The Famous Red Tiled Roofs In Portugal scaled

The Perfect Portugal Itinerary: A 2-Week Road Trip

Having just finished our first-ever Transatlantic cruise, we are following up this eastward passage with a two-week road trip through Portugal. In a daring move, we scheduled our flight from Rome’s Fiumicino Airport to Lisbon at 12:05 pm the day we made port in Civitavecchia.

Luck is on our side; we make our noon flight. I soon find myself peering out the plane window as we fly over the Ponte 25 de Abril. I can’t help but wonder why a bridge that looks just like my hometown’s Golden Gate is in Lisbon. I take this as a good omen and feel we are at the start of the perfect Portugal itinerary.

Perfect Portugal Itinerary - A Photo of Ponte 25 de Abril in Lisbon

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First, a quick note for our readers. Please use the Table of Contents. There is a lot to write about a two-week trip to Portugal. And this is a long post. But, You don’t have to read this post in chronological order. Feel free to jump around, even leave, and then come back. Focus on the best places for what interests you the most.

This was the perfect Portugal itinerary for us because we were not in a rush. You can see a lot of Portugal in less than two weeks. Even with a car and a road trip, there were parts of the country we did not see. At the end of this post, I will discuss how you can shorten your journey or choose alternate regions to visit. After all, the best part of travel is making it your own.

Day 1: Arriving in Lisbon For The Start Of Our Portugal Itinerary

Airport Pick Up And Drive To Heritage Avenida da Liberdade

We know nothing about Portugal. This is our introductory trip. So In a change of pace for us, we used Portugal Trails to assist us with planning our Portugal Itinerary and some of the bookings for our 2-week road trip through the country.

Portugal Trails assists travelers in putting together a self-guided itinerary tailored to the locations they wish to see. They give you a personalized road book and pre-programmed GPS unit for your trip, so you’ll never get lost. The best part is the driver who meets you at the airport with your welcome package and transports you to your first destination, in our case, a lovely hotel in the heart of Lisbon.

The Heritage Avenida da Liberdade: Home For The Next 5 Nights

The Heritage Avenida da Liberdade is a quaint boutique hotel in the Principe Real district. This area is conveniently adjacent to Bairro Alto and the Alfama, the two communities with the most history in Lisbon. This is a fantastic central location for your visit to Lisbon.

A Photo of the Heritage Avenida da Liberdade Bar/Breakfast Room
Hotel Lobby also serves as the location for breakfast each morning and coffee or tea time throughout the day.

After unpacking and freshening up, we head out to explore our surroundings.

Walking The Neighborhood Around Our Hotel

This evening, we decided to walk around the neighborhood close to our hotel. Rua das Portas de Santo Antao, a primarily pedestrian street lined with shops and restaurants, is one block behind our hotel, making for a leisurely stroll.

A building in Lisbon covered with the famous Azulejo Tiles

We reach the end of the avenue on the north edge of Rossio Square next to the Teatro Nacional. This is where my DH recognizes the shops where Anthony Bourdain and Phil Rosenthal (at separate times) stopped to have a quick shot of Ginjinha (sour cherry liqueur). Well, in Bourdain’s case, I think he closed down the shop.

Purchase your shot of Ginjinha (costs about €1.20) and either right there in the store or out at the table; shoot it down!

Day 2: The First Day Of Our Perfect Portugal Itinerary – A Walking Tour of Lisbon

Best Ways To Get Around Lisbon

In Lisbon, you can pick up a Viva Viagem card for use on public transport. The card is €0.50; you then load the amount you think you will use onto the card. A day pass costs between €6.40 and €9.50. The higher price includes the ferries.

However, in Lisbon, we have been using Uber and walking as our means of transportation. Ubers are abundant and inexpensive. The average ride cost for the two of us has been around €5.00. Additionally, we took this trip in 2022, and the world is still fighting Covid. No need to push our luck.

3-Hour Guided Walking Tour Of Lisbon

This morning we have a guided walking tour of Lisbon that we booked through ToursByLocals. We like to take guided tours when we first get to a city to get a good orientation from a local guide. Our guide today is Adriana, and she does not disappoint.

Note that I say this is a walking tour. Bring good walking shoes. Lisbon is built on many hills. Additionally, the whole country has cobblestone streets and sidewalks made from limestone (white) and basalt (black). If wet, the stones can be slick and, even when dry, may cause visual confusion.

A picture of a cobblestone street in Lisbon Portugal

I always recommend Skechers for a comfortable walking shoe that is reasonably priced. These slip-on style shoes are perfect for going through TSA at the airport too!

Skechers - Gray Slip On Walking Shoe

When all is said and done, we walk over six miles, according to my iWatch. Here are some of our favorite sites

Church of St Dominic – Igreja Sao Domingos

Igreja Sao Domingos was consecrated in 1241. Known today for its fire-scorched walls survived many disasters in its long life.

Getting To And Seeing The Great Views of Lisbon From Castelo de Sao Jorge

Castelo de Sao Jorge usually involves walking up steep streets or riding the historic Tram “Miradouro Santa Luzia” (Tram Line 28). Unfortunately, this line is so popular with tourists you can wait for over an hour in long lines to get on a tram.

But Adriana has some great secrets for getting around the steep hills of Lisbon. With a short walk to her favorite elevators, we are up the hills and at the park in no time. The views are worth the climb, whichever way you go.

Walking Down The Steep Hills Of The Alfama

The Alfama is the oldest district in Lisbon. Here the homes are close together, usually with business on the bottom floor. There aren’t a lot of cars, and most of the area is left to pedestrians. The walkways are generally quite steep steps.

Visiting The Oldest Operating Bookstore In The World

Did you know Lisbon is home to the oldest continuously operating bookstore in the world? Livraria Bertrand is located in the Chiado district and has served customers since 1732. The shop is beautiful.

A Book Display at Livraria Bertrand

See The Views From The Santa Justa Lift

The Santa Justa Lift in Bairro Alto is another spot in Lisbon that affords you great views of the City. Built in 1902, the elevator was a way for people to get from the relatively low street of Rua Aurea up to Rua do Carmo avoiding more steep hills.

Lago do Carmo The Square The Location Of The Carnation Revolution

This is the square where the famous Carnation Revolution took place on April 25, 1974, marking the end of the dictatorship of the Estado Novo regime and Marcello Caetano.

the square at the Convento and Igreja do Carmo in Chiado
The square at the Convento and Igreja do Carmo in Chiado in the City of Lisbon in Portugal.

I like this story of a peaceful revolution, but there is more to it. If you are interested in history, read up on the reasons for this conflict here on Wikipedia.

Ending The Walk Full Of New Information And More Curious Than Ever

We head for our hotel and have a light snack in the hotel reception coffee, cookies, and nuts. Reviewing all we saw today makes us eager and curious to see Lisbon more. This afternoon is for rest to get ready for the Fado Dinner tonight. Fado dinners start late, generally not before 8:00 pm, and go long. It will be a late night.

Fado Dinner In The Alfama

Fado (which translates to destiny or fate) is a music genre unique to Portugal. Generally characterized as mournful tunes that employ “Dorian” or “Ionian” modes and lyrics that tell stories of the sea, fate, and longing. The Fado in Lisbon is likely to differ from the Fado you hear from other parts of Portugal as each region puts its own spin on the music.

Fado was inscribed by UNESCO on the Representative List of the Intangible Cultural Heritage of Humanity in November 2011.

A native of Lisbon would likely head over to their local Tasca to listen to this soulful music. Fado dinners are definitely more formal. We head to Mesa de Frades in the Alfama, located in a former chapel, offering just one seating for dinner each night at 8:30 pm.

The atmosphere at Mesa de Fredes can’t be beaten, with the original frescos on the chapel walls and the musicians performing in front of the massive oak doors.

Dinner is a preset menu of three courses: appetizer, entrée, and dessert, with your choice of one of the three traditional Portuguese entrees.


My husband had the white fish. My dinner was traditional Bacalhau com Natas, a dish of potatoes, onions, fish, and bread crumbs. Wine is included with your dinner if you choose.

After dessert is served, the music begins. In this ancient setting, the performance seems somewhat otherworldly.

You can book an evening similar to this and enjoy this hauntingly beautiful music during your stay in Lisbon.

Day 3: Belem And Pasteis

Today we are checking out the neighborhood west of Ponta 25 de Abril, Belem. This will be a day of history, architecture, and food.

The Monument To The Discoveries And Belem Tower

The Monument to the Discoveries is at the Northern anchorage of the Ponta 25 de Abril. This massive project was conceived to honor the five-hundredth anniversary of the death of Henry the Navigator; the monument was constructed in the 1900s and took nearly half a century to complete.

Photo of the Monument of the Discoveries

Surrounding the large stone sail are Portuguese heroes such as Bartolomeu Dias, the first person to cross the Cape of Good Hope, and Pedro Alvares Cabral, who discovered Brazil.

A bit further along the Tagus River is Belem Tower, the 16th-century fortification and ceremonial gateway to Lisbon. This was also the embarkation point for many Portuguese explorers heading to sea.

Photograph of Belem Tower in Lisbon, Portugal

Built in the Manueline style of Architecture (also known as Portuguese late Gothic), the fort on the sea’s edge stands strong these five centuries later. Belem Tower was built to protect this crucial port and the Jeronimos Monastery.

Mosteiro dos Jeronimos (Gothic Monastery) And the Museu de Marinha (Maritime Museum)

The Jeronimos Monastery is one of Portugal’s many world heritage sites. Also known as the Royal Monastery of Santa Maria de Belem is a masterwork of Portuguese Architecture. The monastery’s patron was King D. Manuel I, and it is one of the best examples of Portuguese Gothic Manueline Architecture.

The southern end of the monastery houses the Museu de Marinha (the Maritime Museum). There are over 17,000 (2,500 on permanent display) artifacts of Portuguese naval and maritime explorations going back to the time of Henry the Navigator.

Entrance to the Maritime Museum in Lisbon Portugal

Interesting side note; Henry, the 4th child of King John I, never actually set sail on any of the voyages of discovery. Instead, he was the great patron that helped start the Age of Exploration.

Just when you think you are done, head over to see the Portuguese Navy’s first aircraft, an FBA Type B Flying Boat, and walk through the exhibit of Royal Barges. Imagine being part of the”Gentry,” putting on your Sunday best and sailing along the Tagus for all to see.

Portuguese Riber Barges

Everyone Comes to Belem For Pasteis de Belem

We’ve done a lot of walking and learning so far today and are ready for a break. Fortunately, we planned this walk to end near the famous Pasteis de Belem

Photograph of the line of shoppers at Pasteis de Belem

You hear about pasteis from the first moment you think about a trip to Portugal. Don’t be put off by the seemingly endless line out front; it moves pretty fast. If you sit inside, you may have a short wait for a table. But you will be fully surprised by how large the restaurant is and also get to see the enormous bakery.

You will eat more sweet little egg custard pies than you ever thought possible while in Portugal. Belem is the home of the original pasteis de nata, but it is not the only place to find them.

Dinner Tonight Blends Portugal With India at Jesus E Goes

In another nod to the many travel shows we watch, my DH has located the Indian/Portuguese restaurant Jesus E Goes. This local hole-in-the-wall was featured in the same “Somebody Feed Phil” episode that introduced us to Gijinha.

Not all the restaurants featured on travel shows are accessible to non-celebrity travelers, but Jesus E Goes is! If you like spicy Indian foods at reasonable prices, this is a fantastic find. Just be sure to come early or late. The restaurant has only about seven tables, so there may be a wait.

Day 4: Sintra And The Westernmost Point of Europe

Sintra is the most popular day trip out of Lisbon, and there are several ways to get there. You can purchase a tour package like one of these from Get Your Guide:

Or, of you are an independent and perhaps budget-minded traveler, catch the train from Rossio Station (a return ticket is just €5).

The Entrance to Rossio Train Station in Lisbon

Once you reach Sintra station, you will need to either walk or get transport up the hill to the Pena Palace. Taxis are available, as are Tuk-Tuks. I asked a Tuk-Tuk driver and was told the typical cost is €10 to go up and €5 to come down.

Taxis and Tuk-Tuks only take you as far as the ticket gate. From there, it is another long walk up to the Palace.

Or you can be crazy like us. Since we are touring more than just Sintra today, we chose the luxury of hiring a private car and driver to guide us on our day trip. Our guide, Andre, picks us up bright and early at our hotel.

Palacio da Pena (Pena Palace)

Start your day in Sintra at the Pena Palace. This Unesco World Heritage Site is the highest point of the trip (literally and figuratively) and the most popular. Get here early as the crowds grow as the day goes on. The earliest tickets available each day are for a 9:30 entrance. You can buy tickets online in advance, but be mindful that the entrance time is for the Palace.

Palacio Pena - Sintra Portugal

You can also purchase the audioguide for Pena Palace on the website for €1.09. This is a download for your phone from AppStore or GooglePlay.

The Palace is a 30-minute walk from the ticket gate. The park has a bus if you don’t want to walk. This is the “Transfer” offered on the website for €3 round trip. The “transfer” takes only about 10 minutes, but there may be a slight wait for the bus

No matter what time slot you purchase, ensure enough time for transportation to the Royal Palace. As the website says, “There is no delay tolerance!” You don’t want to miss your time slot to view what may be the purest expression of the Romantic Movement.

The Town of Sintra

After visiting Pena Palace, head back down the hill to the town of Sintra. Walk around the city oohing and awing over the 18th century surrounds.

There is much more to see around Sintra; it can be a full day trip. Spend some time in the National Palace of Sintra and the Moorish Castle. Also, check out the Convent of the Capuchos and the Park of Pena, a fantastic garden.

Entrance tickets for all these sites can be purchased at Parques de Sintra.

Lunch at Curral dos Caprinos

Our driver/guide, Adre, made lunch reservations at one of his favorite local restaurants, Curral dos Caprinos. You’ll never guess the specialty of the house at …Goat.

The food and service were fantastic. One of the advantages of hiring a local driver is their knowledge of these types of places. Having lunch together allows us to learn more about the locals’ lives.

A Drive along the Westernmost Point of Europe, including Cascais and Estoril

After lunch, we head over the mountains to the westernmost point of Europe, Cabo da Rocha. The coast is beautiful and really windy. It feels odd to be standing on these cliffs facing the Atlantic Ocean and realizing we are as far west as we can go in Europe

Adre, who lives close to Sintra, is also an avid mountain bike rider. He tells us he often makes this trek on his bike.

Cascais and Estoril

We drive through Cascais and Estoril. This is the place to go if you want a resort-style beach day. Only about an hour-long train ride west of Lisbon, These seaside towns have long been the summer getaway for the Portuguese.

 Public beach in Estoril i

Grab lunch at one of the many cafés overlooking the shore, shop in the many upscale boutiques, or just lay in the sun on the beach.

Day 5: Free Wheeling It In Lisbon

LX Factory

This morning we head over to LX Factory to see the reawakening of Lisbon’s old factory district. This area had gone by the wayside.

A little rough on the outside, the old buildings now house creative ventures of all types. You will find makers, chefs, architects, and artists all working and selling their goods here. There is even a hostel with a rooftop terrace if you are a traveler who enjoys this lodging.

Why LX? Lisbon is commonly abbreviated as “LX.” This is a throwback to the antiquated spelling of Lisbon as ”Lixbõa.” BTW, you will see Lisbon often as Lisboa, the Portuguese name, not the Anglicized version.

Time Out Market

I’m a big fan of Market Halls. I even have a post dedicated to market halls I think everyone should visit! So Time Out Market was definitely on my perfect Portugal itinerary.

Most people see Time Out Market as a food hall, and it is. The portion most folks come to see is lined with fancy food stalls serving everything from raw bars and sushi to sandwiches, pizza and pasta, and everything in between. In the center of the hall are long tables for dining and drinking.

But the market is part of the larger Mercado da Ribeira. On the other side of this enormous warehouse structure is the “Mercado Tradicional.” Where locals can shop for their everyday fish, meat, and produce.

And, of course, Time Out Market is also home to “Manteigaria  – Fabrica de pasteis de Nata.” Yes, more custard pastries. By the way, it’s odd for us from the States, but they do not accept cash at the market. To purchase two of these delicious little pastries, I had to use my Visa… As they say, “Don’t leave home without it!”

Hitting A Few More “Phil” Spots

After wandering around Time Out and tasting a few fun bites, we convince a Tuk-Tuk Driver to take us to a little corner off Rua de Sao Bento for more food: Wurst Salsicharia Austriaca and Nannarella (Ice Cream). Yes, we saw both of these places watching Phil. This area is a bit off the tourist track, but if you like sausages and ice cream, you should make a stop.

Day 6: Picking Up A Rental Car For The Portugal Road Trip Itinerary

Today, we start the road trip part of our perfect Portugal itinerary. We’ve rented a car with Europcar we find this to be the most reliable agency when renting in Europe. Portugal Trails provided a Garmin navigation device pre-programmed with our driving destinations, so we declined the in-car navi. But we do opt to include the EasyToll system (Via Verde). There are many toll roads in Portugal.

Tip #1: We take all the insurance offered when renting a car overseas. You may think you are covered by your insurance policy back home or even the credit card you use for the rental. But these things won’t help if you are in an accident in a foreign country. The insurance from the rental agency will come to your aid, and you won’t be left with a huge bill.

Tip #2: It’s a good idea to obtain an International Driving Permit before driving outside the US. Rental Car Companies don’t always ask for this, but some do. It’s easy and inexpensive, and I have an article about the process for getting your own International Driving Permit.

Driving Through Arrabida Nature Park And On To Evora

Breakfast this morning includes yet another Pasteis de Nata (yes, these pastries are among the hotel’s goodies for breakfast). Then we pick up our car, load up our suitcases, plug in the GPS navi, and hit the road.

We say goodbye to Lisbon as we drive south across the Ponte 25 de Abril. On the bridge’s east side is a good view of Lisbon’s Santuario de Cristo Rei (which looks curiously like Rio’s famous Christ the Redeemer).

Photo of Lisbon's Christ the Redeemer From The Ponte 25th de Abril

The first stop of our perfect Portugal itinerary road trip is the beautiful Parque Natural da Arrabida (Arrabida Nature Park). On a warm day, the beaches along the shore in the park would be a fantastic place to enjoy the sun. But the fog is still hugging the coast, so we drive on, enjoying the scenery.

A view of the ocean covered by fog in the Arrabida Nature Park

If you drive straight through from Lisbon to Evora, it only takes about two hours. The distance is around 150 km or 90 miles. But we take a few detours to look at the scenery and have a bio break along the way. After our leisurely start and drive, we arrive at our hotel, Convento do Espinheiro, around 2:00 pm.

Where To Stay In Evora

We originally wanted to stay at Pousada Convento de Evora, located in the middle of the old town. Unfortunately, this lovingly refurbished old property was completely booked at the time of our stay.  

Fortunately, we found Convento do Espinheiro available. This hotel is about 5 miles from the ancient town, making our stay less convenient. But the old part of the hotel and the spa and pool areas made up for some of the charms we missed in town.

Convento do Espinheiro

At registration, the concierge invites us for a hotel tour followed by a wine tasting later that evening. We graciously accept.

The concierge also assists us with booking tours for the cork factory and olive oil tasting for the day after tomorrow.

Tonight we dine at the hotel. A four-star presentation!

Day 7: Evora And Monsaraz

Evora is the capital of the Alentejo region of Portugal. There is more to this region than the city’s historic center, but to be honest, this 12th-century walled town is what most people travel to see.

Having driven through the old city on our way to the hotel the night before, we know there is virtually no parking. But even in this remote area, there is Uber. We call one up on the app and head to town for our 9:00 am city walk starting in the historic center.  

Walking Tour Of Evora

Jose, our guide for this morning, meets us at the fountain in front of Igreja de Santo Anatao in the center of the old town for this walking tour of Evora.

Leaving the square, we head up the small streets toward the Cathedral of Evora.

From here, we head over to the Templo Romano Evora, a temple ruin built for Emperor Augustus in the 1st century CE, and the Garden of Diana. While admiring the ancient ruins, we are serenaded by the local high school marching band!

After a quick walkthrough of Pousada Convento Evora (the hotel we wanted to stay at), we headed to the Chapel of Bones. Adjacent to the Church of St. Francis, this 16th-century chapel’s walls are lined with the bones of the monks. The purpose of these ossuaries is to provoke reflection on the transience of human life.

E Chapel of Bones
Chapel of the Bones

The Hilltown of Monsaraz

Along Portugal’s border with Spain are several fortified hilltowns. This afternoon, we drive to Monsaraz, a  walled city that may be one of the oldest settlements in Southern Portugal. Archaeologists have found neolithic remains and megalithic monuments surrounding the town.

 It’s Sunday, and many local shops and restaurants are closed. But we haven’t eaten today except for a pastry and coffee in Evora. So before exploring Monsaraz, we find a small eatery for a bite of lunch.

Monsaraz has been” conquered” over the ages by Romans, Visigoths, Arabs, and Jews. In 1232 the Knights Templar aided King Sancho II in retaking the citadel and town. All of their influences can be seen as we stroll through the narrow cobblestone streets.

We end our day relaxing by the pool and enjoying another great dinner at the hotel.

Author Relaxing By The Pool

Day 8: Learning About Agriculture In The Alentejo

A note for my fellow travelers with allergies: Halfway through the morning in Evora, my “hay fever” kicked in strong. Alentejo is an agricultural area, and many of the crops are trees. Olive trees and Oak trees are everywhere. These trees are known to be in high pollen season in late spring and early fall. If you are sensitive to pollens, you should consider the time of year you travel in this region.

The Cork Factory

The Quercus suber or Cork Oak loves the Mediterranean climate here in southern Portugal and Spain. It’s the bark of this tree that we use for wine bottle stoppers.

But cultivating these trees is generational farming. Why? Because a cork oak must be at least 25 years old before the bark can be harvested.

Here at the cork factory, we learn how the cork is harvested from the trees and processed. First, the bark’s outer layer is removed, and then the cork is softened by boiling it. This makes the cork easier to work with.

The bottle stoppers are made from the best grades of cork. The leftover scraps and the inferior qualities of cork are then ground up and molded together. These blocks are used to make other products, such as cork flooring and all the crazy things you see here.

Amor E Cego Takes Olive Oil To The Next Level

60-plus years ago, Joao Miguel Rosado’s grandfather bought a small olive orchard and farm to provide food and income for his family. In 2015 Joao took the first steps towards his dream of producing olive oil from the trees planted here. At least one of the trees in Joao’s orchard is around 2,000 years old.

The Galega tree is unique to this area of Portugal, growing a small, firm olive. It took a few harvests to perfect the process. Still, today they have a beautiful 100% extra virgin Galega olive oil, Amor E Cego.

For culinary junkies spending the afternoon tasting the oil in the old farmhouse in the orchard where the olives have grown is the type of experience we are always looking for  

When seated for the tasting, Joao tells of his and his wife’s journey to produce Amor E Cego. When they started, all of their friends thought they were crazy, but they pushed forward. Their brand, Amor E Cego, means “love is blind” in English and reflects their passion for the Galega olives.  

This day spent in the orchards was a highlight of our time in the Alentejo.

Day 9: Evora to Belmonte (With A Strange Side Trip)

Our Failed Attempt To Capture Monsanto

We leave Evora planning to spend the morning in another hilltop fortress, Monsanto. Our pre-programmed GPS almost gets us there. But we have a problem. We start out a bit late in the morning, opting to have breakfast at the hotel and then hit the road.

By the time we get to Monsanto, there is no parking anywhere! We tried to drive around the village at the base of the hillside, hoping we could find a suitable way to get up the hill, but to no avail.

The narrow cobbled streets of Monsanto

Also, this is an old village, and the roads are barely wide enough for one car, but traffic is two-way!

Unfortunately, after an hour or so, we give up our attempt to take the town. Hilltop fortresses were built for just this reason. To make it difficult for others to get to the town!

Pousada Convento de Belmonte

We end our day at Pousada Convento de Belmonte, our lodging for the evening. You might notice a recurring theme in naming the hotels we find ourselves at on our Portugal road trip.

“Pousada” is the Portuguese word for an Inn, and clearly, “Convento” is Portuguese for convent (or monastery).

A hotel group has purchased these old convents around Portugal, restored the ancient buildings, and in many cases, added gourmet restaurants and other facilities. Guests get to stay in a lovingly restored 18th-century or older property with all the modern amenities.

We book a table for dinner and head to the room to relax and unwind from the crazy driving we did today.

Day 10: Belmonte Castle and The Douro Valley

The Douro Valley is Portugal’s most famous wine region. But before heading there today, we take an hour or so to visit Belmonte’s sites and finish our tour of central Portugal.

Belmonte’s Castle and Jewish Quarter

The village’s key attraction is Belmonte Castle. Built by King Sancho I in the 12th century, the castle was later gifted to Fernao Cabral, the first Mayor – Alcaide in the 15th century. Fernao Cabal is the father of Pedro Alvares Cabral (born at the castle), the Portuguese navigator and discoverer of Brazil.

Belmonte is also known for its well-preserved Jewish Quarter, with a lovingly restored synagogue below the castle walls. During the Inquisition, many Jews fled Portugal. Their story is told at the nearby Museu Judaico (Jewish Museum).

Now we head off for our perfect Portugal itinerary wine-drinking portion: the Douro Valley.

Ponte Rodoviaria da Regua (A Fantastic Bridge) And The Hamlet Of Peso da Regua

Heading in a northern direction from Belmonte on the A24, we finally cross the Douro on the Ponte Rodoviaria da Regua and stop in Peso da Regua to find a bit of lunch. This small town on the north bank of the Douro is also the train station’s location, which conveniently has shops and restaurants.

After a short walk to stretch our legs, we grab a table at Locomotiva Wine & Gourmet. We take some time to review our trip so far over a simple lunch of a white bean salad with tuna, a charcuterie & cheese board with local bread and wine.

Lunch at Locomotiva - Charcuterie, White bean salad and fresh bread

Bodies refueled; it’s time to find our lodging for the next two nights.

Quinta do … (The Farm Of …)

Small boutique inns are perched on the Douro’s steep, sloped banks. These inns are usually attached to a vineyard and a vintner’s property. A quick glance at a map of the region and you will quickly see a dozen or more.

You will also see many Quinta “da” or “das” or “dos.” These are wineries with tasting rooms but generally no lodging. I do not know the grammar of Portuguese. In fact, I only know very fundamental words like Bon Dia (Good Day) and Obrigado (Thank you). So, I can’t begin to help you understand how these “connective words” are chosen or why.

North of the Douro off a tributary called the Corgo is where we find our quinta …“Quinta do Vallado.”We check into the Inn around 2:00. Our room is one of what is called the “traditional houses.” These rooms are private and separate from the Inn’s hotel, spa, and dining areas.

At check-in, we are asked if we’d like to join the tour and tasting this afternoon, and we eagerly agree. We also choose a time for dinner at the hotel’s 4-star restaurant.

Tour of the Vineyard, Including Tasting

Dinner With A View

Dinner at Quinta do Vallado is a pre-fixe four-course meal served al fresco. The meat entrée this evening is octopus. They eat a lot of octopus in Portugal, but I am not a fan, so I opt for the vegetarian entree. Everything is perfect, including the view.

Day 11: Pinhao For A Private Cruise On the Douro River, Followed By More Port Wine

Today we drive about 30 minutes up the Douro for a private boat trip on the river. The tour company is Anima Durius, and our boat for today is the Unbelievable. We are captained by Paulo and co-piloted by his adorable pup.

The sky has been threatening rain all morning, and as we start our river cruise, we feel a few raindrops. But we are in luck, and the sky gives way to beautiful sunshine as we glide along the river.

Paulo tells us that he and his wife run the boats on the river. His family owns Quinta dos Pocos on the Douro and provides wine tasting, lunches, and guided winery tours.

However, for most of the year, they live in Porto. The schools in the city are better for the children. And Paulo says the kids like the city better than the country. On the return to Pinhao, Paulo breaks out the port wine, and we toast to a successful cruise on the Douro.

Quinta do Bomfim

For the second half of our day in Pinhao, we have a guided tour of Quinta do Bomfim, a Port Wine House, and a wine tasting with regional cheeses.

These vineyards are part of the Symington Family Estates. You will note that most of the port winemakers have British-sounding names. Cockburn, Dow, Taylor, and Graham, to name a few. We learn why during our tour of Bomfirm.

Portugal and England signed a treaty In 1386 to establish a political and commercial alliance. By the late 15th century, a large amount of Portuguese wine was shipped to England to sate the British appetites. In exchange, Portugal got salt cod, known as “bacalhau.”

The reason for the sweet port wine was one of necessity. A small amount of brandy was added to the wines shipped to England. This prevented the wine from going bad during the long voyage.

Dinner Tonight? The Famous (Or Dare I Say Infamous) Franchescina

Tonight we venture back over to Peso de Regua for a less fancy dinner. Still, a meal everyone who goes to Portugal should try, Franchescina!

This sandwich contains ham, sausage, cheese, and steak between two thick pieces of white bread. They then cover the sandwich with more cheese and place it in an oven to melt the cheese. A sauce of beer and tomatoes is poured over the entire plate, and lastly, if you wish, you can top off the whole thing with a fried egg.


Of course, the sandwich is served with a side of fries. Unless you are a strapping young person who just finished up a marathon, I suggest you share your Franchescina with a friend.

Day 12: To Porto, We Go

We are staying at the Yeatman, yes it is as fancy as it sounds. We were initially concerned that this luxury hotel was not in Porto proper but across the Douro in Vila Nova de Gaia. And this is true. But again, we were traveling at a busy time, and choices were limited.

The upside of being in Vila Nova de Gaia is you are close to all the Port Houses, and tasting some lovely wines will be easy. The downside is that you will spend most of your time on the north side of the Douro. Picking a more centrally located hotel in the Ribeira district is a great option for your time in Porto.

Porto Is The End of our Road Trip

The drive from the Douro Valley to Porto is a straight shot and only takes an hour or so. We drive to our hotel in Vila Nova to drop off our luggage and then head across the Douro to return the rental car. You do not want to drive in Porto; the streets are crazy.

On our very first trip to Europe in 1996, we went to London and had to stop at the original Hard Rock Café. Since then, we have visited every Hard Rock Café on our travels to pick up a shot glass and city pin. So from the car return, we call an Uber and head over to the Hard Rock.

We don’t always eat at the café, but today we do. Then we grab our memorabilia, including a scarf for me and a t-shirt for hubby. After our bite, we walk around the Porto a bit to get our bearings. Then call an Uber to return to our Hotel across the river.

The Yeatman has a fantastic bar/restaurant with a vast terrace that looks across the Douro River to Porto. We have a light meal tonight while watching the boats sail out to the sea and the lights twinkle on the hills of the City.

Day 13: Walking Tour Of Porto

Clerigos Tower In Porto
Clerigos Tower

We are up early today, but a bit worried. The weather has changed, it’s raining, and we have our walking tour of Porto this morning. Hubs gives our guide, Marta, a call to see if she thinks the walk makes sense. Marta believes the rain will be very light and will stop soon and encourages us to continue the plan. So off we go.

Marta starts our tour at Clerigos Tower, the 75-meter-tall bell tower for Igreja dos Clerigos (the Church of the Clergymen). This was one of the first baroque churches in Portugal to adopt the grand elliptical floor plan.

People can climb to the top of the bell tower, and as this is the highest point in Porto, the views would be outstanding. But with the rain today and the typically long lines, we admire the tower and church from outside.

A quick one-minute walk north of the church is Livraria Lello. If you are a Harry Potter fan, you’ve probably heard the rumor that JK Rowling was inspired by this bookstore for much of the famous Hogwarts scenery she wrote about in her books.  

I’m sure the store is grand from the pictures I’ve seen, but I’m not willing to wait in line for over an hour and pay €5 to visit the shop. (Yes, there are a lot of Harry Potter fans!).

Onward we go to Igreja do Carmo & Igreja dos Carmelitas. Here are two churches nearly side by side, except that there is a one-meter house separating the two structures. In the 1700s, the church figured this space would be enough to discourage any hanky-panky between the monks and the nuns.

Photograph of Igreja do Carmo and Igreja dos Carmelitas. Two Gothic Style churches in Porto

From here, we walk through town a bit while Marta shares information about the sites, parks, and buildings on our way to Sao Bento Train Station. This is not the central train station for Porto. However, it is nonetheless as crowded as any train station in Europe.

Tourists come from far and wide to see the famous Azulejo tiles representing moments in Portuguese history.

Interior of Sao Bento Train Station
Interior of Sao Bento Train Station

The 12th-century Romanesque Porto Cathedral sits on yet another hilltop with commanding views of the city. The Cathedral is also a point on the Camino de Santiago. Our good friend and his daughter did the Camino de Santiago pilgrimage a couple of years ago.

After the Cathedral, Marta walks us down Rua Pena Ventosa, one of the oldest streets in Porto. The narrow cobblestone streets in this area a pedestrian-only. We continue to walk downhill towards the river to the end point of our tour near the Mercado Ferreira Borges.

Photograph of the narrow Rua Pena Ventosa in Porto, Portugal

Day 14: The Hop On Hop Off Bus

After all the walking we did yesterday, we chose to tour Porto’s outer reaches by hopping on the Hop On Hop Off Bus. This bus service is called the Yellow Bus Tour here.

The Orange Route Bus, called the Historical Porto Tour, has a stop just outside our hotel. We Hop on and ride over to the Porto side of the river, where we hop off at stop 1 and hop on the Purple Route Bus, known as the Porto Castles tour.

This is a lazy way to see the city. We’ve been on the go for 13 days now, and it feels good to sit and have a narration of the sites we are driving past.

At the end of the first bus route, we waited for about 30 minutes for the Orange Route Bus, but it seems there is an issue with traffic, and the bus does not arrive.

We are very close to the Luis I Bridge. Everyone has said we should walk across this bridge as it has a great river view. Since it is primarily flat or downhill back to Nova de Gaia, we decide to walk.

Back on the south side of the river, we stop at one of the many riverside restaurants for our final meal in Portugal. As we enjoy our food, we are serenaded by a local guitarist while watching the steady parade of people walking by.

Tomorrow we head to the Porto Airport and fly home.

Modifications For Your Perfect Portugal Itinerary

You may have less time on your journey or want to see other places. Here are some ways to modify this trip; different travelers are looking for different experiences.

Spend Less Time In Lisbon

You can easily shorten your time here to two full days in Lisbon and one day to visit Sintra and still see much of the rich history. This cuts two days off the Lisbon portion of the trip, but it is still enough time to see all the main attractions.

Don’t Stop over in Belmonte On The Way To The Douro Valley

If you have already seen Monsaraz, you don’t need to see Monsanto. And while the Pousada Convento de Belmonte is a beautiful hotel, there really is not much to see in Belmonte. Drive straight through to your Quinta in the Douro, it’s only about a 4-hour drive, and you can even stop and see Belmonte Castle if you choose. Another day saved.

Take A Day Trip From Porto To The Douro Valley

We enjoyed our two nights in the Douro, but except for staying at a Quinta, you can do everything we did on a day trip from Porto. And if you do this instead of the Hop On Hop Off bus in Porto, it is another day saved.

This takes the timeline down another 2 days, cutting a two-week trip down to a 10-day Portugal itinerary. Yes, it’s more rushed, but not everyone has the luxury of time.

Does Your Perfect Portugal Itinerary Have To Include The Algarve Region? – Skip Evora

The Algarve is at the southern end of Portugal. For many Europeans, this is the go-to place for a beach holiday. The southern coast is dotted with beautiful beaches and quaint beach towns.

Almost everyone wants to see the three main places in Portugal: Porto, Lisbon, and the Algarve. You can make this trip in 7 – 10 days. No matter the length, I recommend starting this trip in Porto. For a seven-day trip, plan for 2 days in Porto, 3 days in Lisbon, and 2 days in the Algarve

If you have more time, you can add the day trip from Porto to the Douro Valley and another night in the Algarve, making this the perfect 10-day itinerary.

When Is The Best Time Of Year To Visit Portugal

Portugal has a very Mediterranean-like climate. It can be pretty warm in the summer, with even coastal cities like Lisbon reaching the high 80⁰’s. Winter is more temperate.

As I mentioned above, if you plan to travel in the Alentejo region and have allergies, I would avoid spring when the trees are pollinating. But with its generally sunny climate, almost any time of the year can be the best time to visit Portugal.

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