If You Have 2 Days
Public transportation is preferable if you’re just hitting the main sights, but renting a car is a good way to get a little off the beaten track and pack a lot of experiences into a short time. Start in Lisbon and drive to Estoril, where you can soak up the atmosphere in the gardens and on the seafront promenade. From here, it’s only a short distance to Cascais, the perfect place for an alfresco lunch. Afterward, explore the little cove beaches and the Boca do Inferno. The next day, it’s less than an hour’s ride to Sintra, where before lunch you’ll have time to find a place to park and admire Sintra National Palace before making the climb to the Castelo dos Mouros (there is no car access to the castle, but buses and tuktuks make the trip if you don’t fancy a stiff hike). After lunch, return to Lisbon, stopping in Queluz to see the Palácio Nacional. For dinner, you might cross the Rio Tejo from Lisbon to Cacilhas for seafood.
If You Have 4 Days
From Lisbon, head for Queluz and its Palácio Nacional. In the afternoon, make the short drive to Sintra, where you can spend the rest of the day seeing the sights in and around the town. Consider having dinner in the adjacent village of São Pedro de Sintra. Head out early the next day to the extraordinary Palácio Nacional de Pena. Note that there is no car access to the palace, so allow time to park in the town center and make the ascent on foot or by bus. To contrast this ostentatious palace with a more humble sight, travel west to the Convento dos Capuchos before continuing to the headland of Cabo da Roca. Wind south to the wonderful beach at Guincho to catch the late-afternoon sun and have a bite to eat. Stick to the coastal road as it heads east toward Cascais, where you can spend the night.
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On the third day, drive back into Lisbon through Estoril. Cross the Rio Tejo via the mighty Ponte 25 de Abril, and detour for lunch at either Cacilhas or Costa da Caparica. It’s then only an hour’s drive to the mighty hilltop castle at Palmela,from where it is possible to take in views over the entire region before driving (6 miles) down the road to soak up sunny plazas and colorful street art in Setúbal. On the fourth morning drive through the Serra da Arrábida, taking in the jaw-dropping views and stopping for lunch at an esplanade restaurant in Sesimbra. From here, you can return to Lisbon in around 40 minutes.
If You Have 7 Days
Seven days exploring this region will allow the luxury of two nights in Sintra, providing time to see all the surrounding sights with ease. On the third day, drive straight to Cabo da Roca and then south to Guincho, if you fancy a half day at the beach, before following the coast around to Cascais. Two nights spent here will allow you to really get to know the town and travel to and from Estoril.
From Cascais, return to Lisbon and aim for lunch at either Cacilhas or Costa da Caparica. Spend the night at the pousada in Palmela On the final day, plan to have lunch in Vila Nogueira de Azeitão and continue on a drive through the Serra da Arrábida. Spend the night in the pretty fishing port and resort town of Sesimbra, where you can feast on some of the best seafood in the region. You’ll have time to visit the windswept Cabo Espichel the next day, before driving back to Lisbon.