An eight day, self-guided cycling holiday that follows a coastal circuit of Madeira, travelling in an anti-clockwise direction starting in Caniço and ending in the capital, Funchal. Stay in small, traditional Madeiran hotels, and have your luggage transferred for you, as you enjoy coastal trails, Madeiran culture and traditional villages. Swim in the island’s famous natural pools, explore São Vicente’s ancient caves and grottoes and cycle along tranquil, forested trails of the west. Although there are some mountainous ascents on this holiday, there is also an option to rent an e-bike.
- Natural swimming pools
- Funchal and cable car
- Madeira’s levadas
- São Vicente caves and grottoes
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Day 1: Arrival in Caniço
Enjoy a day of leisure at the hotel in this historical town or enjoy a dip in the sea. In the evening, a welcome briefing will be held at the hotel.
- Accommodation: Four Views Oásis or similar
Day 2: Caniço – Camacha – Porto da Cruz | 25km
The morning starts with a transfer to Camacha, to collect the rental bikes before heading towards the east coast to the fishing village of Porto da Cruz. Relax on the volcanic beach or visit one of the last working sugar cane mills before cycling to your next hotel.
- Accommodation: Costa Linda or similar
- Cycling distance for the day: 25km
Day 3: Porto da Cruz – Santana – São Vicente | 40km
A bus transfer this morning assists with the steep ascent to Santana, known for its traditionally thatched Madeiran farmhouses. Following the east coast, the route then leads through several small villages before arriving at São Vicente, where you can visit ancient caves and grottoes.
- Accommodation: Estalagem do Mar or similar
- Cycling distance for the day: 40km + transfer
Day 4: São Vicente – Rocha Negra – Porto Moniz | 35km
You are transferred to the high plateau of Paúl da Serra. From here, the route then follows the high road before beginning a long descent to the west coast of the island and eventually to Porto Moniz. This area is famous for its natural swimming pools, formed by volcanic lava, which fill with clear ocean water as the tide rises.
- Accommodation: Hotel Aqua Natura or similar
- Distance for the day: 35km + transfer
Day 5: Porto Moniz – Estreito da Calheta | 45km
Today’s cycle begins along the west coast of the island and passes through multiple forests and small villages, with each bend offering a new photo opportunity. The tour concludes in the historic town of Estreito da Calheta, the largest municipality in the archipelago.
- Accommodation: Savoy Saccharum or similar
- Distance for the day: 45km
Day 6: Estreito da Calheta – Funchal | 50km
The first part of today’s route begins by following the coast to Ribeira Brava, before ascending toward Cabo Girão, where a transparent platform stands 580m above sea level. After taking in the views, a long descent returns toward the coast before eventually heading into the centre of the island’s capital, Funchal.
- Accommodation: Four Views Baía or similar
- Distance for the day: 50km
Day 7: Funchal – Monte – Funchal
Today’s bike-free day gets off to an exciting start by taking the cable car to Monte, with panoramic views over Funchal Bay. Visit the pilgrimage church of Nossa Senhora do Monte or the tropical garden, Jardim Tropical Monte Pala and take a walk along one of the island’s famous levadas, man-made irrigation channels that also serve as superb walking trails. Conclude the day by descending back toward Funchal in a traditional basket car, a wicker toboggan originally used as means of rapid transportation between Monte and the city of Funchal (optional, not included).
- Accommodation: Four Views Baía or similar
Day 8: Departure
Departure day or additional days can be arranged upon request.
What to expect
Accommodation on this tour includes a mix of small, locally-owned hotels, B&Bs and traditional guesthouses. They have been carefully selected based on a variety of criteria including their location, warm hospitality, fine local food or commitment to responsible tourism. All rooms have en-suite or private bathrooms.
Click to view default hotels
- Four Views Oásis (Caniço)
- Costa Linda (Porto da Cruz)
- Estalagem do Mar (Sao Vicente)
- Hotel Aqua Natura (Porto Moniz)
- Savoy Saccharum (Calheta)
- Four Views Baía (Funchal)
Hotels are subject to availability. In the event of a particular hotel being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Click to view upgraded hotel options
Sao Vicente: Solar da Bica 3*
This traditional country house is situated amidst the rugged rocks of the Sao Vicente-valley, nestling in a magical garden full of local fruit and plants. The stunning gardens allow you to feel the calm pulse of Madeira and cater for deep relaxation after your hiking tour. The rooms are furnished in a modern style. Take the time to try the heated saltwater-pool and the sauna available year round. Breakfast is served daily, featuring local dishes from all over the island.
Funchal: Arts in Hotel Conde Carvalhal 4*
This small, very family-run hotel surprises with a comfortable location directly in the heart of the old part of Funchal. Both the harbour promenade and the famous market hall are only a few steps away. Individually designed rooms with lots of amenities and generous gardens offer a tranquil place to relax after a days cycle. From the terrace of your suite you have a view onto the town below and the busy harbour.
Note that hotels are subject to availability. In case a particular hotel (from the ones pictured above) is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.
A breakfast buffet is provided each day. When no restaurant location is available, lunches and snacks should either be bought from local shops, or pre-ordered from your hotel the night before.
Difficulty and terrain
Due to the topography of the area, you will need to have a good level of fitness and confidence on a bike for this tour. The route is mostly on quiet roads however short sections will require cycling on busier roads. (read more about difficulty grades).
We strongly advise you to only follow marked trails and never shorten the path through unknown and unmarked terrain. We will provide you with detailed route notes and maps, and you can call our 24/7 local assistance phone number anytime. More detailed information on route navigation will be included in your holiday information pack.
When to go
This trip is available all year with departures every Tuesday, Thursday and Saturday.
Alternative departure dates may be possible upon request.
Click to view travel options
Our recommended airport for this tour is Madeira.
By train or bus
- 7 nights accommodation as listed in the itinerary
- 7 breakfasts
- Welcome briefing
- Luggage transfer between hotels
- Detailed travel documents (one set per room) including maps and route descriptions (opt for a digital route book to receive a discount)
- Bus transfers Caniço–Camacha, Porto da Cruz-Santana and São Vicente–Rocha Negra
- Return ticket for cable car, Funchal–Monte
- GPS tracks and navigation app
- 24/7 phone assistance from our local office/representative
- Airfare and connecting land transfers
- Lunches, dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Personal expenses such as phone calls, additional transfers and tips
- Local tourist taxes
- Any items not specifically mentioned as included in the programme
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
- Bike/e-bike rental, including bike insurance
- Half-board accommodation
- Extra night(s) in Caniço or Funchal
On this tour, we offer rental of both standard 27-gear trekking bikes and e-bikes.
A high-quality, well-equipped touring bike with a unisex frame and 21 gears.
This bike assists with electric support only when you are pedaling. The bike is easy to handle and has a low balance point.