Escape the Crowds, but not the Luxury on the Alentejo Coast

If you've spent any amount of time in Portugal, one of the first things that strikes you is the impeccably blue sky that dominates from above so many days a year. They call Montana open sky country, but I beg to differ: Having now lived outside Portugal after five years as a resident, the sky still floors me immediately upon my return. As I roll out of Lisbon on my way to the Alentejo across the EU's longest bridge (the cable-stayed Ponte Vasco da Gama), the blinding blue sky is in full spectacle mode. I'm back, baby. 

You know you've reached the Alentejo when you see the cork trees which pepper the landscape throughout the region (Portugal is the world's largest cork producer). I head off the main highway towards the beach at Melides, where a fine patch of golden sand separates the sea from the lagoon. The rustic beach bar here is the kind of place folks dream about escaping to, beer in hand, and losing a few days. It's just a pit stop for me, though. My sights are set on a different piece of paradise.

A gravely road outside of small village of Cercal, 25 miles south of Melides, leads me past an arsenal of tall, slender Eucalyptus groves on my way to Herdade da Matinha, an idyllic countryside house that floors me from arrival. In the heart of Parque Natural do Sudoeste Alentejano e Costa Vicentina, this expanded home is a peak into the eccentric mind of charismatic owner Alfredo Moreira da Silva, whose fantastically colorful paintings and wonderfully mismatched décor combine to create a rural utopia of art and design. Baroque mirrors and hand-painted vases - generations of antiques dot the property – sit alongside sink-into sofas and wicker patio furniture enveloped by bright throws and vibrant pillows. Each room is infused with a dash of carefully curated contemporary art as well. There's a pool and wonderful food and wine, too, but truth be written it's hard to tear yourself away from each lounge's whimsical and fascinating ornamentation. 

The next morning, I head for Porto Côvo, an archetypal traditional Portuguese fishing village surrounded by some of the Alentejo's most sun-kissed sands. Bang in the village, Praia dos Buizinhos is a sight to see: A small cusp of golden sand backed by a semi-circle of jagged coastal cliffs. From there, it's one doozy after leading to the spectacular Praia da Samoqueira, which seems as though its sands connect between a fjord-like series of craggy bluffs. 

I stop for lunch at Arte e Sal on the coast near Sines, a family-run seafooder that attracts droves for doing what Portugal does: Pummel you with a cavalcade of fine seafood and homespun hospitality. Filipe Barros, the heir to this seaside seaside gem, showers me with regional specialties: A perfect vinegary octopus salad, a simple but seamless grilled grouper, wonderful migas de espigos (a savory bread crumb pudding made with garlic, olive oil, stale bread and broccoli rabe) and shrimp swimming in a sauce of coconut milk and fresh coriander — of which nothing survived after I sopped up all that remaining goodness with pão alentejano (Alentejo bread).

Suitably stuffed, I make my way to my next stopover, Monte do Zambujeiro, just outside what is easily one of my favorite seaside villages in Portugal, the remarkable Vila Nova de Milfontes. With rooms and a pool perched above the Mira River, Monte do Zambujeiro feels perfectly isolated, yet sits a mere 3 miles from the town. It's a perfect getaway from a getaway. I manage to snag the self-standing Casa do Rio (River House), which, with its outdoor shower, barbecue and river view patio along with a fully equipped kitchen, temps me to move in. 

Back in Vila Nova de Milfontes, one of the most striking seaside setups in the country never ceases to amaze. As the sea gives way to the Mira, river beaches border both sides, all of which sit harmoniously under the village, which is elevated above in all its whitewashed glory. Dinner here means Tasca do Celso, a local taverna boasting a near-legendary status.