First up on this western Portugal road trip, Lisbon has been grabbing everyone’s attention in recent years. Its reputation as a hub of all that’s cool and creative is well known — which makes it the perfect place to start a holiday.

Get ready for incredible scenery, amazing food, great prices — oh, and lots of walking uphill. The city is set out over seven hills, which makes for both a serious thigh workout and spectacular views.

Begin with a stroll through the Moorish Alfama, one of the most characterful neighbourhoods in the city. Then hop on Tram 28E up to Castelo de São Jorge and wander the ramparts. In Belém, visit the beautiful Mosteiro dos Jerónimos, or head to the site of Lisbon’s Expo 98 and explore the aquarium.

Enjoy exquisite seafood, from octopus to snails, as well as those famous custard tarts. Finish with a shot of ginjinha, the cherry liqueur, then head out to explore Lisbon’s late-night scene in Bairro Alto.

Surfers already know Peniche; its beaches are rated among the best for waves in the country. For those on a road trip through western Portugal, Peniche is the perfect follow-up after a few late nights indulging in the Portuguese capital. It has an authentic, slightly gritty feel, and you’ll still see fishermen mending their nets by the harbour.

In August the town holds the Nossa Senhora da Boa Viagem festival. So head to your next stop to enjoy the fresh sea breeze and even fresher sardines.

To see what makes the waves so good, go to Praia dos Supertubos, which in October hosts the Rip Curl Pro. Another must is Ilha da Berlenga, a granite island and nature reserve about 11 km off the coast.

Check out the local artisan speciality, Renda de Bilros — bobbin lace. And for sunset, head to Cabo Carvoeiro, right at the tip of the peninsula.

Running between Peniche and Coimbra (next on this western Portugal road trip) lies a route of three towns famous for their incredible, UNESCO-listed monasteries. Famous being relative here because the towns of Alcobaça, Batalha, and Tomar are very far off the tourist trail.

Situated in the Leiria region of central Portugal, the monasteries of Alcobaça, Batalha, and Tomar (situated in the Santarém region) are all within a 65 km stretch of one another. All are exceedingly old and pretty, yet have very different histories—both culturally and architecturally. A road trip between these sites is easily done and well worth it.

First up is Alcobaça, an old town straddling the Alcoa and Baça rivers. Its monastery, the Royal Abbey of Santa Maria, was founded in 1153 by Cistercian monks who had the land donated by Dom Afonso Henriques, Portugal’s very first king. Talk about legendary.

Second, Batalha literally means 'battle'. The Monastery of Batalha commemorates the victory of the Portuguese over the Castilians in 1385. A masterpiece of Gothic architecture, it was the country’s principal religious building for two centuries thereafter.

Lastly, Tomar’s monastery is called the Convent of Christ. It’s arguably the most interesting of the three, as it was originally a Templar stronghold from the 12th century. Not sure why that makes it so interesting? Well, the Templars might be European Christianity’s most controversial order and they remained active in Portugal long after they were outlawed by the Pope.

Next up, back to more urban pleasures as you arrive at your next western Portugal road trip destination.

Beautiful Coimbra is famous for being the hilltop home of Portugal’s oldest and most distinguished university. But aside from buzzing with its really bright student population, the city has loads of gorgeous architecture for you to admire and is basically a history lesson in the form of a city. A history lesson with a fun side, though, thanks to its many affordable bars.

Visit the university’s Baroque library with its elaborate frescoes. Also check out St Michael's Chapel with its 3,000-pipe organ. Then there’s the Sé Velha, the city’s 12th-century cathedral. On your way, look out for students dressed in traditional black capes, carrying briefcases with coloured ribbons.

Also make sure to catch one of the hourly performances at the Fado Centre on the Escada do Quebra-Costas — a street whose name roughly translates as ‘Backbreaker.’ Because, yep, Coimbra, like Lisbon, is painfully hilly.

Last stop on your Portuguese coastal adventure is Porto. Like Lisbon, Porto is making a name for itself as a hip and happening city.

A thriving centre for art, fashion and nightlife, with a gritty grandeur and arty edge, it’s also home to a rather famous fortified wine — another plus. So there’s no better place to spend your last few nights in Portugal than in Porto, your final western Portugal road‑trip destination.

Art lovers must visit the famous Serralves art centre, home to a major collection of works by Joan Miró. But there’s also cool street art to be seen everywhere, as well as the stunning azulejos, or blue ceramic tiles, in places like São Bento railway station. For views, head up to Jardim do Morro.

When it comes to dining, there are Michelin-starred restaurants or equally good local petiscarias. Plus, across the water in Vila Nova de Gaia, barrels of maturing port can be heard calling your name.