Cascais has been rich for a long time. It began as a fishing village at the mouth of the Tagus estuary, became a royal summer retreat in the nineteenth century when the Portuguese court started spending the warm months by the sea, and has since turned into a pleasant seaside town for Lisbon's well-off and its visitors. The small citadel stands over the harbour, fishing boats bob on the water, and the old centre has patterned pavements, pastel houses and a pedestrian main street lined with cafés.
The riding on the way in is a classic. The N247 follows the Atlantic coast from the west, past Guincho beach with its wind and kite-surfers and the rocky cape of Cabo da Roca, the westernmost point of mainland Europe, then curves into Cascais through pine and dune. The road has long open bends, sea views and a surface that is mostly good, but traffic is dense on summer weekends and the wind off the ocean can be strong enough to lean on. Just along the coast, the Boca do Inferno, a chasm where waves crash into a sea cave, draws crowds who lean over the railings.
As a stop, Cascais works best for fuel, coffee and a wander. With thirty-odd thousand residents and the neighbouring Estoril merging into it, the town has petrol stations, supermarkets and every kind of restaurant. Fish is the thing to eat, grilled sardines in summer, sea bream or bacalhau, followed by an espresso and a pastel de nata if you like. The fish market by the harbour has a good morning atmosphere, and the promenade towards Estoril is pleasant to walk, with the casino at the other end for those so inclined.
Parking for motorcycles is easier than for cars, but expect narrow streets and the occasional one-way detour. The town is busiest on weekends and warm evenings, so mid-morning on a weekday is far calmer. If you have time, the park at the former royal residence, with its peacocks and shaded paths, is a quiet place to cool down.
Lisbon is about thirty kilometres away along the coast, which makes Cascais an easy bookend to a day on the headland roads.