In-Depth Exploration Tour of Portugal: History, Culture, and Discovery

A More than 18 day trip to Portugal 
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Portugal has style that has stretched through the centuries to include everything from frontier towns to Moorish fishing villages, Templar Knights to Manuelino facades and Baroque ceramics. You will be whisked away on a carpet of seduction and charm and into an atmosphere packed with tradition. With well over two weeks to travel, you will settle into the stylish rhythm of the country to explore the nuance as you hop between the untouched legends of the past. From Lisbon to Porto, this is a complete tour of Portugal on a private tour designed just for you.

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General Information

Detailed Itinerary

Places Visited 

Lisbon, St. George Castle, Se Cathedral, Calouste Gulbenkian Collection, Jeronimos Monastery, Belem Tower, Museo Nacional de Arte Antigua, Palacio Nacional de Marfa, Palacio Nacional de Queluz, Palacio de Pena, Palacio Nacional, Evora, Roman Temple of Diana, Arraiolos, Redondo, Merida, Museum of Roman Art, Elvas, Castelo de Vide, Marvao, Almourol, Templar Castle of Almourol, Convento de Cristo, Tomar, Fatima, Nazare, Obidos, Alcobaca, Batalha, Monastery of Batalha, Coimbra, University of Coimbra, Aveiro, Barcelos, Guimaraes, Braga, Monastery of Sao Martinho de Tibaes, Vila Real, Amarante, Porto 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Lisbon – Begin With the Charming Streets of the Capital

Lisbon has soul, and it is a city that will pick you up and whisk you off in its atmosphere as every street has something that will excite your inquisitive eyes. After being greeted at the airport, you will be transferred to a boutique hotel in Baixa, the grand heart of Lisbon. The day will be at your leisure, and there is a lot to discover within walking distance. From the elegant avenues lined with Baroque architecture to the steep cobbled streets that are dotted with local cafes, you will have no shortage of options. On this first day, you will also notice how proficient the Portuguese are in understanding and speaking English, certainly more so than their Spanish neighbors, so you will easily find the many excellent restaurants are within a five-minute walk of your hotel.

What’s Included: airport transfer, accommodation

Day 2: Lisbon – Evocative Links to the Past and a Fabulous Private Art Collection

An iconic yellow tramcar will carry you along the hills as you weave away from Baixa and to the Castle of St. George, the impressive show of power that has been warding off invaders since the 12th century. Your tram will screech and rattle as it takes you onwards, a historical vessel ascending to Lisbon Cathedral, where Gothic adoration contrasts with the Romanesque style. After a traditional lunch, you will spend the afternoon discovering one of the greatest private art collections in Europe. Old masters like Rembrandt and Van der Weyden fill one gallery, Manet, and Monet another, and then exquisite collections of Islamic and Asian art will introduce you to new names from ancient artistic realms. The evening is at your leisure to enjoy the city nightlife as you would like to.

What’s Included: accommodation, tour, breakfast, lunch

Day 3: Lisbon – Art and Architecture of Belem

Portugal’s stylistic history stretches along the riverside as the district of Belem is one of few that survived the earthquake in 1755. Torre de Belem guards the entrance to the city, with its Moorish-inspired turrets and Renaissance archways exposed above a haunting Gothic interior. Mosteiro dos Jeronimos is equally unusual as a building that blends Gothic with Renaissance and Baroque. In the early 16th century, as the city grew rich from New World discoveries, local architects handpicked what they liked from a full array of styles. The result is unique to Portugal, known as Manueline. The monuments you see this morning are the best and most complete examples of this style. You will also visit Museu Nacional de Arte Antigua, where a fabulous array of Portuguese art is complemented by a regal collection of Flemish and Spanish painters.

What’s Included: accommodation, tour, breakfast

Day 4: Lisbon – Palaces and Poignant Beauty Outside Lisbon

Palaces dwarf towns on the outskirts of Lisbon. Mafra, which is part monastery and part palace, is gilded with gold that was brought back from Brazil. Wander through the basilica and into the library beneath the eyes of sculpted guardians who line the walls. Move next to Queluz, standing like a royal sentinel on green plains, where porcelain and paintings line the walls towards the official reception rooms. Both glisten with excess and extravagance for a detailed insight into the distinctive tastes of Portugal’s royal family. After touring the palace with your local guide, take some time to wander the gardens before a small boat takes across the ornamental lakes and tiled canals.

What’s Included: accommodation, tour, breakfast, lunch

Day 5: Lisbon – Extraordinary Sintra and Haunting Fado Music

More palaces will fill this morning, and the royal complex in Sintra will feel reminiscent of a fairytale. Rising from the thick woods, you will see strange chimneys and pink turrets, sloping blue facades and fortress windows. Yesterday’s palaces showcased classic opulence while those around Sintra seem to come from fiction with a mix of Moorish and Manueline that only gets more beautiful when you explore the interiors. Combine the fantasy palaces with a very relaxed afternoon in Sintra itself, a town that emanates a romantic air. This will be a huge contrast to the atmosphere in a local Fado bar, where two guitarists pluck a haunting melancholy rhythm. A lone voice wings out, soulful and sad, reminiscing of love and loss and the life that did not happen. Fado is a cultural institution, and a very moving portrait onto both Lisbon and Portugal.

What’s Included: accommodation, tour, breakfast, lunch

Day 6: Lisbon – Day at Leisure in the Portuguese Capital

Tiny doorways lead you to antique stores in Bairro Alto while trendy cafes juxtapose with traditional taverns in the district of Baixa. A promenade might lead you past townhouses with a thousand contrasting hues. Plazas are broad and welcoming, and great places to pass a day at leisure. Museums are intriguing and inspiring and cover their particular pieces of history or art. About a week is just about enough to explore Lisbon’s eclectic landscape, and enough time to follow personal interests and discover districts that love to surprise. This day is deliberately left free, and by now you should have an idea of where to focus your final day exploring.

What’s Included: accommodation, breakfast

Day 7: Evora to Arraiolos to Redondo – Portugal’s Perfect Medieval City and a Convent in Rural Alentejo

Redolent and remote, Alentejo is Portugal’s expression on the unchanged past, a region of dusty plains and sublime towns frozen in the past. Today you stop briefly at a neolithic stone circle before spending half the day in Evora, a medieval town of cobblestone and allure. Footsteps echo past a Roman Temple, a 12th-century cathedral that will baffle with its décor, and the harmony of sandstone has a soothing effect all over the pedestrianized city. Enjoy a leisurely lunch on the central square of this UNESCO World Heritage Site, and then discover the castle and clock tower at Arraiolos. You will spend the night at a converted convent in Redondo, a village seemingly stuck in the 12th century while your accommodation combines antique glamour with contemporary comfort.

What’s Included: accommodation, tour, breakfast, lunch

Day 8: Redondo – Day Trip to the Fortress Outposts of Merida and Elvas

Elvas and Merida straddle the frontier as fortress cities full of legendary tales with battles and barricades, Roman invasions and roving swords, ruins piled upon ruins. On the Portuguese side, you will find Elvas, a UNESCO World Heritage city with a medieval frontier feel that is dominated by the thick stone of its castle. Hop across the border to Spain, and Merida is equally ambient, a nostalgic portrait of distant centuries. Both cities are enhanced by remarkable structure as an arched Roman bridge leads you to a 2,000-year-old amphitheater in Merida while Elvas has a 15th-century aqueduct made of 843 stone arches. Return to Redondo for a second night in your unique accommodation.

What’s Included: accommodation, tour, breakfast

Day 9: Marvao – Where Few Visitors Venture: Weaving Along the Portuguese Frontier

All along the Portuguese frontier are odes to Iberian history, towns, and villages where quarrels left churches and castles in ruins. Some of them have been left in a semi-dilapidated state while others have been restored with fortified gates and thick walls that guard labyrinthine interior lanes. This is an area where few visitors travel, and it will make for a great day of going off the beaten track. Not simply into the towns, but also into local traditions with food, art, and wine distinct from what you have sampled so far. Spend the night in Marvao, beneath the looming frame of the frontier’s best-preserved castle.

What’s Included: accommodation, tour, breakfast

Day 10: Almourol to Tomar – Legend of the Templar Knights

The Knights Templar come from a time of fable and fiction and when the stories were elaborated in whispers that crossed the plains. More than 800 years later, the legend of the Templar is just as dreamlike, even when you are exploring the vast Templar Convento de Cristo or feeling the energy of Almourol Castle. Today’s unique route will connect the dots of Templar history, from the first to the last of the towns and then onwards to the Templar’s role in New Age Discovery. You will spend the night in Tomar, which will allow for a full afternoon to experience the rich architectural beauty of the convent, one of the finest yet most understated monuments on the Iberian Peninsula.

What’s Included: accommodation, tour, breakfast

Day 11: Tomar – Picturesque Moorish Fishing Villages of the Atlantic Coast

Fatima is an unusual place as two enormous basilicas dominate the tiny fishing town that is dedicated to visions received by local children. Nazare is also mythologized, where fishing boats are painted with eyes to ward off evil spirits. Both are whitewashed and back-dropped by the cliffs of a rugged Atlantic Ocean coastline, and both are also soothing destinations for dipping your feet into both the sand and the traditions. After a seafood lunch, you can visit Obidos, and the harmonious white facade allows the vibrant balconies to shine in the light of the afternoon. The castle here is exquisite, and a contrasting style to the one above your accommodation in Tomar.

What’s Included: accommodation, tour, breakfast

Day 12: Tomar – Comparing the Gothic Wonders of Alcobaca and Batalha

Gothic architecture has morphed and meandered over three centuries, so is a style that is packed with nuance to the trained eye. Nowhere in Europe are the Gothic contrasts better illustrated than the Cistercian Abbey of Alcobaca and Batalha Monastery. The former is the original that others were based upon, and a welcome visual break from the sober Romanesque style that came before. The latter is ridiculously flamboyant, with extraordinary detail lining every archway and chapel. Gothic architects always pushed boundaries, so by the time Batalha was constructed, there were few architectural boundaries left to fall. After this historical tour, you will return to Tomar for a third relaxed night spent beneath the castle as the terraces still hum of Templar Knight tales.

What’s Included: accommodation, tour, breakfast

Day 13: Coimbra – Portugal’s Ancient University City

This 19-day luxury tour visits ten UNESCO World Heritage sites and perhaps none will be as memorable as the Coimbra University buildings, an ensemble of extravagance that has been added to since the 12th century. From Romanesque to Gothic to Baroque, the artistic style in Coimbra has valued style over substance. Buildings lean towards each other in narrow alleys, but they are exquisitely covered in ceramics. Stunning mosaic pavements date to the time of ancient Portugal while public cafes drip with the grandeur from a past age. You will have a guided tour in the morning before an afternoon and evening at leisure in Coimbra.

What’s Included: accommodation, transfer, tour, breakfast

Day 14: Aveiro to Barcelos to Guimaraes – Cities From the Past and the Atmosphere of the North

Portugal excels in the unique, and one of the country’s highlights is the eclectic nature of the old cities as each has its own character. Aveiro is where the blue ceramics shimmer above the canals and narrow plazas. Barcelos is full of life when the traditional Thursday market is in town, and Guimaraes is full of the opulence and the excess you might expect from the first capital of a country. Hopping north on a full-day tour, you will experience all three of these destinations before spending the night amid a beautiful suburb of 18th-century mansions. Dinner is included tonight with a traditional fine cuisine served on a terrace overlooking Guimaraes.

What’s Included: accommodation, tour, breakfast

Day 15: Guimaraes – Day Trip Exploring Portugal’s Early Christian History

It will have been over two weeks in Portugal, and still, the destinations compete with their originality. Braga has few similarities with Guimaraes, a city of churches that is rich in scale and detail. Horseshoe arches from pre-Romanesque times and Corinthian columns guard the entrance to the empty tombs of saints while rococo and Baroque art elaborate the once solemn monasteries. This enchanting little city is a great day trip from Guimaraes, and you will have a local guide to lead your discovery. Rather than travel with a single guide for the whole 19 days in Portugal, you will be led by the insiders. Their knowledge will allow each day to be customized to your particular interests, as well as offer an encyclopedia of knowledge that will make every destination feel even more alive.

What’s Included: accommodation, tour, breakfast

Day 16: Vila Real to Amarante to Porto – The Extravagance of the Baroque

Vineyards will dominate the panorama on your journey through the Douro Valley as the vine terraces are punctuated by stone farmhouses and 18th-century manor houses. Allegorical statues and golden stone bridges will add further mystique to the vistas, along with Baroque facades and porticoes from the past. The whole valley is a UNESCO World Heritage Site, and you will travel slowly and weave along country lanes as you stop to taste at two historical vineyards. Also today, you will visit the monastery in Villa Nova de Gaia and then cross the iconic bridge into the heart of another UNESCO World Heritage site, Oporto.

What’s Included: accommodation, tour, breakfast

Days 17 – 18: Porto – Relaxed and Redolent Two Days in a World Heritage City

The traditional style that many associate with Portugal has its origins in Porto. Blue ceramic tiles create mosaics that cover buildings with aperitifs of sweet wine and lunches that mix pork with fresh fish.  Many imagine terraces where strangers become friends over an espresso or a small beer while a hundred colors fill the sky and nothing seems out of place. Porto delights in tradition that overflows from the art and the architecture to the food and wine. You can feel the local atmosphere every time you step from your hotel, but your local guide will tailor the discovery for you and piece together the most elaborate sights and settings.

Roman mosaics in storage houses, palaces of Arabian halls gilded in gold, fine art from the 19th century and a working hospital of sublime Palladian architecture are all yours to be explored. Then move to the mazy streets of cafes that exude charm, viewpoints that overlook the Douro, and a boat trip in one of the traditional vessels used to transport grapes. Of course, at some point during these two days, you will tour one of the port cellars and taste various vintages. There are also churches that changed over the centuries, magnificent panoramas and gilt carvings, ornate bookshops, and staircases that seem to come from fiction. Your guide will assist in making dinner reservations at the most renowned restaurants, and you can adjust the pace of your days to suit your energy levels with options for touring outer Porto on bikes or by tramcar.

What’s Included: accommodation, tour, breakfast

Day 19: Porto – Departure

After your 19-day tour in Portugal, you will depart with a stellar collection of photos and memories. Looking back, it will be hard to imagine that you have seen so much in this time away as every destination has been so different from the last. But after your airport transfer and as you are flying back home, you will realize that there is something that ties the country’s patchwork together: a spirited and friendly character that always made you feel at home.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.