A Rural Road Trip from Lisbon to the Alentejo, Staying in Boutique Hotels

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.

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.

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.

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.