A Road Trip Through Portugal

Join Monica Frim on a winding drive from Lisbon to Braga in the far north to the beaches of the Algarve in the south. Along the way Portugal's great cities mix old and new, and tiny, whitewashed villages nestle in the hillsides dominated by old stone castles. Cliffs rise out of the ocean, vineyards cascade into river valleys, and ancient caves and stone circles riddle the countryside. There's something for everyone — from glitzy nightlife to rustic retreats.

Whenever possible I'm all for serendipity and a loosely structured travel schedule. I look forward to getting lost, whether on crowded city streets or in isolated rustic places, because I've learned that experiences that first appear as setbacks often lead to enriching encounters otherwise missed. John and I had three weeks to scout about Portugal and, like the early explorers, we occasionally drifted off-course, although our circumnavigation was not of the globe but a crazily skewed clockwise loop of a small country, and our caravel a rented Alfa Romeo.

Portugal packs a prodigious amount of history, culture and geology into a small footprint. It was Portugal's adventuresome seafarers who opened the eyes of Europe, the then-known world, to the existence of islands — Madeira, Azores and Cape Verde — that sprinkled the Atlantic Ocean well before it dropped into a presumed abyss. Their 15th century explorations unflattened the world and rolled it into a ball of continental masses — Africa, Asia, the Americas — that for a time made Lisbon the richest capital in Europe.

But on its own turf, the country was barely penetrable. Foreboding cliffs, narrow headlands, a mountainous interior riddled with caves and tortuous rivers chopped the country into secluded settlements with few means of traveling or communicating amongst them. For centuries the isolated beauty of the land remained largely ignored by travelers who had more accessible options in other parts of Europe.

Portugal is still somewhat of an isolated destination, separated from the rest of Europe by Spain and from the Americas by the Atlantic Ocean. But in a world collapsed by fast jets and split-second communications, it has become one of the world's top tourist destinations. The 2013 Report on Nation Brands listed Portugal as the fourth country with the highest increase in tourism.

Roads spider across the country like mottled veins of marble, which is a fitting metaphor given that Portugal is the second largest exporter of marble in the world, most of it from the Estremoz area east of Lisbon near Spain. Like the marble markings, the roads are erratic with confusing forks and tortuous branches that end in the unlikeliest places — lone farmhouses, cliff edges, empty fields, river banks or rocky outcroppings that sit like abandoned castles brooding over impossible habitats where only the hardiest — perhaps foolhardiest — survive. While the roads are poorly marked and narrow, they are surprisingly well preserved and don't chew up the tires. This is a good thing for tourists who, having taken the wrong turn, must often drive great distances before they can find a place to turn around. One can't just veer around the block to recoup because grid roads are rare outside of Lisbon's "Baixa," the lower quarter that was rebuilt to geometric specifications by the Marquis of Pombal after the Great Lisbon Earthquake of 1755. The Portuguese, born navigators, wend their way just fine and free; foreigners, bereft of the blood of da Gama and Magellan, do better paying the hefty tolls on Portugal's "autoestradas."

In Lisbon the sun rises over the Tagus River and sets over the Atlantic Ocean. It is the perfect place to begin and end a journey. And so we did, leaving behind the seven hills that make up the city to follow the sun to the princely playgrounds of Estoril and Cascais 19 miles away. The two towns are connected with a stone walkway called Paredão (which translates as sea wall) that meanders among sandy beaches, rocky outcroppings and restaurants.

King Luís I planted the first cosmopolitan seed in Cascais in the late 19th century when he turned the 16th century citadel into a summer residence for the royal family, thereby spawning a movement for aristocratic families to build their own elegant mansions nearby. After World War II many exiled royal families of Europe followed suit. They established elaborate homes in Cascais and Estoril and launched the area as a sophisticated tourist destination for both international and national jet-setters with luxury hotels to match. Today the Citadel is a "pousada" (historical hotel) that continues to attract a discerning clientele.

Eleven miles north of Cascais, Sintra anchors with dreamlike spontaneity (but nightmarish parking) a patchwork of castles and their protective hilltop fort in a dramatic, mystical setting. The effect is fairytale eclectic, indebted as much to the architectural whims of the various kings and aristocrats who built a pastiche of palaces as to the exuberant gifts of nature: a granite mountain of megalithic rocks and woodlands that imbue the entire area with romance and lore. A massive Moorish Castle dominates the skyline, but the crowning glory is the pseudo-medieval Pena Palace, whose "bricoleur" king, Ferdinand of Cobourg, creatively mixed Moorish, Gothic and Manueline details to turn a 16th century monastery into a royal summer home complete with exotic gardens, fountains, lakes and meandering paths. It seems that the architectural olio of royalty and a moneyed bourgeoisie was in itself a method of creating order out of many styles. Monserrate, a nearby neo-Gothic palace, bears Moorish and Indian touches; the Sintra National Palace mixes Gothic, Manueline and Mudéjar elements; and, the Quinta da Regaleira is a Gothic, Manueline and Renaissance combination. Its leafy grounds and tentacled paths make getting lost among mystical gardens, grottos, tunnels, fountains and lagoons a pleasurable pastime. One could almost picture fairies and "duendes" (goblin-like sprites) crouching under the foliage.

Portugal has a thing for storybook creatures. Medieval maps depict mythical monsters that kindled the imaginations of sailors with frightening scenarios of what would happen if they ventured too far from shore. At Cabo da Roca, the westernmost point of continental Europe, the wind whistles across the desolate headland and the Atlantic beats a mean tempo as it crashes 144 feet below the cliff top. The horizon looks flat as the earth was once believed to have been and it doesn't take much to imagine legendary sea monsters churning up the sea. Visitors can buy commemorative certificates complete with an official red wax seal over a blue and yellow ribbon to prove their arrival at the end of the old continent. Yes, it's gimmicky but the certificates are attractive. I'm admiring mine as I write this.

With a coastline of promontories and beaches of all shapes and sizes tucked willy-nilly among them, there's no such thing as a coastal road with constant views of the sea. Portugal's roads may weave, but more often they sprout. Take one of the offshoots to a fishing village or sandy beach and the only way to drive to the next one is to retrace your route back to the main road, then take another offshoot. The practice can be tedious, but the reward, sometimes, is a beach to yourself.

At every turn there seems to be a town with a hilltop monastery or castle: Mafra's National Palace-cum-convent, with a footprint the size of 11 football fields, looms over everything else including some mountains; the white-walled town of Óbidos beckons a walk along its crenellated ramparts and a taste of the town's trademark "ginjinha," a cherry liqueur served in edible chocolate cups; Fátima, one of the world's holiest sites, weaves a curious mix of piety and trade where even kitschy souvenirs seem to attract a pilgrim following; and nearby caves offer a refreshing geological detour. The Grutas da Moeda are small but the natural display of the exquisite formations (no harsh or multi-colored lights) and the friendliness of the knowledgeable guides renders them appealing.

The Portuguese have a saying that loosely translates as: "Coimbra studies, Braga prays; Porto works and Lisbon plays." Having checked out Lisbon's playgrounds of Cascais and Sintra, we needed to see if the other places also lived up to their reputations. We soon realized they did. Coimbra's centuries old university buildings, with a library where even the spines of the books were gilded, were classified as a World Heritage Site by UNESCO in 2013. And Braga definitely prayed. The Santuário do Bom Jesús, with its moss-covered statues and 500 steps leading past the Stations of the Cross, is one of the most photographed places of worship in the country.

However, my first impression of Porto was not so much that the city worked, but that it needed work. A somber grey seemed to penetrate the air, the buildings, the very souls of the people — the old woman who dusted the carvings in Clérigos Church, the bent old-timers who trudged the steep streets in a drizzle, even the young man handing out bedrizzled flyers on the street corner. On closer inspection, many of the dilapidated mansions and abandoned warehouses were being turned into hotspots, with trendy restaurants and nightclubs. Minimalist and modern buildings like the National Contemporary Art Museum, The Music Hall and the glassy hotels of the Foz (mouth), where the Douro River meets the Atlantic Ocean, were proving that Porto was not so much a dour city (Douro means golden), but a balance of old and new, and a fusion of the two when appropriate — but still a work in progress.

The next day, the sun bleached the clouds and kindled the buildings ochre, white and well, yes, some stayed just plain grey, but it was a fine day for walking the crenellated walls of the cathedral, admiring the 20,000 hand-painted tiles in the São Bento train station, climbing the famous glossy red staircase of the Lello Bookshop and taking a Douro bridge cruise aboard the "Carlota do Douro," a rabelo boat operated by DouruAzul. Rabelos, known only on the Douro, once carried wine from the valley to the cellars of Gaia, opposite Porto, where it was aged, blended and bottled. Today they serve as Porto's answer to Venice's gondolas, and the wine is transported to Gaia by truck.

Porto is the gateway to the world's oldest demarcated wine region, the port-producing Douro Valley. We have the early 17th century English traders to thank for the port. Early Portuguese vintners added a dash of brandy to red wine to stabilize it for the long trip to England and, lo, the elite gentlemen in the clubs of London liked it.

We drove the wine country via valleys that rose like giant amphitheaters, their scallop-edged terraces tumbling in slathering greens and browns to a watery stage where cruise boats plied in place of rabelos. Here and there the manors of wine estates poked out of the greenery, their tangerine-tiled roofs in brilliant contrast to the surrounding foliage.

Near the border with Spain where the Douro River is joined by the Coa, the vineyards make room for olive and almond trees … and the largest collection of prehistoric (more than 20,000 years old) cave drawings in the world. Visitors can take pre-arranged guided tours by jeep to three sites in the Coa Valley or visit the excellent Coa Museum with its representational drawings in Vila Nova de Foz.

Portugal's interior is full of surprises: prehistoric rocks and caves, hidden hamlets with medieval ruins, neolithic dolmens (megalithic tombs) and other stone monuments. Many are scattered throughout the Alentejo, an expanse of granite hills and rolling plains between the Tagus River and the Algarve anchored among cork trees, olive trees and wheat fields. Enotourism has made inroads here, thanks to the region's nascent winemaking industry that now rivals that of the Douro Valley. The wines pair nicely with the area's other savory industry: a delirious assortment of cheeses made from goat's, sheep's and cow's milk, or a blend of all three known as "mistura."

Encostas de Estremoz is a tiny hilltop winery that launched its label in 2001 and surprisingly produces a variety of wines. We toured the facility, attended a wine tasting and, armed with three bottles — a TE branco (white), Grande Escola tinto (red) and the Grand Gold Medal Winner for 2012 at the Concours Mondial de Bruxelles, a 2009 Reserva tinto — wended our way to évora, the upper Alentejo's historic walled capital.

The Portuguese call Évora a "cidade-museu," and, indeed, the whole town is a museum where almost every building — from the beautiful to the macabre — oozes with history. In the Capela dos Ossos (bone chapel) in the church of São Francisco, the remains of 5,000 monks decorate the walls and pillars of the chapel. It's gruesome, but somehow the dimly lit 500-year-old bones and skulls, artistically laid in carefully thought-out patterns, looked — dare I say it? — more graceful than ghastly.

From Évora, the beaches of the Algarve are a mere two-hour drive south, but the history-infused villages en route can stretch into a full day of stop-and-go sightseeing. Alcoutím on the Guardiara River that separates Portugal from Spain, the Roman ruins at Lanjeiros and the castle of Castro Marím are among some of the worthy stops.

You can travel the entire southern route of the Algarve from Vila Real de Santo António to Sagres in less than two hours — or several days if you stop at every beach and golf course. From whitewashed villages in the east where a farm-and-fish lifestyle prevails, through crowded resorts near Albufeira and Faro that are about as Portuguese as the Queen of England, to the towering cliffs of the west where the Atlantic slams the coast with Swiss-cheese results, there seems to be a beach for everyone. Grottos and caves riddle the coast, sandy beaches form horseshoe-shaped webs between rock walls that rise straight out of the sea and rocky islands pop from the surf like monsters pickled in brine.

Such is the force of the Atlantic at Sagres and Cabo de São Vicente, the Algarve's westernmost headlands, that its spray can be felt on the cliff tops 200 feet above the ocean. To the north are the uncrowded beaches where mostly surfers find their paradise. We watched them at Castelejo and again at Amado before heading inland, back through the Alentejo to close off our loop in Lisbon.

With streets that dip, wind and twist among diverse neighborhoods, Lisbon's somewhat schizoid personality reveals itself in small eccentricities. In Bairro Alto, it's the nightlife of raucous bars; in Alfama, the tangle of color and shabbiness of the daily grind; and in Chiado, the designer boutiques and cultural sites of a style-conscious crowd. Yet somehow Lisbon manages to present a cohesive front where old monuments and sleek, modern buildings accommodate each other, albeit in an odd-couple-Felix-and-Oscar kind of way.

Baixa (downtown), perhaps Lisbon's sanest neighborhood, has grid streets that rise from the arcaded Praça do Comércio, one of the grandest squares in the world. Its Rua Augusta Arch provides the best views over the Tagus River and, up the Rua Augusta, a pedestrian walkway of shops and restaurants. On the east side of the square, the Lisbon Story Centre takes visitors on an audio-guided tour through the history of the capital and sets the groundwork for the panoply of sights and monuments that are best appreciated with a little knowledge at the outset.

The city spreads itself along the Tagus River in skyward swirls of ochre and white façades. The hills undulate with the red clay tiles of roofs that gradually taper toward the city's bookend suburbs: Belém with its ancient port and imposing monastery, the Mosteiro dos Jerónimos in the west and the Parque das Nações, with its soaring concrete and glass buildings, remnants of the 1998 World Fair, in the east. One looks to the past, the other to the future. Together they hold not only the essence of Lisbon — what it was, what it could be — but the soul of a country.

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