Portugal Road Trip: 2 Weeks of Culture, Coast & Countryside

The beautiful city of Lisbon lies draped across a string of seven hills on the western Iberian Peninsula and is the westernmost and oldest city in western Europe. Its long and tumultuous history has resulted in an aesthetic characterised by a haphazard combination of old and new; however, the aesthetic chaos of Lisbon only adds to its appeal and its undeniable charm. Bright yellow centenarian trams rattle their way up steep, tree-lined, cobbled streets; ornate ironwork balconies overrun with bougainvillaea sit above elegant outdoor cafes housed in ancient whitewashed, red-roofed stone houses; and a flurry of detailed mosaics decorate the sidewalks. Ancient statues adorn grand squares and hidden gardens. A diverse culinary scene, a plethora of fascinating museums, and numerous castles make it easy to see why Lisbon is one of Europe’s most misunderstood and underrated cities.

The Algarve’s southernmost city, Faro, has an elegant marina backed by a historical quarter dotted with white-washed Portuguese buildings, stately Catholic churches and age-old Moorish architecture. Its atmospheric squares and boulevards are paved with white and grey stone and lined with boutiques, designer stores, cafes and bars. There is no shortage of entertainment in this university town - it has a lively nightlife and a thriving arts and culture scene that caters to a wide array of audiences. There is plenty of opportunity for swimming and sunbathing on the area’s golden coast, and nature lovers will be in their element in the nearby Ria Formosa Reserve, with its incredibly biodiverse lagoon and coastal zone.

Located in the Alentejo region of Portugal, Beja is the capital city of the district of the same name, set at the heart of the ‘Golden Plain’ tourism area. Often referred to as the ‘Bread Basket’ of Portugal, it is surrounded by golden wheat fields, vineyards and olive groves, and produces delicious pastries, olives and wines. Home to charming squares, a glorious thirteenth-century castle, a wonderful traditional market and plenty of excellent restaurants, Beja provides a serene and delightful holiday spot and an authentic taste of Portuguese village life. Top attractions include the lavish Regional Museum, housed in a 15th-century convent; the fairy-tale-like castle, featuring a fantastic lookout point; numerous fascinating and well-protected ancient ruins; and the picturesque Jardim Gago Coutinho e Sacadura Cabral.

Located in the District of Évora in Portugal, the Vila Viçosa is rich in history, culture and architecture. Dubbed the ‘Princess of Alentejo,’ this charming village is an open-air museum. Surrounded by incredibly fertile soil, the town is known for its rich agricultural yields and marble, which is harvested in the area. Visitors to this little gem can look forward to an array of attractions, including the Marble Museum, showcasing the region's natural materials, the Old Church of Santa Maria do Castelo, Vila Viçosa’s main church; and the Ducal Palace of Vila Viçosa, an impressive royal palace. Don’t miss the opportunity to wander the quaint streets lined with a collection of beautiful heritage buildings, stay overnight at the Hotel Vila Viçosa, which is rich in history; and sample a wide variety of delicious Portuguese dishes.

Set roughly halfway between Lisbon and Porto, Coimbra is a vibrant, historical university town that flanks both sides of the Mondego River, with the old quarter on one side and the modern district on the other. A walk down the ancient town’s main street will take you past shops and cafes, culminating in an atmospheric plaza. The square is crowned by the 12th-century Santa Cruz Monastery, a majestic building of ivory-coloured stone with an elaborate arched entrance and an exquisitely detailed interior decorated with blue tiles. The University of Coimbra, dating to 1537, is Europe’s oldest university and the town’s main architectural attraction, while the Quinta das Lagrimas estate, with its forests, bamboo groves, poppy fields, and manicured gardens, provides a tranquil oasis just outside the city.

Located in northern Portugal along the Douro River estuary, the old sailing port of Porto is a World Heritage Site and the second-largest city in the country. While retaining the timeless charm of a small town, Porto also has many of the modern advantages of a metropolis. Browse the expansive art collection at the Soares dos Reis National Museum, view the ornate interior of the Church of Sao Francisco, and explore the medieval maze of stairways and terraces in the old quarter of Ribeira. Don’t miss the chance to visit the Vila Nova de Gaia area to sample some of Porto’s famous Port wine. Other popular attractions include the 12th-century Porto Cathedral, Clerigos Tower and the Harry-Potteresque Livraria Lello bookshop, showcasing some magnificent neo-gothic architecture.

Located in Portugal's Oeste Subregion, Obidos is a 12th-century city enclosed by walls that once protected it from medieval marauders. The town’s piece de resistance is its imposing stone castle that dominates the skyline with its crenellated walls and towers and now functions as a high-end hotel. Another highlight is the view from the town’s ancient walls: it is possible to walk around the entire fort in about one hour, taking in superb 360-degree vistas of the city and its surrounds. After navigating the whole perimeter, there’s no better way to relax than by popping into one of the local cafes for a shot of Ginja de Obidos, a strong, sweet cherry liqueur traditionally served in chocolate cups. Art lovers will delight in the exhibits of 16th-, 17th- and 18th-century Portuguese works at the Municipal Museum.

Set on the west coast of Portugal in the foothills of the Sintra Mountains, the town of the same name is a wonderland of historical castles and palaces. These architectural jewels range from the 12th-century Moorish fortress, with its imposing stone walls and the elegant white facade of the medieval Sintra National Palace, to the eerie Gothic extravagance and exquisite gardens of the Quinta Regaleira. The most famous of its ancient citadels is the hilltop Pena Palace, a Romanticist masterpiece with fantastical turrets, domes, vaulted arches and crenellated walls, recently restored to its original purple and ochre colours. Make sure to take a wander through the city’s old quarter, where a network of narrow alleys lead past exclusive boutiques and souvenir shops, cosy taverns and traditional bakeries; or head to Pena Park for a stroll along its beautiful forested trails.