Luxury Portugal Tour 2019

A 10 day trip to Portugal 
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Luxury is found throughout every experience with this celebration of Portugal. From three eclectic bases, you will journey into the culture and charms of a nation. Enjoy tasting with the winemakers in Porto cellars, sailing around Madeira and insider insight in Lisbon. Move through fairytale palaces, medieval walled towns, volcanic mountains, fishing villages, ceramic baroque masterpieces and everything in between. Privately guided, this 10-day luxury tour has been handcrafted especially for 2019 to take you well beyond the guidebooks.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Madeira, Porto, Douro River, Palacio da Bolsa, Se do Porto, Livraria Lello, Casa da Musica, Douro Valley, Coimbra, Obidos, Lisbon, Alfama, Bairro Alto, Belem, Belem Tower, Mosteiro dos Jeronimos, Sintra, National Palace of Sintra, Alentejo, Evora, Chapel of Bones

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Madeira – Wilderness and Charm on a Remote Volcanic Island

Dazzling cliffs set the scene on Madeira for a rugged and lush backdrop to the waves of the Atlantic Ocean. The cliffs twist and turn around the island and bring a feeling of wilderness that stretches across the interior of the island. From these cliffs, you can watch pods of dolphins rising in unison as they surf the waves. Picturesque fishing villages also hide down below, their scents of coffee and seafood carried on a breeze. Farming hamlets dot the interior hills, serene and picture perfect as they mark the panorama. Madeira is a perfect place for you quickly succumb to nature and overcome any travel fatigue.

You will be greeted at the airport and transferred to a timeless hotel that will overlook the ocean. Your hotel has been entertaining luminaries for over a century and is a place of indulgence and decadence to complement the wild feel of the island. Enjoy a welcome drink with your Madeira guide and discuss the itinerary for the next few days. A high level of customization is possible with the private four-wheel drive tour and the yacht expedition, with options to discover different parts of Madeira dependent on your interests and mood. You will not need to decide now, but while introducing the region’s history, the guide is likely to inspire your imagination.

What’s Included: airport transfer, accommodation

Day 2: Madeira – From Fishing Villages to Dramatic Mountains and Coastline: A Private Four-Wheel Drive Tour

Exploring Madeira is always an adventure. Bump along the rugged coastal roads to find fishing villages hiding beneath the cliffs. Bounce through the interior to viewpoints that epitomize the wilderness feel. Choose to spend an hour or two hiking the canal trails, iconic routes through the excesses of nature. Or spend more time in the villages to understand how local culture has been mostly unchanged for centuries. To the smells of wildflowers and the sound of birdsong, you can fully explore Madeira as you stop at wineries, markets, gardens and embroidery studios unbeknown to the world. It could be a full-day tour by four-wheel drive, or something a little shorter depending on your energy levels with your guide able to tailor the stops to your liking. A traditional lunch at a legendary island eatery will also be part of your experience.

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

Day 3: Madeira – Private Yacht Expedition and Natural Rock Pools of the Northern Coast

From the water, you can enjoy a very different perspective of Madeira as a private yacht will use the power of wind to sweep you along the coastline. Impenetrable cliffs rise starkly, hiding beaches that you cannot see or access from the land. The scent of the salty ocean accompanies you past the tiny fishing villages, where whitewashed facades shimmer from afar. There are various places to dock in sheltered bays, and you can jump into the cooling waters of the Atlantic, a must on a balmy summer day. You can also explore the natural rock pools of the northern coast, try deep-sea fishing at spots that only the locals know about, and finish the day with a private cooking lesson in one of the fishing villages. While a day of sailing provides a degree of contemporary indulgence, you will be firmly settled into the natural rhythm of an island cut off from the edge of Africa.

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

Day 4: Porto – Overlooking the Port Cellars and Celebrating the History of the City

Fly to Porto, and the view from your hotel terrace will reveal an essential part of local history. Beneath you are the wine cellars, the faded bricks emanating a rustic, industrial charm. Look down further to the Douro River, and then across to the historical waterfront of Porto, your focus for an afternoon of private discovery. Painted in blue and liberally cobbled, this a living UNESCO World Heritage Site immerses you in styles from across the centuries.

Add your footsteps to the echoes that float over the staircases and inhale the scents in the narrow lanes with wine mingling with local kitchens and the musty fumes of a distant era. Admire the lavish murals that cover so many of the walls that are made up of individually painted blue tiles that look like jigsaw pieces that stretch for hundreds of square meters. Avoid the tourist riffraff and browse the best specialty shops with your local guide, particularly those renowned for their porcelain. With a full afternoon in Porto, your private tour can be handcrafted to your interests, perhaps venturing further afield to highlights like Casa da la Musica and the Serralves Museum.

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

Day 5: Porto – Private Cruise on the Douro River and the Wines of the Douro Valley

Porto stands at the mouth of the Douro River, and since the 18th century, wooden rabelo boats have transported grapes and barrels from the green valleys upriver.  You will replicate this journey on a private cruise, and as you weave away from the city, you will be slowly enveloped by the canyon walls that rise higher and higher with crumbling fortresses dotting the hills in the distance. Soon, the terraced vineyards take over, dominating the vista as the river narrows. These vines are too steep for machinery, meaning the most traditional methods of viticulture have been continued into the 21st century.

Disembark at a couple of the vineyards and taste with a winemaker for an excellent introduction to the wines of Portugal. Those from the Douro Valley are fruity and full-bodied, the best vintages rounded further by extensive oak barrel aging. Grapes used for Port also originate here, and you will get a tour of one of the old vineyards to discover how the steep terraces ensure a wine that benefits from a high level of natural sugars. After an indulgent lunch in the Douro Valley, you can cruise back into Porto, the rabelo a window onto both wild and rural northern Portugal. Disembark at one of the port cellars for a private port tasting, the sommelier opening up old vintages as you taste ports that date back many centuries. While all the port cellars offer a tasting, only through local connections are you able to taste the vintages that are revered all across the world. The evening will be at your leisure, and the guide can recommend Porto restaurants on both sides of the river.

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

Day 6: Porto to Coimbra to Obidos to Lisbon – Connecting Culture and History on a Beautiful Route Through Northern Portugal

Cultures are connected on the journey between Portugal’s two major cities. With a new private guide, you will drive south, ascending into the hills and the cute little town of Coimbra, where many buildings have a scent of the 13th century. Passing tiny villages and ruined fortresses, you will continue south, stopping for lunch in the whitewashed medieval town of Obidos. Surrounded by city walls, you can dine on the past, Portugal’s food a real celebration of raw ingredients and traditional recipes. Then it will be onwards, beneath the hills to the next colorful city on the river. By traveling with different guides, you can get to  understand the local context and discover with specialists. Their knowledge of the destinations does not just provide a historical overview, but a chance to share tales with the locals who define their city.

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

Day 7: Lisbon – Insider Tour of Lisbon’s Distinctive Neighborhoods

Crossing Lisbon, you will feel the atmosphere change. Built across the seven hills, the Portuguese capital is a patchwork of neighborhoods, each with a distinctive style. Standard tours follow a standard route that bustle with crowds from the tour buses. But this is a city that is perfect for a tailored tour, one that can lead you in multiple directions dependent on your mood and interests. Portuguese specialties are found in backstreet shops, from golden jewelry to Indo-Portuguese furniture and all manner of antiques. Moorish and Manueline architecture is celebrated at postcard icons, but also on lanes that are far from the typical tourist’s eye.

Handcrafting your itinerary, your local guide will reveal their city beginning with the heritage of Alfama district to the vibrant Bairro Alto and the monuments of Belem. Museums can be selected according to your interests, be it the royal glamour of the National Coach Museum, the exquisite design in the National Tile Museum or a private art collection at the Calouste Gulbenkian Museum. Make a private stop at the Ricardo do Espirito Santo Silva Foundation for a wonderful insight into traditional decorative art. Make stops at Lisbon’s most revered eateries, from a pasteleria where pastel de nata, a sweet fluffy custard pastry, originated, to dinner reservations at Michelin-starred restaurants. By the end of the day, it may feel that you have discovered many cities. One element ties the neighborhoods together is the enthusiasm and zest for life that contradicts most capitals of the world.

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

Day 8: Lisbon – Private Tour to the Fairytale Palaces and Hills of Sintra

There is a plaque outside the National Palace of Sintra that narrates the building’s mystical history and declares how the first records of the palace come from the Moors in the eighth century. That is not when the palace was constructed, but just when it was first documented by a civilization through written language. This is just the start of the fairytale in Sintra, a delightful village of winding streets that are dotted with these sublime memoirs to the past. More palaces are found in the forested hills around the village, resplendent in their narration of a pre-medieval time.

Poet Lord Byron came to Sintra in 1809, and his immortalized words retain their poignancy into the present day. “Lo! Cintra’s glorious Eden intervenes...who to the awe-struck world unlocked Elysium’s gates?” (from Childe Harolds Pilgrimage). Travel further to find that this fairytale world is not merely humanmade, but also defined by nature. Beaches nestle beneath cliffs, holes, and caves hide deep within the landscape, and you will have options to explore by road and by hiking trail. As part of your day, you could have lunch at an iconic seafood restaurant in nearby Cascais, or enjoy the royal cuisine of Sintra in one of the small village restaurants.

What’s Included: accommodation, tour, breakfast

Day 9: Lisbon – Rural Portugal at its Best: Private Tour to Evora and Alentejo Region

Leaving Lisbon for the day, you will embark on a discovery of rural Portugal as the Alentejo region is proud of its traditions and roots. Olive groves line the road, vineyards focus on quality over quantity, vast forests of cork are harvested and sent around the world. Hiding in Alentejo, you will also find beautiful old cities where narrow lanes are lined with whitewashed houses and crumpled Roman ruins. Moorish architecture becomes more apparent as you wind closer to the coast, its white simplicity enhancing calligraphy and geometry painted in all manner of colors. With an Alentejo expert, you can travel in many directions to follow the scent of food and wine or delve deeper into history.

Stop in Evora, the UNESCO World Heritage symbol of the region and a city with an atmosphere of the old world. Admire the Chapel of Bones and muse about the heritage, which seems to step out from every corner in the city. Step into the dense cork forest to find the Neolithic ruins of Cromlech and Menhir of Almendres. Enjoy lunch at one of the region’s most renowned wine estates, and then customize the afternoon to your desires. While these last two days will take you away from Lisbon, you will return in time for enchanting evenings spent in the hills, perhaps watching the sunset from a restaurant or maybe going off the beaten track to neighborhoods of culinary tradition.

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

Day 10: Lisbon – Departure

After a leisurely morning, you are transferred privately to the airport, where this luxury 2019 Portugal tour ends.

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.