Portugal’s mountainous archipelago is just a two hour flight from Lisbon and Porto. Known for its wine, landscape, and futbal player Cristiano Ronaldo, the island is just 35 miles long and 14 miles wide, making it a great destination to road trip. Along the coastal highway, villages and towns sit in pockets and dot the rising mountainsides up into the clouds.

With her rugged terrain and lazy resorts, Madeira attracts both the adventurous and the idle.

Madeira, however, isn’t necessarily a beach destination. While much of the ocean front is highly developed with resorts, rocky swimming areas, and oceanside dining, only a few sandy beaches exist on the island, artificially created with sand from the mainland. Neighboring island Porto Santo, just a boat ride away, is a great alternative for those looking for flat land and a day at the beach. Others hike or mountain bike in search of hidden waterfalls, seaside cliffs, green laurel forests, and mountain views above the clouds.

We did not drink poncha, the island’s signature drink, or take a wicker toboggan down the mountain from Monte. In fact, there was much we were unable to see and do, like stand at Mirador de Balcões over the mountains, or stroll through the tropical gardens of Monte Palace, or swim in the natural swimming pools of Porto Moniz. But we spent four long days on an island in the clouds, dangling precariously over narrow switchbacks and breathless from the views.

Madeira Itinerary

• Day 1: Ponta do Pargo, Catamaran Cruise
• Day 2: Pico do Arieiro, São Martinho neighborhood
• Day 3: Caldeirao Verde levada walk, Campanário neighborhood walk
• Day 4: Porto Santo

Day One

Our two hour flight from Lisbon to Madeira, despite a bumpy landing, was quick and painless. We picked up our rental car from Sixt, and sped along the coastal highway past the capital Funchal and towards the Campanário neighborhood, where we had found a spacious but affordable Airbnb.

We chose the Campanário neighborhood, knowing we would have a car rental to get around the island but also space to park it at night. The neighborhood is very residential, and near a somewhat sleepy Ribeira Brava. Like other parts of the island, stray dogs and cats roar and holler into the night. You’ve been warned.

On our first day, we knew we would be anxious to see as much as possible. We started out on a driving tour along the southern coast heading west. The drive took us through deep tunnels, high above valleys, and past lush resorts.

We stopped once to enjoy an ice cream cone at Praia da Calheta (beach) before continuing through rural villages and farms to Ponta do Pargo (lighthouse).

Our GPS took us to a dirt road unsuitable for driving on (though we attempted). Once close to Ponta do Pargo, we suggest following road signs that lead to a nice paved road, right to the edge of the water.

The sun was high and air hazy from the salt water, but nothing could keep us from dropping our jaws at the sight of the water below. There’s a flat spot to walk out to and take in more views, though visitors should use their own discretion when nearing the edge of the cliff.

That night, our Airbnb host invited us to join a catamaran tour during sunset. We mingled with her and her Campanário neighbors, as the catamaran crashed into waves towards the setting sun.

From the water, Funchal sprawled up into the mountains, and east to west.

The crowd cheered as dolphins rode the waves alongside the boat. A few brave souls, including a young child, dove into the ocean as we anchored.

We were treated to a plated dinner of fish, pork, and vegetables with red and white Madeira wine. In the darkness, we sailed back to a sparkling Funchal while listening to Portuguese music and learning about Madeira from an old (and drunk) local.

Day Two

On our second day on the island, we grabbed some snacks at the grocery store and set out for our road trip to Pico do Arieiro, the 3rd highest peak on the island. We aimlessly chose the route that would wind us up the mountainside. We drove through a couple towns before the scene became rural with pastures and a sole cow here and there.

If you are a daredevil and like very steep and skinny (but well paved) roads, take road ER107 north from Funchal to get to Pico do Arieiro. This is the route we took…with some regret and a new fear of heights. If you prefer wider and more manageable roads, take road ER103 north from Funchal to get there.

Once at the top, we parked at the lot next to the visitor center. We arrived around noon and were lucky enough to find a parking spot, while others had to park down the hill on the side of the road.

At the well equipped, cafeteria-style restaurant, we had pizza and a quick coffee. From the patio, we could see tiny specks of hikers off in the distance.

There are clean bathrooms here, but be prepared to pay €.20-€.50 to gain access.

We weren’t prepared (or willing) for a strenuous hike, so we only hiked about 30 minutes down the trail, stopped at a couple viewpoints, and turned back around. Our short hike provided us with incredible views, so don’t feel as if you need to hike for hours in order to get great pictures.

If you’re prepared for a long hike, the main trail from Pico do Arieiro splits before Pico das Torres, both ending at Pico Ruivo. It will take you 5-6 hours round trip, with the easternmost trail being an extra 45 minutes.

After our hour long hike, Ali was ready to find flat ground, so we drove straight down to Funchal where we found a steamy rooftop cafe.

That afternoon we drove to the São Martinho neighborhood to explore the resorts and waterfront, and then dined at Sabor da Índia (we recommend!).

Day Three

Not to be missed is one of the many levada walking tours. The island boasts 1,350 miles of walking trails that follow a network of levadas, or aqueducts, built into the mountain originally meant to bring water to drier parts of the island.

We chose the Caldeirao Verde levada walk with company Madeira Best to take us through the Laurisilva forest. It takes about 5 hours and can be done with or without a tour guide.

Check out our Caldeirao Verde Levada hiking page for more details.

The path was wide at first, bumpy from tree roots, but narrowed eventually to a stone ledge about 2 feet wide. To our left the silent levada stream flowed downhill as we went up.

Moisture dripped from the lichens and ferns covering the rocky mountainside. To our right, the mountainside dropped to steep heights. One by one we filed through the narrow tunnels, some longer than others, in the faint light of our cell phones. And then the views!

Midway, the trail opened up to the Green Cauldron, a canyon nourished by the tall, slim waterfall. We rested for about 30 minutes and backtracked the way we came.

At the end of the day, we snagged photos of the neighborhood we stayed in. It was the most beautiful, but precarious place.

Day Four

On our final day, we were in serious need of something lazy. In the morning, we parked at a ramp near the water and bought two tickets for the small cruise ship that swims to and from neighboring island, Porto Santo. This is where you go if you want to lay on a beach all day!

Check out our page about Porto Santo for more travel details.

In the name of honeymooning, we paid extra for first class tickets. First class was smaller with a complimentary buffet, bar service, and couches for seating.

The “tourist class” was much larger with multiple food options including a more formal dining area with movie theater style seating in the common areas. We would have been comfortable either way.

After docking at Porto Santo, you will have multiple options of getting to Vila Baleira, just 2 miles away; a great spot to start if you want to grab some food and walk down to the beach.

The quickest and easiest way to get here is by one of the many taxis that will be waiting for the boat to dock. This will cost you about €8. You could also walk (a little over an hour) or rent a bicycle.

From Vila Baleira, we walked down the Cais do Porto Santo pier before walking west down the beach and finding two chairs and an umbrella, right next to the O Corsario Beach Bar. Chairs and umbrellas are only for hire. We suggest reading the signs and sticking to that price, or the approaching man may upcharge you €7.

And there we sat, enjoying the sun, the waves, and cold gin and tonics from the bar nearby.

For dinner we ate at Restauração E Animação Turística, overlooking the beach.

As the afternoon grew long, we grabbed some ice cream and strolled along the sand, all the way back to the cruise ship. The walk takes about an hour from the Cais do Porto Santo pier, give or take, so keep this in mind when making it back to the boat on time!