Seven days is the length at which Madeira stops feeling like a sampler and starts feeling like a place you know. You cover all six regions, walk the island’s flagship traverse from Pico do Arieiro to Pico Ruivo, take a real rest day instead of pretending you do not need one, and finish on the sand of Porto Santo, the beach the main island lacks.

This plan keeps a single base in or near Funchal for the Madeira nights, then moves to Porto Santo for the last two. A rental car is assumed for every Madeira day except the rest day. Madeira’s weather changes sharply between coasts and altitudes, so treat the day order as flexible: do each region on its best-looking morning.

The plan in one paragraph

Day 1: Funchal, the market, the Monte cable car and the old town. Day 2: the full Pico Arieiro to Pico Ruivo traverse. Day 3: the north coast, São Vicente, Porto Moniz and Santana. Day 4: the west, the 25 Fontes levada and the Calheta sand. Day 5: a genuine rest day in and around Funchal. Day 6: the east, the Ponta de São Lourenço walk, then the afternoon ferry to Porto Santo. Day 7: Porto Santo, the nine-kilometre beach. The plan finishes with a second Porto Santo night before the return.

Day 1: Funchal

Ease in. Start at the Mercado dos Lavradores, the covered market, in the morning, then walk the centre and the cathedral. In the afternoon, ride the Monte cable car up to Monte and take the wicker toboggan back down toward Livramento. Dinner in the Zona Velha, the old town. No car needed today; collect the rental in the evening or first thing tomorrow.

Day 2: the Pico Arieiro to Pico Ruivo traverse

The big walk. The PR1 traverse runs from the summit of Pico do Arieiro across a knife-edge ridge to Pico Ruivo, at 1,862 m the highest point on the island. It is around seven kilometres one way, five to six hours of real walking, with stone steps, tunnels (bring a torch) and serious exposure. It is not a casual stroll, and it closes in bad weather.

The logistics matter. The simplest version walks from Arieiro to the Achada do Teixeira car park below Pico Ruivo, which means you need either two cars, a taxi arranged for the far end, or a guide with transport. Start at first light to walk in cool air and clear views, and check the forecast the night before. If the weather is wrong, swap this day with Day 3 or Day 4.

Day 3: the north coast

Cross the island to its wild, green side. The tunnelled expressway reaches São Vicente in under an hour, a tidy valley town and a good first stop. Continue west to Porto Moniz, where old lava flows have been shaped into natural sea pools that are calm enough to swim on a settled day. On the way back, stop in Santana for its painted, thatched A-frame houses. For the scenic version, swap the tunnels for a stretch of the old cliff-edge coast road and allow extra time.

Day 4: the west and the 25 Fontes levada

A second walk, gentler than Day 2. Drive into the western highlands to Rabaçal and follow the 25 Fontes levada trail, a level forest path to a rock amphitheatre of springs and a green pool. Allow three to four hours and start before the trail gets busy. In the afternoon, drop to Calheta for an hour on the golden sand, the easiest swimming beach on the main island.

Day 5: a real rest day

After three big days, take one that asks nothing of your legs. No car. The morning is for whatever you skipped on Day 1: a slower wander through Funchal, the botanical garden, or the small museums. Late morning is a good slot for a whale and dolphin watching trip out of the marina, three hours on calm water with no walking involved.

The afternoon is deliberately empty. A wine lodge tasting in town, a long lunch in Câmara de Lobos, the fishing village just west of Funchal, or simply a book and a coffee. The point of this day is that the back half of the week starts fresh.

Day 6: the east, then the ferry to Porto Santo

A morning walk and an afternoon crossing. Drive east to the Ponta de São Lourenço peninsula, the bare red-rock trail at the island’s eastern tip, around two and a half hours return. It is exposed and treeless, with no shade, so go early. Lunch in Machico or near Caniçal, then drive to the Porto Santo ferry terminal at Funchal for the afternoon crossing, about two and a quarter hours. Leave the rental car in Funchal; you will not need one on Porto Santo. Check in and walk the seafront of Vila Baleira in the evening.

Day 7: Porto Santo

A full day on the beach the main island does not have. Porto Santo is a flat, sandy island with nine kilometres of pale beach and far less to see than Madeira, which is the point. The day is for swimming, walking the sand, renting a bike along the seafront path, and a long lunch. The water is warmer and clearer than most of Madeira’s rocky south coast. If you want a little more, the Pico do Castelo viewpoint and the small Christopher Columbus house museum in Vila Baleira fill a couple of hours without effort.

The plan finishes with a second night on Porto Santo, then the ferry or the short flight back the next morning, timed to your departure.

Costs at a glance

A rough per-person estimate at a mid-range standard, excluding flights.

Item	Per person
Accommodation, 7 nights mid-range	€490 to €910
Rental car, 5 days (split per person)	€120 to €240
Fuel and tolls	€40 to €65
Porto Santo ferry, return	€70 to €110
Cable car, toboggan, whale trip, entries	€110 to €180
Restaurant meals	€280 to €460
Coffees, snacks, drinks	€80 to €150
Total per person (estimate)	€1,190 to €2,115

Variations

The two-base version. Instead of commuting from Funchal all week, spend the first four nights in Funchal and the next ones in the north or the west, near São Vicente or in Calheta. The trade-off is one hotel change and slightly higher cost; the gain is shorter drives to the north and west on Days 3 and 4, and quiet evenings away from the city. Travellers who like rural calm tend to rate the second base higher in hindsight.

Skip Porto Santo, deepen Madeira. If a beach island does not appeal, drop Days 6 and 7’s crossing and use the time for Curral das Freiras, the Caldeirão Verde levada in the north, and a second slow day in Funchal. The week stays on the main island.

The premium version. Trade the mid-range hotel for a hillside quinta or a five-star Lido property, fly rather than ferry to Porto Santo, and add a guided walk or a private driver for the traverse and north-coast days.

The budget version. Stay in central guesthouses, walk the levadas and the peninsula independently rather than guided, and eat the lunchtime prato do dia to keep restaurant costs down.

What this itinerary skips

Multi-day hikes. Madeira’s walks are all day walks or shorter. There is no hut-to-hut backpacking circuit, so a week is plenty for the walking on offer.

Canyoning and diving. Both are excellent and both would mean cutting something else. If an adventure activity matters to you, swap it into the rest day and accept a slightly less restful Day 5; see canyoning and Garajau diving.

A second visit to the central massif. This plan touches the centre once, on the traverse. For a trail-led week with a graded walk every day, see the hiking itinerary.

For the wider picture before you book, start with the regions overview and the activities catalogue.