Five days is enough to get a real sense of Madeira without rushing. Because the island is small and the expressway network is fast, this itinerary keeps a single base in or near Funchal and treats every region as a day trip. You unpack once and let the car do the work.

This plan assumes a rental car for the days you head out of the city. It also assumes some flexibility: Madeira’s weather varies sharply between coasts and altitudes, so the smartest move is to keep the order loose and do each region on its best-looking day.

The plan in one paragraph

Day 1: Funchal itself, the market, the Monte cable car and toboggan, the old town. Day 2: the central mountains, sunrise at Pico do Arieiro and a laurel- forest levada walk. Day 3: the north coast, São Vicente, the Porto Moniz lava pools and Santana. Day 4: the big walk, the 25 Fontes levada in the west, with an afternoon on the Calheta sand. Day 5: a flexible day, the Ponta de São Lourenço peninsula if it is bright, or wine and gardens in Funchal if it is not.

Base in or near Funchal for all five nights. With an extra day or two, add an overnight on Porto Santo for the beach.

Day 1: Funchal

Start in the city. The Mercado dos Lavradores, the covered market, is best in the morning, when the fruit and the fish hall are at their liveliest. From there, wander the centre and the cathedral before heading up.

In the afternoon, ride the Monte cable car out of the old town to the hillside village of Monte, with its church and tropical garden, and take the wicker toboggan back down toward Livramento. Finish in the Zona Velha, the old town, where the painted doors and the restaurant terraces make the obvious place for dinner.

Day 2: the central mountains

This is an early start. Drive up to Pico do Arieiro in the dark to watch the sun rise over a sea of cloud, one of the most memorable things on the island when the weather cooperates. Dress for real cold at the summit.

Once the day is properly up, move down to Ribeiro Frio and walk a level levada trail through the laurisilva, the ancient laurel forest, out to the Balcões viewpoint. In the afternoon, drive to Curral das Freiras, the village deep in its near-vertical valley, and look down into the bowl from the Eira do Serrado viewpoint before returning to Funchal.

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 town set deep in its valley and a good first stop. Continue west along the coast to Porto Moniz, where old lava flows have been shaped into natural sea pools, calm enough to swim on a settled day.

On the way back, take in Santana and its painted, thatched A-frame houses. For the most scenic version of the day, swap the tunnels for a stretch of the old cliff-edge coast road, allowing extra time for it.

Day 4: the big walk and the west

Day four is the levada walk. Drive into the western highlands to Rabaçal and follow the 25 Fontes trail, a level forest path to a rock amphitheatre of trickling springs and a green pool. Start in the morning, before the trail gets busy.

In the afternoon, drop down to the coast at Calheta, where the island’s most usable beach, made of imported golden sand, is the place to rest your legs before the drive home.

Day 5: a flexible last day

Leave the final day loose, and decide it the evening before based on the forecast.

If the weather is bright, drive east for the Ponta de São Lourenço peninsula walk, the bare red-rock trail at the island’s eastern tip, and have lunch in the old town of Machico on the way back. If it is grey or wet, stay in Funchal instead for a slower day of wine lodges and gardens, neither of which needs good weather.

Costs at a glance

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

Item	Per person
Accommodation, 5 nights mid-range	€350 to €650
Rental car, 5 days (split)	€120 to €220
Fuel and tolls	€30 to €50
Cable car, toboggan, levada shuttle, entries	€60 to €120
Restaurant meals	€200 to €350
Coffees, snacks, drinks	€60 to €110
Total per person (estimate)	€820 to €1,500

Variations

The premium version. Trade the mid-range hotel for a hillside quinta or a five-star Lido property, eat at the top tier, and add a guided walk or a private driver for the mountain and north-coast days.

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

Add Porto Santo. With two extra days, take the ferry or the short flight to Porto Santo for the long sand beach the main island lacks, and slow the trip right down at the end.

This plan covers four of Madeira’s six regions. For the full picture before you book, start with the regions overview and the activities catalogue.