Off the Beaten Path Exploration of Portugal: Evora, Estremoz and Elvas

A 12 day trip to Portugal 
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Portugal hides its secrets and rewards the patient traveler that is willing to explore down the narrow lanes and journey behind the obvious highlights.  Find elegiac music in little taverns and ancient towns built from marble, and then turn to find seductive outposts and cities from the 16th century. With expert insider guides, this 12-day luxury tour will take you off the beaten track and into the authenticity of Portugal’s lesser known destinations of Evora, Estremoz, and Elvas.

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General Information

Detailed Itinerary

Places Visited 

Lisbon, Alfama, Baixa, Lisbon Castle, Se Cathedral, Belem, River Tagus, Belem Tower, Mosteiro dos Jeronimos, Park of Nations, Avenida da Liberdade, Campo Pequeno, Sintra, Pena Palace, Moors Castle, Palacio Nacional, Cascais, Elvas, Forte de Santa Luzia, Praca da Republica, Estremoz, Borbo, Vila Vicosa, Igreja de Santa Maria, Evora, Se Cathedral

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Lisbon – Grandeur and Charm of Baixa and Alfama Districts

Lisbon is the iconic introduction to Portugal’s character as every district is distinct and feel as if the locals are deliberately creating contrasts. Touch down in the capital and a local guide will lead your exploration, Alfama, and Baixa the classic example of a city with many characters. Rebuilt following the 1755 earthquake, Baixa is the grand heart of Lisbon and home to opulent avenues and grand plazas, a celebration of glamour and entirely different from Alfama, a distinct a dozen stops away on the tram. Narrow lanes are flanked by tiny graffiti-scathed houses to bring the old working-class neighborhood to be one that is packed with charm.

It will be here that you can hear the elegiac sounds of the Fado, a mournful style of traditional music that emanates from the taverns. While in Baixa, you can stop for a coffee on a grand al fresco terrace, but in Alfama, you will feel the heat and intensity of the tavern music with beautiful songs that drift with the smells of barbecued seafood or boiled pork. This is just your first day in Portugal, and you already have settled into the style of this luxury tour. The timing of the day will be very flexible and will allow you to move at a pace that reflects your energy levels.

What’s Included: airport transfer, accommodation, tour

Day 2: Lisbon – Contrasts of the Capital: Belem to Bairro Alto

Continue to celebrate the contrasts with your day that will start in Belem. It will be here that you will find the city’s popularized postcard images like the suspension bridge over the Tagus and the whitened beauty of Belem Tower. The city is less crowded with tourists in the morning hours, which will allow you to appreciate the grandeur without too many spoiling your photos. Back in the heart of the city, Bairro Alto is the old working-class neighborhood now redefined with vintage stores and artisans. There is color everywhere with painted tiles on the buildings and vibrant secrets hiding down the steep pedestrianized lanes. It will be another excellent district for the evening, with its vast array of underground venues and quirky hangouts.

What’s Included: accommodation, tour, breakfast

Day 3: Lisbon – Modern and Forgotten Side to Lisbon

As visitors clamber to see the old districts, the modern side of Lisbon is mostly forgotten. The modern areas of the city are just as authentic as anywhere else as a contemporary interpretation of tradition. Trendy and fashionable, the Park of Nations is where the locals come to chat and is packed with restaurants, bars, and benches beneath the trees. Nearby is the Moorish-inspired bull ring, along with the chic Avenida da Liberdade. Taking the cable car through the park and along the river is an iconic experience on this side of the city, as is wiling away a couple of hours in the park sharing stories with the locals.

What’s Included: accommodation, tour, breakfast

Day 4: Sintra – Palaces and Ruins of the Glorious Eden

The Palacio Nacional stands in the heart of Sintra with a strange coned chimney reaching out from its kitchens for a memorable first impression as you enter the city of royalty. But before you head inside, you will explore the surrounding hills of Sintra, which exhale with a sense of history full of both battles and beauty. Clamber up to the restored ruins of a Moorish castle, and then admire the extravagance of Pena Palace. Stone carvings mark the façade, and vibrant colors fill the interior and all scream of a regal excess. This is a wild and beautiful area that is crisscrossed by hiking trails that are perfect for taking a picnic. From 20 minutes to two hours, there are some sublime trails of discovery.

It will be later in the afternoon when you will return to Sintra, just as the day-tripping tourists have left. You can now have the Palacio Nacional all to yourself, a castle that the Portuguese monarchy have occupied for centuries. The castle has been here since before the Moors, enhanced with snippets of typically unique Portuguese style. With the tourists gone, you can also wander through the authenticity of Lord Byron’s glorious Eden and hear your own footsteps on the cobbles. With very few other people around, you will experience precisely why Lord Bryon was so moved.

What’s Included: accommodation, tour, breakfast

Day 5: Cascais – A Charming Seaside Town With a Regal History

From Sintra, you will follow the coast for a relaxed day in the regal getaways from yesteryear. Even since the 19th century, Cascais was the resort destination for aristocrats and the wealthy, and it has retained its charisma as the grand old dame of Portuguese destinations. You will be transferred privately from Sintra, and the day will be at your leisure with an opportunity to wander through the old part of town and take a stroll along the promenade. There are various beaches for a languid afternoon, as well as an outstanding collection of seafood restaurants standing over the sand.

What’s Included: accommodation, transfer, breakfast

Days 6 – 7: Elvas – The Seductive Outpost on the Spanish Border

Alentejo is the wild region found beyond the Tagus, where dust swirls on the plains and cork forests tumble across the hills. Empty roads slice past vineyards, forts stand isolated on the hills, and you will be unable to understand why the region is so under-visited. The region is a poem to the tradition and heritage of Portugal, happy to maintain its rurality and authenticity. You will see it and sense it on your journey out to Elvas, where the seduction of Alentejo is inescapable. Found just along the Spanish border, this is the outpost that repelled an invasion from neighbors with three staggering forts that greet you from afar, the star-shaped Forte de Santa Luzia an insight into the enormity.

From the walls of a 15th-century castle, you will gaze past the frontier and out across the plains of dust and cork. Then you will enter through the old city gate and bask in the beauty of the city’s design, encased in an epic wall from the medieval period. Battlements rise, an aqueduct stretches out into the valley, snippets of marble are found along the walls. Elvas was the first line of defense against the Spanish, but behind the yellow city walls, you will find a serious dedication to style and grandeur. Whitewashed townhouses line the cobbled streets, family-run taverns beckon you inside, and ancient churches ring their bells through the evening. Your local guide will take you on a tour of the iconic fortress sites, and then the following day, you can go behind the scenes to meet the locals who can narrate the history.

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

Days 8 – 9: Estremoz – Surreal Marble Towns of Alentejo

Alentejo has always been a region of natural splendor. Not just the cork and the cliffs, but the vast landscapes of marble as well. While the region has traditionally been poor, the towns have a facade that seems to appear more lavish by the century. Marble was the local building material, and entire plazas are paved in its opulence. The marble can be slippery beneath your feet, polished over the centuries by footsteps. Estremoz is your base for the exploration of the marble cities, a quaint little place that delights in its tradition. Admire the decoration of Igreja de Santa Maria, marvel at the beauty of chapels crafted from marble, and hear all of the stories from your private guide. Spend the day here to find a city where nearly every building could be a postcard. Lounge on the square during the evening, sip on local wines and dine on the food from the plains.

The next day, discover the surroundings, where smaller villages and towns are also dominated by the glamour of marble. Taste fruity wines with the winemaker in Borba, where the snow-white marble makes for fascinating churches and fountains. Wander down the tiny lanes of Vila Vicosa, a one-time hunting retreat for the dukes and kings and the most liberal of all in the use of marble. Convents and hermitages shimmer, statues and mosaics are polished white, and a 13th-century castle reveals further royal excess. These two towns glisten from afar and will have enough sites to keep you enchanted for days. But like so much of Alentejo, your experience is not about sightseeing but absorbing the atmosphere of destinations from the past. Witnessing such huge collections of marble makes you really wonder why there are so few other international visitors.

What’s Included: accommodation, tour, breakfast

Days 10 – 11: Evora – Cobbled Streets, Painted Houses, and 16th-Century Allure

Evora’s history is immediately apparent as a Roman aqueduct enters the city from the valley and leads you towards the Diana Roman Temple, where the columns rise proudly after 2,000 years. Sounds echo across the temple, the hum of terrace chatter mixing with church bells and the clatter of footsteps on cobbles. This is a city that rewards slow travel and one that implores you to look beyond famous monuments like the Diana Roman Temple. Evora is a living, breathing city that brings a captivating cultural experience. Family-run restaurants reveal timeless Alentejo delicacies, tiny taverns and terraces take you from evening to night, and traditional houses are unchanged for centuries.

While Evora has two millennia of history, it is frozen in the 16th century when the city grew rich from the wealth brought home by explorers. Your guide will act as a gatekeeper, affording access to houses that are closed to the public. These are painted in traditional colors to create a harmony that is laced with nuance when you explore slowly. Strange findings hide when you head inside, like at the Chapel of Bones, where femurs and skulls are embedded into the walls, haunting and ghoulish in their abundance. Or at the Se Cathedral, where unique statues hide beneath the mystifyingly mismatched towers.  You might also spend an afternoon nearby, where bizarre Neolithic formations show that the landscape is many thousands of years older than the Roman temple.

What’s Included: accommodation, tour, breakfast

Day 12: Evora to Lisbon – Departure

From Evora, it is just a 90-minute journey back to Lisbon. Spend your morning at leisure with perhaps one last stroll around Evora or coffee on the central plaza. Returning to the capital, you will enjoy a quick glimpse at the landscapes of Alentejo as you arrive at the international airport with plenty of time before your flight.

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.