Lisbon and the Alentejo: A Chic Luxury Holiday in Portugal


May - October


From £5,200pp excl. flights
(based on 2 ppl sharing)

How long

6 nights ideal length

Sitting snugly in the crook between Spain and the warm tides of the Atlantic, Portugal has all the vibrancy of its neighbour to the east, but with fewer crowds and a number of added hidden gems. From the whir of Lisbon’s iconic tramlines to the regal splendour of Cascais, and the wild corner of Portugal’s unspoilt Alentejo region home to the chic rural hideaway São Lourenço do Barrocal, Portugal is never short on fascinating culture and spellbinding beauty. Our travel experts have travelled the length and breadth of the Seven Hills of Lisbon to curate a trip that will see you swaying along to the tones of the Fado, and mastering the art of the Pastel de Nata. So, spend a week living as the trendy Lisboans do as you take in the history and nightlife of Lisbon before heading inland to discover the beauty and history of the Alentejo region. We won’t just take you away from the crowds, but get you ahead of them too.

The View from Up Top

The perfect start to any trendsetting trip to Portugal, get a feel for historical elegance in its capital, Lisbon. Framed by the Seven Hills, lapped by the waters of the Rio Tejo and cobbled up to the hilt, this is a city that comes postcard-ready and needs no filter to show off its beauty. Make yourself at home on one of the hills at the grand Four Seasons Ritz and spend three days living like royalty amid lavish 18th-century decor.

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First things first, you’ll get your bearings on a private tour of the city’s most happening neighbourhoods as you hop on board the city’s iconic tram and head into Bairro Alto. Lively and full of energy, this is the place to sway along to the melancholic tones of the fado. Continue onto Chiado and discover a cultural enclave where the great writers and philosophers of the 20th-century used to gather to hone their ideas. Ticking off the city’s hills as you go, next up is the picture-perfect neighbourhood of Alfama. Here, you’ll get a feel for traditional Lisbon with its narrow cobblestoned streets and the stunning 12th-century Sé de Lisboa Cathedral before learning to cook petiscos like a local in a private cooking class, before turning your hand to the famous Pastel de Nata. From there, the only way is up; up to one of the cities most iconic miradouros at Castelo de São Jorge. Looking out over centuries of history as the sun glints and turns the city a dusky shade of pink; it’s Lisbon at its most magical.

In the evening, you’ll head back into Bairro Alto and enjoy a night at one of the city’s best fado restaurants, where good food, the perfect setting and the melancholic tones of the fado come together for a truly authentic night in Lisbon.

Culture by the Sea

Tomorrow, you’ll get a taste for Portuguese royal life as you take a trip out of Lisbon to the beautiful seaside town of Sintra. A UNESCO World Heritage Site, this charming town is studded with pastel-hued villages and palaces. Head into the historic centre for a picturesque stroll and discover historic buildings that now house quaint handicraft stores. The best sights in Sintra, however, belong hands down to Pena Palace, a hilltop palace of whimsical design and boasting sweeping views.

In the afternoon, you’ll continue onto the town of Cascais, stopping off at Europe’s most westerly point at Cabo da Roca on the way. Here, you’ll discover the cosmopolitan side to coastal living as you stroll from the Nossa Senhora da Luz Fort in the Old Town down to the sandy beaches of the Atlantic. From here, it’s a short drive back to Lisbon; but it’s not without its stunning vistas as you cruise along the famous ‘Marginal’ Road, taking in the stunning contrast of white sandy beaches that run along one side of the road and opulent fortresses that dot the other.

Laid Back Living in the Alentejo

After a few days of city exploration, we suggest taking some time out to relax and experience a slower side to Portugal. Luckily our travel experts know the perfect secret spot which has been in the same family for over 200 years located in Alentejo. São Lourenço is the ideal place to experience the Portuguese countryside by taking a stroll to see the organic farm or take a horseback ride to explore the sprawling estate. For vintners, the estate has an impressive wine cellar where they produce their own delectable wine, there’s also the possibility to participate in the activity of the Harvesting. In addition, this estate also offers wine tastings, balloon rides, star-trekking, cycling tours and many more activities, all perfect for a relaxing end to your stay in Portugal.

Where to rest your head

Four Seasons Hotel Ritz, Lisbon

Sitting right at the heart of all the buzz of Lisbon, the Four Seasons Hotel Ritz is the perfect base to rest your head whether…
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Sao Lourenco do Barrocal, Alentejo

Set in the rolling landscapes of The Alentejo, amid ancient holm trees, olive groves and vineyards, São Lourenço do Barrocal is a step back in…
View hotel

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