The Highlights of Portugal

Duration 9 days
Price guide
From the historic beauty of Alentejo and the highlights of Lisbon, to the pretty coastal town of Cascais and Porto’s ancient port cellars, Portugal can easily hold your attention for weeks. This nine-day trip combines history and natural beauty with plenty of opportunities for good food and wine. You'll head home with wonderful new memories and a deeper understanding of Portuguese culture.

Trip highlights

  • Taste wines at an 18th-century estate in Alentejo
  • Explore the 2,000 year old city of Evora
  • Experience the power of fado, traditional Portuguese music
  • Discover the charming towns of Estoril, Cascais and Sintra
  • Tour the city of Porto on foot and by boat
  • Sip on the finest vintages of port at Churchill’s and Graham’s

Our bespoke trips include

We design one-of-a-kind journeys incorporating luxury in all its forms. Our bespoke trips include:

  • Luxury accommodation throughout
  • Privately guided tours
  • Private transfers
  • Meticulously selected experiences
  • Expertise and support from your Jacada Concierge
Black and white illustration of two guides pointing to a building in the distance
  • Days 1–3 Alentejo
  • Days 3–6 Lisbon
  • Days 6–9 Porto
The Highlights of Portugal
Price guide
  • Days 1–3 Alentejo
  • Days 3–6 Lisbon
  • Days 6–9 Porto

Itinerary in detail

Every Jacada trip is tailored to your personal preferences and interests. Below you’ll find a sample itinerary to inspire your own custom-designed journey.

Days 1–3

Two nights in the heart of Alentejo

Covering almost a third of the country, Alentejo is a vast region of cork plantations, wheat fields, vineyards and clusters of historic hilltop towns. Its name means beyond the Tajo, and it stretches south from the River Tajo to the northern mountain ranges of the Algarve encompassing rolling hillsides, rugged peaks, endless plains and sweeping Atlantic beaches.

Vast swathes of sand lay sheltered between rocky cliffs and over 100km of the coastline is part of the South West Alentejo and Costa Vicentina National Park, an area rich in animal and plant life.

Heading inland, Alentejo is littered with Roman ruins, crumbling Moorish castles, marble towns and whitewashed villages. The UNESCO towns of Evora and Elvas are home to baroque bell towers, temples and mighty fortresses, plus there are plenty of smaller atmospheric towns with winding cobbled streets to explore.

Evora old town in Portugal

The highlights of Alentejo

Quinta Dona Maria

This palace-like 18th-century estate is world-renowned for its beauty and the quality of its wines. At one point, it was acquired by King João V as a gift for Dona Maria, a lady of the court with whom he was madly in love. Explore the grounds and the gorgeous walled garden, learning the stories of the aristocrats that once spent hot summer afternoons here. Inside, the owner will invite you to enjoy a wine tasting and traditional lunch.

The town of Evora in Portugal

Exploring Evora

A UNESCO World Heritage Site known as the ‘museum city’, Évora traces some 2000 years of history. On your private tour, start in the main square, Praça do Giraldo, the heart of the city where you can see the 16th Century St. Anton’s Church. Beyond, explore the Gothic and Manueline influenced Church of St. Francis and the Capela dos Ossos, the Chapel of Bones. Évora’s Cathedral, by far the most dominating site in the whole town and the largest cathedral in Portugal.

Herdade da Mata Farm

At the Herdade Da Mata farm, we’ll arrange a tour and a picnic lunch. The Swiss owners live on the grounds and are delighted to share life on a typical Alentejo farm, from breeding cattle horses and goats to running the equestrian school. You will have the opportunity to meet endangered Garvonesa cows, enjoy spectacular views and spot many different species of birds.

Days 3–6

See Lisbon in luxury

Europe’s second-oldest capital, Lisbon is an effortlessly elegant city, full of old-world charm. Winding your way through its streets, you’ll pass rows of houses in warm shades of orange, yellow and rust red. Washing is strung from wrought iron balconies and window boxes overflow with flowers. Weaving their way through this pretty patchwork are the city’s trams, a great way to hop between the different districts.

There’s lots to see as you explore with an expert local guide: a plethora of museums and galleries as well as beautiful buildings covered in azelujo tiles. The city is built on seven hills, each one offering spectacular views, and is known for its lively restaurant scene.  There are plenty of places to stop, sip a coffee and savour a Portuguese custard tart.

Outside the city, you can spend a day discovering the charming traditional towns of Estoril, Cascais and Sintra.

Lisbon's Gloria funicular

Sightseeing and culture

Panoramic view of Alfama rooftops in Lisbon, Portugal

A historical tour of Lisbon

Your private tour will allows you to dig deeper into the history of Portugal’s capital. Visit the Castle of Saint Jorge and Alfama, Lisbon’s oldest quarter, before learning about the heroic deeds of the Portuguese maritime exploration in the 15th and 16th centuries. This was the Golden Era of Portugal, when Lisbon transformed into the opulent center of a vast empire. Monuments from this era can still be seen today.

The brightly coloured Pena Palace in Sintra, Portugal

Visit Sintra, Cascais and Estoril

In Sintra, hundreds of years of history and culture await. You’ll walk through the city centre and visit the 19th-century Pena Palace, the greatest expression of 19th-century romanticism in Portugal. Cascais is a coastal town, once a small fishing village, that became popular with artists and writers thanks to its idyllic scenery. You will also have time to explore the pretty seaside resort of Estoril.

Enjoy a fado performance and dinner

Many Portuguese would argue that you can’t truly know their country without hearing and understanding the traditional music. Fado is the melancholic song of Portugal, usually performed in a dark tavern by a singer and a small band of guitars, violas and basses. Tonight, you will be welcomed into the soul of Portugal in one of Lisbon’s most emblematic fado locales for a traditional Portuguese meal and a show.

Explore Tomar and Fatima

Venture out of Lisbon to visit Tomar, one of Portugal’s most historic cities. Its Templar Castle and Christ Convent became the national headquarters of the Templar Knights in the middle ages, and later was at the forefront of the Order of Christ. In Fatima, visit one of the most important catholic shrines in the world dedicated to the Virgin Mary, which welcomes millions of pilgrims and tourists from all over the world.

Days 6–9

Three nights in Portugal's second city

Porto is one of Europe’s most charming cities. Built on a steep riverbank, its jumble of colourful medieval houses hug the calm waters of the Douro River where wooden boats bob on the surface and people spill out of its cafes and bars.

Once you’ve settled into your accommodation, you’ll be joined by a guide for a walking tour of the city, followed by a boat tour. Enjoy the views of the old town and bridges as you slip by in the fading evening light.

Finally, raise a glass or two of port to an amazing Portuguese trip as you visit Churchill’s and Graham’s Port Wineries and sample some of their finest vintages. What better way to bring your adventure to a close?

A traditional tiled church in central Porto

The best of Porto




A private tour of Porto

This tour is a great introduction to Porto, its history and its cultural treasures. Discover medieval relics, soaring bell towers, extravagant baroque churches and stately beaux-arts buildings piled on top of one another. Along the way you’ll visit landmarks such as the Stock Exchange Palace, the Church of Saint Francis, the Cathedral and the ornate Lello Bookstore in the historic Ribera district.

An evening on the Douro

The best way to discover the romantic and mythical city of Porto is from the water. Cruise along the Douro River on your private boat and enjoy a glass of local wine as the views of soaring bell towers, baroque churches, and stately beaux-arts buildings are illuminated by the last rays of the sun. Once the sun has set, the lit-up homes seem to dance along Porto’s hills, and the city takes on a whole new character.


Tasting the finest ports

Churchill’s winery was founded by John Graham in 1981, and was the first British port wine company to be established in 50 years. It was named for. his wife, Caroline Churchill. Their unique ports are produced from vineyards on the south bank of the River Douro, in the prestigious Cima Corgo sub-region. You’ll also stop for a tasting the historic Graham’s winery, built in 1890 on a hilltop in Vila Nova de Gaia, a strategic location between river, ocean and the lush green hills.