Madeira and Porto Santo are usually sold as one destination, but they are two very different islands and an eight-day trip is the natural length to do both justice. This itinerary spends the first five days on the main island covering the essentials, then crosses to Porto Santo for three nights of the long sandy beach that Madeira simply does not have. The two halves balance each other: green and vertical, then flat and pale gold.

The plan keeps a single base in or near Funchal for the first five nights, then moves to Porto Santo for the last three. A rental car is assumed for the Madeira days and is not needed on Porto Santo. The single most important practical decision is how you cross between the islands, so the ferry-versus-flight comparison below comes before the day plan.

Ferry versus flight: how to cross to Porto Santo

There are two ways across, and they suit different travellers.

The ferry. The Lobo Marinho sails between Funchal and Porto Santo, usually once a day in each direction, with a crossing time of about two and a quarter hours. It takes foot passengers and cars. A return fare for a foot passenger is roughly €70 to €110 depending on season; taking a car across adds a significant amount and is rarely worth it for a short stay, since Porto Santo is small and walkable. The ferry leaves from the centre of Funchal, so there is no airport transfer at the Madeira end. The crossing can be rough in winter swell, and the boat occasionally cancels in bad weather, so build a buffer day if your trip is tight.

The flight. A short hop links Madeira Airport and Porto Santo Airport in about fifteen minutes. Fares vary widely and can be cheap if booked early. The flight is the better choice if the sea forecast is bad, if anyone in the group is prone to seasickness, or if your Porto Santo time is short and you want to maximise it. The catch is the airport transfers at both ends, which eat into the time the flight saves, and the baggage allowance on a small aircraft.

The recommendation for this plan. Take the ferry out, on Day 6, when you have a full afternoon and no schedule pressure, and decide the return by the forecast: ferry if calm, flight if rough or if your departure from Madeira is tight. This plan is written for the ferry out and a flexible return.

The plan in one paragraph

Day 1: arrive, Funchal, the market and the old town. Day 2: the central mountains, the Pico Arieiro sunrise and a short levada. Day 3: the Monte cable car, the toboggan and a wine lodge. Day 4: the west, the 25 Fontes levada and the Calheta sand. Day 5: Câmara de Lobos, Cabo Girão and a slow Funchal afternoon. Day 6: the afternoon ferry to Porto Santo. Day 7: a full Porto Santo beach day. Day 8: a last Porto Santo morning, then the return. Base in Funchal for nights one to five, Porto Santo for nights six to eight.

Day 1: arrival and Funchal

Arrive at Madeira Airport, collect the rental car, and drive about 25 minutes into Funchal. Settle in, then take the city at an easy pace: the Mercado dos Lavradores if it is still open, the cathedral, the streets of the old town. Dinner in the Zona Velha. A light first day to absorb the flight.

Day 2: the central mountains

An early start. Drive up to Pico do Arieiro in the dark to watch the sun rise over a sea of cloud, the best single sight on the main island when the weather cooperates. Dress for real cold at the summit. Once the day is up, drop to Ribeiro Frio and walk the level levada to the Balcões viewpoint, about 30 minutes each way through the laurel forest. Trout lunch in Ribeiro Frio, then an easy drive back to Funchal.

Day 3: Monte, the toboggan and the wine

A lighter day after the early start. Ride the Monte cable car from the old town up to Monte, walk the gardens, and come back down in a wicker toboggan toward Livramento. In the afternoon, spend an hour on a Madeira wine tasting at one of the old city lodges. The rest of the day stays open for a café or the seafront.

Day 4: the west and the 25 Fontes levada

The trip’s main walk. Drive an hour 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, three to four hours return. Start in the morning before the trail fills. In the afternoon, drop to Calheta for an hour on the imported golden sand, a preview of the beach time waiting on Porto Santo.

Day 5: the working coast and a slow afternoon

A short, easy day to close the Madeira half. Drive a few minutes west to Câmara de Lobos, the fishing village with boats pulled up on the shingle, for a coffee by the harbour. Continue to the Cabo Girão skywalk, a glass platform over one of Europe’s highest sea cliffs, a quick stop with a long view. Back in Funchal, keep the afternoon slow: a botanical garden, a long lunch, packing for the crossing. Return the rental car this evening or first thing tomorrow, since you will not need it on Porto Santo.

Day 6: the crossing to Porto Santo

A travel day, taken at an easy pace. Spend the morning finishing anything left in Funchal, then make your way to the ferry terminal in the centre of the city for the afternoon sailing to Porto Santo, about two and a quarter hours. The boat usually leaves in the early afternoon, so check the current timetable when you book. Arrive in Vila Baleira, check in, and walk the seafront in the evening light. The change of scale is immediate: after five days of mountains, Porto Santo is flat, low and built around its beach.

Day 7: a full Porto Santo beach day

The day the trip was building toward. Porto Santo has nine kilometres of pale, gently shelving sand and water that is warmer and clearer than Madeira’s rocky south coast. The day is for swimming, walking the length of the beach, and a long lunch at a seafront café. Renting a bike on the flat coastal path is an easy way to see more of the island without effort. If you want a little sightseeing, the small Christopher Columbus house museum in Vila Baleira and the Pico do Castelo viewpoint each fill an hour, but the beach is the point.

Day 8: a last morning, then the return

An unhurried final morning. More beach while the light is soft, a last swim, a coffee in Vila Baleira. Then the return to Madeira, by ferry if the sea is calm or by the short flight if it is rough or if your onward departure is tight. If you fly home from Madeira Airport the same day, leave a comfortable margin: the ferry docks in central Funchal and still needs an airport transfer, and the inter-island flight, though quick, has its own check-in.

Costs at a glance

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

Item	Per person
Accommodation, 5 nights Funchal mid-range	€350 to €650
Accommodation, 3 nights Porto Santo mid-range	€210 to €420
Rental car, 5 days Madeira (split per person)	€120 to €240
Fuel and tolls	€30 to €50
Porto Santo crossing, ferry or flight return	€60 to €130
Cable car, toboggan, wine tasting, entries	€70 to €130
Restaurant meals	€300 to €490
Coffees, snacks, drinks	€90 to €160
Total per person (estimate)	€1,230 to €2,270

Variations

Fly both ways. If anyone in the group is prone to seasickness, or if the winter sea forecast looks poor for your dates, swap the Day 6 ferry for the fifteen-minute flight. You lose the slow-travel feel of the crossing and gain two airport transfers, but the timing becomes more predictable.

More Porto Santo, less Madeira. Travellers who mainly want the beach can cut the Day 5 working-coast day and cross a day earlier, giving four nights on Porto Santo. The Madeira half then covers only the mountains, Monte and the 25 Fontes walk.

More Madeira, less Porto Santo. If two nights on a beach island feels enough, trim Porto Santo to two nights and add the north coast to the Madeira half: São Vicente, Porto Moniz and Santana make a full extra day. See the 5-day plan for that day’s shape.

Add the big traverse. Strong walkers can replace the Day 3 Monte day with the Pico Arieiro to Pico Ruivo traverse, the island’s flagship ridge walk. It needs a shuttle or two cars and a clear forecast.

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