The Most Beautiful Towns and Villages in Alentejo, Portugal

The biggest fortified city in Europe is a faded beauty, and well worth the two-hour road trip east from Lisbon. History buffs will love the unvarnished, crenellated castle, while romantics will lap up the pretty white-and-peach alleys that branch off of it. Stumble upon fondant-fancy mansions and churches trimming the city squares, as well as fabulous viewpoints from the city walls. There are spectacular historic sites just minutes from the historic centre, too. Don’t miss the four-tiered Amoreira Aqueduct or the immaculately star-shaped city walls of the Fort of Nossa Senhora da Graça.

This hilltop “museum village” of gnarled, sun-bleached buildings overlooks the tranquil Guadiana River, a stone’s throw from the Spanish border. The time-worn arches of its four city gates beautifully frame the dry countryside around it – a photographer’s dream. Venturing through them, you’ll find cobbled streets of wrought-iron balconies and swinging street lamps, with dinky 14th-century chapels and tiny museums to seek shade in. Need a proper break from the summer heat? Head for the smooth lakeside sands of Praia Fluvial de Monsaraz, a five-minute drive out of town.

Widely regarded as Portugal’s prettiest coastal town, pastel-painted Vila Nova is trimmed by a waterfront scattered with petite fishing boats. Compact enough to discover in a day – but with chic hotels that are well worth a night or two of your trip – this is Instagram heaven thanks to its wide drift of vanilla-sugar beach and sea-view restaurants serving simmering pots of pork or seafood stew. A reasonably lively centre with mini-marts and taxi firms also makes this a hub for solo travellers and self-caterers.

This crumbling, sleepy town might be most famous for its fantastically preserved Roman temple, but its historic centre has stories from every era. Home to Portugal’s kings in the 15th century, its features have been sculpted by Celts, Visigoths, Lusitanians and Moors. Take a walking tour to discover ornate buildings like the dainty azulejo-tiled Igreja dos Lóios, or the eerie bones and skulls lining the Church of St Francis. Along with Elvas, it’s one of a handful of Portuguese towns designated as a Unesco World Heritage site.

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.

The spectacular riverside location of this ancient settlement, which spills down a hillside towards the Guadiana River, makes it a must-see. Snap the views from the film-set medieval castle and Moorish city walls, then visit the town’s former mosque (now a church). Mértola is enveloped by green countryside, with forests of cork trees and water-based activities on hand. In the summer months, potter around the historic town in the cooler early morning, then make the short drive to one of the manmade lake beaches in the area, such as the sandy Praia Fluvial da Mina de São Domingos.

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.