Perfect 2-Week Portugal Itinerary – Including a Wonderful Week in Madeira

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Last updated Jun 28, 2023

You would not know by the looks of it now, but Portugal once was Europe’s greatest power. Now it is a tiny country on the Iberian Peninsula bordering Spain on the east coast, with two paradise islands in the Atlantic Ocean: Azores and Madeira. This post is a perfect guide if looking for suggestions on a Portugal itinerary.

This itinerary includes a visit to Lisbon, Porto, Douro Valley (Portugal’s wine country), and beautiful Madeira Island. The 2-week Portugal itinerary includes exploring cities, enjoying Fado, hiking, tasting amazing wine, and celebrating New Year’s Eve on Madeira Island. One of the note-worthy celebrations.

This Portugal itinerary is good for

  • City explorers: Lisbon, Porto, and Funchal
  • Nature lovers & hikers
  • Scenic drivers
  • Food lovers
  • Wine lovers

2-Week Portugal Itinerary

Day 1: Arrive in Lisbon
Day 2: Lisbon
Day 3: Fly to Madeira
Day 4-7: Hike in Madeira
Day 8: Drive Around Madeira
Day 9: Funchal
Day 10: Fly Back to Mainland Portugal
Day 11: Porto
Day 12-13: Douro Valley
Day 14: Fly Back Home

Day 1: Arrive in Lisbon

Portugal Itinerary
Lisbon | Perfect 2-Week Portugal Itinerary

Hopefully, your flight is arriving in the morning or early afternoon, this gives you a chance to check in to your accommodations, take a nap if needed, and save the late afternoon and evening for exploring.

A good thing to do on your first day is to make your way to the Time Out Market where they have fresh and prepared food. You can try different Portuguese dishes and forget about the airplane food. From the Time Out Market, you can get on the metro and head to the Belém Tower to get the city views from the rooftop tower.

If Belém Tower is of no interest to you, you can head over to Santa Justa Elevator for a view of the city via Pink Street, Rua Cor-de-Rosa. Pink Street was painted to turn around the area’s reputation from the “Red Light District” into the effluent bar and nightclub scene which turned out to be a success.

Portugal Itinerary
Pink Street, Lison | Perfect 2-Week Portugal Itinerary

Another quick stop should be made at the oldest operating bookstore in the world, founded in 1732, Livraria Bertrand.

From the bookstore walk up to the Fernando Pessoa sculpture, a Portuguese poet, sitting in front of the Brasileira. Brasileira is a good spot to stop for a refreshment and people-watch.

We completed our day at Tasca do Chico, Fado club, munching on some Chourico Assado and Pasteis Bacalhau and drinking Vinho Verde while listening to Fado performance.

Portugal Itinerary
Chourico Assado | Perfect 2-Week Portugal Itinerary


Bairro Alto and Alfama neighborhoods are where most of the action is happening and the most convenient neighborhoods for tourists to stay at.

We rented an apartment in Bairro Alto with a splendid view of the São Jorge castle.

Day 2: Lisbon

Start the day off with breakfast/brunch at Manifest Lisbon – claimed by many as the best breakfast in Lisbon. After breakfast, especially on a clear day, make your way to the São Jorge Castle for 360° views of the city.

Portugal Itinerary
View from São Jorge Castle | Perfect 2-Week Portugal Itinerary

On your way to the castle, stroll through the São Cristóvão street, and if still hungry stop for delicious baked empanadas and Sagers mini at the Union Portugal. Right across from it is a historic old potted tree, you could not tell by the looks of it.

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Once at the castle, you can spend a couple of hours walking around, enjoying the garden, city views, history, and peacocks roaming around the property. The entrance fee to the castle is €10 per adult and buying online ahead of time is advisable.

Portugal itinerary

There are a lot of shops, cafes, and restaurants around the castle to buy souvenirs or enjoy some local specialties.

From the castle, make a stop at Miradouro do Recolhimento, where you can catch some live performers on your way to the Lisbon Cathedral.

Lisbon Cathedral is the oldest church in the city and has been destroyed and rebuilt after many earthquakes. It is not as grand as some other churches in major cities in Europe, but it does have quite a history.

Finish your day with another dinner and Fado show at the Clube de Fado or tiny Lisboa Tu & Eu with a traditional Portuguese fair.

Portugal Itinerary

Day 3: Fly to Madeira

Lisbon to Funchal flight is a little less than 2 hrs. long, however, delays and long flights can be expected due to unpredictable weather in Funchal for landing and take-off.

Once you arrive in Funchal, pick up a rental car as that is the best way to get around the island, and settle in your accommodations. You may have some daylight left for a walk by the water.

2-Week Portugal Itinerary
Funchal | Perfect 2-Week Portugal Itinerary

And maybe even luck out with one of Madeira’s epic sunsets.

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Celebrate your arrival to this beautiful island with dinner at Kampo where you can watch chef Julio Pereire prepare every dish in front of his customers. The food and wine were excellent.

Day 4-7: Hike Madeira

Madeira is a hiker’s wonderland. There are endless numbers of hikes to do on this island for every fitness ability.

The weather is going to play a crucial role in the hikes you decided to do on what day. Madeira has a lot of live webcams all over the island, so make sure you check them out to better understand the weather in the location you are going to.


This is one of the more popular and challenging hikes on the island. It is a hike from Pico do Arieiro at 5965 ft. down some stairs, valleys, and tunnels to Pico do Ruivo at elevation 6106 ft.

The wind and sun can be brutal. I would recommend a wind/waterproof jacket, plenty of sunscreen, and water.

Starting the hike as the sunrises offer magnificent views from Miradouro do Pico do Arieiro and a peaceful beginning to the hike as not that many people start the hike this early. However, the café and bathroom facilities will be closed that early.

2-Week Portugal Itinerary
Miradouro do Pico do Arieiro | Perfect 2-Week Portugal Itinerary

Starting Point: Miradouro do Pico do Arieiro Parking Lot – 30–40-minute drive from Funchal
Facilities: Cafes and restrooms are available at both Pico do Arieiro and Pico Ruivo. Restrooms are €0.50 for each use and may not be open early in the morning.
Difficulty: The trail is well maintained and most of the way has a safety cable around it. However, there are some very steep staircases, some stone some metal. There are multiple tunnels where headlamps are recommended. And the wind can be brutal. I would rate this hike as difficult.
Length: an 8.7-mile hike, out and back.
Elevation: 3250 ft.
Alternative Routes:
Option 1: To avoid the elevation gain with an out-and-back hike from peak to peak, you can take an alternative route Achada do Teixeira from Pico Ruivo that takes you to the parking lot from which you can call a cab to take you back to Miradouro do Pico do Arieiro. This shortens the hike to 6.0 miles.
Option 2: You can just hike out and back to Pico Ruivo from Achada do Teixeira parking lot. This is a 3.5-mile hike with minimal elevation gain, but still some amazing views.

TIP: If you decide to drive to Achada do Teixeira it is a great opportunity to drive through Ribeiro Frio Natural Park and stop at Balcões Viewpoint.

PONTA DE SAO LOURENÇO – out and back

This was our favorite hike as far as the views are concerned. The entire time you are surrounded by breathtaking views. However, the famous ‘Dragon Tail’ is a remarkably busy trail.

2-Week Portugal Itinerary
Dragon Tail, Madeira | Perfect 2-Week Portugal Itinerary

TIP: If you climb all the way to Pico do Furando you will be able to see Pico do Arieiro.

The trail is well-maintained, and you will come across many viewpoints of the steep cliffs, colorful rocks, and sea stacks.

Starting Point: Ponta de Sao Lourenço Parking Lot – a 35-minute drive from Funchal
Facilities: Food trucks are available in the parking lot. Sardinha café and restrooms are located at the end of the trail before the last climb to Pico do Furando. Restrooms are €1.00 for each use.
Difficulty: The trail is well maintained and most of the way has a safety cable around it. However, there are some steep sections. It is easy to moderate hike.
Length: a 5.0-mile hike, out and back.
Elevation: 1355 ft.


This is one of the most popular levada walks in Madeira. We saw tour guides taking large and small groups out for this hike and if you do not like crowds this would be one hike to skip. The waterfall and the weeping streams are beautiful, but you would not notice anything else much different on this hike than any other levada hike.

Portugal Itinerary
Waterfall at Levada das 25 Fontas | Perfect 2-Week Portugal Itinerary

There are two ways to start this hike either by parking at the Rabaçal parking lot and walking down the paved road to the Rabaçal house and starting the loop there. Or by parking off the road ER211 at Parque estacionamento levada do Risco and using a long dark tunnel to get to the levada.

We opted for the tunnel, and it was a nice and peaceful part of the hike.

Rabaçal house has food and refreshments as well as bathrooms, we stopped here for soup and beers at the end of the hike.

Starting Point: Rabaçal parking lot or Parque estacionamento levada do Risco – 45-minute drive from Funchal
Facilities: Cafe and restrooms available at Rabaçal house. Restrooms are €0.50 for each use and may not be open early in the morning.
Difficulty: The trail is well maintained and most of the way has a safety cable around it. However, there are some stairs and, in our case, a long tunnel where the headlamp is needed to see. It is easy to moderate hike.
Length: a 7.4-mile hike, loop.
Elevation: ~2000 ft.
Alternative Routes:
Option 1: If you are starting at the Rabaçal parking lot there is a shuttle you can take to the Rabaçal house and shorten the hike by 2.5 miles total.
Option 2: Add a short hike to Risco waterfalls which adds about 1.0 miles to the total distance.


PRO TIP: Levadas are irrigation channels or aqueducts created to supply island with water for agriculture. The construction of levadas started in 16th century and is unique to Madeira Island.

This hike is an effortless walk through lush vegetation and weeping walls to a tall waterfall – Caldeirão Verde. There are also 4 tunnels on this hike, 3 in the last 1-mile of the hike, and some of them are very long, dark, and low – recommend bringing a headlamp.

Besides a headlamp, it is a good idea to bring a poncho, waterproof jacket with a hood, or an umbrella with you as the weeping walls rain quite a bit on you as you walk under them.

Portugal Itinerary

You can add a hike to Caldeirão do Inferno to this route which adds another 2.5 miles total.

The path is very narrow in some areas, and it gets difficult when crossing paths with other hikers. We started this hike late in the afternoon and hardly came across anyone on our way back. I would recommend starting early in the morning or late in the afternoon to minimize encounters with other hikers.

Starting Point: Parque Florestal de Queimadas – a 45-minute drive from Funchal
Facilities: Cafe and restrooms available at the parking lot. Restrooms are €0.50 for each use.
Difficulty: The trail is well maintained and most of the way has a safety cable around it. It is an easy hike by the levada.
Length: a 7.7-mile hike, out and back.
Elevation: ~500 ft.
Alternative Routes:
Option 1: Instead of returning after reaching the waterfall, you can continue to the Caldeirão do Inferno, an additional 2.5-miles total.


Unfortunately, we ran out of time and good weather to do this hike, but it was on our list of hikes to do. It is a coastal hike, a cliff-side trail along the easter side of the island, from Machico to Porto da Cruz. From here you get stunning views of the Penha de Aquia, hill by the sea.

Portugal Itinerary

It is an 8.0-mile one-way hike. We recommend making your way to Porto da Cruz and taking a cab or Bolt back to Machico.

Starting Point: Vereda do Larano, limited parking in the neighborhood – a 30-minute drive from Funchal
Facilities: There is a Snack Bar at the start of the trail and many different restaurants in Porto da Cruz. However, we recommend A Pipa
Difficulty: It is an easy hike that starts in the levada.
Length: an 8.0-mile hike, one way.
Elevation: ~500 ft.
Alternative Routes:
Option 1: The first 3.0 miles of this hike are through the Levada do Caniçal and a lot of hikers find this boring. To avoid this, you can start in Porto da Cruz and just do Vereda do Larano portion out and back.

There are many other hikes to do here, these are just the ones that we enjoyed.

Day 8: Drive Around the Madeira Island

Driving around the island is the best way to see the island and requires having a car. Madeira is a tiny island, approximately 35 miles at the longest point and maximum width of 14 miles. The entire island can be driven in less than 4 hours. This makes driving around and stopping at different viewpoints a great thing to do for someone visiting an island.

While driving, you can see amazing waterfalls, mountain peaks, cliffs, and rock formations and experience different weather patterns.

TIP: Warning, driving in Madeira can be nerve-wracking. Majority of the roads are paved, but not all of them are wide enough for two-way traffic, and inclines and switchbacks can be very steep. Oh, and a lot of tunnels! Which I learned to appreciate since I cannot see the road drop-offs when in the tunnel 😊

Starting from Funchal, you can drive in either direction (clockwise or counterclockwise) around the island. I would dedicate a minimum of one full day to this or split it up into two days and tag on more attractions.

Below are some of the main attractions:

Pont Do Sol: Past the city center on road ER101 you will drive through an old tunnel and come across an old stone bridge off the main road, now a walking bridge that leads to an open arch. It is a great location to watch the sunset from.

Portugal Itinerary

Pont Do Sol: Cascata dos Anjos – waterfall cascading onto the road ER101 which people drive on to pass through town. Many people find this attraction cool to us it seemed more of a hazard with people not paying any attention to the passing cars just to get a photo.

Paul Do Mar: A quiet and secluded fishing village that attracts surfers from all over the world. The drive into the village down a steep road full of switchbacks can be nerve-wracking. The restaurants here serve some of the freshest seafood – an octopus salad at Restaurante Sol e Mar is to die for.

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Miradouro do Fio – on the western tip of the island, offers a viewpoint of the cliffs on the southwestern part of the island. There is a nice tea house next to the viewpoint if you would like to pop in for some tea and dessert.

Portugal Itinerary

Porto Moniz – is known for the lava pools that are popular with tourists and locals alike. A couple of miles down the road is a viewpoint for some unique rock formations in the water.

Portugal Itinerary

Miradouro do Véu da Noiva – is a viewpoint of a waterfall cascading into the ocean. Driving from this viewpoint to São Vicente you will continue to see waterfalls coming down every few hundred feet.

Portugal Itinerary

São Vicente – One of the main attractions in São Vicente is visiting caves on a guided tour. However, due to COVID-19, they are indefinitely closed. Instead, you can stop at Porto de Abrigo, an old traditional winehouse turned into a bar for some ponchas (traditional Madeiran cocktail) or Madeira wine.

Portugal Itinerary
Poncha | Perfect 2-Week Portugal Itinerary

Santana – between São Vicente and Santana there are many amazing viewpoints: Miradouro das Quebradas, de São Cristovão, da Santinha, da Beira da Quinta and many more you can pick from. In Santana, the site of the traditional tiny houses is what brings a lot of tourists in.

Portugal Itinerary
Tiny House, Santana | Perfect 2-Week Portugal Itinerary

Porto da Cruz – a popular town with surfers and hikers also has a sugar cane factory and the North Mill Distillery. East of the town is Penha d’Águia (Eagle’s Rock) one of the country’s geological symbols and a great hiking trail. A Pipa is a great place to stop for some food. You can skip stopping at Porto da Cruz if you are planning to do Verado do Larano hike.

Ponta de São Lourenço – a wonderful place to stop at if you are not planning to do the hike to the Pico do Furando. The views of the “dragon tail” are still good from here. However, if you are planning to hike out there skip this and head directly to Funchal.

Portugal Itinerary
Ponta de São Lourenço | PErfect 2-Week Portugal Itineray

If you would like to split this into a two-day adventure, make your way to São Vicente from Funchal and cross the island back to Funchal using road VE4. Then next day, head in the opposite direction back to São Vicente. You will not regret spending more time on the north side of the island. It is the quieter side of the island and more local, than touristy.

Day 9: Funchal

Funchal, the capital city of Madeira is worth exploring. It has a beautiful harbor, many historic sites, museums, and botanical gardens worth exploring.

Here is a list of some of the things to do in Funchal:

Take a Stroll by the Harbor – the waterfront area is beautiful and designed for walking. There may be a fair going on there, great for families. You will see a lot of docked boats there and this is where Whale and Dolphin Watching tours leave from.

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Explore the Old Town – Old Town is a lively place full of restaurants and shops. You will be hackled by many restaurants to have a seat at their place as you are walking by. We usually try to look for a place without such practices.

Check Out Madeira Farmer’s Market – the Mercado dos Lavradores is not a big market and is mostly visited for colorful and unique fruits, flowers, and tons of different chili peppers. Be aware that the prices can be unreasonably high, but you will probably try some fruit you never even heard of before.

Ride Teleférico do Funchal – Taking the cable car gives you a magnificent view of the town and the harbor. The ride from the Old Town to Monte takes about 20 minutes and there are a ton of things to do up there. The church Our Lady of Monte is at the top standing tall and looking over Funchal. You can also visit Monte Palace Tropical Garden, next to the cable car, or take another cable car to the Botanical Gardens of Madeira.

Portugal Itinerary

Take a Toboggan Sled Ride – When you are done exploring all the attractions at the Monte you can take a Wicker Toboggan Sled Ride, partway back. The toboggans are pushed and steered by two men dressed in traditional white costumes with straw hats. The ride is only 2 km down the road and the rest of the way back to town you either can get a cab or walk back.

Portugal Itinerary
Toboggan Sled Ride in Madeira | Perfect 2-Week Portugal Itinerary

Taste Madeira WineThe Blandy’s Wine Lodge is the most popular place to go for Madeira Wine Tasting and to learn about how the wine is made and aged. However, most restaurants will have Madeira Wine on the menu if you would just like to try some.

Visit CR7 Museum – If you are a Cristiano Ronaldo fan this is a must-stop.

Some of the restaurants we enjoyed in Funchal:

Basmati Indian & Nepali Restaurant
Restaurante Casal de Penha

Day 10: Fly back to Mainland Portugal

From Funchal you can either fly back to Lisbon or Porto, there are a couple of flights a day to each city. We decided to fly to Lisbon, rent a car and drive to the Douro Valley because we wanted to stop at Nazare and check out the waves. If you are visiting Portugal in winter, you may get lucky to see some massive waves in Nazare.

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Nazare Waves | Perfect 2-Week Portugal Itinerary

Either way, rent a car and position yourself to spend the next two days exploring Douro Wine Region and Porto before flying back home.

We stayed at Casa de Pousadouro in the Baião village. We were the only guest there in January and the staff could not be nicer to us. We just had a wonderful experience here.

Day 11: Porto

Porto took our breath away and right away we knew that one day here is not enough. But that was all we had and were able to hit some high points.

Here is a list of some of the things to do in Porto:

Explore the Riverfront from the South Bank – from the south bank of the Douro River, you get splendid views of the Porto’s stacked-up houses. From here you can visit a Port Factory, we visited Churchill’s, to taste some ports and learn about process making. You will also get a great glimpse of Dom Luis I Bridge, and from here you can take a funicular up to the Jardim de Morro.

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Porto | Perfect 2-Week Portugal Itinerary

Porto Cathedral – from the outside of the cathedral you get great views of the area that you just came from – the Port side of the town.

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Visit a Beautiful Bookstore Livraria Lello is a beautiful bookstore, but expect a line to get in.

Climb Torre de Clérigos – the tower is one of the most recognizable landmarks of Porto and you can climb it for a wonderful bird’s-eye view of the city. Just be ready to climb over 200 steps.

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São Bento Train Station – you may have arrived in the city by train, you can take a train from Douro Valley to Porto, and have already seen this beauty. But if you have not, it is worth checking out as it is covered with beautiful Portuguese azulejos.

We finished our day with dinner at Taberna Dos Mercadores, a tiny family-owned restaurant with delicious local specialties.

Day 12-13: Winery Visits in Douro Valley

Douro Valley may be the oldest demarcated wine region in the world, but it is only recently that visitors have started exploring it and making a point to visit some wineries. For years, Port factories would offer river cruises to their visitors to take them directly to the wineries that they own while the rest of the winemakers felt bypassed and forgotten.

Luckily, in the recent past visitors have caught on to the quality of Douro wine and started visiting wineries on their own. This has energized some of the younger generations to get into the wine/port-making business.

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Douro Valley | Perfect 2-Week Portugal Itinerary

Douro Valley is like no other wine region we have visited, it is very steep and takes a lot of manual labor to work the land. And driving through the region can either be an overly exciting experience or the scariest thing you have done, depending on what side of the driving spectrum you are.

Wineries to Visit:

Quinta Do Crasto – this is one of the few Portuguese wines we can find in our local wine store and have enjoyed it very much. We were worried that this would be a big production, but it was a very informative tour and tasting for just the two of us.

Portugal Itinerary
Quinta de Crasto Winery | Perfect 2-Week Portugal Itinerary

Gueda Wines – Even though the land has been in the family for 36 generations, a brother and sister just started making delicious wine, port, and olive oil recently. The tour starts as a self-guided walk through the vineyards and the private tasting with an assortment of cheeses and meats. Make sure you ask about the chickens!

Portugal Itinerary

Quinta Seara D’Ordens – Another small family-owned winery with an excellent mix of whites, reds, and Ports. You can book a Jeep Tour of the estate and wine tasting after for some amazing views of the region.

Quinta de Marrcoso – if you are looking for a superior quality port from a small family-owned business, you will find it at Quinta de Marrcoso.

Some other delicious gems that you will find in this region are olives, olive oil, walnuts, and the most delicious almonds.

Restaurants in the Area to Try Out:
Restaurante da Lama
Restaurante Pena
Restaurante Primavera

Restaurante O Alpendre
Restaurante Limonete

Day 14: Fly Back Home

Both Porto and Lisbon have international flights, but it would be more convenient if you can fly out of Porto because of your current location. We flew out of Lisbon and truly regretted that decision by this point in the trip.

Additional Suggestion For Portugal Itinerary

For explorers that are not as crazy about wine as we are, you can skip a visit to Douro Valley (even though the region is stunning wine or no wine) you can explore the Peneda-Gerês National Park, north of Porto where you can find hiking trails, wildlife, villages with medieval castles, and stone granaries.

If you are interested in visiting both Lisbon and Porto I would suggest flying into one city and flying out of the other to minimize driving.

Portugal is one of the most welcoming countries we visited and wherever you go you will feel welcome. While here try to immerse yourself into the culture and appreciate the beauty you are surrounded with and if you skip a few things and do not get to see everything you wanted, that is ok. There is always a next time.

Other helpful posts…
Things to Know About Madeira Island
One Perfect Day in Châteauneuf-du-Pape – The Village And The Wine
Self-guided Walking Tour of Nice
Italy, Slovenia and Croatia – 15-Day Adventure Filled Itinerary
Tips for Renting a Car in Europe




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