Portugal: A Country Full Of Surprises

From Lisbon's Elegant Streets to the Algarve's Wild Coast

And Everything in Between!

Portugal has a habit of making people feel like they've found something the rest of the world is slightly late to. The strange thing is that millions of people visit every year, and the feeling persists. The light is different here, particularly in the south and in the hour before sunset. The cities have a quality that's genuinely hard to name: a combination of lived-in beauty and unhurriedness that other European capitals spend a great deal of money trying to manufacture.



We plan many trips to Portugal. Let us plan yours.


Why Portugal?

Portugal sits under three hours from the UK – under three hours from London to Faro – and yet manages to pack in more variety than destinations twice the flight time away. That’s the reason it keeps surprising people who thought they already knew what it was.


The food is outstanding and still underappreciated internationally. Proper fresh seafood, extraordinary pastries, wine that sits well above its reputation. The history runs deep in a way that keeps revealing itself: Lisbon and Porto are cities where Moorish, Phoenician and Roman traces turn up in street corners and market buildings and church walls, and you keep encountering them even when you weren’t looking. Compared to other major European destinations, Portugal also represents exceptional value.


It’s also a country that rewards people who like to move around. Hire a car, and you can spend a few nights in a city, drop down into wine country, stop at a medieval hilltop town and still make it to a beach hotel in time for sunset – all without a single long-haul flight. The Douro Valley is one of Europe’s great wine landscapes. The Alentejo has been quietly turning out some of the continent’s most interesting reds for two decades. The Algarve has more championship golf courses per mile than almost anywhere in Europe. And the coastal stretch around Comporta, just 90 minutes from Lisbon, has become one of the most sought-after spots on the Atlantic – wild beaches, rice fields, and a handful of genuinely beautiful places to stay.


For families with young children who need warm weather, luxury beach hotels and a short flight, Portugal is difficult to beat. For couples who want wine, history, walking and good restaurants without the crowds of France or Italy, it’s even better. And for anyone who wants to build a trip that mixes golf, culture, coastline and exceptional food – hopping between regions by hire car with a round or two of golf along the way – it’s the most underrated multi-centre destination in Europe.


Beyond all of that, the country has a pace that suits the kind of travelling we love planning. It doesn’t rush you.


Lisbon – One of Europe's Great Capital Cities

Most people expect somewhere pleasant and slightly faded. What Lisbon actually is takes a moment to absorb.


The miradouros are viewpoints perched above the old city, and from them the Tagus stretches wide and silver towards the sea. The azulejo tiles covering facades, church interiors, and metro station walls are extraordinary, and they're everywhere. The neighbourhoods of Alfama and Mouraria have been continuously inhabited since the Moorish period, and walking through them at night, when the streets are quieter, you can feel that in a way that's hard to manufacture anywhere newer.


The food scene has evolved significantly over the past decade. The classic tasca, where the fish is whatever came in that morning and the wine is cheap and good, still thrives. It now sits alongside more ambitious restaurants that have brought serious international attention to Portuguese cooking. Both are worth your time.


Allow at least three nights. Two will leave you with a list of places you didn't get to. And if you don’t eat Pastel de Nata – Portuguese custard tarts – every day you’re in Lisbon, you clearly didn’t try one on day one!


Our favourite hotel in Lisbon: Bairro Alto Hotel


The Douro Valley – Wine, Silence and One of Europe's Most Beautiful Landscapes

The wine terraces here were carved into near-vertical hillsides over centuries, mostly by hand, and the scale of it only becomes clear when you're standing in the middle of it. UNESCO gave the valley World Heritage status, which feels like an understatement once you've seen it in October light.


A visit to a quinta is one of the great pleasures of a Portugal trip. The wine estates line both sides of the river, and most offer tastings in cellars that have been producing Port since before Britain and Portugal signed the trade treaty that made it fashionable. Lunch afterwards, with slow-cooked local kid goat and sheep's cheese from the hills above, tends to run long. It's that kind of place.


See the valley by train if you can. The vintage service from Porto to Pinhão is one of Europe's most beautiful rail journeys, and it costs almost nothing. A river cruise through the valley, stopping at estates along the way, is the more indulgent option and equally worth it.


Our favourite hotel in the Douro: Six Senses Douro Valley


  • Livraria Lello Bookshop Porto

    Livraria Lello Bookshop Porto

    Livraria Lello Bookshop Porto

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    Livraria Lello Bookshop Porto

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    Livraria Lello Bookshop Porto

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Porto – Compact, Beautiful and Increasingly Hard to Leave

Porto is compact enough to explore on foot and has enough substance to fill several days without repetition.


The Ribeira district earns its reputation: medieval buildings stacked along the riverside, the port wine caves of Vila Nova de Gaia just across the bridge, the Dom Luís I bridge itself looming over it all. But the smaller details stay longer. The covered market at Bolhão. The baroque interior of São Francisco church, which is one of the most astonishing rooms in Portugal. The bookshop Livraria Lello, always full, is always worth the queue. The neighbourhood of Foz do Douro, at the western edge of the city where the river finally meets the Atlantic, is almost entirely overlooked by visitors.


Our favourite hotels in Porto are: The Yeatman and Hotel Pestana Vintage Porto


The Alentejo – Rolling Plains, Ancient Towns and Exceptional Wine

Most visitors who've been to Lisbon and the Algarve come back wanting to know what they missed in between. The answer is the Alentejo.


Cork oak and olive groves stretch to every horizon. Whitewashed villages appear in the heat. The hilltop town of Évora has a Roman temple standing in its centre as if it were built last century, intact and nonchalant in a way that catches you off guard. Monsaraz, perched above the Alqueva reservoir, is a preserved medieval village with views across the plain that go on long past the point where they should stop.


The wine has quietly made the Alentejo one of Europe's more interesting regions over the past two decades. The reds are warm, complex, and suited to long lunches in the shade. There are worse ways to spend an afternoon in the interior.


On the western edge of the Alentejo, where the land meets the Atlantic, is Comporta – a stretch of coastline that has spent years being described as Portugal’s best-kept secret while quietly becoming one of Europe’s most fashionable addresses. The beaches here are extraordinary: miles of white sand backed by pine trees and rice paddies, with almost no development in sight. It sits about 90 minutes south of Lisbon, making it an easy add-on to a city stay or a destination in its own right.


Our favourite hotels and wine retreats in the Alentejo and Comporta are: Quinta do Paral - Vidigueira, L'and Vineyards - Exclusive Wine Retreat and Quinta da Comporta – Wellness Boutique Resort


The Algarve – More Than Its Reputation Suggests

The Algarve has been a British favourite for so long that its reputation has slightly overtaken it in both directions: some people expect too much, others dismiss it too quickly.


The western end of the region is where the coastal drama is. Around Sagres and the Costa Vicentina, the cliffs face the Atlantic head-on and the beaches are broad, wild, and largely empty. The surfing is world-class. The walking is extraordinary. This is a different country from the golf resorts an hour east, and it's worth knowing the distinction before you choose where to base yourself.


The stretch between Lagos and Albufeira delivers what most families and couples are actually looking for: good weather, beautiful beaches, reliable restaurants. The key there is hotel selection, which makes a significant difference and is something we put real thought into.


Our favourite hotels in the Algarve are: Vila Vita Parc, Tivoli Algarve, and Bela Vista Hotel & Spa


The Azores – If You Want Something Extraordinary

These nine volcanic islands in the middle of the Atlantic are technically part of Portugal and feel like somewhere else entirely.


Calderas filled with lakes. Whales pass close enough to the boat that you can hear them. Hot springs on black volcanic beaches. The Azores are not a conventional beach holiday, and the weather can be unpredictable, but for the right kind of traveller, they are genuinely unforgettable. São Miguel is the natural starting point. Flores and Corvo, at the far western end of the archipelago, are as remote and beautiful as anywhere in Europe.


When to Go

May and June are the months we recommend most for Lisbon, Porto and the Douro. The temperature is ideal for walking, the evenings are long, and the summer crowds haven't yet arrived. September is excellent everywhere: still genuinely warm, noticeably quieter than August, and with a quality of light that rewards anyone with a camera.



The Alentejo gets fiercely hot in July and August, which suits some travellers entirely and deters others. Lisbon and Porto are rewarding year-round, with mild winters that make them very good short-break destinations from the UK.


How Tailormade Escapes Puts It Together


Portugal works well as a single-centre escape and equally well as a multi-stop journey – and the multi-stop version is something we think is genuinely underrated. Fly into Lisbon, spend a couple of nights in the city, pick up a hire car and head north to the Douro Valley for wine and stunning scenery, then south through the Alentejo – perhaps a night on the Comporta coast – and finish with a few days in the Algarve for sunshine, beaches and a round of golf before flying home. The whole thing is under three hours from London and doesn’t involve a single complicated transfer. For families, that combination – city, countryside, beach – works particularly well: children get the beach they want, parents get the culture and wine they want, and everyone gets the weather. For couples who want to build in golf, the Algarve courses are right there at the end. We design a lot of these combinations, and the logistics of doing them well are less obvious than they look on a map.


We'll ensure the hotels are right, the car hire and transfers are sorted, and that you arrive at each place knowing what's worth doing and where to eat. If Portugal is on your mind, get in touch, and we'll start building something around you.


Come see what we're all about

Ready to plan your escape?


At Tailormade Escapes, we create bespoke luxury holidays built entirely around you. From choosing the right island and resort to arranging flights, transfers and special experiences, your personal travel consultant will take care of every detail.


With full ATOL protection, access to the whole of the market and expert destination knowledge, you can relax knowing your holiday is in safe hands from start to finish.


Whether you’re dreaming of winter sun, a relaxed family holiday or a stylish escape by the sea, get in touch to start planning your getaway – designed just for you.


Contact Tailormade Escapes today and let us create your perfect escape.


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