Built on a series of hills overlooking the broad Tagus Estuary, Lisbon is one of Europe’s most visually striking cities. But its elegantly homogeneous appearance is partly the result of a catastrophic earthquake and tsunami that destroyed much of the city in 1755. Only the Alfama neighborhood, clinging to the hillside underneath the Castelo São Jorge, retains its original medieval alleyways and an air of Moorish influence.

The Portuguese rebuilt in grand style, and now Lisbon’s buildings and monuments provide a constant reminder that the city was once the hub of a far-flung colonial empire. It remains at the center of a Portuguese-speaking world that includes Brazil, Angola, Mozambique, East Timor, Goa and Macau. The city can now boast an excellent subway system, an array of new museums and an old port that has been renovated into a stylish restaurant and nightlife district. Yet it is also wonderfully unchanged. The sidewalks are still paved with small squares of white stone, wooden trolley cars rattle by, laundry is still strung between the shuttered windows of ancient houses with tiled façades, and at nighttime a mournful snatch of fado (the national song that evokes the sorrow and wistfulness of life) creates an atmosphere that is sepia-toned and utterly unique.

Set close to the Atlantic, Lisbon’s climate is relatively mild from May through October, but even in winter the city makes a very pleasant change of pace from the northern half of the United States. The following itinerary includes the top sights in the city and its surroundings. It could be a fantastic week-long vacation in itself, or continue on to explore the Douro Valley or the Algarve.

Day 1

Arrive in Lisbon and transfer to the Olissippo Lapa Palace, a lavish hotel on a hilltop overlooking the Tagus River, or the Palácio Belmonte, occupying an exquisitely restored 15th-century palace in Alfama. In the afternoon, explore the evocative Alfama district and ascend to the Castle of St. George for panoramic views of the city.

Days 2 & 3

Dig deeper into Lisbon. Visit the extraordinary National Coach Museum and the ornate St. Jerónimos Monastery where Vasco da Gama is buried. Wander the white streets of the Baixa, lined with outdoor cafés and restaurants. Mr. Harper notes that Lisbon’s best wine shop, Manuel Tavares, is at the top of this district on Rua da Betesga. The fashionable and atmospheric Bairro Alto district, just to the west of Baixa, is the traditional home of fado music.

Day 4

Sintra was once the favorite summer retreat of the Portuguese royal court, and it continues to rank as a top day-trip destination. Major sights include the 19th-century Palácio Nacional da Pena, which looks straight out of a fairy tale, and the equally enchanting Palácio Nacional de Sintra, the summer residence of the kings of Portugal. Many people miss the elaborate Quinta da Regaleira, a Manueline/Gothic mansion filled with enigmatic symbols relating to the Freemasons, Rosicrucians and Knights Templar.

Day 5

A former fishing village, Cascais is now a wealthy suburb of Lisbon and an excellent place to spend a relaxing day outside the city. Its beaches can be crowded on summer weekends, but even then, it’s a pleasure to stroll the pedestrianized old quarter and visit sights such as the Museu Condes de Castro Guimarães, a converted 19th-century mansion. Among other intriguing and beautiful decorative objects, this museum houses a 16th-century book with an illustration of how Lisbon appeared before the devastating earthquake.

Day 6

The white hill town of Obidos is no stranger to tourists— an overabundance of souvenir shops clutters its main pedestrian street—but off the beaten track, the city still has plenty of atmosphere within its dramatic defensive walls. The balconies of whitewashed houses overflow with colorful flowers, and charming cafés and restaurants set up outdoor tables along the winding side streets. Have lunch at whichever catches your fancy. For something more upscale, opt instead for the stylish restaurant in the Pousada de Obidos (open daily) or the fine Restaurant Cozinha das Rainhas (closed Tuesdays and Wednesdays).

Day 7

An hour and a half inland from Lisbon, the walled city of Evora has been declared a World Heritage site, and the ruins of a Roman temple stand in one of its main squares. Renaissance palaces and medieval mansions line the narrow streets of the center, making Evora an ideal city to explore on foot. Besides the temple, visit the Praça do Giraldo (a vibrant market square), the medieval cathedral, the ornate church of St. Francis and the well-preserved remains of some Roman baths. Also consider stopping in one or two of the fine wineries between Evora and Lisbon to do some tastings (the unusual and lightly fortified Moscatel de Setúbal, made on a peninsula across the Tagus from Lisbon, is particularly worth seeking out, especially if well-aged).

This article was originally featured in the Traveler magazine.