Gretchen Stuppy Carlson
Madeira is an incredible island with dramatic views, incredible hiking, local culture and so many places to explore. We spent 4 incredible days on the island (we were scheduled for 5 but they closed the airport due to winds and we arrived a day late). This 4 day Madiera Itinerary is exactly what we did and enjoyed with a few additional suggestions based directly on our experience.
Quick Look at our 4 Day Madeira Itinerary
Day 1: Arrive, check in to our rental. Hike Vereda da Ponta de São Lourenço (PR8) for incredible coastal views. Dinner in town
Day 2: Spend the morning at Seixal Swimming Pools, and drive over the center of the island. Stop at the Fanal Forest and explore Funchal
Day 3: Sunrise at the Pico do Arieiro Trail, lunch and a swim, then afternoon hike at Levada do Caldeirão Verde, visit the ‘Typical Houses’
Day 4: Sleep in and explore Funchal, spend the afternoon at Prainha do Caniçal, do a tour, try a toboggan, or visit the gardens
Where to Stay in Madeira
One of the most important decisioun you will make when you are planning your visit is where to stay. This is very important as the island is very mountainous and it takes a long time to get places. We rented a house in Machico which was an excellent choice. Not only is it relatively close to the airport but you can get to some of the best hikes within an hour.
Besides this cute town, Funchal is also well located for most of the activities. You can also stay in the west or north parts of the island, just note that these are further from some of the best hikes and while they are quieter they offer a very different experience.
We found a lot of great options for both hotels and house rentals through booking.com.
Renting a Car and Getting around Maderia
I strongly recommend renting a car in Madeira. It is the easiest way to get to come of the hikes and hidden spots without spending a lot on a tour. We rented through Discover Cars which is a great resource to find the best deals. Book your car well in advance.
There was mixed cell service on the island, so I recommend downloading hiking and road maps in advance. Driving is not too bad although there are windy roads, tunnels and plenty of hills.
Details of our 4 Day Madeira Itinerary
The itinerary below is the order we explored the island, but you can really flip flop the days depending on the weather. The itinerary prioritizes hiking and adventures. There are so many trails on the island, so this itineraryreally highlights our favorites!
Day 1: Arrive and enjoy a Coastal hike
We were originally supposed to have 5 days on Medeira, but after closing the airport due to wind, our flight re-routed to the Canary Islands where we spent the night. This meant we arrived middayinto Funchal with enough time to squeeze in a hike.
Since we were already staying in the eastern part of the island, the drive was short and we spent the afternoon hiking Vereda da Ponta de São Lourenço (PR8). This was easily one of our favorite hikes and is a stark contrast to the other more lush side of the island.
Distance: 4.3 miles
Elevation Gain: 1,058 feet
Difficulty: Moderate
When we hiked this trail in July 2025, the final section leading to the summit was closed to hikers, so be sure to check current conditions before you go.
Plan for about 2 hours to complete the hike. This popular trail offers incredible coastal views and follows an out-and-back route with a short loop at the end. The path is well-marked, and you can do the loop in either direction. Although the total elevation gain is around 1,000 feet, it’s spread out along the route with plenty of rolling terrain rather than one long climb.
Located on the east side of the island, the trail tends to be dry and sunny, with cactus-lined sections and fewer clouds than many other island hikes, though it was still somewhat cloudy when we visited. It’s a great option if you’re looking for a scenic, less foggy alternative to the island’s cloudier trails.
Get your first dinner on the island. We found a few good restaurants in Machico but there are excellent options in Funchal and all over the island. We found dining more expensive than mainland Europe although this is expected on an island.
Day 2: Seixal Swimming Pools, Fanal Forest and Funchal
You can do this day in any order. We chose to visit the swimming pools in the morning as the sun was out, but the water is chilly here. These pools are located on the north side of the island and are mostly formed by the natural rocks that form beautiful swimming pools. We visit Seixal, but you can also visit some of the other swimming spots.
Top Swimming Holes – North Madeira
- Porto Moniz Natural Swimming Pools – The most famous volcanic pools; great facilities and stunning ocean views.
- Cachalote Natural Pools (Porto Moniz) – Quieter, more natural alternative right next to the main Porto Moniz pools.
- Seixal Natural Pools (Poça das Lesmas) – Beautiful lava pools with dramatic cliffs and fewer crowds.
- Poça do Mata Sete (Seixal) – A smaller, more rugged natural pool known for its scenic rock formations.
- Ribeira da Janela Natural Pools – Near the impressive sea stacks; less developed but wild and beautiful.
- Ponta Delgada Natural Pools – Local favorite with easy access and calm waters protected by rock walls.
- São Vicente Natural Pools – Scenic oceanfront spot with views of the cliffs and a nearby seaside promenade.
Grab lunch in town.
From here drive up over the top of the island and stop at the Fanal Forest.
This is often in the clouds and makes for a beautiful, but eerie forest you can wander through the trees. There are some walking trails, but this isn’t really a hike. Plan to spend about 30-60 minutes at the forest.
If you have time in the afternoon, spend some time exploring the town and area of Funchal. The town has a fun pedestrian area to walk and we enjoyed visiting some shops, checking out the waterfront and getting dinner. Here are some other things worth exploring in town:
Take the Cable Car to Monte – Enjoy incredible views over Funchal Bay as you glide up to the hilltop village.
Visit Monte Palace Tropical Garden – Explore exotic plants, koi ponds, and beautiful tile artwork in this lush garden.
Ride the Monte Toboggan – Hop into a wicker sled guided by men in straw hats for a thrilling ride down the hill.
Stroll the Funchal Old Town (Zona Velha) – Wander cobbled streets filled with street art, cafes, and local shops.
Tour the Mercado dos Lavradores (Farmers’ Market) – Sample tropical fruits and admire Madeira’s vibrant flowers.
Explore the Funchal Cathedral (Sé Cathedral) – Visit this 15th-century Gothic church with intricate wood carvings.
Visit the CR7 Museum – Learn about Cristiano Ronaldo’s life and career — a must for football fans.
Relax at the Funchal Marina or Promenade – Enjoy a drink by the water or catch a dolphin-watching boat tour.
Take a Wine Tasting Tour – Visit Blandy’s Wine Lodge or other cellars to try Madeira’s famous fortified wine.
Watch the Sunset at Pico dos Barcelos Viewpoint – Get panoramic views over the city and ocean, especially at golden hour.
Day 3: Sunrise at the Pico do Arieiro Trail, lunch and a swim, afternoon hike at Levada do Caldeirão Verde
This is an early start day! Start by finding the time of sunrise and then plan an early start to watch the sunrise from the highest point on the island. Plan enough time to arrive at the parking lot early and walk out on the trail for the best morning views. I’ve written a full article about sunrise at the Pico do Arieiro Trail which should be helpful.
After sunrise – head somewhere on the island for breakfast. We then took a morning rest at the Primitive Centre of the parish of São Jorge, in Calhau de São Jorge. This is a rocky beach with so gorgeous views. We spent about 1 hour relaxing here after an early start. You can also take a short walk from this ‘beach’
Spend the afternoon hiking the Levada do Caldeirão Verde. This hike is inland on the island along one of the many levadas. The Levada do Caldeirão Verde hike is one of Madeira’s most breathtaking trails, winding through lush Laurisilva forest in the island’s northern mountains.
This moderate, 8.7 km (5.4-mile) out-and-back hike follows a historic irrigation channel, or “levada,” carved into the cliffs, offering a peaceful walk surrounded by moss-covered trees, ferns, and waterfalls. The path passes through several dark tunnels, so bring a flashlight. The trail ends at the Caldeirão Verde waterfall, where a thin ribbon of water plunges into a deep emerald pool.
Before leaving the area, make sure to stop and admire the houses typico or the Casas de Santana.
Day 4: Sleep in and explore Funchal, spend the afternoon at Prainha do Caniçal, do a tour, try a toboggan, or visit the gardens
The final day is perfect for rounding out some sites and doing anything you missed on the first 3 days. We spent a good part of the day at the black sand beach: Prainha do Caniçal. This is one of the few sand beaches on the island and is very pretty with lots of little lizards.
We enjoyed the day here and had lunch at the little restarant.
There is a short walk to get from the parking lot down to the beach.
If you have more time, consider visiting some more of the sites in Funchal.
