Portugal’s Historic Highlights - North to South with experts Portugal by Travel Tailors DMC.
Portugal’s history is a rich tapestry woven of countless influences and upheavals - from its ancient Celtic roots to its maritime trailblazers; Roman and Moorish occupation to monarchy; republicanism to revolution. The result is a captivating, colourful canvas of history, culture and architecture. With all this and more on offer, it’s important to offer your guests the best guides around - and that’s why we work with Portugal by TravelTailors DMC.
Portuguese cities are living museums, with Lisbon and Porto boasting intricate, centuries-old neighbourhoods bursting with ornate Manueline architecture, Moorish influences and Gothic grandeur.
In the verdant, rolling hills of the North, ancient capitals and castle-topped hills sit alongside the stunning terraced vineyards of the Douro Valley, with its famously aromatic wines.
And to the South, Moorish architecture, charming, whitewashed villages and dramatic limestone cliffs create the perfect setting to savour the region’s unique culinary heritage of fresh seafood and delicious pastries against the soulful backdrop of its breathtaking coastal views.
Tailor-made by Portugal by TravelTailors
Led by Paula, a passionate Portuguese and US citizen, their handcrafted itineraries don’t only take in the very best of Portugal and its hidden gems - they place an unrivalled range of unexpected, unique and downright delightful experiences at your guests’ fingertips for the tour of a lifetime.
Like what, you might ask?
Well, perhaps they’d like to ride award-winning thoroughbreds along the beach, the taste of ocean salt on their lips and the Atlantic breeze whipping their hair.
Romantics could choose to make their proposal in a mediaeval palace, beautifully serenaded in centuries-old surroundings.
Wine lovers can enjoy a private lunch, hosted by nobility in their family home set amongst stunning vineyards; gastronomes can learn to cook delicious, authentic Portuguese dishes on the seashore under the guidance of a prestigious Chef…
… with Portugal by TravelTailors, there’s something special to suit everyone.
Read on to discover the experiences on offer to your guests for their perfect, slow travel history and culture exploration of Portugal.
First stop - Porto
There’s nowhere better to begin a tour of Portugal’s historic highlights than Porto.
A UNESCO World Heritage Site, this captivating city is a perfect marriage of history and modernity, perched prettily on the slopes of the Douro River.
In the capable hands of a licensed guide, a private tour is the best way for your guests to take in the endless sights of this stunning city - from its grand Cathedral and iconic Clerics Tower to its charming alleys, where nightclubs sit alongside museums and cosy cafés are the perfect spots to recharge after tackling Porto’s hilly terrain.
Travelling up from downtown, the Church and Tower dos Clérigos offer panoramic city views, while the renowned Lello bookshop, famed for its lavishly fantastical décor, is a must-see.
Architecture buffs have plenty to fall for - from bustling streets adorned with Art Nouveau accents to the iconic tiled entrance to the São Bento railway station; the baroque façade of the Church of Misericórdia to the charming cloisters of the 12th century Cathedral.
And back down on the riverfront, the Ribeira district immerses you in Porto's ancient, vernacular charm, its most unmissable sights being the gothic Church of S. Francisco, whose baroque interior is completely covered in gilt, and the opulent 19th-century Palácio da Bolsa.
The perfect end to a perfect day? Hop on a Douro river cruise from the riverfront and take in the sunset over picturesque villages and lush greenery, before heading back to the luxury of the incredible Vila Foz Hotel or the historic Torel 1884 Suites & Apartments,
Portugal’s historic past - and its innovative future
The next stop on your guests’ historic tour has to be Guimarães, the birthplace of Afonso Henriques, the first Portuguese King and some say of the country itself.
Within the city’s ancient walls, travellers can roam its well-preserved historical centre, recognised as a World Heritage site.
Amongst the mediaeval arches and historic mansions, towers and cloisters, visitors can immerse themselves in the ambience of Portugal past, heading from the old Castle on the city’s highest hill to view the maritime tapestries of the Dukes of Bragança Palace, before strolling narrow streets through to the charming cafés of Oliveira Square.
Beyond, the cable car rises high to Monte da Penha where guests can discover the Shrine of Our Lady of Penha and gaze over one of Portugal’s most beautiful panoramas.
In complete contrast, Braga, the third-largest city in Portugal, is a wonderful next stop.
Young, vibrant and forward-looking, here huge emphasis is placed on sustainability, innovation and a modern arts culture.
Visitors to Braga will discover a friendly place that’s full of contemporary life, bursting with future-focused learning, eco-friendly initiatives and projects designed to revive and revitalise the city and its surroundings - a wonderful juxtaposition to the ancient heritage of Guimarães.
After a day of diverse and thrilling exploration, guests can head back to the charming boutique country house Terra Rosa Country House and Vineyards, a beautiful family estate dating back to the year 1758, and still a working farm.
The Kingdom of Portugal and the Knights Templar
Stopping off en route to discover the canals, Art Nouveau architecture and delicious foodie treats of Aveiro, head on to Coimbra, the capital of the Kingdom of Portugal from 1131 to 1255.
With its roots in Roman times, this is a city doused in ancient cultures and steeped in romantic tales, including the ill-fated love story of King Pedro I and Lady Ines de Castro.
Nestled on the banks of the River Mondego, Coimbra's charms are clear - from the legendary spaces of the Coimbra Republics to the narrow mediaeval streets adorned with courtyards, arches, cafes and bookstores.
Here, guests can explore with a private walking tour that takes in the city’s historical monuments, mediaeval churches, cathedrals and temples, as well as Portugal's most important library - before heading to the Old University, with its beautiful chapel and baroque library.
After, a stroll through the gateway to the old Moorish walled city reveals historically significant sites like the Inquisition Courtyard, St. James Church and Santa Cruz Church, where the first King of Portugal is buried and St. Anthony graduated as an Augustine monk.
But that’s not the end of this, the ultimate 2-day experience for mediaeval history enthusiasts!
After a night staying at the sumptuous Octant Palácio da Lousã, with its stunning views over the Lousã forest and mountains, a former place located in the city centre of the charming town of Lousã, the itinerary moves on to Tomar, the former seat of the Order of the Knights Templar.
Today, Tomar is a city wealthy with artistic and cultural treasures, and its Convent of Christ stands as a perfectly preserved example of Portuguese Renaissance architecture.
Climbing up to the Templar castle, this remarkable complex includes the Charola, a 12th-century Templar chapel, which (along with the castle) represented cutting-edge military fortifications inspired by the Holy Land. Its splendid 16th-century restoration was kept intact to modern times, earning the chapel UNESCO World Heritage status.
In Tomar’s fascinating mediaeval centre, traditional shops line the surrounding streets and guests can feast on delectable local pastries, from almond and squash queijadas to the unique Fatias de Tomar, a rich, sugar-syrup-drenched sponge originally concocted by the nuns of the Convent of Christ.
Here, stay at Here, stay at the luxurious Hotel Républica in the heart of Tomar…
Monasteries and Mediaeval Life on the Iberian Peninsula
At Batalha, don’t miss the Monastery of Santa Maria de Vitória.
This remarkable site on the Iberian Peninsula gained UNESCO World Heritage status in 1983 in recognition of its fabulous Gothic architecture, whose construction spanned seven reigns and incorporated the work of generations of skilled masons.
To this day, the monastery remains home to some of Portugal’s most important and beautiful stained glass windows, and is a wonderful site to explore in the company of an experienced guide.
But the charms of Alcobaça and Óbidos are most lovely when discovered slowly by the guests themselves.
Alcobaça is home to the Cistercian Royal Abbey of Santa Maria, founded in 1153.
The monastery’s architectural beauty, inspired by the Abbey of Claraval in France, led to its own UNESCO World Heritage recognition - and, if a morning spent exploring leaves your guests feeling peckish, Alcobaça has a delicious secret to discover.
This unique town has unique cuisine and confectionary traditions influenced by local Cistercian monasteries and convents, including the rightly famous "Pão de ló" cake, a luscious 15th-century delicacy.
Meanwhile, the beautiful mediaeval town of Óbidos is one of Portugal’s best-preserved heritage spots.
A gift from King Dinis to Queen Isabel in the 13th century, the town’s stunning castle is surrounded by a network of charming streets and white houses.
It also boasts a rich collection of churches, museums, Manueline architecture and artistic treasures ripe for discovery.
A year-round calendar of events means that there’s never a bad time to visit this peaceful, romantic place.
Whether your guests arrive for the International Chocolate or open-air Opera Festival, the Mediaeval market or to experience it in festive glory at Christmas, the welcome is always warm and the local bouillabaisse is always incredible, especially when washed down with wines from the Oeste region or the famous Ginjinha de Óbidos (sour cherry brandy).
The gorgeous Montebelo Mosteiro de Alcobaça is the place to stay in the region- for a truly special night! Imagine yourself spending the night at one of the biggest monasteries of Portugal, now renovated by the prestigious architect Souto Moura, winner of the Pritzker Prize 2011. It is located in the unique setting of the Rachadouro Cloister, perfectly integrated into the Monastery of Alcobaça, one of the Seven Wonders of Portugal and classified as a National Monument and Heritage of Humanity by UNESCO.
Lisbon, Sintra and Cascais
Next, to the capital!
The unique charm of Lisbon lies in its harmonious blend of historic beauty, stunning architecture, vibrant culture and warm people, creating a place that's both rich in heritage and welcoming to all.
A private walking tour begins in Bairro Alto, a neighbourhood that resonates with "Fado" music as trams pass by, before treading in the footsteps of early 20th-century writers and philosophers in Chiado and exploring Baixa Pombalina, the historic centre rebuilt and reshaped after the 1755 earthquake.
Up to the iconic Alfama district, where life beyond the city walls began during Roman times. Here, guests explore the 12th-century Sé de Lisboa (Cathedral) before moving to São Jorge Castle, a vantage point offering breathtaking views of Lisbon, the Tejo River and centuries of history.
Stay at the stunning and recently restored, Palácio Principe Real Hotel located in the heart of the city.
Another day, another stunning UNESCO World Heritage Site - this time a privately guided tour of beautiful Sintra.
Steeped in history, myth and magic, Sintra has provided inspiration for centuries of romantics captivated by its mystical charms, arts, music and literature.
In its time, the town has seen Celtic bards, Moorish legends and Christian reconquests, leaving behind a place of palaces, culture and art, where the narrow streets of its historical centre are filled with flowers, local crafts and delicious traditional sweets.
With so much to see in Sintra, Portugal by TravelTailors feel the best way is to offer a tasting menu of select experiences for guests to choose from!
Travellers can pick to suit their individual interests from:
The Queluz Royal Palace - An extravagant 18th-century rococo palace set amidst stunning gardens which showcases the opulent lifestyle of Portuguese royalty.
The National Palace of Sintra - A unique mediaeval palace with significant historical importance, whose remarkable interior is filled with valuable artefacts.
Pena Royal Palace - Ranked among the world's most beautiful palaces, this 19th-century masterpiece boasts an enchanting blend of architectural styles.
The Moorish Castle - Perched on the Serra de Sintra's ridges, this ancient fortress dates back to the 8th century and offers awe-inspiring panoramic views.
The Palace and Gardens of Quinta da Regaleira - A magical estate built in the early 20th century, filled with mythological statues, intricate gardens and enigmatic grottoes.
The Palace and Gardens of Monserrate - Here, guests can wander through the enchanting park, which contains a diverse array of plant species from around the world, before heading inside for an indulgent exploration of the palace’s luxurious interior.
Leaving Sintra, a delightful traditional lunch is followed by a scenic drive to the coastal town of Cascais, passing through the natural beauty of Sintra-Cascais Nature Park.
Cascais, once a humble fishing village, seamlessly combines its seafaring heritage with aristocratic influences from 19th and 20th-century royal visitors.
Soaking up its cosmopolitan vibe on the edge of the Atlantic is a wonderful treat, and sets the tone nicely for a return to Lisbon via the picturesque “Marginal” road route, skirting sandy beaches, 17th-century fortresses and Estoril, known for its famous casino.
After another fabulous day of history and culture, guests searching for the charm of the golden era, can kick back and relax at The Estoril Vintage Hotel - a perfect match.
Estates and Evora, Capes and Cooking!
What would a cultural trip to Portugal be without a visit to a winery - and believe us, this experience is one of the best around.
An extraordinary day of fine wines and delicious food is hosted at the opulent Wine Estate Dona Maria, a historic 18th-century palace in Estremoz, North Alentejo.
Here, in the company of the Lady of the House, guests will indulge in a premium wine-tasting session and sumptuous lunch, accompanied by some truly remarkable, award-winning estate wines.
Each is named after Dona Maria, a lady of the court who was gifted the house and its extensive grounds by King João V as a token of his love.
Afterwards, full, happy and pampered in the lap of noble luxury, guests can retire to the sophisticated surroundings of Dá Licença Hotel. Only a 45-minute drive from Évora, in the calm and relaxing fields of Estremoz.
In Évora, every corner tells a story of its illustrious past..
Alongside an experienced local guide, visitors can spend an enchanting day exploring the long history of this mediaeval UNESCO World Heritage City, with its beautifully preserved historic centre that holds traces right back to the Romans, and walls that have safeguarded its streets and structures for centuries.
A walking tour is the perfect way to take in all the many, many sights on offer and soak up the ambience of this ancient place - from the Church of St. Francis and its intriguing Chapel of Bones to the historic Giraldo Square; the ancient Roman Temple and the 13th-century cathedral to the prestigious 16th-century university, which has been a hub of culture and tradition through the ages.
Spend the night at the Torre de Palma Hotel sat amongst vineyards of Monforte, in the heart of the Alentejo. This is a hotel steeped in history dating back to 1338.
Next stop, the coast.
Lagos, a picturesque city on the Western Algarve, is steeped in history and boasts a rich seafaring heritage amidst dramatic coastal scenery.
Today, it’s one of the Algarve's top holiday destinations, offering beautiful beaches, vibrant nightlife and excellent tourist amenities while retaining its unique character.
The historic centre is proudly Portuguese, with cobbled streets, authentic eateries and a relaxed, welcoming atmosphere that blends traditional culture with modern comforts.
Beyond its stunning beaches, picturesque harbour estuary and the remarkable Ponta da Piedade headland, Lagos offers diverse activities alongside its heritage of ancient Moorish walls, 17th-century fort and extravagant Baroque churches, offering adventurous souls the option to indulge in something active to complement this tour of cultural exploration.
After a long lunch, guests can take a self-drive trip to the Cape of Sagres. This village perched on the cliffs of the Algarve has a captivating "end-of-the-world" ambience that comes complete with wind-sculpted fortresses.
Nearby, a short stop at Cabo de São Vicente on the continent's southwestern tip allows the exploration of stunning cliffs and beautiful beaches - but sunset has to be enjoyed a little further along the coast at Cape S. Vicente, a revered spot in Roman times with spectacular, uninterrupted ocean vistas.
After an indulgent night at Casa Mãe, Tavira, with its enchanting streets along the River Gilão and captivating oriental allure, beckons exploration.
This charming town of whitewashed houses, exceptional regional cuisine (don’t miss the seafood!) and historic features still bears visible traces of Arab influence amongst its winding streets, together with a vibrant character all of its own that travellers can view from the Castle Tower above, or discover in the bustling Jardim do Coreto and vivacious Mercado da Ribeira, now devoted to entertainment and leisure.
Beyond the town, a leisurely afternoon can be spent at the Ria Formosa's scenic estuary, whose pristine beaches invite relaxation and are a haven for twitchers, while Cacela Velha, a quaint village overlooking the paradise setting of the Ria Formosa, marks the beginning of a nature park extending to Ancão Peninsula west of Faro.
Following a rewarding and relaxing day, visitors will relish a night’s repose in the Grand House Hotel, almost on the border with Spain…
A final culinary flourish
What’s the most idyllic way to cap this cultural and historical tour of Portugal’s hidden highlights?
Portugal by TravelTailors highly recommends a fabulous traditional cooking workshop that allows guests to taste and take home the secrets of the traditional dishes of the Algarve.
Beginning with a local market visit to choose the freshest ingredients, a renowned Chef will guide guests through preparing and cooking the fish, seafood and accompaniments to perfection, using recipes based on the healthy Mediterranean diet so characteristic of the stunning Southern coast of Portugal.
We hope we’ve given you plenty to inspire your guests for an enriching journey through Portugal's rich tapestry, discovering captivating heritage sites, mediaeval towns and stunning architecture, soaking up its scenic wonders and indulging in the finest of its cuisines and wines.
If your guests are longing to uncover the historic and cultural soul of this fascinating nation, Portugal by TravelTailors are peerless in their ability to create a bespoke itinerary that speaks to their every need.
