Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Flights
available
11.0Kg CO2e
Printed route
directions
Due to the popularity of this holiday some peak dates in 2025 are filling up quickly, particularly in April and May. Please do call for further advice and if possible do consider travelling outside of the peak times for better availability.
Madeira is an island of fascinating natural beauty and enticing climate. Known as the pearl of the Atlantic, it rises steeply along with its small island neighbour in splendid isolation off the coast of Africa. An island of volcanic origin, it is a haven for those seeking a relaxing holiday in close proximity to nature. Bursting with the exotic colours of subtropical flowers and lush laurisilva forests. Gardens and parks are everywhere planted with all manner of exotic trees, shrubs and blooms.
Its mountains are rugged and inspiring, with jagged peaks and plunging valleys filled with lush vegetation. Here you will find the more challenging walking, where dramatic cliff top walks zig zag along paths with the Atlantic lapping below. There is also plenty of easier walking suitable for even the least experienced walker. A network of Levada's contour the mountain sides their banks planted with wild hydrangeas, lilies and agapanthus. Built to carry water from the abundant springs in the north to the cultivated areas of the south. These irrigation channels provide gentle walks through the wilds, allowing you to explore some of the dramatic mountainscapes at the heart of the island. Stroll alongside the constant stream of bubbling water with ever-changing views of deep valleys and hillsides often with splendid sea views in the background.
The historic and beautiful town of Funchal, set in a natural amphitheatre by the sea in the south of the island, is an ideal location for your walking holiday in Madeira. It has a lively commercial centre with contrasting quiet pedestrianised streets and pretty squares (many painstakingly restored with mosaic-like miniature cobblestones) and an abundance of parks and gardens. The Old Town is atmospheric with its street flower-sellers, narrow streets and period buildings. Its vibrant restaurants specialise in delicious fresh seafood and very many have folk groups and dancing. A cable car will take you quickly up to Monte where you can enjoy magnificent panoramic views over Funchal. A visit to the Monte Palace Tropical Gardens is a must, with the option of returning by wicker basket!
Choose from the 3 star Hotel Orqueida or the 5 star Quintinha Sao Joao.
The paths are generally of good quality, with some uneven sections and tunnels. Some walks, particularly those which follow the levadas, do require a head for heights and may not be suitable for vertigo sufferers as paths are narrow with drops to the side, sometimes without barriers. The description of each walk will indicate if it has vertiginous sections.
Arrive at your hotel in Funchal, your base for the week. The walks can be done in any order, depending on weather conditions. For all of the walks public transport will be needed to get to the start/from the end (payable locally).
You stay at Hotel Orquidea or Quintinha Sao Joao.
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Aircon
You stay at the 3* Hotel Orquidea, ideally situated in the heart of Funchal. A large rooftop terrace offers views over the bay of Funchal. Rooms are spacious and most have balconies some with baths and some with showers. Breakfast is a hot and cold buffet, and dinner can be taken at the onsite Villa Mare restaurant serving typical Madeiran cuisine. With easy access to a wealth of atmospheric restaurants you may prefer to eat out. Enjoy the islands fare in a family run establishment in the old town or marvel at the fantastic array of fresh fish at a harbour side café.
All rooms feature free Wi-Fi, television, telephone, air conditioning and private bathroom with WC, shower/bath and hairdryer.
Room upgrades: Please contact us for details.
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The Quintinha São João is set in lush, landscaped gardens and features a spa and indoor and outdoor heated swimming pools.
The hotel has 2 bars and a restaurant serving a selection of Portuguese and international cuisine, as well as Goan specialities.
This is a half day coastal walk on the most easterly point of the island. It is a walk like no other on the island, in a Nature Reserve (payable locally) where some of the plants are not just endemic to Madeira, but to this part of the island. Along with the flora, you'll enjoy spectacular cliff scenery.
Alternatively a sunrise breakfast and half or full day guided walk can be pre-booked for this day, please call our team for more details.
This is a classical levada walk, along the Levada do Furado and Levada da Portela. Whilst walking through the thick laurel forest the views are restricted, but from Rocha dos Pingos onwards there are increasing opportunities of views to the sea at Faial and Porto da Cruz. The levada passes through a number of interesting rock arches before arriving at a good viewpoint over the Machico valley.
This is an attractive walk covering a small amount of open hillside to start, a steep and secretive descent beside a small swiftly flowing levada, a more level section (but rough underfoot) beside a levada (where you can see trout swimming), and a walk along and down a wooded ridge to finish. Weather permitting, you should obtain good views over the north coast, embracing Faial, Aguia (Eagle Rock) and Porto da Cruz.
Enjoy a day exploring Funchal, . You can visit its magnificent gardens, wander along picturesque streets vibrant with jacaranda and squares with Portuguese cobblestone pavements, or perhaps simply stop and relax at one of the pavement cafes and watch the world go by. Funchal's museums and historical buildings are also well worth a visit and there are art galleries with works by national and international artists. Funchal's market happens on a Friday when all the flowers, fruit, vegetables and fish sellers on the island set up shop in the old central market place. The sheer range, colour and smell of the produce are quite amazing, and it is difficult to pass through without buying anything! With stunning views overlooking Funchal, Monte is certainly worth a few hours of your time. Take the cable car up for a wonderful way to appreciate the fabulous views of Funchal and its surrounding valleys.
This walk starts in the village of Camacha, the centre of Madeira’s willow craft industry and worth an explore before starting the walk. Following the Levada dos Tornos, as the name suggests there will be many twists and turns along the way, along with some tunnels. After the first tunnel you emerge into a luxuriant landscape of eucalyptus, mimosa and sweet chestnut and many flowers. The terraces the levada was built to water can be seen below you.
All year round this is a walk with a sun-blessed aspect, through landscape rich in cultivation. Here in early autumn the grapes are harvested for some of Madeira's best-known wines, and the valleys are thick with cherry trees, full of blossom in spring, and banana farms. It is possible to extend this walk to the viewpoint at Cabo Girão.
These tour only prices are based on two people sharing. Single supplement from £148.
We can book your flights, protected by ATOL and ABTA. Please ask at time of enquiry.
Unfortunately this holiday is not suitable for solo travellers due to remoteness and terrain of some walks.
If you choose a flight inclusive package with us, you will fly into Funchal airport. We can provide transfers from the airport, please contact us for details and prices.
We hold an ATOL License and are fully ABTA bonded, so you can book your flights with us in confidence. We can book most airlines and will advise you of your most convenient airport and flight options.
Flight prices vary massively and change quickly. At Headwater we will sell you your flights at the same price you can buy them yourself. We simply add £35 per person to cover your flight protection, to learn more please click here.
Subject to availability and dependent on service provider, please ask at time of enquiry and book early to avoid disappointment. *Unfortunately, due to the airline themselves we are unable to book Ryanair.
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Flights
available
11.0Kg CO2e
Printed route
directions
