An Unforgettable 5-Day Madeira Itinerary for First-timers

Madeira – a small island off the coast of Northwest Africa that closely resembles paradise – is becoming an increasingly popular destination for travelers all over the world.

Known for its lush, green mountains and quaint oceanside villages, Madeira is a spectacular island you MUST add to your travel bucket list!

With a mix of breathtaking landscapes, ranging from vibrant blue natural pools beside the roaring waves of the North Atlantic Ocean to the sharp, jagged peaks along the island’s best hiking trails, there’s a beautiful adventure waiting for all types of travelers in Madeira. 

In São Martinho, the sparkling ripples of ocean waves meeting the rough cliff sides are enough to draw in those seeking serenity – a quiet refuge for laid-back travelers hoping to escape the bustling scenes of everyday life. 

High above the capital city of Funchal, the jagged, awe-inspiring peaks along the PR1 trail (Pico do Areeiro to Pico Ruivo) invite those seeking adventure – a challenging journey for avid hikers and active travelers hoping to explore the rugged beauty of the island’s mountainous landscapes.

I was lucky to experience a fraction of the many landscapes and microclimates all over Madeira, and I am already planning for another island escape to this incredible Portuguese island! I loved every moment spent sunbathing along the cliffs of Funchal and exploring the northwest side of the island. Here’s my ultimate guide to Madeira to help you plan an unforgettable Madeira itinerary!

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Planning a Trip to Madeira

During the summer season, June – August, Madeira welcomes considerably more tourists than the shoulder- and off-seasons. I recommend visiting Madeira during the shoulder seasons, May and September, when the weather is still enjoyable and there are fewer tourists visiting during summer vacation.

Fall and winter are also a great time to visit Madeira if you are hoping to escape the cold in your hometown. As a Colorado girl well-acquainted with chilly, snowy winter days, I always look forward to a warm island getaway.

Fall and winter in Madeira still experience warm temperatures, however the island gets the most rainfall during the fall and winter seasons. If you plan on spending lots of time hiking in the mountainous regions of the island, I recommend visiting during spring or summer to enjoy rain-free outdoor activities.

Temperatures during the peak summer season usually soar to a high of 80°F, with evenings reaching an enjoyable 70°F. In the wintertime, the temperatures rarely fall below 60°F, oftentimes reaching a high of 70°F.

I visited Madeira in late August and I experienced a multitude of the island’s microclimates.

In the oceanside capital city of Funchal, sunny days are greeted with enjoyable temperatures, even in the “coldest” winter months. In the mountainous regions of the island, you can expect heavy fog, and cinematic rainfall during all seasons! It’s best to prepare for all kinds of weather when you visit Madeira, even if you plan to travel during the busy summer season!

I flew to Madeira directly from Lisbon and found this flight to be easy and enjoyable – only ninety minutes! Snag a window seat so you can enjoy birds-eye views of the incredible island!

Another way to visit Madeira is via cruise! Most cruises stop at the Port of Funchal and will usually dock for a few days, giving travelers time to explore the city of Funchal and venture around the island.

If you prefer to budget travel and are looking for affordable hostels or guesthouses, there are plenty of budget-friendly accommodations in Madeira. Seeking a lavish, luxury resort-style getaway? The capital city of Funchal has a variety of five-star resorts for lux travelers wanting a relaxing oceanside vacation.

I found the food prices to be very reasonable in Funchal. If you have the means to pay for fancy dining experiences like those offered at Il Gallo d’Oro restaurant, a lavish Michelin-star dining experience in the Cliff Bay Resort in Funchal, there’s a long list of incredible fine-dining restaurants in Funchal. 

On the other hand, local Portuguese restaurants often offer travelers affordable meals for as low as €20-30 for two people. Visit restaurant A Bica for an affordable, local-approved Portuguese restaurant in Funchal!

Tours and activities in Funchal and around the island were the most expensive purchases I made during my time in Madeira. There’s lots of incredible things to do in Madeira, so budget accordingly to make the most of your island adventure!

The island also offers travelers with a love for fantasy the chance to visit a UNESCO World Heritage “enchanted forest” called the Fanal Forest, which experiences mystical foggy conditions that closely embody fantasy landscapes straight from a novel.

Aside from the unique landscapes that draw adventurers from around the world, Madeira is also known for its wine — characterized by a distinctive fermentation process that includes a gentle heating step. This method was originally developed to replicate the conditions the wine experienced during long sea voyages when Madeira first began exporting it by ship. When you visit Madeira, make sure to taste the delectable Madeira wine!

When I visited Madeira, I chose not to rent a car. Instead, I booked a variety of guided tours of Madeira to explore the island with a professional guide. There are a number of day trips that start and end in Funchal, allowing travelers who stay in the capital city the chance to explore other parts of Madeira. 

I booked a 4X4 tour of northwest Madeira, and I found this activity to be an incredibly fun way to visit the beautiful towns along the Northwest coast. This guided adventure tour was the perfect way to explore Madeira’s Fanal Forest, the natural pools at Porto Moniz, and see the black sand beach of Seixal…without the need to rent a car. 

If you don’t plan on renting a car, I recommend booking guided activities to other parts of the island. Many local tour companies make pick-up and drop off as easy as possible!

If you would rather enjoy Madeira on your own pace with a rental car, I recommend booking your vehicle with Discover Cars – an affordable rental car booking platform that provides the best option for your budget!

Madeira History

Like most islands, Madeira was formed millions of years ago by a series of volcanic eruptions. It wasn’t until Portuguese navigator and explorer, João Gonçalves Zarco, discovered the nearby island of Porto Santo on an expedition originally destined for Western Africa in 1419, that the series of beautiful Portuguese islands were found. 

Under the service of Prince Henry the Navigator, João Gonçalves Zarco returned to the location a year later, soon discovering a nearby island, densely packed with lush green vegetation. Because of its abundant vegetation, the island was given its name, Madeira, which translates to “wood”. The trees scattered all over the island would eventually be used in Portuguese ship building. 

Upon its discovery, Prince Henry the Navigator divided the archipelago into three regions: Porto Santo, Eastern Madeira, and the area known today as Funchal, the capital city. 

The island’s rich biodiversity made Madeira a perfect place for growing grapes and sugarcane. The economy grew rapidly with the export of wine, sugarcane, and exotic island fruits. And with the economic growth, Madeira saw rapid urbanization of its capital city, Funchal. Many explorers stopped at Madeira as they traversed global trade routes, stocking up on the famous “Madeira wine”. 

Known as an island paradise, Madeira became one of the first popular tourist destinations in the 19th and 20th centuries, mostly visited by wealthy European aristocracy. Over sixty years after Portugal became a republic in 1910, the island gained its own autonomy, remaining an independent Portuguese colony. The growth of the island continued into the 21st century and Madeira has become a popular travel destination, known for its beautiful landscapes, lush mountains, and sapphire blue waters.

Top Things to Do in Madeira

There are so many incredible things to do in Funchal and around the island of Madeira, but the most memorable activity from my island adventure was a “rough-riding” 4X4 tour of Northwest Madeira!

I knew it would be an adventure when our guide picked us up in a bright green vehicle with the roof completely off! We explored the many beautiful landscapes of Northwest Madeira, including the UNESCO World Heritage Fanal Forest, a mystical fairytale escape to the foggy Laurel forest, the Porto Moniz natural pools, and the black sand beach of Seixal. 

There are a variety of other day trips to other parts of Madeira directly from Funchal, but the 4X4 tour of Northwest Madeira was my absolute favorite tour on the island!

Where to Stay in Madeira

Madeira’s capital city, Funchal, is a beautiful coastal landscape nestled among jungle-like green hills. Many people like to venture around the island, staying in hidden towns and quaint Portuguese villages, but for those who don’t rent a car (myself included), the archipelago’s capital city is a great place to stay for your trip to Madeira! 

Many tours around the island begin in Funchal, so even without a rental car, you can visit villages all over Madeira. With a plethora of activities including the Funchal Cable Car, the Monte Palace Botanical Garden, local markets, and breathtaking ocean views, Funchal is the place to stay!

For the first half of our island getaway, we stayed in Funchal Old Town, in a boutique hotel called Hotel Cajú. Funchal Old Town is the BEST place to stay in Madeira for first-time visitors.

With beautifully exposed stone walls and a delicious free breakfast (call ahead if you have limited time to eat!), Hotel Cajú is the best boutique hotel in Madeira. A fifteen minute walk from the farmer’s market, Mercado dos Lavradores, and the Funchal Cable Car, this centrally located hotel was perfect for its proximity to Funchal Old Town. 

After staying in Funchal Old Town for several days, we then decided to splurge on a two-night, five-star experience at The Cliff Bay Hotel.

Located west of Funchal Old Town in the resort part of the capital city (São Martinho), this luxury hotel was probably one of the nicest hotels I’ve ever stayed at! The Cliff Bay boasts an amazing buffet breakfast, afternoon tea experiences, the island’s top spa, and private beach access (definitely rent snorkel gear!). This hotel is the best five-star hotel in Madeira and will satisfy even the most opulent of travelers!

If you don’t plan on renting a car for your time in Madeira, I recommend finding accommodation in Funchal for the duration of your trip. Many tours allow guided access to all parts of the island without the need to book a rental!

Madeira Itinerary: How to Spend an Unforgettable 5 Days in Madeira

Day 1 – Explore the Historic Side of Funchal

Day 1 of your Madeira itinerary should be spent exploring the historic side of Funchal and its beautiful neighboring villages.

When I first arrived in Madeira, I was captivated by the contrast between the bright orange rooftops that dotted the capital and the vibrant sapphire waves of the North Atlantic. Funchal is a burst of color — with pastel houses scattered across lush green hillsides, all framed by the brilliant blue of the sea.

There are so many incredible things to do in Funchal, you’ll want to spend a whole day exploring the capital city before embarking on your next adventure around the island of Madeira.

Start your morning with a delectable Portuguese delicacy, pastéis de nata. This creamy custard tart that pairs well with espresso can be found in bakeries all over Funchal. One of my favorite places to get pastéis de nata is at Nata 7, a local Portuguese bakery that specializes in the mouth watering morning bite.

After breakfast, I recommend joining a guided tour of Funchal to learn more about the city’s unique history. This guided tour will take you all around Funchal Old Town, the historic city center where the settlement first began in the early 1400s. 

This guided tour will bring you to Funchal’s historic landmarks including the Sé Cathedral, one of the oldest structures in the city, and Mercado dos Lavradores, the local farmer’s market (a great place to get fresh exotic fruit!).

For a quick lunch in Funchal, I recommend stopping at Bela 5 Snack Bar, a local favorite serving up fresh fish and local cuisine for an affordable price. 

After lunch, catch the Funchal Cable Car up to the hillside town of Monte which offers travelers beautiful views of the city of Funchal and the ocean surrounding it. One of my favorite activities in Funchal was a visit to the Monte Palace Tropical Gardens which features over 100,000 plant species from all over the world.

If you’re a daring adventurer like I am, you’ll enjoy a ride on the Funchal Toboggan, a transportation tradition in Madeira where adventurers are whooshed down the hillside in wicker toboggans with the help of carreiros, a “toboggan guide”. This is a thrilling way to traverse the hillside if you’d rather take the road-less-taken! Otherwise, the Funchal Cable Car will get you back down to the historic old town. 

Once you’ve made it back to the city, it’s time to experience one of the many incredible things Madeira is known for…wine. At H.M. Borges Winery, located in the heart of the historic old town, you’ll have the chance to learn about the unique fermentation process that makes Madeira wine so noteworthy. Local Madeira wine makes for a great souvenir, if you have checked luggage!

By now you’re probably tipsy off the sweet island nectar and ready for some local Portuguese food. Head to A Bica restaurant in Funchal Old Town for affordable Portuguese dishes, local-approved! This restaurant was a recommendation from our tour guide on the Funchal walking tour and I really enjoyed the fresh fish and the large portions. 

If you have time after dinner to catch the sunset, Praia do Almirante Reis is a beautiful place to enjoy the setting sun after a long day exploring Madeira’s capital city!

Day 2 – Explore the Northwest Side of Madeira

Day 2 of your Madeira itinerary will have you exploring the mystical and magical landscapes of the northwest side of Madeira!

A guided 4X4 tour of the northwest side of the island (4X4 Enchanted Terraces tour) is a great way to explore other landscapes without needing to rent a car. This full-day tour was my absolute favorite activity we did while exploring Madeira!

Why choose northwest Madeira for a day trip and not anywhere else?

The northwest side of Madeira contains many of the mystical, fairytale landscapes including the famous Fanal Forest – a UNESCO World Heritage Site that features twisted, contorted laurel trees shrouded in fog. This is one of Madeira’s most incredible landscapes.

We also got to explore the black sand beach of Seixal and its neighboring natural pools (Poças das Lesmas) and dive into the chilly natural pools of Porto Moniz. 

Along the way, our tour guide stopped at several of Madeira’s incredible waterfalls allowing plenty of time for the group to get photos.

Is the 4X4 Enchanted Terraces tour family-friendly?

Yes – the 4X4 northwest Madeira island tour is family-friendly! Many of the local tours and day trips are kid-friendly. On my 4X4 tour I was surprised to see a couple with their young toddler enjoying the “rough riding” experience! It was a lot of fun and I highly recommend booking the guided tour for you and your family!

Day 3 – Hike to Madeira’s Tallest Peak

Day 3 of your Madeira itinerary should be spent making the difficult but rewarding trek to the top of Madeira – Pico Ruivo, Madeira’s tallest peak. 

Before I even set foot on the beautiful island of Madeira, I had already seen hundreds of videos of the “Stairway to Heaven” – a surreal stairwell ascending high above the island’s jagged peaks.

The mountain landscapes looked like something out of a dream. How could a place draped in vibrant green ridges and clouded by otherworldly fog actually exist — let alone be accessible for an avid hiker, like me, to climb?

It was the postcard landscapes – the ocean-meets-mountains photographs – that enticed me to visit Madeira. 

If you’re willing and able to explore the beautiful ridges of Madeira’s mountains, I highly recommend you trek along the PR1 trail to Madeira’s tallest peak, Pico Ruivo.

This challenging but rewarding ~10km hike to the top of Madeira features beautiful views of the mountains with the cerulean sea as a backdrop. 

Hiking from Pico do Areeiro, Madeira’s third tallest peak, to Pico Ruivo, Madeira’s tallest peak was a difficult adventure but SO WORTH the climb!

Day 4 – A Day of Relaxation in Madeira

After a long day of hiking to the top of Madeira’s tallest peak, you’ll want to spend day 4 of your Madeira itinerary relaxing!

The best way to catch up on relaxation is to enjoy the sounds of the waves lapping against the shoreline. If you’re staying in the São Martinho area, the resort side of Funchal, there are a variety of hotels with private ocean access. Otherwise, Funchal has a few great beaches – Praia Formosa and Praia do Almirante Reis – and a plethora of natural pools – Doca do Cavacas – for relaxation. 

Note: many of the beaches are pebble beaches, so don’t forget sandals or flip flops!

After spending several days in Funchal Old Town, I decided to splurge and move to an incredible five-star hotel in Funchal (The Cliff Bay Resort) to experience luxury relaxation and private beach access. 

If you’re staying at a luxury resort like the Cliff Bay Hotel, one of the BEST five-star hotels in Funchal, I highly recommend looking into the spa packages. I budgeted some extra money for a fancy couples massage with my boyfriend, and I thoroughly enjoyed the release of tension it gave me after hiking the day prior. 

In addition to the fancy hotel pools, many resorts in São Martinho offer guests the option to rent snorkeling gear. The Cliff Bay Hotel even has its own private dock for travelers who want to dive into the refreshing waters of the North Atlantic. Let day four of your Madeira itinerary be the time where you enjoy every amenity at your hotel or guesthouse!

If you want to take an afternoon lunch break, I also recommend enjoying afternoon tea at The Cliff Bay Resort or one of the other luxury resorts. There’s nothing quite like enjoying a cup of tea and some warm scones with an incredible view of the ocean!

To wrap up your ultimate day of relaxation, I recommend getting out on the water and enjoying a sunset cruise! The landscapes of Madeira can easily be seen by car or on foot. But why not enjoy the beautiful hillside city of Funchal by boat? A sunset cruise along the gorgeous island coastline is the perfect way to end a day of relaxation!

Day 5 – Choose Your Own Adventure

The final day of your Madeira 5 day itinerary is a choose-your-own-adventure day!

I love to include a you-pick option in all my itinerary recommendations with a choice of incredible activities for the type of traveler you are! If you want to explore more of the island, venturing towards the East side of Madeira, I have a great tour option for you! And if you want to spend that extra day soaking up the sun, there’s plenty of time for more relaxation!

Here are the best options for the final day in your Madeira itinerary:

If you loved your tour along the northwest side of Madeira as much as I did, you’ll probably want to explore the east side of Madeira as well!

A guided tour of the east side of Madeira will take you to incredible places like the easternmost part of the island, Ponta de São Lourenço, and the magnificent town of Santana, home of the “Santana houses”. This option is great for adventurous travelers who want to round out their exploration and see every part of Madeira.

Beyond the high-elevation peaks and mystical forests lie some of Madeira’s most incredible pathways.

Levadas, walking paths running parallel to the irrigation channels in Madeira, are the gems of Madeira – beautiful walkways through the awe-inspiring natural landscapes. The most popular levada walk is Levada das 25 Fontes (PR6), which is ~45-60 minutes from Funchal. This option is great for outdoorsy travelers who have access to a car (or are willing to hire a taxi!).

Enjoy the soothing sounds of crashing waves while you reminisce on an incredible island getaway in Madeira! This option is great for slow travelers who want an extra day to soak up the sun!

That concludes day five of your Madeira itinerary! I hope you have as much fun on the incredible Portuguese island as I did! Enjoy Madeira!