Itinerary Highlights
    • After the sweetness of Lisbon, enjoy the Alentejo, the scent of the scrubland and the ocean, and the wild beaches of the Serra d'Arrabida

    • We'll show you secret spots to visit, and chic refuges for nature-loving adventurers

    • Lisbon with a Lisbon native, a private discovery of Evora, a visit to wine estates: it's all included in the itinerary

    • Car, our app loaded with places to visit, local Concierge service, all our usual additional services

Contact one of our specialists + 44 (0) 20 3958 6120

The capital city, secret locations

From the vibrant capital to the oceanic charm of the Alentejo, to its hinterland and promising hillsides, this trip offers a range of delights as only Portugal could provide. It is on foot that Lisbon best reveals the charm of its shaded terraces and facades of azulejo tiles. In Alfama, you'll tap into the soul of these popular, tangled streets. When they get too steep, locals and tourists alike take the funicular lines, the most common means of transport in the capital, using the Eletrico. Then head south. Just half an hour from Lisbon and easily reachable by car, the Alentejo feels like another country entirely. In Grandola, your first stop, the waves seem to come from the end of the world, completing their journey on the coast a few minutes from your hotel.
But try to resist the lure of the sea for a moment. Try taking your time; getting lost in the shades of green of the plains, noticing the hills covered with oaks and olive trees, wandering through the villages of white houses dotted with flowers along the irregular cobblestones. The town is close to Comporta. It's a place to whisper about, afraid the secret will get out. You'll then head east and through genuine backcountry. The bucolic region of Monsaraz is not lacking in quality wine-producing areas and generous gastronomy. Finally, at the end of the Troia peninsula, the ferry will take you to Setubal, a former sardine port. You'll take the road to the Serra d'Arrabida Natural Park, a beautiful park overlooking the mouth of the Sado. Here the hills melt into the sea and the cliffs plunge steeply.

Your Journey

Travelling with us means benefiting from a range of customised services. Like freely discovering Lisbon in the footsteps of a local during an informal and personal meeting. Or try regional specialties at Herdade do Esporao and visit its cellars thanks to our advance reservation. How best to explore the sublime Evora? Rely on your private, knowledgeable guide to answer any questions you might have. The Alentejo is still a little-known wine-growing region which runs along the hillside. You'll have a reservation at Casa Ermelinda Freitas to get to know it better. Throughout this gentle road trip, you'll enjoy the assistance of our local Concierge, who will be at the ready for last-minute reservations, or, for example, to postpone a visit by an hour so you can sleep late.


Everything is 100% tailored to you

Flight to Lisbon

Private transfer to your hotel, just a short stroll from the Tagus. Its neo-Moorish style dates back to the late 1800s, with interiors resembling the Brazilian Art Nouveau style that was in vogue at the time of its construction. Despite a recent renovation, the property has retained all of its original features, as well as the decorative and architectural elements that comprise the building's interior and exterior. This gentle facelift makes it a great choice to lay your head for your two-night stay.



Included in the itinerary - A walk to experience Lisbon like a local, with a local guide. A fine connoisseur of the city, they will share little-known spots and favourite places with you. You'll walk through cobblestone streets as they regale you with amazing stories, and explore some mansions and small churches that are usually closed to the public, along with art galleries and flea markets. It's an improvised walk where you can spend a few hours living the Lisbon life; you set the pace with your preferences and questions.
Optional - Dinner at Chef Jose Avillez's Cafe Lisboa restaurant.


Lisbon - Grandola

Pick up rental car and drive to Grandola. Two-night stay at a property in the heart of the Serra de Grandola, a typical village of Alentejo set about nine miles from the ocean. The small 'aldeia' is inland, bordered by hills of cork oaks as well as farmland. Modern history gave it its name during the 1974 Carnation Revolution, when the song 'Grandola, Vila Morena', previously banned under the Salazar regime, became the Portuguese revolutionary anthem. Your hotel looks like a contemporary cabin, a mirage of pristine trapezoids and pure lines. The serene surroundings are redolent of olive trees, enveloping the grounds - and its guests - in a sense of total wellbeing. The same feel continues indoors, in the sizeable rooms highlighted by large windows and extended private terraces. A few laps in the pool will complete the blissful picture.



The Alentejo region seems to exist to make those who venture there happy, whether you're drawn by the Atlantic beaches, inland pastures, or explorations along winding and hilly roads. Comporta appears like a mirage a few miles north of Grandola, a stone's throw away from the Sado estuary and its nature reserve. This small seaside village has all the essentials for chic adventuring. The picture-postcard landscape - sand as far as the eye can see and authentic fishermen's huts - also contains a handful of trendy spots. Comporta is still a secret oasis bathed in sunshine, where Lisbon natives head on weekends, and travellers in search of sunny calm linger. Comporta is best kept a secret.
Optional - Go riding in Comporta.


Grandola - Monsaraz

Drive east and inland. Two-night stay just minutes from the charming village of Monsaraz. This 19th-century estate has been carefully restored by the family that owns the property, and a renowned architect, with the express purpose of preserving the area's soul, ancient farming traditions and history. The result is superb: delightful tranquillity, exquisite refinement, discreet luxury and great service. Meals are brimming with local produce and recipes; the organic breakfast is wonderful, and the pool is very nice as well. Also on site: a spa, Pilates sessions, and visits to a winery followed by tastings. Bikes are available to explore the area.



We head upwards in Monsaraz. From the hill, which rises to almost 984ft, the Guadiana River flows quietly and the landscape of the Alentejo stretches as far as the eye can see. Get lost in the medieval streets lined with white houses with red rooftops. Visit the castle and dungeon, the former court, and the church of Nossa Senhora da Lagoa. Around the city are numerous megaliths and neolithic tombs. A few hundred yards from Monsaraz is Xerez with its spectacular neolithic menhirs (standing stones) and dolmen (a stone resting flat on others); and a few miles to the north is the carved menhir of Bulhoa. proof that man has been taken by the Alentejo region for some time.
Already in the itinerary - Lunch at the Herdade do Esporao winery, with a visit to its cellars.


Monsaraz - Setubal

As you head to Setubal, you may choose to bypass the mouth of the Sado through the hinterland. But it would be a shame to miss out on the panorama of the Troia Peninsula, a striking strip of land in balance between river and ocean. At the end is the village of the same name, its Roman ruins and a ferry which sails to Setubal. Quiet two-night stay, a little away from the coastal city. Your hotel is bordered by 17th-century quinta (estate) vineyards. Everything here celebrates tranquility, from the spacious and beautifully thought out rooms to the pool, set above the vineyards.
Already included in the itinerary en route - A tour of Evora with a private guide. Evora is the capital of the Alentejo region and a UNESCO World Heritage site. A white hilltop city sheltered by its walls, it has long been a favourite residence of Portuguese rulers. Apart from an exceptional density of churches and monuments, the city has preserved its gentle lifestyle. Evora is a living museum of a city with great historical and cultural richness. The famous temple of Diana is a good example of the Roman presence in the city, and the cathedral bears witness to medieval times. The historic centre is surrounded by walls built in the 17th century. Visits include the Cathedral and Basilica of Our Lady of the Assumption and the Chapel of Bones.



From Setubal, head a few miles west to Arrabida Natural Park. Fun fact: it may be located on the Atlantic side, but its vegetation recalls the landscapes of the Mediterranean. Pines and scrubland protect secret beaches and unexplored coves. Cliffs and stunning views appear along rolling trails. They continue to the summit, where the convent of Arrabida, built in the 16th century, stands. The white buildings contrast with shades of green and blue.
Included in the itinerary - A private visit to the Casa Ermelinda Freitas estate to discover the best local wines.


Setubal - Return flight

Drive to Lisbon and return the rental car. Priority clearance through airport formalities and return flight.

A la carte

Dinner at a Lisbon restaurant

The official restaurant of the Teatro Nacional Sao Carlos, Cafe Lisboa is headed by Jose Avillez. The country's most renowned chef, he offers gourmet bistro cuisine, combining reimagined burgers with updated Portuguese classics. The refined setting is a must for its elegance and simplicity. When the weather is warm, the very pleasant terrace serves as an open-air theatre for divine concerts under the stars. It is this mosaic of qualities that makes it successful.


Riding in Comporta

Nestled in the Sado estuary, the small fishing village of Comporta is the perfect setting for a ride. The walk begins through stork-filled rice fields, ending at a huge white sandy beach, where horses can gallop freely along the shore.


The Alentejo is home to prehistoric remains because it has been inhabited since the dawn of time. The towns and villages of Monsaraz, Alqueva, and Mourao sparkle white, and you can marvel at the unspoiled nature of Serra da Estrela.


A Rough Idea of Price

Dependent on season, accommodation and activities
The estimated cost for this trip starts from £3,245 to £5,180 per person. The final cost of the trip depends on the way we tailor it especially for you. The final cost will vary according to several factors, including the level of service, length of trip and advance booking time. The exact price will be shown on your personalised quote. The average starting price for this trip is £4,145 per person.
  • Flights to and from Lisbon

  • Airline taxes and fuel surcharge

  • Private transfer upon arrival

  • Seven-day car hire

  • Two-night stay in Lisbon, suite with breakfast included

  • Two-night stay in Grandola in a suite with breakfast included

  • Two-night stay in Monsaraz in a double room with breakfast included

  • Two-night stay in Setubal in a double room with breakfast included

  • Private tour of Lisbon in the footsteps of a local

  • Lunch and wine tour at Herdade do Esporao

  • A visit to Evora with a private guide

  • Private tour of the cellars of Casa Ermelinda Freitas, with tasting

  • Priority clearance through checks at Lisbon airport

  • Our local Concierge service

A few of the benefits of travelling with us
Get in touch
Our experts have the inside track on the destinations they sell and will tailor-make a holiday to your unique requirements.
Contact one of our Portugal specialists