Sintra is a charming town located in the lush hills of the Serra de Sintra amidst an evergreen pine forest known for its whimsical villas and the ruins of a 10th-century Moorish castle. The main attractions include the vibrancy-coloured yellow Palácio Nacional de Pena, the Neo-Gothic mansion of Quinta da Regaleira and the medieval Palácio Nacional de Sintra. The town's entire centre is a UNESCO World Heritage Site. Some day tours to Sintra will also include a visit to Cabo da Roca — the westernmost point in Europe, as well as a stop in the Cascais bay area.

The largest cultural institution in Portugal was founded in 1955 when Calouste Gulbenkian, the Armenian oil millionaire, donated his estate to the country that had welcomed him during World War II. This museum houses his extensive collections and is part of a larger complex that includes concert halls, a park, restaurants and a museum of modern art.

These lavish gardens were constructed in 1694 as a residential retreat for Mitsutomo, the second Lord of the Owari clan. Sadly, however, most of the garden and its buildings were destroyed during World War II. The restoration took a long time, with the garden being finally opened as a public park in 2004. If time permits, visit the adjacent Tokugawa Art Museum, the third oldest private museum in Japan, which miraculously survived the World War II air raids.

The Dales is one of the Island's iconic sites and one of the few places with permanent flowing water and stunning wet areas, providing significant habitat for endemic blue crabs and impressive stands of Tahitian chestnut trees. The drive through the Dales leads through rainforest to a scenic and tranquil area, which has two walking trails starting from the Dales 4WD car park. The first trail is mostly a boardwalk, leading to Hugh's Dale Waterfall, about 1 kilometre each way from the car park. Signage along the trail offers information on the island's plants and animals. For the adventurous, the second trail leads on from Hugh's Dale for about 800 metres to Anderson's Dale, a small gorge with a stream that flows to the sea.