First up on this West Portugal road trip, Lisbon has caught everyone’s attention in recent years. Its reputation as a hub of all that is cool and creative has become common knowledge. Which is why it’s the perfect start for 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 but also spectacular views.

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

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

Surfers already know about Peniche, whose beaches are rated some of the best for waves in the country. But for those on a West Portugal road trip, Peniche is the perfect follow up to a few days of late nights and indulgence in the Portuguese capital. It has an authentic, slightly gritty feel, and you’ll still come across fishermen mending their nets by the harbour.

In August, the town has its Nossa Senhora da Boa Viagem festival. So head on to your next destination to enjoy the fresh sea breeze and even fresher sardines.

To find out what makes these waves so great, head to Praia dos Supertubos, which, in October, is the location for the Rip Curl Pro competition. Another must is the Ilha da Berlenga, a granite island and nature reserve 7 miles off the coast.

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

Running between Peniche and Coimbra (next on this West 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 general tourist track.

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 from one another. All are exceedingly old and pretty, yet have very different histories—both culturally and architecturally. A road trip between said sites is easily done and very rewarding.

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

Second, Batalha literally means battle. The Monastery of the Battle 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 out of the three, as it’s 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 West 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 super-smart student population, the city has heaps 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 up 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, which is another plus. So no better place to spend your last few nights in Portugal than in Porto, your final West 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.