Pico do Arieiro Retreat
Hotel or lodge, twin sharing
6 days, planned by Cypress & Stone
The Monte toboggans are wicker sleds on greased runners, steered by two men on foot. They started as transport in the 1850s and never stopped.
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| Funchal old town |
| Monte Palace gardens |
| Toboggan run |
The PR1 crosses a knife ridge with cut tunnels and several hundred steps, usually above the cloud layer. Head torches are needed for the tunnels.
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| Pico do Arieiro |
| Pico Ruivo |
| Ninho da Manta |
| Rock tunnels |
Levadas are irrigation channels cut across the island from the wet north to the dry south, with maintenance paths beside them — about two thousand kilometres of them.
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| 25 Fontes |
| Risco waterfall |
| Laurisilva forest |
The pools at Porto Moniz are natural lava basins that fill and flush with the tide.
| LANDMARKS |
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| Porto Moniz pools |
| Seixal |
| Old ER101 coast road |
The eastern tip gets almost no rain and looks like a different island — bare red and ochre rock, with the Atlantic on both sides.
| LANDMARKS |
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| Ponta de Sao Lourenco |
| Casa do Sardinha |
| Volcanic cliffs |
Madeira airport has one of the shortest and most exposed runways in Europe, built out on pillars over the sea. Landings are occasionally diverted.
| LANDMARKS |
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| Mercado dos Lavradores |
| Painted doors of Rua de Santa Maria |
Day 1 · Fri, 18 Sept, 2026
Most of these can be added to your booking later — the operator confirms within a day.
Published by the operator. Nights on the ground can move with weather and permissions.
Hotel or lodge, twin sharing
Hotel or lodge, twin sharing
Hotel or lodge, twin sharing
5 breakfasts and 2 dinners across 6 days, at camp. It opens with dinner on day 1 and closes with breakfast on day 6.
7 meal services named in the itinerary. Vegetarian and vegan covered; Jain, gluten-free and allergies on notice at booking
“Walking in Europe with the timed tickets booked at release”
A walking operator whose main skill is administrative: Alhambra slots, Sagrada tickets and hut beds, booked the day they open.
Did this over 6 days and it was the best walking I've done in years. Rooms were comfortable and the locations meant we could walk most evenings. Good value for what's included.
Did this over 6 days and it was the best walking I've done in years. Hotels were clean and central, which saved a lot of time. Guides answered every question, including the daft ones. Recommended.
Second trek with this operator and they've kept the standard up. Accommodation was a notch better than the price suggested. Simple food, well made, and enough of it.
Did this over 6 days and it was the best walking I've done in years. Rooms were comfortable and the locations meant we could walk most evenings. Would book with them again.
The route is beautiful and the pacing was sensible — nobody was rushed on the climb. Rooms were comfortable and the locations meant we could walk most evenings.
Did this over 6 days and it was the best walking I've done in years. No complaints about any of the hotels — all of them well placed. No hesitation recommending them.
Appreciate the honest feedback; we're looking at the pacing on that section.
An irrigation channel, cut from the sixteenth century onwards, carrying water from the wet north of the island to the dry south. The maintenance paths beside them are now the walking network — around two thousand kilometres of near-level path across very steep terrain.
One other operator runs this trail. See all 2 side by side →