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Travellers staying in Madeira for two weeks or more, on a long holiday or a winter escape, face a different question from those on a short trip: not what to fit in, but how to pace it. With time, the island becomes a place to live in for a while rather than a list to tick off.
A long stay works as a rhythm. Two or three active days a week, a walk, a drive or a boat, then a slow day in Funchal, a day on the coast, a rest. Over two weeks, that covers every classic trail, Porto Santo, the west and the north, with days left for the city's museums, the market and the sea.
Time also changes the costs. The municipal tourist tax stops after seven nights, the trail fees have weekly rates, and the quieter months give more choice. The tourist tax, €2 a night, stops at €14 a stay however long you remain.
Two of the longer outings a long stay has room for.
LevadaMadeira: PR 9 - Levada do Caldeirão Verde Hike Transfer
PR9 to the Caldeirão Verde, on your own schedule
WestFrom Funchal: West Madeira Waterfalls and Fanal Forest Tour
The west and Fanal, without driving
A rhythm, not a list
The common mistake on a long stay is to walk every day in the first week and have nothing left for the second. Pace it.
A good week has two or three active days, a mountain walk, a west or north drive, a boat trip, with city or coast days between. Start with the week-long plan from Funchal: the city, PR1 across the peaks, the west with Rabaçal and Fanal, the north with PR9 and Santana, the east with PR8 and Machico, an easy levada and the coast. The seven-day plan covers it.
In the second week, add what the first left out: PR10, the Levada do Furado, 11 km one way from Ribeiro Frio to Portela; PR13 or PR14 at Fanal; the Levada dos Tornos to Monte; Curral das Freiras, 21 minutes away by route 181; and two nights on Porto Santo. Keep one day a week with no plan at all.
The Levada do Furado is listed as an addition for the second week of travel, running 11 km one way from Ribeiro Frio to Portela.Every classic trail
Visitors on a long stay often want to walk them all. With two weeks, you can.
The classic classified trails from Funchal are PR1 across the peaks, 6.1 km one way; PR6 to the 25 Fontes and PR6.1 to the Risco at Rabaçal; PR8 on the Ponta de São Lourenço, about 4 km each way; PR9 to the Caldeirão Verde, 8.7 km each way; PR10, the Levada do Furado, 11 km one way; PR11 to the Balcões, 1.5 km each way; and PR13 and PR14 at Fanal. Add the Levada dos Tornos, unclassified and free.
Spread them across the stay, with the long ones, PR1, PR9 and PR10, on the clearest days and a rest day after each. The combined rates help: two or more classified trails in 7 days cost €52.50, not including PR1, which is €10.50 on its own.
The hiking hub lists every trail with its start and fee.
The PR1 trail across the peaks is 6.1 km one way and requires booking via SIMplifica.Porto Santo, and the festivals
The mistake is to treat Porto Santo as an afterthought. On a long stay, it deserves its nights.
The Lobo Marinho ferry from Funchal to Porto Santo starts at €33.90 and takes about 2 hours 15 minutes each way, with a break for maintenance in January. Its beach runs for 9 km. Two or three nights there turn it from a long day trip into a stay of its own.
A long stay also has time for a festival. Carnival fills early February, the Flower Festival late April and May, the Atlantic Festival's fireworks the Saturdays of June, the jazz early July, the Wine Festival late August to mid-September, the Nature Festival early October, and the Christmas season from 1 December to 10 January. The festivals calendar has the dates.

Ribeiro Frio / Portela - Levada Walk
★ 4.5 · 21 reviewsThe Levada do Furado from Ribeiro Frio to Portela with a guide, for the second week.
Winter sun stays
People escaping a northern winter often ask whether Madeira is warm enough for a month. On the south coast, it is mild.
From November to April, Funchal's average highs stay between 19.9 °C and 22.8 °C, and the nights between 13.9 °C and 17.0 °C, by the IPMA normals. Rain comes in spells, heaviest in December, 94.8 mm, and the sea is 17.6 to 20.9 °C.
Winter is also the quietest season for hotels: regional occupancy was 52.8% in December 2025 and 54.1% in January, against 76.7% in August. For a long stay, that means more choice of rooms.
The trade-off is the mountains: they are wet and cold in winter, with 391.0 mm of rain in November at Queimadas. Keep the high walks for clear days, and the coast, the city and the east for the rest.
What a long stay changes
- Tourist tax
- €2 a night, at most 7 nights (€14 a stay)
- Trail rate
- €52.50 for two or more trails in 7 days, not PR1
- Bus
- €1.45 a trip on a GIRO card
- Quietest months
- December and January
- US licence
- Valid for up to 185 days for non-residents
Costs that fall with time
The mistake is to budget a long stay as a short one multiplied. Several costs cap or fall.
Funchal's municipal tourist tax is €2 per guest per night for visitors over 12, charged for at most 7 consecutive nights, so it stops at €14 a stay however long you remain. The trail fees have combined rates, €9.00 for a day, €22.50 for three days and €52.50 for seven, not including PR1.
For moving around, a pre-paid GIRO bus card, €0.50, brings the city fare down from €2.05 to €1.45 a trip, and day tickets start at €4.95. A hire car can be taken for the active weeks only, and collected in the city rather than at the airport.
The quieter months, from November to March, when occupancy stays below 66%, add more choice and space.
A two-week rhythm
| Week | Active days | Slow days |
|---|---|---|
| One | PR1, the west, the north (PR9), the east (PR8) | Funchal and Monte, the coast, a rest |
| Two | PR10 Furado, Fanal (PR13 or PR14), Porto Santo | Curral das Freiras, the lodges, a free day |
- Active days
- PR1, the west, the north (PR9), the east (PR8)
- Slow days
- Funchal and Monte, the coast, a rest
- Active days
- PR10 Furado, Fanal (PR13 or PR14), Porto Santo
- Slow days
- Curral das Freiras, the lodges, a free day
Living in Funchal for a while
People on a long stay often want to feel less like tourists. Funchal makes that easy.
Shop at the Mercado dos Lavradores, open Monday to Friday from 07:00 to 19:00 and on Saturday to 14:00. Take the city buses rather than taxis: with a GIRO card, a trip costs €1.45, and the 59 urban routes of Horários do Funchal reach every part of the city, from Monte and the Botanical Garden to Praia Formosa and Santa Luzia. Learn the rhythm of the week: the market and the cathedral close on Sundays, and the city fills with festival nights through the year.
Explore the neighbourhoods one by one: the old town's streets, the museums of São Pedro, the views from Santa Luzia, the hotel zone of the Lido, and Monte on the hill. Each has its own page in the neighbourhoods guide.
For the wine, the lodges run tours all year, from €17 at Blandy's, and the Wine Festival from late August turns a long stay into a season of tastings.

Madeira: Food and Wine Walking Tour in Funchal
★ 4.8 · 517 reviewsA food and wine walking tour of Funchal, to start a long stay well.
Practicalities
The mistake is to plan a long stay around a single forecast. Plan it around the week's.
Check the IPMA forecast each evening, and put the long walks on the clear days; with two weeks or more, there is always another chance. Book the classified trails on SIMplifica close to the day: the fee is refunded only if a trail is officially closed.
Drivers from the United States can use a US licence for up to 185 days if they are not residents; UK drivers can use a photocard licence. Travellers from outside the Schengen area pass the EU's Entry/Exit System at their first Schengen border.
For choosing the month, see the best time to visit Madeira. The IFCN's FAQ on trail fees has the combined rates, and the IPMA the forecast.
Common questions
Is two weeks too long for Madeira?
No. At a slower pace, two weeks cover every classic trail, the west and north, Porto Santo and the city, with rest days between.
Do I pay the tourist tax for my whole stay?
No. Funchal's tax is €2 per guest per night for visitors over 12, for at most 7 consecutive nights: €14 a stay.
Is Madeira warm enough for a winter month?
On the south coast, mild: Funchal's highs stay around 20 to 23 °C from November to April, with rain in spells.
Is there a weekly trail pass?
There is a combined rate of €52.50 for two or more classified trails in 7 days, not including PR1.
