Beautiful historic cities and a scenic, rugged coastline; spectacular monasteries and a James Bond casino; great food and excellent wines to match – all part of the route that takes you from Lisbon to Oporto. Explore the land of the medieval explorers: a three-day self-drive holiday itinerary that leads you to some of Portugal’s outstanding World Heritage sites along the way.

Belem: the Monument to the Discoveries

Day 1  Lisbon-Caiscas-Estoril-Sintra-Estoril   Approx 104 kms
Start the morning with a drive west along the Marginal de Cascais (N6), the coastal road that leads to Estoril and Cascais. As you leave Lisbon you pass through Santa Maria de Belem, which sits at the mouth of the long flowing River Tagus. It’s known as Belem to the locals: the name means Bethlehem.

Much of Belem dates back to the early 18th century, when royal residences and aristocratic homes were built there in the wake of the devastating earthquake and tsunami of 1755. Belem is also home to the historic Jeronimos Monastery, which was constructed by King Manuel I at the end of the 15th century to commemorate Vasco de Gama's successful voyage to India.

Treasures from Portuguese explorations in Africa, Asia, and South America, as well as a heavy tax on the lucrative Portuguese-controlled spice trade with Africa and the East funded the building of the richly ornate monastery. The Treaty of Lisbon, which laid down the basis for the reform of the European Union, was signed there at the end of 2007.

Between May and September the monastery is open from 10.00 to 18.00: it closes an hour earlier the rest of the year; and like most museums in Portugal, it is closed on Mondays throughout the year. There is no charge to visit the church, but there is a set of age-related entrance fees to explore the cloisters: 4.50 Euros for those 26 and older; 2.25 for those between 15 and 25; with free admittance for those over 65 or under 14.

Here’s a money saving tip. If you are intending to visit several museums while in the Lisbon area, consider buying a LisboaCard: it gives free accesss to museums and public monuments, plus local trams and cable cars – as well as a 50 per cent discount on entry fees at many other places.

The Portuguese were once great explorers: the majestic Monument to the Discoveries (Padrao dos Descobrimentos), located on the edge of the northern shore of the River Tagus, was erected in 1960 to commemorate the 500th anniversary of the death of Henry the Navigator. The son of King John I (a Portuguese king also known as John of Happy Memory and, less flatteringly, John the Bastard), Henry is regarded as the true patron of Portuguese exploration: he played a very important role in developing the country’s maritime trade with other continents in the 15th century.

Something for foodies: on Rua de Belem (close to the beautifully laid out avenue called Praca do Imperio) you’ll find the famous pastry shop Fabrica de Pasteis de Belem, known for a Portuguese confectionery called the pastel de Belém (an egg tart made with flaky pastry). What makes them so good? Nobody can say -- the locals will tell you that the secret recipe invented by two Catholic nuns from the neighbouring Jeronimos Monastery back in the mid-1800s has been heavily guarded over the years.

Cascais

From Belem it’s a little over half an hour’s drive along the Atlantic coast (depending on the time of the year and holiday traffic) to the pretty towns of Estoril and Cascais, an area known for excellent beaches and the Estoril Casino; one of the oldest casinos in Europe. Ian Fleming based his James Bond thriller Casino Royale on Estoril’s casino.

With its elegant shops and wide choice of cafes, bars and restaurants, Cascais has come a long way from being a small, sleepy fishing village. You can transport yourself back to earlier times at the sea museum, which brings alive the town's close association with the Atlantic. Also visit the 16th-century citadela, part of a whole line of fortresses once built along the Tagus estuary to protect Lisbon from invasion: you’ll get a beautiful panoramic view of the area from the fortress.

The Mouth of Hell

Nature lovers will want to head for the nearby Boca do Inferno (Mouth of Hell), an unusual crater-shaped rock formation constantly pounded by noisy, foaming Atlantic waves. It’s just a couple of kilometres west of Cascais. Further along the coast is the sandy Guincho beach, a favourite with surfers and windsurfers.

From Cascais take the road that winds north to Azoia, where you make a small detour along the Estrada do Cabo da Roca to a lighthouse that sits at the the most westerly tip of continental Europe. Until the early 15th century, the rugged Cabo da Roca was considered by the Portuguese to be the end of the known world, beyond which lived all sorts of fearful monsters: today it has a lookout point, a café (tasty pastries) and a souvenir shop (usual kitsch).

A bit of trivia: at Cabo da Roca you can buy a document to certify that you have visited The Most Westerly Point in Europe. All you need to do after that is visit the Russian Urals in the east, Cape Nordkinn in the north of Norway, and Punta de Tarifa in southern Spain to complete your collection.

Cabo da Roca lighthouse

Carry on in the direction of Sintra, and if you are thinking of lunch stop off in the hillside village of Colares, about twenty minutes from the Cabo da Roca. Colares is best known for its rich red wine, which makes a stop here that much more interesting.The vines of the Colares region are some of the oldest in Portugal, the vineyards having survived the devastating phylloxera, which destroyed most of Portugal's grapes in the late 19th century.

Colares gets a foodies’ thumbs up for one or two local restaurants, including the Refugio de Roca ( a bit on the pricey side, but serving excellent seafood dishes) and Toca do Julio (try the succulent young goat meat, roasted on a spit).

From Colares the road weaves it way east to Sintra, a drive that should take about twenty minutes, but can often take almost double that, depending on local traffic.

Surrounded by green forests, Sintra is one of the oldest places in Portugal. First settled by the Romans, it is known for its magnificent palaces, built centuries ago as summer retreats for Portuguese royals. Cool and breezy Sintra was the perfect place for them to sit out the summer; away from the sizzling heat and city scents of Lisbon. Lord Byron, the English poet, described Sintra as 'glorious Eden' in his autobiographical poem, Childe Harold.

Pena Palace, Sintra

There are several historic attractions to explore in Sintra, starting with the National Palace on the main square, which dates back to 14th century: a superb collection of paintings, sculptures, tapestries and furniture. Sitting on a mountaintop overlooking Sintra, Pena Palace is a breathtakingly rich mix of architectural styles: impressive drawbridge, towers, impenetrable battlements and exquisitely furnished royal chambers. This extravaganza, built by the Germanic husband of Portugal’s Queen Maria II, Ferdinand of Saxe-Coburg-Gotha, means negotiating a steepish climb on foot through the woods of Pena Park – but it’s worth the effort. Ferdinand was a nephew of the eccentric King Ludwig II of Bavaria, who built the fairy-tale Neuschwanstein castle on southern Germany’s famous Romantic Road.

The Castelo dos Mouros (Moorish castle) on the opposite hill is much older, and was the scene of bitter warfare in the mid-1100s when the Crusaders captured Sintra from the Moors. Snaking along the mountain ridge, it boasts superb views that stretch far along the coast – though like the Pena Palace, it means some uphill walking. The Castelo dos Mouros, the Pena Palace and the Sintra National Palace, are all UN World Heritage sites.

If you are travelling with children, you might want to head for the Museu do Brinquedo, or Toy Museum on Rua Visconde Monserrate: it’s open daily (except Mondays) and has a vast and eclectic collection of more than 20,000 toys exhibited over four floors – everything from toys from the Roman days to dolls and Dinky cars. The entrance fee is three Euros.

A top tip: if you were thinking of spending the night in Sintra and want to do it in style, Lawrence’s, an elegant, small boutique hotel in the centre of town, is said to be the oldest hotel on the Iberian Peninsula, dating back to the mid-1700s.

From Sintra you return to Lisbon on IC19, a drive of less than thirty kilometres. It’s a road that can get very busy in rush hours as people commute into and out of Lisbon. That is why it’s best to make this day trip from Lisbon in a clockwise direction.

Accommodation options: Altis Avenida Hotel, Hotel Avenida Palace, Eurostars Das Letras.

Day 2: Depart: Lisbon   O/night: Coimbra  Approx: 232 kms
Head north for Coimbra, visiting Obidos and Batalha along the way. Just a hundred kilometres north of Lisbon, Obidos is a beautiful small medieval town, surrounded by ancient city walls. Walking around the ramparts it is difficult to believe that this little town was once a significant port: the sea inlet silted up in the 16th century and destroyed its trade. The ramparts walk rewards you with marvellous views of stubby Don Quixote-style windmills, sprawling vineyards and surrounding farmlands.

The whitewashed houses along the narrow cobblestone streets within the town’s walls are carefully decorated with coloured flowerbeds -- in spring Obidos is ablaze with geraniums and bougainvillaea.

A bit of royal history: the town was given by the King Dinis I (known as the Farmer King) to his new wife Isabel as a wedding present in 1282. And the church of Santa Maria in Obidos is where the King Afonso V married his cousin, Isabella of Coimbra – they were both fifteen years old at the time. Afonso had taken the throne on the death of his father in 1438 when he was only six years old. He later became the most powerful man in Portugal and one of the richest men in Europe. Afonso and Isabella had three children before she died aged only twenty-three. Some say she was poisoned.

There are two entrances to Obidos: one is from the main parking area in the south, through a narrow gateway lined with 18th century blue tiles: the other is at the north of the town, reached through the 13th century castle, which is now home to a fairly luxurious yet small pousada: it has only nine rooms.

Monastery of Santa Maria de Alcobaca

Between Obidos and Batalha is Alcobaca, a town dominated by the 12th-century Monastery of Santa Maria de Alcobaca, the first Gothic building in Portugal, and once one of the most important monasteries in Portugal.

This route could so easily turn into a tour of Portuguese monasteries – there are so many fine examples. One you should not miss visiting is the stunning Monastery of Santa Maria da Vitoria, more commonly known as the Batalha Monastery. It took more than 130 years to build, spanning the reign of seven kings: work began in the 15th and was completed the following century. A true Gothic masterpiece, it is considered to be among the finest structures in southern Europe.

Batalha Monastery

Batalha Monastery has one of the most remarkable cloisters in the world. The ‘imperfect chapels’ (Capelas Imperfeitas) are so named because they were never finished, but the intricate stonework is incredible, with a style that reflects the Italian Renaissance.

The monasteries of Alcobaca and Batalha, along with the Monastery of Santa Cruz in Coimbra, are all listed as UN World Heritage sites

Coimbra, the final destination of the day, is just over 85 kilometres further north on the A1, but you might want to make a detour south-east from Batalha to visit Fatima and savour its religious mysticism. Fatima became one of the Catholic world’s most famous pilgrimage sites following reported sightings of the Virgin Mary early in the last century: it’s a little less than a 20-kilometre drive on Route 356.

Once a desolate, god-forsaken piece of countryside, Fatima has become what somebody has termed ‘an industrial-strength religious centre’, attracting both the devout and the curious. If you do not have strong religious beliefs, you may choose to leave Fatima off your itinerary, but it is interesting to see what has become of the remote village since the reported sighting in October 1917, said to have been predicted by three shepherd children. The statue of the Virgin Mary in the Chapel of Apparitions marks the exact spot where she is alleged to have appeared – and attracts four million pilgrims every year: the basilica, with its fifteen altars took a quarter of a century to complete.

The birthplace of six Portuguese kings and home of the country’s first university, said to be the second-oldest in the world, Coimbra's tradition as a seat of learning runs deep: black-caped students throng the town during term times – a sort of Oxbridge on the Iberian Peninsula.

Once a royal palace, Coimbra’s university was founded in 1307 by King Dinis. Its library is widely considered to have the most striking interior in Portugal, and one of the richest book collections in the world. The university sits above a lazy stretch of the Rio Mondego, and the picture-postcard maze of  narrow medieval streets that clamber up its monumental halls and libraries is scene of boisterous student life at night.

Here’s a foodie tip: there are many great little student-priced restaurants in Coimbra’s university area -- check out Ze Manel dos Oss. It’s hidden down a small alleyway on Beco do Forno and open for lunch and dinner (lunch only on Saturday, and closed on Sunday). It’s small, lively and inexpensive, but does not take reservations. Try the feijoada á leitao (a stew of beans and suckling pig).

Coimbra

You should include a visit to Coimbra's ancient cathedral, which is one of the finest examples of Romanesque architecture in Portugal: it was built in the 12th century on the site of a Moorish mosque. And you might want to explore the Old Convent of Santa Clara on the other side of the Mondego River. It was was built in the 14th century, but had to be abandoned by the nuns three hundred years later because of frequent floods. The well-preserved Gothic ruins of the monastery were excavated at the end of the last century, and the church has reopened to the public, complete with a visitor centre, after many years of restoration.

Accommodation options: Hotel Astoria, Tryp Coimbra Hotel, Ibis Coimbra

Top tip: if you are looking for a really unforgettable experience, spend the night at the five-star Palace Hotel in Bucaco, located in a national forest about 30 kilometres northeast of Coimbra. Pricey, but worth biting into your plastic for a night. In the days of the Portuguese monarchy it was a royal hunting lodge. All 62 rooms are elegantly furnished with period pieces, from the 18-century to Art Nouveau -- and they all have free wi-fi. Try to get a room overlooking the hotel’s extensive gardens.

Day 3; Depart: Coimba   O/night: Oporto Approx: 232 kms
Continue north to Oporto, with a stop in Aveiro, a city of canals and home to the famous Vista Alegre porcelain factory. Not surprizingly, Aveiro has been dubbed the ‘Portuguese Venice’, and one of the attractions is its fleet of moliceiros, boats with brightly painted prows used for gathering seaweed.

Aveiro, the ‘Portuguese Venice’

The town, which is surrounded by saltpans, beaches and lagoons, was once a busy and prosperous port, but the entrance to the harbour silted up several centuries ago leaving Aveiro landlocked. An entrance was cut through the sandbar in the early 1800s, but Aveiro never regained its status as a major port.

The Vista Alegre Museum is located in Ilhavo, about four kilometres south of Aveiro. It boasts a fascinating collection of ceramic, glass and crystal, and traces the history of the famous Vista Alegre porcelain from the 1850s to the present day. It’s open daily, except Mondays, throughout the year (it closes for lunch) and there’s a 2.50 Euro entry fee. Recommended.

A foodie note, especially for those with a sweet tooth: Aveiro is known in Portugal for its traditional sweets, ovos moles, trouxas de ovos, both made from eggs and tripa de aveiro, a sort of waffle. Aveiro’s ovos moles have a long tradition, and were first made in a local convent back at the beginning of the 16th century for King Manuel I.

From Aveiro to Oporto is about a ninety-minutes drive, but you will want to stop off in picturesque Ovar and Santa Maria da Feira along the way.

Ovar is also surrounded by saltpans and lagoons -- an unusual town where some of the women still wear black pork-pie hats and walk around the streets barefooted. Many of the local inhabitants are descendants of Phoenician sailors who settled in the area centuries ago. Nearby Santa Maria da Feira is set against a background of tall trees, with a castle that is one of the best-preserved fortresses in Portugal.

Oporto, the gracious capital of the north, is Portugal's second largest city (it is known as Porto in Portuguese). Rich from centuries of trade, modern Oporto is as much a cosmopolitan centre as it is a city steeped in the historical events of the past. It sits on the great gorge of the River Douro, which spills into the Atlantic after its scenic journey of more than 900 kilometres from neighbouring Spain.

Often called the 'granite city', Oporto is best known for its much celebrated port wine, which is another good reason for making the drive from Lisbon. But its attractions are much more than just the wine. Classified as UN World Heritage site, Oporto’s ancient Ribeira riverside district is a warren of narrow, twisting streets and shadowy arches. The ongoing restoration of this lively quarter includes an array of restaurants, bars and nightclubs.

Oporto’s Ribeira riverside district

Two ‘musts’ are the 12th century Se Cathedral and the spectacular Sao Francisco Church with its striking gold-encrusted interior.

Crossing the spectacular two-tiered Dom Luís bridge brings you to Vila Nova da Gaia, the real home of port wine. You can tour the cellars of household names such as Cockburns, Sandeman, Taylor's and Grahams. Typically, a tour of a port winery includes a guided walk through the barreling and distillery areas of the winery with all your questions answered along with samples of two to three types of port wine. Once the tour is over, you have the option of buying bottles of port wine, as well as chocolates and other foodie items

While Oporto’s port wineries are located in Vila Nova da Gaia, the grapes for port wine are grown along the Douro Valley. just south of Oporto.

Foodies will want to drive out to the fishing towns of Matosinhos and Leca da Palmeira to the north of Oporto -- they boast some of the best fish and seafood restaurants to be found in Portugal. Within easy reach of the city to the south, Espinho is a laid-back beach side resort with hotels and a casino.

Accommodation options:  Eurostar das Artes, Hotel Porto Trindade, Hotel Ibis Porto Centro

This itinerary is for visitors flying into Lisbon and renting a car. If you are planning to arrive from neighbouring Spain there are several possible routes. Crossing the northern border at Valenca takes you to Guimaraes -- from where you would follow our Best Self Drive Route in reverse  If you're driving from England, you might want to consider the Plymouth-Santander or Portsmouth-Bilbao ferries to northern Spain and then drive west to Portugal.