A 79 km loop
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A proper escape from Lisbon with roads worth waking up for. A 79 km loop that starts and ends near Lisbon, about 1 h 26 of riding. It goes by way of Sintra and Cascais. It was put together for the scenery rather than the shortest line.
Lisbon is built on hills, as the old joke goes, to give the trams something to do. The city rises from the north bank of the Tagus river on seven hills, a tumble of tiled houses, church domes and steep cobbled lanes, with yellow trams creaking up the slopes, and the great red suspension bridge, the 25 de Abril, spanning the estuary. In 1755 a huge earthquake, followed by a tsunami and fires, destroyed much of the centre and killed tens of thousands, and the flat grid of the Baixa district was rebuilt afterwards under the Marquis of Pombal. The hill quarters of Alfama and Mouraria, which came through, still have their medieval twists and turns.
The city's character lies in small things. Fado, the melancholic music of longing, comes from cellars in Alfama and Bairro Alto, and the best places are small and quiet. Tiled walls cover buildings in blue, white and yellow. At Belém, just west of the centre, the Tower of Belém and the Jerónimos Monastery commemorate the age of exploration, when Portuguese ships sailed to India and Brazil, and a bakery nearby sells custard tarts, the pastéis de Belém, made to a recipe that is a close secret. Cod, grilled sardines and strong coffee fill the rest of the day.
The ride out of town toward the Atlantic is a favourite. The N247 follows the coast west from Cascais, passing Guincho beach, a windy surfing spot backed by dunes, and then reaching Cabo da Roca, the westernmost point of continental Europe, a cliff of about a hundred and forty metres above the ocean. Inland lies Sintra, with its palaces hidden in misty hills. Roads are generally good but busy, and the cobbled streets in town are very slippery when wet, so take care on tram tracks, which can catch a front tyre. Wind and sea fog are common on the coast.
Fuel is easy to find, though on the city's one-way streets finding parking can take time. Motorway tolls are electronic, so check how to pay if you plan to use them. Late spring and early autumn are the best seasons, and August brings crowds and heat.
Lord Byron called Sintra a glorious Eden, and for once the poet was not exaggerating. The Serra de Sintra is a granite ridge that catches Atlantic cloud and holds it, so while Lisbon bakes the hills above Sintra are green, cool and often wrapped in mist. Up in the trees stand fantasies built by Portuguese royals and rich romantics: the Pena Palace in yellow, red and blue, built in the nineteenth century for Ferdinand II, a German-born prince consort with a taste for the theatrical, and the Moorish Castle, whose walls snake along the ridge above.
Further down are Quinta da Regaleira, with its spiral initiation well, and the Monserrate gardens, with plants from every continent. All of this explains why the town is on the world heritage list, and why the visitor numbers are enormous. In the old centre the pastries are the local religion: travesseiros, flaky pillows filled with almond and egg cream, and queijadas, small sweet cheese tarts.
For a rider, Sintra is two things at once. The roads climbing through the serra are delightful: narrow, wooded, twisting between moss-covered walls and huge boulders, with the odd view of the sea far below. But they are also shared with tour buses, tuk-tuks, hire cars and queues. Early weekday mornings or the off season are the only sensible times, and even then expect cobbles in the village and wet leaves on shaded bends. West of town the road runs out to Cabo da Roca, the westernmost point of mainland Europe, where a lighthouse stands above cliffs that fall straight to the surf. Wind there is fierce, so tuck in and keep your visor down.
The municipality has hundreds of thousands of people, with big suburbs like Algueirão and Mem Martins running into town, so fuel, supermarkets and repair shops are easy to find on the lower side, away from the hills. Parking a motorbike near the historic centre is usually easier than for a car, though there is no guarantee in high season. Pack a layer, since the serra is often ten degrees cooler and damper than the coast, and leave time for a pastry.
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.