Alentejo's Countryside & Coast

Your journey begins in Portugal’s vibrant capital city, Lisbon. This is one of the oldest continually inhabited cities in the world, and it wears its heritage on its sleeve with beautiful historic architecture and cultural attractions. A historic tour of the city should take in the magnificent Jeronimo Monastery and the Castelo Sao Jorge, which looms impressively over the city.

The UNESCO-listed Belem is dotted with relics of Portugal’s seafaring golden era in the Age of Discovery, while artistic masterpieces from across Portugal and beyond can be marvelled at in the Museu Nacional de Arte Antiga. To get a taste for Portuguese folk culture, attend a fado show – a form of traditional music, normally comprised of voice and guitar.

Your home during your cultural exploration of Lisbon is the Olissippo Lapa Palace, an impressive 19th-century mansion on the banks of the Tagus River.

Your road trip adventure starts here, as you pick up your car and hit the road for a couple of hours of driving inland to Evora. With its crumbling city walls, narrow cobbled streets and impressive medieval churches, Evora is a snapshot of the past; its older buildings are in varying states of decay, but some are incredibly well preserved, especially considering they date back to the 14th century.

Highlights include the Capela dos Ossos (Chapel of Bones), a church lined with the skulls and bones of thousands of people – an eerily beautiful memento mori. Even more majestic is the town’s cathedral, while Evora’s ancient history is evident in the Templo Romano, the ruins of which still stand on the site of the town’s Roman Forum.

You’ll spend two nights in Evora at the suitably historic Convento de Espinheiro, a luxury hotel housed in a former convent and set in sprawling olive and fig groves.

The next leg of your journey sees you enjoy a scenic drive south of around an hour and a half, to the wine country of Baixo Alentejo. You’ll stay for the next couple of nights at Herdade da Malhadinha Nova, a rural wine estate and five-star hotel.

With cows and black pigs roaming the olive groves and vineyards, this is a relaxed spot and a great place to get a feel for Portuguese country life – and, of course, enjoy some fantastic wine. The estate produces red, white and rosé wines, and you can sample each variety at either regular tasting sessions or on a peaceful picnic out in the grounds of the estate. A range of cultural activities are also on offer, from pottery to boot-making classes.

The final leg of your journey sees you driving from the countryside to the coast, arriving at the beautiful rugged scenery of the Costa Vicentina.

Your final hotel, Herdade do Touril, combines an oceanfront location with a rustic setting, surrounded by hundreds of hectares of unspoilt farmland. It sits on the Rota Vicentina, a collection of hiking trails which are perfect for exploring the beautiful landscapes of this coastal region. There are two trails on offer: the Fisherman’s Trail, which winds along the coast, and the History Walk, which connects historic towns and villages inland. There’s no need to choose between the two, though – walking both of them on separate days is the best way to really immerse yourself in the environment. Of course, if all that sounds a bit too much effort, there’s nothing stopping you from swimming, surfing, or just lazing in the sand at the stunning Odeceixe Beach.

After three nights exploring the coast and countryside of the Costa Vicentina, your self-drive adventure reaches its end, and you’ll return your car at Faro airport before your flight home.