Itinerary: Our magical 5-day Madeira Island road trip

Life on much of Madeira is a battle between man and nature. Moments from the coastline, sharp, jagged mountains rise out of the earth covered in thick, green foliage that few manage to tame. A scattering of typical Portuguese houses with terracotta roofs dot the ridges and valleys. We catch but a glimpse as we shoot in and out of small tunnels along a smooth, fast road. Wafts of mountain mist rise and fall, fighting for space with thick and humid sea air. 

We’d just picked up the rental car and were making the short drive from the airport to a small seaside village by the name of Porto da Cruz. That’s all the time it took to feel the magic of Madeira.

Madeira Island itinerary & road trip overview

I’m based in Lisbon and there are plenty of daily flights to Madeira. I’ve visited the Portuguese archipelago a few ties now, and spent more than two weeks on the island.

I’ve designed this trip as a self-drive Madeira itinerary, but there are lots of reasonably priced guided day trips from Funchal or transfers to the start of popular hikes. I’ll include some in the mini guide below.

How long to spend on Madeira Island?

When deciding how long to spend on Madeira, I’d suggest at a minimum three days. You could easily entertain yourself for weeks – particularly if you love hiking – but I think five days is the ideal length for a real taste of Madeira. With five days you’ll tick off the main sights and have time for a couple of half-day hikes.

If you’re a keen hiker you might like to extend another day or two to include more magical hikes through the ancient laurisilva forest.

What’s unique about this 5-day Madeira Island itinerary?

This trip splits the island, starting on the east coast, dropping into Funchal and finishing on the west. If you prefer one base, you can stay in Funchal or somewhere central and day trip around the island. Nothing is more than an hour drive away at any time.

If you’re a return reader to my Portugal travel blog, you’ll know I’m a food and culture-focused traveller based in Lisbon – so while this Madeira Island itinerary contains some spectacular half-day hikes, it’s not purely focused on adventure (like some others I’ve seen). I research in both English and Portuguese to find the best tips and restaurants to try.

What if I don’t want to rent a car?

I highly recommend renting a car for Madeira. But if I didn’t have a car, I would definitely stay in the capital Funchal. There is lots happening in the small city, plus it’s the perfect base for guided small-group day trips.

Accommodation on Madeira Island

Madeira Island is small enough that it’s easy to base yourself in one place, yet there’s enough to do to entertain you for weeks. I’ve stayed in four different towns or locations on Madeira Island, and this itinerary splits your time across two smaller destinations.

• Favourite stay: Casas da Levada – I’ll dream about this spot forever. Restored houses that sleep 2-9 people. With an infinity pool and a Hobbit-themed honesty bar. I can’t wait to return.
• Budget stay: Jaca Hostel – convenient and chic spot in Funchal with budget double rooms or shared bunks.

What would I do differently? Things to do consider when planning your Madeira trip

• I hadn’t grasped how touristic Madeira was before visiting. If you like your peace and quiet, and dislike large coaches of tourists, then wake up early and beat the crowds to popular hikes.
• Another tip is to check the cruise ship schedule – if a ship is docked, Funchal will be rammed. On the second visit we missed the Monte basket ride one day due to crowds.
• I’d spend less time in Funchal (and more time at Talho do Caniço – two visits were not enough, more on that down further). Funchal is a great small city, but for me Madeira is about the nature.
• Choose your hikes carefully – consider your ability and preferences. The Ponta de São Lourenço coastal hike is very cool, but I love deep, dense forests so the Levada do Caldeirão Verde hike was more my jam.

➼ Wish someone could shortcut your Madeira or Portugal research? ➼ Talk to me – I offer 1:1 video calls to help people cut through the noise and plan a perfect Portugal itinerary. Find out more here.

Madeira Island road trip itinerary

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Day 1: North-east Madeira Island: Porto da Cruz, Santana & Balcões or Caldeirão Verde

42.5km \\ 75 minutes driving

Guided tour option: Best of the East

Let’s assume you fly in early (or the night before like we did), pick up a rental car and hit the road to Porto da Cruz, a magnificent coastal village with a buzzing, youthful vibe.

We were hoping to snag a private room at the Jaca Hostel there but settled for a room at Hotel Bela Vila, which had the bonus of breakfast by the seafront each morning. Check out the view from our room below! Surreal. Next time, I hope to stay at Hotel Quinta Do Furao – a 4-star spot where the pool is set within a clifftop vineyard.

Morning: Go for a hike – choose from Vereda dos Balcões or Levada do Caldeirão Verde.

Madeira Island is all about the nature and hiking, so don’t forget to pack good sneakers or hiking boots. Personally, I’m a novice hiker. I have no idea and none of the gear, but I do love setting off for half-day hikes. I can highly recommend two hikes over in the northwest of the island:

Option 1: Vereda dos Balcões, one of the easiest and most rewarding walks on Madeira. Perhaps even better than the easy, 20-minute Vereda dos Balcões walk is the drive out there – winding road around steep mountainside covered with dense, lush forest. Stunning and worth squeezing in. I’ve done this twice – it was very very busy in the morning, but quieter in the afternoon. Either way, it’s just a short 1.5km trail and reach the lookout. If you’re luckier than us you’ll actually see the view over a deep valley (instead of being inside a thick cloud).

Tip: If the lookout is packed, don’t panic – just wait for people to leave so you can appreciate the serenity and beauty of Madeira.

Option 2: PR9 Levada do Caldeirão Verde. Of the four hikes I’ve done on Madeira Island, this one is my favourite. This half-day out-and-back trail starts like a fairytale in Parque Florestal das Queimadas, where you’ll feel like you’ve stepped into Hansel & Gretel. You’ll follow the levada stream into the Laurissilva forest, through lush oak trees, past verdant ferns, and pass through four tunnels. If you plan for this option, set off early to beat the crowds. Arriving around 8am or 8.30am should be sufficient.

Read next… The 4 best hikes (that I’ve done) on Madeira Island

Afternoon: traditional Santana houses and the rum factory

For first-time visitors to Madeira, you can’t skip Santana – unless you can resist the charms of those little 16th-century-style traditional houses with thatched roofs?

For lunch, Cantinho da Serra is a recommendation that came via a local. The sopa de tomate e cebola (tomato and onion soup) and the octopus, which came out bubbling from the oven with potatoes, are both fantastic (read about more traditional Madeiran dishes here). Maybe the best octopus of my Portuguese life – definitely order this dish.

Do a quick round of the Santana tourist houses – snapping cheesy pictures – then return to Porto da Cruz. 

You can visit all year round, but between March and May, the Porto da Cruz rum factory is buzzing with burly men and the sound of 19th-century steam pistons, firing at full speed to churn through the fresh sugar cane arriving by the truckload. At Engenhos do Norte they make agricola rum, which means rum from fresh sugar cane juice.

It turns out this method is actually rather rare as most rum is made from sugar-cane molasses or evaporated sugar (from cane or beets). If you’re using fresh cane juice to make rum, you have to start the fermentation within a day or it spoils like milk – meaning it has to be produced near the source. It’s free to wander about the factory.

Before or after you can pop into the bar to sample the six-year-old aged rum, and order a poncha of your choice. They had all four main poncha flavours – fisherman’s lemon (pescador), passionfruit, tangerine and orange-lemon (regional).

Read next… 8 best poncha bars on Madeira Island

For dinner, try Pipa or Praça Velha in Porto da Cruz.

Where to stay: Porto da Cruz (or, if easier, Funchal)

• We stayed: budget and beachfront Hotel Bela Vila
• Dream stay: Hotel Quinta Do Furao – 4-star with pool set within a clifftop vineyard
• Chic hostel: Jaca Hostel – Friday is social pizza night
• Guesthouse: Casa da Tia Clementina – has a Santana house on the property

Sunday market: If you happen to be in Madeira on a Sunday, try to squeeze in a visit to the Santo da Serra Farmers Market. This local mercado is a great place to try Madeiran specialities you won’t find on menus and see what produce is really in season. Read more about it: Sunday in Madeira at the Santo da Serra Farmers Market

Day 2: Ponta de São Lourenço Hike + Funchal

57km \\ 1 hour driving

Morning: Half-day Ponta de São Lourenço hike

Today’s hike is in stark contrast to the lush laurisilva forest of yesterday. At Ponta de São Lourenço the semi-arid climate and strong north winds mean there are no trees and only low vegetation. For this reason, it’s best to leave the house early to beat the crowds and the sunshine.

This two-to-three-hour hike that explores the rugged basalt and limestone cliffs of a long, thin peninsula is not one to do in the midday sun. Trek out past magnificent coastal and cliff scenery to the cafe and bar at the end, or enjoy a swim at Sardinha Port beach.

In spring it was a gorgeous walk with coastal wildflowers of all varieties covering the ground. You’ll be able to see the Ilhas Desertas (Deserted Islands) and Madeira’s other inhabited island, Porto Santo.

Need a transfer to the start point? This top-rated driver will get you there.

Afternoon: Talho do Caniço (best espetadas!) and Funchal

For lunch, head to my favourite place on the island. The super casual Talho do Caniço is a super local experience that was so nice we went twice during the first trip. I’ve detailed the spot in my Where to Eat in Madeira guide and my partner Jorge wrote a short love-letter about the place – but essentially it’s a butcher shop with a DIY barbecue around the back.

Pick your meat, take your skewers to a table then grill while munching on bread and red wine for less than €14 each. It’s communal, it’s fun! Alternatively, you could try seaside MaréAlta for fish, shellfish and other seafood dishes.

Then drive on over to the capital of Madeira, the small city of Funchal. There’s so much to do here, so I’ll list loads of ideas below. Make a choice then tick off most of what you want in just one day. 

Things to do in downtown Funchal:

• Visit the famous Market – Mercado dos Lavradores (best on Saturdays, but good all other days!)
• Explore the Sé Cathedral (climb onto the roof!)
• Wander down the open-air gallery that is Rua Santa Catarina, where all the doors are painted
• Join a dolphin and whale watching cruise and see Madeira from the water
• Go scuba diving in the ocean
• Join a food and drink tour of Funchal to learn about local dishes and drinks
• Do a Madeira wine lodge tour at Blandy’s, pictured below 
• Drop in for a free Madeira wine tasting at D’Oliveira
• Dive into the ocean at Fort São Tiago, a small beach by a historic fort
• Climb the tower of the Igreja de São João Evangelista
• See the local embroidery at Bordal
• Learn about the islands at Madeira Story Centre

For sunset, I’d roll around to Barreirinha Bar Café. Set right on the ocean’s edge, this cool but casual cocktail bar has a great terrace that overlooks the bathing complex. Come earlier and have a swim if that’s your style. Order any drink with passionfruit, because #madeira. I loved the one I had with passionfruit and fortified Madeira wine.

For dinner, swing into Taberna do Ruel on the famous Rua Santa Catarina. I didn’t have high hopes given the central location but this recommendation from a local didn’t steer us wrong. The peixe espada preto here (black scabbardfish) with banana and sweet potato was fantastic. Alternatively, try Fugacidade beer bar for casual snacks and crafty brews.

Read next… What to eat in Madeira

STAY: Funchal (or squeeze tomorrow morning’s activities into today and stay three nights in the west)

Where to stay in Funchal

Funchal is a small city, so you can choose to stay in the historic centre, or to the west of the city the area of São Martinho is a popular spot with large hotels that offer more resort-style facilities.

• Dream stay: Reid’s Palace, A Belmond Hotel – 5-star luxury historic clifftop hotel in São Martinho, set within 10 acres of subtropical gardens with 3 pools and ocean access.
• Old town: Three House Hotel – 4-star stay next to Funchal’s historic centre with a rooftop pool.
• Cool hotel: NEXT Savoy Signature – this 4-star spot has a very cool pool lounge in São Martinho.
• Guesthouse: Vila Vicência – historic house with a lush garden and pool.

Day 3: Carreiros do Monte + Southwest Madeira Island (Madalena do Mar)

48km \\ 1 hour driving

Morning: basket toboggan time in Monte, above Funchal

Picture yourself careering down the steep streets of Funchal in a giant wicker basket while two men dressed in white with cute boater hats steer with their huge rubber boots. Combining thrills and artisanal basketry, obviously this was the number one thing I wanted to do on Madeira Island.

The Carreiros do Monte is one of the oldest forms of public transport on the mountain. You’ll find them lined up in Monte, high above the city waiting for guests. 

To get up there we caught the (expensive) cable car from downtown Funchal. While the views were nice, you could save your €14.50 each (€20 return) and get the bus or a cab – or drive up yourself (look for carparks on Google Maps, and take care of the very steep streets).

It took 15-20 minutes to reach the top of Monte, where we stopped for a brilliant flat white with lush mountain views at Local Shop Coffee before heading over to meet the carreiros.

There’s actually loads to do in the hilltop neighbourhood of Monte. You could wander the Monte Palace Gardens before flinging yourself down the mountain roads.

Afternoon: Slow drive to the west, with lunch at Madalena do Mar

For lunch, cruise over to the sweet banana town of Madalena do Mar and eat a fish stew (fragateira) at A Poita. Madalena do Mar is one of my favourite little villages on Madeira Island. There seems to be 100 times more banana trees than houses squished onto a small, semi-flat patch of land between the mountains and the sea.

If you don’t go to A Poita for lunch, try Casa de Pedra for apparently the best lapas (grilled limpets). After, you can follow a short and easy trail around the banana plantations

Read next: Where to eat and drink in Madeira

I’m a big believer in having fast days and slow days on your vacation, so use this afternoon to take it easy. You could visit the town of Ponta do Sol for a swim – famously it’s always sunny here while the rest of the island is under cloud. Or stop for an afternoon coffee and slice of apple pie at XS Coffee in Prazeres, the last place I expected to find locally roasted specialty coffee. Nearby you can visit Quinta Pedagógica dos Prazeres, a cool farm project.

Where to stay: Casas da Levada, an all-time favourite stay.

Casas da Levada is an absolute wonderland. The family who owns it restored the estate, renovating old stone buildings and adding a couple more to make half a dozen cute stays that sleep 2-9 people. The garden is magnificent, filled with fruit trees and exotic species. There are sheep, chicken, rabbits and chirping frogs.

The infinity pool overlooks the sea, resulting in endless blue vistas. The Hobbit Bar is the best honesty bar I’ve ever seen, with cocktail supplies, an ice machine, music, games, and a wall of booze to choose from.

If you’re lucky enough to find availability here during your time on Madeira Island, leave time to enjoy the estate, tan by the pool, pat the cats, and wander the gardens. #NotSponsored (but please, invite me back!).

➡️ Book a stay at Casas da Levada

Day 4: Northwest Madeira: Fanal, Seixal + Porto Moniz

84km \\ 2 hours driving split across the day

Morning: Chase the fog at Fanal Forest

The plan was to arrive early to see the magical Fanal forest enveloped in a blanket of mist. Problems with our rental car’s brakes (not something you want on this steep island) meant we didn’t arrive until midday, finding fields of beautiful gnarly trees under a clear blue sky. At first I was disappointed with the still ridiculously beautiful sight, but then out of nowhere the cloud rose up around us.

Soon enough we were standing in fog so thick we couldn’t see more than 10m in front. This made it tricky to find the car again! There is a long Fanal hiking trail you can follow if you’re an eager hiker – but if you just park at this point you’ll find where the patch of magical trees are. If you need inspiration for a fantasy novel or don’t believe in fairies, come here and feel inspired.

Afternoon: Visit Europe’s third most beautiful beach, Seixal

On the drive down the mountain to Seixal, stop and admire the views at Miradouro da Ribeira da Janela before reaching the town. Praia do Seixal was voted Europe’s third best beach in 2022, but it’s not what you’d expect. A wide black sand beach with a small waterfall, protected by a port wall on one side and framed by rainforest that appears to all but cascade into the ocean, it’s a special spot for sure.

Before laying out on the sand we dropped into the seafront Clube Naval de Seixal for a relaxed lunch. We ate a sandwich of marinated octopus jammed between bolo de caco and shared the best lapas (grilled limpets) we had on this trip. Super good.

If you’re not a fan of beaches, maybe a wine tasting at Quinta do Babusano is more your vibe, or continue westward to the pools of Porto Moniz. While I’d dreamed of visiting the Piscinas do Porto Moniz, it didn’t quite have the charm I’d seen in pictures. What I hadn’t heard of was the Piscinas Velhas (old pools) next door, which were not only free to enter but spectacular. Both pools are set within lava flows, but while the new one is more shiny concrete than dark, rough volcanic rock, the old ones feel more natural (pictured below).

You could structure this afternoon differently – head to Porto Moniz first, then Seixal and drive back to the southern part of the island via Serra de Agua, where the famous Taberna da Poncha is a must-stop.

STAY: Casas da Levada

➼ Wish someone could shortcut your Portugal research? ➼ Talk to me – I offer 1:1 video calls to help people cut through the noise and plan a perfect Portugal itinerary. Find out more here.

Day 5: 25 Fontes hike + Câmara de Lobos or Curral das Freiras

90km \\ 2 hours driving split across the day

Morning: 25 Fontes hike

One of my favourite things we did on Madeira Island was the lush Levada das 25 Fontes hike. One of the most famous hikes on the island, we realised this trail would get super busy so we arrived at the trailhead a little after 8am to tackle the three-to-four hour hike. Boy, I’m glad we did. I was disappointed to see a dozen cars there already but while passing huge tour groups and loads of tourists on the return part of the hike I was glad we went early.

The hike itself is magnificent. You drop into a valley and wander through the vibrant green laurisilva forest, following a levada along most of the way. A levada is essentially a little canal of water that the early inhabitants of Madeira built some 500 years ago to funnel water from the mountains to where they needed it. They are all over the island with accompanying hikes.

At the end of the hike you reach a brilliant blue pool with one great waterfall and 25 or so little waterfalls gushing into it. We took some photos and sat here for quite a while, which meant watching the end point fill up as hikers arrived en masse. The return trip was trickier as the levada is very skinny in some parts, making passing difficult, so I really truly recommend going early to get the best experience.

Read next… The 4 best hikes (that I’ve done) on Madeira Island

Afternoon: Câmara de Lobos and/or Curral das Freiras

For lunch, you could drop into the town of Câmara de Lobos, just outside Funchal. The colorful fishing village is famous for its espetadas (meat skewers) and you can taste them at: Santo António, Viola, O Polar or As Vides, just above the town. Or in the historic village, I loved a restaurant called Gavião do Ilhéu that has a great range of local seafood.

If you have the time, drive 25 minutes into to Curral das Freitas, a remote inland village set within a valley. Legend has it that nuns ran in here to hide from invading pirates. Aim first for the Miradouro da Eira do Serrado, where you’ll gain a view over the secluded valley. Then head into town for coffee and chestnut cakes, the local specialty.

If you have less time before your afternoon flight, make your way to A Venda do André for excellent poncha at this vintage spot. I loved going here. Or you could try Os Castrinhos.

And if you’re killing time – you could venture back to Talho do Caniço – as we did. A place so nice we went twice! With an 8.30pm flight we need something to eat, and few places do non-stop service through the afternoon. We went for 5.30pm espetadas, which FYI I believe is considered a late lunch not an early dinner. As expected, it was brilliant and a high note to end our trip on.

Planning a trip to Madeira? Read Where to Eat on Madeira Island and What to eat and drink on Madeira.

Keep reading…

• Ultimate guide to exploring Madeira Island
• It’s worth a flight to Madeira just to eat these espetadas
• The 4 best hikes (that I’ve done) on Madeira Island
• Sunday in Madeira at the Santo da Serra Farmers Market
• What to eat and drink in Madeira: the best local dishes to try
• Where to eat and drink in Madeira
• 8 best poncha bars on Madeira Island
• Best medieval and historic events in Portugal
• Food Festival Guide: Best Gastronomic Events in Portugal