Our trail runs through Funchal’s São Martinho district. The starting point sits in an area largely lived-in by locals, but these days it’s also well stocked with hotels and tourist stays. If you’re based in Funchal, you might be in luck—the start could be just a short walk away. Otherwise, you can drive and park on Rua António de Sousa, or hop on one of the city buses. The stop closest to the trailhead is called Redondo Barreiros, served by lines 45 and 50.

Right from the outset you’ll get the classic levada feel: a narrow path alongside a surprisingly clean, fast-flowing channel. You’ll likely meet plenty of animals—nothing wild, mostly cats and dogs that belong to residents living along the levada. Before long, the route leaves the waterway and ducks into city streets, guiding you to the foot of Pico da Cruz. The ascent is very easy—there are homes almost all the way to the top, so a paved road leads right up near the summit.

You may want to linger at the top—perfect spot for a picnic. As you arrive you’ll see a small parking area (yes, that’s an option) and a transmitter tower. The tower itself isn’t much to look at, but follow the worn footpath along the fence and it opens onto a lovely, slightly wild grassy patch where you can sit, take in the views, and stay a while. From different points on the summit you’ll catch different angles of Funchal, but the main panorama stretches over São Martinho. You’ll also spot Praia Formosa beach, the sheer face of Cabo Girão rising beyond Câmara de Lobos, and the Igreja de São Martinho.

The second-best viewpoint is roughly where you first reached the top and the asphalt gives way to a dusty parking area—here, the view opens over downtown Funchal, the ocean, the port, and the headland that closes the city on its eastern side. After descending from Pico da Cruz, quiet streets lead you gently back to the start, which is also the end point. On the way, keep an eye out for a striking layered sandstone outcrop that livens up the otherwise residential Rua da Amoreira.