How To Spend 16 Days in Portugal

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Over 23 years guiding US travelers

Small Private Tours

Explore Portugal your way

Our 16 day ultimate Portugal tour itinerary ensures that you will truly get to sample everything that makes Portugal such an attractive, inviting, and unique destination to visit.

Everything that comes to mind when you dream of Portugal is included here.

Tour Highlights: 

What’s Included?

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We are extremely proud that the Institute for Spanish Tourism has granted our team the “Safe Tourism Certified” seal of approval. In addition to the security and peace of mind this provides to our clients, we have extended our cancellation policy to entitle guests to a full refund if they are forced to cancel their tour anywhere up to 7 days before the start date. Find out more here.

16 Days Portugal Itinerary

Day 1: Central Porto

Private tour of Porto old town.
Porto, Portugal

Your first day in Porto will be spent at the following sites with your private guide:

  • City Center tour
  • Ribeira District
  • Porto Cathedral
  • Wine Experience

Located in a spectacular valley bathed by the Douro River, Porto is known for the beauty of its architecture and the sweet taste of its wine. The center of the city is Avenida dos Aliados, a wide avenue surrounded by Plaza General H. Delgado and Praça da Liberdade. 

The most attractive part of the city, however, is Ribeira, the river district and world heritage site where three of the most elegant bridges in Europe are located. 

Bustling Praça da Liberdade and the adjoining Avenida dos Aliados form the center of the city, where statues stand on mosaic-studded pedestrian pathways. Nearby is the great Porto Cathedral, a colossal fortified Romanesque structure, whose granite foundations, thick walls and small windows enclose a gloomy interior. 

The Ribeira stretches along the river, bordered by a wonderful pier filled with shops and restaurants. Porto’s most characteristic monument, the ornate Torre dos Clérigos, offers a panorama of the city from the top of its 240 steps. 

No visit to Porto would be complete without a stop at one of the many cellars, where the port is stored and bottled. Another must-see is the impressive Lello Library with its spiral staircase, even if you’re not a Harry Potter fan.

Day 2: Porto Architecture Tour & The Old town

Porto in Portugal showing the Cathedral.
Historic center of Porto, Portugal

Porto is a city with an eclectic mix of architectural styles, including Roman, medieval, Baroque, and contemporary. 

Portugal is the cradle of the handmade tile. It is common to find it not only as interior decoration but as facade cladding. Find out all about how the tile was made on an artisan workshop experience.

Porto is a city with Visigothic, Roman, and Arabic heritage, and this will be discussed by your private guide as you walk together down the cobbled streets of the city’s old town on a medieval walking tour.

Best of Spain & Portugal

“I urge everyone who values unforgettable vacations to contact Magical Spain and talk to Dan or Rachel.

Beyond the personalized planning and fine 24-7 tour support, we loved the quality and care of the licensed guides, the delicious tapas, the exotic ambiance of Seville and Granada, Madrid’s majesty and art, medieval Toledo, and meeting the olive oil estate owners, artist, chef & winemaker.”

R. Mathews, wife & friends (Northern Virginia)


Day 3: Braga & Guimarães with Private Driver

Bom Jesus do Monte Sanctuary, Braga.
Bom Jesus do Monte, Braga


Founded by the Romans in the year 16 B.C. and the religious center of the country during the Middle Ages, this city concentrates an immense architectural and archaeological heritage. It has the oldest cathedral in Portugal and its emblematic monument, the sanctuary of Bom Jesus with an incredible baroque staircase.


The pretty medieval town of Guimaraes is known for being the “cradle of Portugal”. Its historic center surrounded by walls, declared a World Heritage Site, stands out for its cobbled streets such as Rua Santa María, its squares with quiet terraces, its churches, palaces, and typical buildings of Portuguese architecture.

Some of the most essential places to see in Guimaraes are the Guimaraes Castle, the Palace of the Dukes of Braganza, the Churches of Our Lady of Oliveira, and Consolation, the Plaza de Oliveira and going up to the Sanctuary of Penha by cable car with magnificent views of the city.

Day 4: Aveiro - The Venice of Portugal

Moliceiro boats at Aveiro, Portugal.
Moliceiro boats at Aveiro, Portugal

The city of Aveiro is known as the “Venice of Portugal” due to the canals that cross the old city. The “Beira Mar” neighborhood houses the essence of the city’s history, old houses between alleys and canals. 

In the estuary, you can see the Moliceiros, typical boats that have traveled these channels for centuries. The tiles are another of the hallmarks of the city’s origin since they are present in all Aveirense architecture.

Day 5: Porto - Off the Beaten Track and Gastronomy Experiences

Duero Valley River Cruise.
Evening Cruise Douro River, Spain

There are many places to visit in Porto such as entering the Lello e Irmão bookstore, one of the most beautiful in the world, getting lost in the Do Barreda neighborhood, seeing the Bolhao Market, climbing the Clérigos Tower, visiting one of the many churches and cloisters full of beautiful tiles or take a walk at sunset along the Ribeira.

For us, one of the best things to do in Porto is to try its delicious gastronomy in which cod predominates and have a glass of wine in one of the famous Vila Nova de Gaia wineries when the day ends and after touring the city, this is the best reward and to finish enjoy a romantic evening cruise along the Douro River.

Day 6: Duero Valley

Cruise Douro River, Vineyard/Wine Experience

There are many places to visit in Porto such as entering the Lello e Irmão bookstore, one of the most beautiful in the world, getting lost in the Do Barreda neighborhood, seeing the Bolhao Market, climbing the Clérigos Tower, visiting one of the many churches and cloisters full of beautiful tiles or take a walk at sunset along the Ribeira.

For us, one of the best things to do in Porto is to try its delicious gastronomy in which cod predominates and have a glass of wine in one of the famous Vila Nova de Gaia wineries when the day ends and after touring the city, this is the best reward and to finish enjoy a romantic evening cruise along the Douro River.

Day 7: Porto - Coimbra - Lisboa

University of Coimbra in Portugal
University of Coimbra in Portugal

Coimbra, located between Porto and Lisbon, the old medieval capital and another essential place to see in Portugal. Crossed by the Mondego River, it is a small city built at various heights and full of charming corners that can be explored in a day.

In the center or the upper part, you can discover hidden courtyards as you stroll through its narrow cobbled streets and old buildings. In this part, in addition to seeing the Old Cathedral and the Almedina Arch, you can go up to the historic campus of the University of Coimbra, a World Heritage Site, and visit the magnificent Joanina Library.

The lower part, the Baixa, revolves around the Praça Do Comércio, it is a commercial area of bourgeois houses, in which the beautiful São Tiago Church and the Santa Cruz Park stand out.

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“Thanks for the great work during our Spanish Food and Wine Adventure…. you guys really know your stuff and are great guides & hosts! We’ll be back for northern Spain in the future!”

The Marshall Clan (Dallas, TX)


Day 8: Lisbon

skyline of alfama at lisbon, portugal at dawn
Lisbon, Portugal

Known as the city of the seven hills or of light, one of the favorite cities in Europe. thanks to its charming neighborhoods such as Alfama, monuments and historic buildings, incredible viewpoints, and lively taverns where you can listen to fado as well as fantastic cuisine featuring exquisite dishes such as bacalhau com Natas and delicious Bélem cakes that are a real treat.

Day 9: Lisbon Sintra

Sintra castle in Portugal
Sintra, Portugal

The magic of Sintra is breathed in the environment. Located 30 kilometers from Lisbon, this Portuguese town stands out for its many picturesque castles, its natural forests, and its golden sand beaches.

Day 10: Obidos & Tomar

Historic town center in Obidos, Portugal.
Obidos, Portugal


Obidos in the north of Lisbon, you will find Óbidos, one of the most beautiful towns in Europe, surrounded by 15th-century walls that enchant you with its white houses and red roofs, the balconies, and terraces full of flowers and its narrow cobblestone streets.

Among the places that you cannot miss is the Porta da Vila, the main access gate to the city, decorated with precious traditional tiles, and the tour of the wall.

Tomar, refuge of the Templars

Half Game of Thrones, half Assassin’s Creed, there is no better place than Tomar to follow in the footsteps of the Knights of the Order of the Temple, the Templars. Created in the twelfth century to help the Christian reconquest of the country.


“Outstanding, seamless planning with a very personalized itinerary executed perfectly…..

In Spain, we felt like VIPs as we met the winemakers in La Rioja and Ribera del Duero, the chefs, the village mayor  and flamenco dancer in Sevilla! The unique experiences and memories beat that of 4 or 5 cruises.  We will be back to do Andalucia or Portugal in a few years”

Scott & Kisha McCann (NYC)


Day 11: Evora

Cloister of the Evora Cathedral, the largest cathedral in Portugal_
Evora Cathedral, Portugal

Évora is the jewel of Alentejo, a region located in the south-central part of the country that makes you fall in love with its medieval villages, fortified cities, and its landscapes full of cork oaks, olive trees, and vineyards. 

The city of Évora, with a historic center, declared a World Heritage Site, and one of the most beautiful cities in Portugal, stands out for its historical monuments, excellent cuisine, and lively nightlife.

Walking through the old streets with their traditional white houses is the best way to get to know the city and you can’t leave Évera without seeing the impressive Roman Temple, the Walls, the University, the Cathedral, or the macabre Chapel of Bones.

Day 12: Algarve

Portugal private tour and Ferragudo village in Algarve.
Algarve, Ferragudo Village

Incredible as it may seem, despite the waves of visitors that arrive each year in the south of Portugal, there are still many lonely corners in the Algarve region, far from mass tourism and winter is perhaps the best time to go looking for them.

Fishing villages, almond trees in bloom, and an artificial reef unique in the world. Hiking routes between cliffs and virgin beaches, mountain stews that alternate on the tables with fish cataplanas, or kilometers of paths adapted for bicycle routes. These are just some of the surprises that we offer you from the most unknown Algarve.

Day 13: Algarve

Private tour of Coves and cliffs at Ponta da Piedade in the Algarve region.
Coves and cliffs at Ponta da Piedade

The Algarve stands out for its spectacular beaches and coves in a privileged natural environment that makes it an ideal and unique place.

Its kilometric coastline hides sandy beaches and turquoise waters, between steep rock cliffs, which place them among the most beautiful in Europe.

Its old villages with white fishermen’s houses and narrow streets are ideal for trying the gastronomy based on fresh fish and visiting the old town of Faro, the capital of the Algarve, getting lost in the town of Tavira, having a good time in the charming Lagos or seeing the sunset in Cabo de San Vicente, are other essentials of the Algarve.

Day 14: Algarve Madeira

Funchal City, Portugal
Funchal City, Portugal

Madeira is a paradise full of sensations and unique landscapes full of winding roads, viewpoints from which you can see vertiginous cliffs, beautiful villages nestled between the mountains, natural pools, fortresses, peaks above the clouds, lush forests, and charming cities.

Its capital, Funchal, is the largest tourist, commercial and cultural center in the entire Madeira archipelago. Situated in a natural basin overlooking the Atlantic Ocean it is surrounded by rugged mountains with labyrinthine cobblestone streets, low hillside houses and elegant architecture, beautiful boutiques, and lively cafes.

Day 15: Madeira

Aerial view from the highest Cabo Girao, Madeira island, Portugal
Cabo Girão

In Funchal, the Cathedral or Sé of basalt with white walls stands out, the Mercado dos Lavradores with a multitude of exotic flowers, tropical fruits, and typical crafts.

And you can’t miss the well-known Carros de Cesto! Wicker carts that move thanks to the unevenness and are skilfully driven by two “carreiros” dressed in white who control the cart with their feet as brakes.

Located on the south coast, Cabo Girão, at 580 meters high, is the highest cape in all of Europe, from where you can see, thanks to a glass platform, the fajãs de Rancho and Cabo Girão, small areas of cultivated land at the foot of the Cliff.

Day 16: Madeira - Departure

The Porto Moniz Natural Pools, Portugal
The Porto Moniz Natural Pools, Portugal

The Porto Moniz Natural Pools, located to the north between the sea and the mountains, is another of the places in Madeira that you cannot miss, formed thanks to volcanic lava and filled with seawater that enters naturally.

If you like hiking you are in luck, on this island the laurel forest prevails, a laurel forest considered a World Heritage Site, and where you can make a route full of gorges and vertiginous areas until you reach an impressive waterfall.

Santana and its traditional houses are another of the attractions of Madeira, triangular houses with thatched roofs and bright colors. Surely you have not seen others like it!

Porto Santo, the other inhabited island from Madeira, its main attractions are an extensive 9-kilometer beach, the Portela Viewpoint, and the Ana Ferreira Peak.

SideBar Tour Request

Meet our Founder & Iberian Tour Expert

Ola! I’m Dan O’Beirne, owner of Magical Spain and Portugal

Originally from America, I worked in the Health and Wellness sector until moving to Iberia over 20 years ago. Ever since then, I have made it my mission to combine classic American hospitality with the fascinating, beguiling, and simply beautiful landscapes, monuments, and cultures found across Spain and Portugal.

Step 1

Fill out the form with the destinations, wish-list, & personal preferences for your perfect trip. If you would like your tour planner to offer some inspiration, then we are happy to provide a suggested itinerary which we can then refine with you until you are 100% delighted with it.

Step 2

Soon after receiving your request, your personal tour planner will be in touch to begin planning your custom tour. You will then receive a tailor-made tour itinerary which can be revised an unlimited number of times to ensure total satisfaction and the perfect vacation.

Step 3

Your officially licensed private guide will meet you at the pre-arranged starting point of your tour. You can count on us for 24/7 in-country support and everything else necessary for a wonderful vacation and seamless tour experience. Welcome to Iberia!

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Fill in the form below with as much detail as you can and our tour planning experts will get in touch with you shortly to help you craft the perfect vacation to Portugal and/or Spain, tailored to you and your group! 

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