Exploring Central and Northern Portugal

14 Days of Old World Architecture and Fine Cuisine

Historically, Portugal has been much farther down on visitors’ lists than France, Italy and Spain. But more and more travelers have begun to discover its appeal: beautifully preserved Old World architecture, a varied landscape dotted with medieval towns, underrated cuisine and lovely, hospitable people. Now flights are being added to meet the booming demand, and the hotels, restaurants and shops are becoming much more sophisticated. The long lag in development means the Portuguese remain refreshingly unpretentious, despite their proud emphasis on their country’s products — from wine and olive oil to wool and ceramics — and cultural heritage. 

Most visitors spend a few days in Lisbon, take a side trip to see Sintra’s romantic palaces and then head to the sunny beaches of the Algarve. But it’s worth spending some time exploring other areas of the country, stopping in the city of Porto, the Douro Valley wine region, the plains and hill towns of the Alentejo, and the chic beach resort of Comporta. Driving is easy — the highways are excellent and well-maintained — and the rail network is extensive. English is widely spoken. You certainly won’t be the only tourists on this itinerary, but it includes a few places off the beaten path. Spring and fall are the optimal times to visit, with warm temperatures, abundant sunshine and fewer crowds than summer. 

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Spend a day in the medieval Alfama district
  • Explore central Lisbon
  • Visit the palaces, castles and gardens of Sintra
  • Tour Jerónimos Monastery in Belém
  • Enjoy the architecture of Porto
  • Visit Ribeira, Porto’s colorful historic center
  • See the bookstore that inspired Harry Potter’s Hogwarts
  • Tour the wineries of the Douro Valley
  • Explore the Alentejo region
  • Visit the hilltop village of Monsaraz
  • Stay in Comporta, a low-profile getaway for in-the-know Europeans

Trip Overview

Day 1 : Arrive in Lisbon
Day 2 : Lisbon
Day 3 : Lisbon – Day Trip to Sintra
Day 4 : Lisbon
Day 5 : Porto
Day 6 : Porto
Day 7 : Douro Valley
Day 8 : Douro Valley
Day 9 : The Alentejo
Day 10 : The Alentejo
Day 11 : Comporta
Day 12 : Comporta
Day 13 : Comporta
Day 14 : Drive to Lisbon and Depart
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Day 1 : Arrive in Lisbon

An increasing number of nonstop flights serve Lisbon from the United States. The flag carrier TAP Portugal, now co-owned by the founder of JetBlue, has improved markedly in recent years with new planes and a popular free stopover program.  

The dining area at Bistro 100 Maneiras in the Alfama district of Lisbon
The dining area at Bistro 100 Maneiras in the Alfama district of Lisbon - Fabrice Demoulin

After you arrive, spend your first day in the medieval Alfama district, whose winding streets and steep staircases will stimulate your post-flight circulation. (If jet lag gets the better of you, take the tram: The popular route 28 passes by many well-known attractions.) At the very top of the hill sits the Castelo de São Jorge, a Moorish citadel; the view from its crenellated towers provides an ideal first-day orientation to the city. 

As the sun sets, enjoy a glass of wine at one of Alfama’s many miradouros (viewpoints), such as Miradouro da Graça or Miradouro das Portas do Sol. Have dinner at a casual spot like Prado or Bistro 100 Maneiras. (See our list of recommended restaurants in Lisbon.)

The view from Castelo de São Jorge in Lisbon
The view from Castelo de São Jorge in Lisbon - Photo by Hideaway Report editor

Overnight at one of our recommended hotels in Lisbon, such as Santiago de Alfama, Santa Clara 1728 or Palácio Belmonte, all in Alfama; central Valverde Hotel or Pousada de Lisboa; or Olissippo Lapa Palace, 10 minutes from downtown.  

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Santa Clara 1728

Set within an 18th-century mansion, this six-suite hotel is located in a relatively quiet section of the Alfama neighborhood.

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Olissippo Lapa Palace

This lavish 109-room hotel overlooks the Tagus River in a quiet residential-embassy district, 10 minutes from downtown.

Day 2 : Lisbon

Spend the day exploring central Lisbon, whose neoclassical architecture — much of it built after the devastating 1755 earthquake — makes for a pleasing visual uniformity. Its compact size allows for easy exploration on foot. From the imposing Praça do Comércio square, walk through the gridded streets of Baixa to Chiado, home to many upscale shops, cafés and restaurants. (Bairro do Avillez, a collection of restaurants from the Portuguese celebrity chef José Avillez, is a solid choice for lunch.) Then head up Rua da Misericórdia, taking in the view at the Miradouro de São Pedro de Alcântara, and enter the Príncipe Real neighborhood. This tony district, centered around a pretty park, contains chic shops as well as the city’s Botanical Garden.    

Taberna restaurant at Bairro do Avillez in Lisbon
Taberna restaurant at Bairro do Avillez in Lisbon - Photo by Hideaway Report editor

Day 3 : Lisbon – Day Trip to Sintra

About 30 minutes west of central Lisbon, the former summer home of Portuguese royalty is a popular excursion; avoid weekends and Mondays, when closures in Lisbon swell the crowds here. A host of fairy tale palaces, castles and gardens are tucked within its forested hills, among them the Moorish-Manueline Palácio Nacional de Sintra, the symbol-laden Quinta da Regaleira and the whimsically romantic Palácio Nacional da Pena.

Palácio Nacional da Pena in Sintra
Palácio Nacional da Pena in Sintra - Photo by Hideaway Report editor

Day 4 : Lisbon

The Belém district of Lisbon, near the mouth of the Tagus River, is associated with Vasco da Gama, Henry the Navigator and their fellow explorers. The Monument to the Discoveries, whose granite prow leans out over the water, honors them all. Long lines are inevitable at the Jerónimos Monastery and the National Coach Museum, but the wait to try one of the famous custardy tarts at Pastéis de Belém is easy to dodge: Simply walk past the counter and find a table inside. On the way back from Belém, stop at LX Factory, a former industrial complex converted into a retail and dining destination; the rooftop bar at funky Rio Maravilha provides a splendid perch for a sunset drink. (See our shopping recommendations in Lisbon.)

The Jerónimos Monastery in Lisbon
The Jerónimos Monastery in Lisbon - Photo by Hideaway Report editor

Day 5 : Porto

High-speed Alfa Pendular trains to Porto leave Lisbon frequently from the Santiago Calatrava-designed Oriente station; the trip is comfortable and takes just under 3 hours. 

Portugal’s second-largest city, Porto charms with its colorful cityscape, Port wineries and superb setting on the Douro River. Prosperity from the maritime trade, wine in particular, left it with a distinct architectural heritage that continues today. The University of Porto School of Architecture counts two faculty members who have received the Pritzker Prize. (Be sure to see these five architectural landmarks in Porto.)

The view of Porto from the terrace of The Yeatman

Spend your first afternoon in Porto wandering the medieval maze of Ribeira, the colorful historic center, not missing the dazzling gold-leafed interior of the Igreja de São Francisco. The neighborhood culminates in a beautiful promenade along the Douro facing the scene-stealing Ponte de Dom Luís I bridge and the Port warehouses on the far bank. Set back slightly from the waterfront, seafood restaurant Terreiro is a low-key option for lunch or dinner. (See all of our Porto restaurant recommendations.)

Overnight at The Yeatman hotel.

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The Yeatman

This stylish 83-room hotel is located on a hillside above the Port lodges of Vila Nova de Gaia with spectacular views of Porto across the Douro river.

Day 6 : Porto

Make the Livraria Lello bookstore your first stop of the day to avoid waiting in a long line: Its exquisite interiors supposedly inspired the Hogwarts School in the Harry Potter books, which explains the crowds swarming its sinuous staircases. From there, explore Porto’s other treasures, including the azulejo-clad São Bento train station, the iconic Clérigos bell tower and Serralves, a cultural institution comprising a contemporary art museum, an art deco villa and beautiful gardens. Later in the day, head across the river for a tasting at one of the Port warehouses in Vila Nova de Gaia.

A dish from Pedro Lemos in Porto
A dish from Pedro Lemos in Porto - Photo by Hideaway Report editor

For an elevated dinner, we recommend Pedro Lemos, a Michelin-starred restaurant in the Foz do Douro neighborhood whose tasting menu puts a modern spin on traditional Portuguese flavors. 

Overnight at The Yeatman.

Day 7 : Douro Valley

Today head out of Porto and into the region to which it owes its riches: the Douro Valley, one of the world’s oldest wine-growing regions and perhaps the most beautiful. Pick up your rental car in Porto (if you’re using Avis, be sure to pop into Rem Koolhaas’s masterly Casa da Música performance hall, just up the street from the downtown location), then drive east for about 90 minutes. The stretch of the N222 that winds along the river between Peso da Régua and Pinhão is a particularly scenic drive. 

Six Senses Douro Valley next to the river in the Douro Valley
Six Senses Douro Valley next to the river in the Douro Valley - Chris Caldicott

Overnight at Six Senses Douro Valley if you want a more traditional resort experience, or at Quinta da Côrte, a winery with an intimate luxury guesthouse feel. (If you choose the latter, the Six Senses property is a good pit stop for lunch.) 

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Quinta da Côrte

This 60-acre family-owned estate comprises a contemporary winery and an eight-room hotel. 

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Six Senses Douro Valley

This striking hotel on a 19-acre vine-planted hillside overlooking a sinuous bend in the Douro combines a traditional 19th-century manor-house and contemporary buildings.

Day 8 : Douro Valley

Start your day with an hourlong cruise on the Douro in a rabelo, the traditional flat-bottomed wooden boats that were used to haul wine downriver to Porto. The landscape here is stunning, the Douro’s steep emerald banks terraced with vines and studded with white-walled, red-roofed quintas, or wine estates.   

A traditional rabelo boat on the Douro River in the Douro Valley
A traditional rabelo boat on the Douro River in the Douro Valley - Photo by Hideaway Report editor

Have a riverside alfresco lunch and tasting at Quinta de la Rosa, a small family-owned quinta perched riverside just outside Pinhão, where the rabelo cruises begin and end. In addition to fine Ports, it also produces excellent red and white table wines, beer and olive oil. The tasting includes a tour of the winemaking facilities, where the grapes are still stomped, Lucy-and-Ethel-style, before being fortified and aged in enormous oak barrels. Table wines are newer to the region but show promise and great value. The best, among them de La Rosa’s Reserve Red, have dark fruit, spice and floral notes that recall Port.

Day 9 : The Alentejo

The drive from the Douro Valley to the central Alentejo plain is scenic, but it takes around five hours. Break the trip up with a stop in Coimbra, the former medieval capital and home to Portugal’s oldest university. The school’s ornate baroque library, the Biblioteca Joanina, is one of the small city’s top sites, along with the 12th-century Sé Velha cathedral and its serene cloister.

A Courtyard Room at São Lourenço do Barrocal in Monsaraz
A Courtyard Room at São Lourenço do Barrocal in Monsaraz - Ash James

As you reach the Alentejo region, the landscape shifts to bucolic rolling plains flecked with olive trees and cork oaks, their trunks neatly stripped of bark. Continue east nearly to the Spanish border and check in at São Lourenço do Barrocal, a 1,900-acre family farm turned stylish resort. 


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São Lourenço do Barrocal

Located about two hours east of Lisbon, this fine countryside hotel is set within what was once a family-owned farming village that produced its own olive oil, wine and grains. 

Day 10 : The Alentejo

Spend a relaxing day at São Lourenço, where the offerings include a spa, horseback riding, hikes and bike rides through the estate, and tastings of the estate-made wine. The food, particularly the excellent breakfast spread and delicious dinners served by a crackling fireplace, is locally sourced and excellent. Consider a late-afternoon visit to Monsaraz, an ancient hilltop village about 10 minutes from the hotel. Its whitewashed cottages and stone fortifications are especially picturesque as the sun goes down.  

The grounds of São Lourenço do Barrocal

(Depending on your countryside-versus-beach druthers, you may choose to spend an additional day and night here and reduce your stay in Comporta by one night.)

Day 11 : Comporta

After departing from São Lourenço, stop at Évora, a gorgeous medieval town and UNESCO World Heritage site that is surrounded by 14th-century walls. Its winding lanes lead past whitewashed houses to several impressive churches, including the gothic Sé (cathedral), the skull- and bone-lined Capela dos Ossos and, opposite the incredibly well-preserved remains of a Roman temple, the Igreja de São João, its nave covered in blue-and-white azulejos. The Enoteca Cartuxa, a cheerful wine bar just across from the Sé, is a nice place to stop for lunch.

A tomb inside the Sé cathedral in Lisbon
A tomb inside the Sé cathedral in Lisbon - Photo by Hideaway Report editor

From Évora, proceed east around 90 minutes to the Tróia Peninsula on the Atlantic coast. Here, the village of Comporta and the surrounding beaches have become a stylish but low-profile getaway for in-the-know Europeans. Christian Louboutin, Jacques Grange and artist Jason Martin are among the homeowners here, but the area has resisted overdevelopment. Check into Sublime Comporta, the area’s best luxury stay, and have dinner at its fine restaurant. (Read our ”Perfect Day In... Comporta” article to get the most of your day there.)

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Sublime Comporta

Set within a 42-acre complex, this resort features a distinctive architecture that references local traditions and magnificent grounds with mature umbrella pines and cork oaks. 

Day 12 : Comporta

Unwind at Sublime’s spa and pool, or head to one of the area beaches, Comporta, Carvalhal or Pêgo. Each is blessed with perfect pale sand and unmarred by commercial activity other than the occasional beachfront restaurant, like Comporta Café and Sal. In the afternoon, drive to the village of Comporta, whose picturesque blue and white buildings include a handful of boutiques selling fashionable clothing and housewares.

The outdoor pool at Sublime Comporta in Grândola
The outdoor pool at Sublime Comporta in Grândola - Nelson Garrido

Overnight at Sublime Comporta.

Day 13 : Comporta

If you’ve had your fill of the beach, the hotel can organize various activities: horseback riding, golf at the challenging Troia course or dolphin- and bird-watching in the Sado Estuary. This evening, have dinner at Museu do Arroz, which serves local seafood in an exuberantly decorated former rice mill. 

Sublime Comporta
Sublime Comporta - Nelson Garrido

Day 14 : Drive to Lisbon and Depart

Ferries depart frequently from near the tip of the Tróia Peninsula to Setúbal, a small city south of Lisbon. From there, the drive to the airport takes around 40 minutes and includes a ride over the Vasco da Gama Bridge, at nearly 8 miles one of Europe’s longest.

Connect to your flight home.

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