Although Portugal is well-known for its beautiful city breaks and surf beaches, its rural breadbasket excels in scenic hillside communities.
Some of Portugal's most picturesque towns and villages may be found throughout the country's central Alentejo area, uniformly whitewashed as if rendered in frosting and capped with toytown red roofs and elegant bell towers. Day trips inland or down the coast will reveal their complex past, seen in vestiges of Moorish and mediaeval architecture, dizzying monasteries, and refractory city walls.
Comporta
Comporta is a chi-chi beach town with a bohemian vibe that rivals Ibiza or Tulum, with thatched fish eateries right on the sand and farmhouse-stle hotels with calm courtyard pools. Its appeal with the wealthy and famous - Madonna owns a mega-villa here - has given it the impression of "Portugal's answer to the Hamptons," but it's far less glitzy. Use it as a base to explore the Troia Peninsula, a 20km (12 mi) sliver of pristine beach that juts out north into Setbal.
Elvas
The world's largest fortified city is a faded beauty worth the two-hour drive east of Lisbon. The unadorned, crenellated castle will appeal to history lovers, while romantics enjoy its lovely white-and-peach alleyways. Discover fondant-fancy houses, cathedrals adorning city squares, and spectacular views from the city walls. There are other outstanding historic places within minutes of the historic centre. The four-tiered Amoreira Aqueduct and the beautifully star-shaped city walls of the Fort of Nossa Senhora da Graça are must-sees.
Évora
This decaying, peaceful town is most known for its magnificently preserved Roman temple, but its historic centre contains tales from every era. In the 15th century, it was home to Portugal's kings, and Celts, Visigoths, Lusitanians, and Moors moulded its characteristics. On a walking tour, explore elaborate buildings like the tiny azulejo-tiled Igreja dos Lóios or the macabre bones and skulls bordering the Church of St Francis. It is one of just a few Portuguese towns listed as a Unesco World Heritage site, along with Elvas.
Monsaraz
A stone's throw from the Spanish border, this hilltop "museum village" of gnarled, sun-bleached cottages overlooks the calm Guadiana River. The time-worn arches of the four city gates frame the parched countryside around it magnificently - a photographer's delight. You'll find cobbled alleyways with wrought-iron balconies, swinging street lamps, dinky 14th-century chapels, and little museums to seek shade. Need to get away from the summer heat? Drive five minutes out of town to the smooth lakeside sands of Praia Fluvial de Monsaraz.
Vila Nova de Milfontes
The pastel-painted Vila Nova is widely recognised as Portugal's most beautiful seaside town, with a coastline dotted with small fishing boats. This is Instagram heaven thanks to its wide drift of vanilla-sugar sand and sea-view eateries serving simmering pork or shrimp stew pots. It's compact enough to see in a day but with sophisticated hotels that are well worth a night or two of your vacation. A relatively active downtown with mini-marts and transportation companies makes this a popular destination for lone tourists and self-caterers.
Castelo de Vide
This walled hill village lies amid a beautiful green hiking area on the Spanish border in Portugal's distant mid-east. Chocolate-box charming, with a magnificent mediaeval castle complex and a Jewish Quarter harbouring many Spanish Jews during the Inquisition. It's a sleepy little place with sloping, cobbled roads, slanted roofs, fluttering laundry, and kittens snuggled beneath flower pots. On your explorations, you'll come across dozens of gorgeous small places. Stay in one of the little guesthouses here to enjoy views of the forested Serra de So Mamede mountains.
Zambujeira do Mar
This low-rise, russet-roofed seaside town, spread across the flat cliffs like marmalade on toast, overlooks a calm, sheltered beach. This is your charming village base for exploring the Costa Vicentina, an unspoiled stretch of coast just north of the Algarve, where you may walk, surf, rock climb, or relax on Blue Flag beaches. The town itself is small and charming. You'll sit on plastic chairs at a blue-checked tablecloth and eat unfussy grilled octopus and clam broth, and you'll stay in cottages transformed as no-frills hostels or B&Bs.
