The Most Beautiful Towns and Villages in Alentejo, Portugal

Right by the Spanish border, in Portugal’s remote mid-east, this walled hill town is in a lush, green hiking area. Often visited in tandem with nearby Marvão, it’s chocolate-box cute, with a pristine medieval castle complex and a Jewish Quarter that sheltered many Spanish Jews during the Inquisition. It’s a soporific little spot with sloping, cobbled lanes and slanted roofs, fluttering laundry and cats curled up beside flower pots. You’ll find dozens of photogenic little corners on your wanders. Stay in one of the dinky guesthouses here to wake to views of the forested Serra de São Mamede mountains.

From its thatched fish restaurants sitting right on the sand to farmhouse-style hotels with serene courtyard pools, Comporta is a chi-chi beach town with a bohemian style that aligns it with the likes of Ibiza or Tulum. Its popularity with the wealthy and famous – Madonna has a mega-villa here – has led to an image of “Portugal’s answer to the Hamptons”, but in reality it’s far less flashy. Use it as a base to explore the 20km (12mi) Troia Peninsula, a wisp of unspoiled beach that juts out north towards Setúbal.

Spread across the flat cliffs like marmalade on toast, this low-rise, russet-roofed coastal town overlooks a smooth, sheltered beach. This is your pretty-village base for the Costa Vicentina – an unspoiled, outdoorsy stretch of coast just north of the Algarve where you can hike, surf, rock climb or laze on Blue Flag beaches. The town itself is compact and quaint. You’ll sit on plastic chairs at a blue-checked tablecloth to tuck into unfussy grilled octopus and clam broth, and stay in cottages repurposed as no-frills hostels or B&Bs.