An Immersive One-Week Privately Guided Tour of Portugal

After breakfast, you depart to the north of Portugal, first traveling along the cliffs that mark the coast. Stop in Obidos, where narrow streets are enclosed by crumbling city walls, and medieval doorways transport you into scenes from the past. So much of Portugal is unchanged, untouched since an era of battles at sea and building castles to repel crusaders. Obidos is a timeless example, and you almost expect the cafes to serve drinks in metallic goblets. Further north is Nazare, the most colorful of all the Portuguese fishing villages. Boats lull gently in the harbor, backdropped by houses that are painted in all manner of vibrant hues. It is a great place to stop for lunch, with the catch of the day fresh from the Atlantic Ocean.

Weaving inland, you traverse green valleys and pass villages that cling to peaks. Batalha Monastery is a monument to the Portuguese victory over the Castilians, a World Heritage Site of splendid Gothic design. Flamboyant in scale and detail, it is just one of the day’s insights into Portugal’s history. Batalha was constructed in the 14th century, while nearby Coimbra has a legacy from the 13th. The University Library and Chapel are among the most impressive of the monuments you will find. It is a delightful town to explore at leisure, and you will need to travel at a leisurely pace given the steepness of the pedestrianized lanes. The evening is free, and Coimbra is a great place to taste traditional food from the interior, like pork and game meats that have boiled for many hours until they redefine the notion of falling off the bone.

Keep traveling north across the hills, less than an hour between Coimbra and the city of canals, Aveiro. You notice the profusion of blue, with different scenes painted on the ceramics that cover the side of buildings like murals. Travel along the canals and onto the lagoon, where the colors of the Atlantic ripple beneath the boat. Then explore on foot, Aveiro a small town with dozens of colorful buildings and traditional stores. It is less than an hour further north to Oporto, a city that extends on two sides of the River Douro.

First, you explore old Porto, a maze of staircases, cobblestones, and charm. Start high, where the Clerigos Tower provides a panorama of down below. Descend through the 16th to 18th-century buildings, the masterpieces of Baroque design that have been neatly restored over the last decade. There is the stock exchange palace, marketplaces that still thrive with trade, and so many houses dominated by the blue tiles that make Porto so picturesque. Later in the afternoon, you are on the opposite side of the river, discovering the port cellars.

Fortified Port needs to be aged, some vintage bottles not released until 50 years after their harvest. Back in the 18th century, the warehouses were built on the Porto side of the river, a place of prime real estate. The authorities banned wine from the city, prompting each of the winemakers to build more expansive cellars on the opposite side of the river. At the time, Nova de Gaia was its own city, although it has now been incorporated into modern Oporto. Inhaling the musty scents, you explore one of the cellars, thousands upon thousands of barrels visible in the gloomy light. Enjoy a special tasting, with access to rare vintage ports, before an evening along the shores of the River Douro.

The north of Portugal is the cradle of the nation, where the oldest battles were fought and an independent country was founded. Three cities make for a classic loop across the north, each with its own colors and style. Guimaraes is a city of ancient hill settlements and towering royal fortresses. It is where Portugal’s identity originated, epitomizing the passion and pride of a nation. A warren of narrow lanes takes you to quaint little plazas, all backdropped by castle ruins. Now a World Heritage Site, it is the sort of city that comes further alive when you are accompanied by an expert guide who knows all the stories.

Next, you stop in Braga, an old center of commerce and culture, and a city of pretty churches that is perfect for a relaxed stroll. Finally, to Barcelos where brightly-painted pottery tumbles out of the shops, and a hundred legends emanate from the city square. While you spend the day on the move, the evening is very relaxed. Porto is a beautiful place to watch the world go by while dining on the traditions of the country.

While Porto has an old-world bustle, the Douro Valley has an old-world charm, with vineyards and pinewoods dominating the panorama. The landscapes help create a serene and soothing atmosphere, enhanced further by the curves of the famous river. Most of the hills are too steep for machinery, so the vineyards are only harvested in the traditional method, by hand. It all makes for a very relaxed day, first in the ancient episcopal city of Lamego. Baroque townhouses surround the square, churches are guarded by 17th-century statuesque ghouls, and you will take a look at the country’s most important shrine. Complete the day in Viseu, following the trail of the great 16th-century artist, Grao Vasco, a local icon who has added so many dashes of color to the country.

Across the north of Portugal, you will witness the scenes beautifully painted onto the ceramic tiles that fill the walls of train stations and townhouses, as well as staircases and sumptuous churches. You can make your own visual interpretation, but with so much fable and legend, it is the insight from a local guide that makes the experience. Through a guide, you gain access to buildings that are sometimes closed to the public, hear the tales that have been passed down through the generations, and savor an insider knowledge that reveals more about your destination. As the tour is private, you can travel at a relaxed pace, stopping longer in the destinations that you find the most compelling. And while the route is specifically designed to take in eclectic highlights, there are always little treats that can be added depending on your interests.

This day starts with an ancient legend, the Order of the Temple in Portugal, also known as the Templar Knights. Explore a 12th-century castle and a fabulous monastery, where marine motifs are draped around Manueline windows, and there is an extravagance you would not expect from the period. An original Templar church, the Charola, is your next stop, a quieter showcase of grandeur. Take your time in the town of Tomar, where vintage stores line Rua de Serpa Pinto, and a Gothic church stands proudly in the city’s heart. There is Jewish heritage to provide another dimension to the local history, along with a 17th-century church with an impressive matchbox collection. Take your time today, and then travel onward to the Portuguese capital, the final stop on this luxury tour of culture and history.

Lisbon is draped elegantly across seven hills, a city where every neighborhood has its own atmosphere, and the only constants are the tramlines. Barrio Alto is the regenerated suburb where the narrow houses are all manner of hues. Alfama is full of elegance and the glamor of the late 18th century. Ascend one hill, and you find a 12th-century cathedral, one of a few buildings to survive the devastating earthquake of 1755. Ascend another, and there is a castle with thick stone walls that warded off aspiring invaders. Then descend, down the bustling lanes to the marble-lined squares along the banks of the Tagus River.

In the afternoon, you discover Lisbon’s proudest jewels, the statues and symbols further along the river in Belem. Jeronimos Monastery and the Tower of Belem are postcard photos of the country, World Heritage Sites with origins in the 16th century. That was a time of luxury and prestige, one that has been continued in all the buildings of Belem. On this last day in Lisbon, you could choose to customize the program and visit nearby Sintra instead, where the palaces have the most peculiar shape and style. Lisbon is famous for its seafood pleasures, and your guide can provide dining recommendations and reservations. One treat you should not miss is a pastel de nata, a small creamy pastry that is served all over the country but originated in a tiny Belem cafe.

Enjoy a free morning in Lisbon, and a further opportunity to soak up the ambience of the city, whether down by the river or on one of the many central plazas. You will be transferred privately to the airport where you leave from the place you started.