One day trip from Lisbon that really rocked. Sintra, Cabo di Roca, legendary Guincho beach...
30 kilometers north of Portuguese capital there is one splendid town, that really doesn't fit into this rough, dry and rocky country of simple pleasures and crumbing estates for sale. Sintra reminds more of Disneyland, though fortunately is not anyhow cheap or kitschy, if anything then fairy-tale like.
Refreshingly green and cool when compared to Lisbon and whole boiling south, this mountainous royal nest gathers some of the most fantastic old villas I have ever seen, plus two castles looking at each other form impressive hill tops. Colorful and palace-style La Pena blends all sorts of naive, roman architecture trends while rough and monumental ruins of Moores' Castle seem to boast of patriotic pride and glorious history. Both require some pleasant hiking and both are worth an effort.
You could most certainly spend whole day in Sintra roaming through cute noble streets, admiring outstanding pieces of architecture and pleasing yourself with local pastries and coffee, but we made it somehow quick and headed west towards very rewarding coast. First on the way is Capo da Roca, westernmost point of mainland Europe, with breathtaking cliffs and great ocean view (as well as possibility to obtain a certificate of reaching that far) and then south towards Lisbon there is most crazy beach, that all the windsurfers and kitesurfers have wet dreams about. Guincho is not really for swimming or suntanning most days, as wind here can be a devil, but live water show is worth seeing even if you don't fell the vibe yourself. Drama of broken sails and torn kites, huge fight with nature, inhuman jumps and stunts - we were left literally speechless, as many other spectators and photographers on land.
In case you didn't make it to Lisbon by night there is accommodation right at Guincho beach (rather basic one) and lots of lodging and eating opportunities in Cascais, cute and stylish summer resort 10 km west from Lisbon. Good hotels are plenty there but we managed to find at local tourism office a very decent room with kitchen for one night for 35 euros for 2.