The Highlights of Portugal
- Duration
- 9 days
- Price guide
- From $11,824 per person
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

Itinerary in detail
Every trip is shaped around you. Below is a sample route to start from; we change any part of it to suit you.
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.

Where you could stay
Days 4-6
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.

Where you could stay
Days 7-9
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?

Where you could stay
★★★★★
“My trip to Portugal was wonderful”
My trip to Portugal was wonderful! I planned it with Meg and Rita, and their suggestions, answers to my questions and support all the way made my trip! I could not have done it without them! I travelled alone, so especially as a senior , my family knew I was really not alone! The drivers I had in Lisbon to…
Bea Lennan · Trustpilot
Why book with Jacada
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Personalised design
We’ll plan your trip around your personal interests, tastes and preferences, providing honest advice based on first-hand knowledge.
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Authentic experiences
Our expert guides and brilliant Concierges are hand-picked for their ability to bring your destination to life with care and passion.
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Positive impact
We seek out unforgettable experiences that benefit both local communities and the environment.
Start planning your trip
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