Cascading down the banks of the Mondego River, Coimbra is a scenic city filled with a mishmash of architectural influences: Romanesque monasteries, baroque libraries and Moorish cathedrals sit side-by-side. At its core is Portugal's oldest and most prestigious university, a huge sugar-cube structure perched on a hill with an imposing 17th-century bell tower that crowns the city. More than just a historical checkpoint famed for its relics, Coimbra has a lively student population that ensures there's always an electric energy running through its veins - visitors will find it in the streets serenaded by the sounds of fado singers and in bars that line the riverbanks. Look out for the political graffiti scrawled across the walls.

Technically a town but with enchanting landscapes that resemble a page torn from a Hans Christian Andersen storybook, Sintra is worthy of a deliberate detour. Crumbling castles, fairy-tale turrets and champagne-bottle-shaped chimneys peak out from the misty wooded hillside that unfolds into the Atlantic. It's easy to see how this was once a summer playground for Portuguese royals. Stroll through the flamboyant estates, exotic gardens and whimsical grottos decorated with mythical creatures that once inspired Byron. Though Sintra is popular with day-trippers (it's just a 40-minute drive or bus ride from Lisbon), lingering a little longer in one of its candy-coloured casas means that you can absorb Sintra's jaw-slacking beauty at your leisure.

Hopeless romantics will feel at home here; in 1282 King Dinis gave Óbidos to a young Queen Isabel of Portugal as a wedding present. It's her you can thank for the town's handsome sun-bleached houses buried beneath creeping bougainvillea and the gothic doorways decorated with intricate tiles. Although, Óbidos doesn't just rest on its good looks. Historic spaces have been remodelled into contemporary bookstores - scout out first editions, design books and coffee-table centrepieces - while cobbled streets lead to artisan chocolate stores serving ginja, the local cherry-flavoured liqueur. Coincide visits with the town's many festivities: come in July for the open-air theatre at the Medieval Fair, bibliophiles should book in October for the literary festival and November sees the town covered in sugared sculptures for the annual International Chocolate Festival.

Once a meeting point for kings in the Middle Ages, Évora has retained all its glory and grandeur. Arguably more photogenic than Lisbon, its narrow lanes reveal whitewashed houses with yellow trimmings the colour of pasteis de natas and expertly preserved Roman ruins dating back to the first century. Take coffee in the pretty Praça do Giraldo square before heading to Paço de São Miguel for views across the rust-coloured rooftops. After seeing the city's main sights, hire a car to explore the rural region outside its walls - the area is a hotbed for agriculture and production. You'll find rolling hills, rows of vineyards and marble quarries glistening in the Alentejo sun.