarts and many other tiny plants that resist the windy environment and grow in soils with high salinity levels. Rocks, sculptured by nature, have a great diversity of colors ranging from black to red, and are in stark contrast to the blue of the ocean. Park rangers watch over the plants and animals that belong to this eastern extremity of the island, around Casa do Sardinha. We return to our hotel in Machico in the afternoon, and there is free time to explore the village or relax at the beach.
Distance covered: 5mi (8km)
Ascent: 787ft (240m); Descent: 787ft (240m); Activity hours: 3hr 30min
Meals included: Breakfast
Machico: Hotel Dom Pedro (nights 1-2)
Monday May 18
Spectacular walk along the north coast path to the village of Porto da Cruz
This morning, we take a transfer and walk a scenic route along a cliff trail on the north coast. We set off along the little Levada do Caniçal, more modest and quieter than yesterday’s path, then begin a gradual climb to the crest of the cliffs at Boca do Risco, where we enjoy amazing views along the north coast. We then head west along the coastal path: a spectacular route, in many places cut right into the cliff. We finally descend to Porto da Cruz, once a bustling port but now a sleepy, picturesque village. Time permitting (and if open), we have a short look around a factory that has been producing Madeira rum for several centuries. Later, we transfer to Porto Moniz for the night.
Distance covered: 7mi (12km)
Ascent: 1,542ft (470m); Descent: 2,231ft (680m); Activity hours: 4hr 30min
Meals included: Breakfast, Dinner
Porto Moniz: Hotel Aqua Natura Bay (nights 3-5)
Tuesday May 19
Transfer to Queimadas; walk along Levada do Caldeirão Verde to the remote village of Ilha
Transfer to Queimadas Natural Park, where we walk along the Levada do Caldeirão Verde. This route has many waterfalls and we may need to pass under some to continue the path. We use our torches/flashlights to walk through tunnels carved into the mountains. We finish the walk with a descent into the village of Ilha before returning to Porto Moniz.
Distance covered: 7mi (12km)
Ascent: 295ft (90m); Descent: 1,640ft (500m); Activity hours: 5
Meals included: Breakfast, Dinner
Porto Moniz: Hotel Aqua Natura Bay (nights 3-5)
Wednesday May 20
Vereda do Fanal, the ancient forest of Madeira
Our walk today starts on the Paul da Serra plateau and ends at the Unesco World Natural Heritage site of Fanal Forest. We walk via open landscapes with fabulous views over the Ribeira da Janela and Chão da Ribeira valleys, and through the largest surviving area of laurisilva forest on the planet (believed to be 90 percent primary forest).
We end the hike at the fairytale Fanal Forest, a small volcanic crater filled with twisted trees and often shrouded in mist. Many of the ocotea foetens trees here predate the founding of Madeira in 1419, and we take time to absorb the unique energy of the forest before returning to Porto Moniz.
Distance covered: 7mi (11km)
Ascent: 623ft (190m); Descent: 1,476ft (450m); Activity hours: 4
Meals included: Breakfast, Dinner
Porto Moniz: Hotel Aqua Natura Bay (nights 3-5)
Thursday May 21
Morning transfer to Funchal; free day to explore the city or join an optional whale-watching excursion
After a morning transfer (approximately one hour) via the mountainous interior, today is free for you to explore Funchal, the island capital and our base for the final two nights of the trip. The city is easily explored on foot and sites of interest include Sé Cathedral, built between 1493 and 1514, and the imposing statue of Madeira founder, João Gonçalves Zarco, on Avenida Arriaga.
Alternatively, take the cable car to Monte Palace and Tropical Gardens to enjoy fascinating installations and magnificent views over the city, learn about the production of Madeira’s ever-popular wine at Blandy’s Wine Lodge, or join a whale-watching tour to spot some of the 28 whale and dolphin species that grace Madeira’s waters throughout the year.
Meals included: Breakfast
Funchal: Pestana Casino Studios (nights 6-7)
Friday May 22
Early departure for Pico Arieiro; continue the path to Pico Ruivo
Today we embark on the most strenuous walk of the trip. We depart early to reach the third highest mountain on the island, Pico Arieiro (5,965ft/1,818m), in time for sunrise, then continue to Pico Ruivo (6,109ft/1,862m), the highest peak, for more fantastic views. We finish by taking the 1.9mi (3km) path to Achado do Teixeira. The path has lots of ascents and descents along the way, but the memorable scenery is ample reward. At the end of the walk, we transfer back to Funchal.
Please note: On occasion, the route to Pico Ruivo may be closed due to mudslides or inclement weather. Our guide will always try to offer another route up to Pico Ruivo, but if this is not possible, an alternative walk from Ribeiro Frio to Portela will be available. This route traverses native forest and offers wonderful coastal views.
*Due to forest fires in August 2024, the route between Pico Arieiro and Pico Ruivo is closed and we do not have a scheduled date when this will re-open. Currently it is possible to still take the same route to Pico Arieiro and instead we will also trek to Pico do Cedro (5,770ft/1,759m) and Curral Martinho (5,856ft/1,785m), giving impressive views over Curral das Freiras and the highlands of Funchal.
Distance covered: 6mi (9km)
Ascent: 2,001ft (610m); Descent: 2,690ft (820m); Activity hours: 5
Meals included: Breakfast
Funchal: Pestana Casino Studios (nights 6-7)
Saturday May 23
End Funchal
The trip ends in Funchal after breakfast. Hop into your free transfer to the airport. Or, if you’d like a little longer on the island, speak to Ilse about extending your stay.
Meals included: Breakfast
Want to learn more about how you can join this extraordinary experience?