For 8 days we will visit Lisbon and the Alentejo region, the southern part of Portugal, to see and experience the overwhelming contrasts of what this 900 year old country offers, sleeping and dining at exclusive places, visiting World Heritage cities and monuments, taking a deep dive into curated experiences that will leave you wondering how in the world can such a small territory offer such great travel memories! Are you up for it?

The hotel choices featured on this trip reflect the many sides and pride of the Portuguese welcoming tradition. Accommodations from early 16th century monasteries to more countryside design atmospheres, as well as renovated and more sophisticated at the heart of Lisbon neighborhoods, these are curated hotel choices that will enhance your Portuguese experience. If you are looking for R&R you can always use some of these hotel’s facilities such as the spa, pool or even, the gym.

Lisbon has been around for many centuries. It has seen Roman and Muslim occupation and was the most cosmopolitan place on Earth during the 15th & 16th century, to being completely rebuilt in 1775 after an earthquake, tsunami and large fire destroyed it. We will visit all these layers of time, from the Muslim castle to the Belém Tower, Jeronimos Monastery, visiting the National Tile Museum and still leaving you in wonder on how vibrant and full of life the Portuguese capital is, with its shops, restaurants and nightlife choices. All these wonderful places that spread between the river and the hills will enhance your Lisbon experience.

After Lisbon, we will head inland to the UNESCO World Heritage town and Alentejo capital of Évora, where different layers of civilizations are at our fingertips (Roman, Muslim and Jewish influences). Here we will experience a wine tasting at a 13th century wine estate followed by a dinner at a typical “Taberna” restaurant - a true portuguese cuisine experience. As we travel through the wine country, we will move further into the Alentejo inland, wondering near the border town of Elvas (home to the largest defensive system in Europe) to enjoy a slow-paced lifestyle, more incredible wine and food, notwithstanding other adventures that will serve as a reminder to the lightness and easygoing rhythm of our journey.

There is a sense of truth when we say that one way to travel is through flavors. With this knowledge, this tour will also take you to very different places using your senses, making you aware of the different inspirations and cultures that go around the typical southern Portuguese food (Alentejo) found in this wine producing region. This will include quaint recommended restaurants which will be paired with other exquisite food experiences, with one underlining idea: the slowly flavoring of the Alentejo traditions, paired with a more sophisticated take, around the city of Lisbon.

Our first stop will be at the Castelo neighborhood where we will have lunch. We will take in amazing scenery, looking over the 25th of April bridge, reminiscent of the Golden Gate bridge built by the same American company. After lunch we will head to our Hotel, check-in, and if you feel like it we can take a stroll around the Bairro Alto and Chiado neighborhoods or you can choose to rest. Before dining we will have a cocktail at one of the most incredible rooftop bars in the area. We will dine at a quaint and easy going restaurant in the Príncepe Real neighborhood.

We will start our day by the Tagus river at the Belém Tower, Jerónimos Monastery and the Discoveries Monument, before we head out to the nearest wine region to Lisbon, to experience a first wine tasting in Colares. We will lunch at an amazing and quaint place, overseeing the Atlantic, by a windmill. Afterwards,  we will still find time for another stop at a wine maker, before heading back to Lisbon, taking the scenic view through Cascais and Estorial and a stop at the most western European tip of the continent. Evening will be free.

We will head in the morning to the Ajuda National Palace where, not only will we visit its royal chambers and Throne Hall, but we will also have time to see the Royal Treasure Museum where some of the royal jewels can be seen. Afterwards, we will drive to the UNESCO Heritage Site of Évora, a city where different layers of history are at our fingertips. Being of so many influences (roman, jewish, muslim and christian) we will have lunch at a popular setting, to eat “Petiscos” (portuguese version for the Spanish “Tapas”) combining Alentejo traditions with Italian inspiration.

In the afternoon, while strolling around the narrow streets of Évora, we will visit the Saint Francis Church, where the Bone Chapel is, followed by The Giraldo Square and the Roman Temple and also, one of the Portuguese Kings residences in Évora, where, hopefully (weather allowing it) will have a wine tasting in its gardens. We will check in at an charming hotel that once was parto fo a monastery. A dinner awaits us at Eugénio de Almeida Foundation, right beside a 15th century Manor, thought to be owned by Vasco da Gama, the portuguese navigator who completed the maritime way to India, crossing the Cape of Good Hope in the southern tip of South Africa.

We will begin our day by driving through the beautiful wine region of Alentejo. We will first stop at Évormonte to see not only one of the most incredible views in the Alentejo region, but also its quietness allowing us to see and hear for miles. Then we will drive to Mainova, one of the most interesting and young wine producers of the Alentejo wine region, not only to taste wine but also to have a picnic/lunch.

We will then head to Pepe Aromas where we will learn more about Cork, one of this region’s most valuable natural products or experience the production of Olive Oil and its different types of tasting, their health benefits and how they are used in regional cuisine. Dinner will be at a nearby and quaint village..

Our first stop will first stop at Vila Viçosa to visit the Braganza Palace where the Portuguese Royal Family spent their summers, welcoming royals from other countries. Then we will head to Estremoz, to have a wine tasting and sightsee the XVIII century Palace given by the Portuguese King John V to one of his mistresses D. Maria. Afterwards we will head out to Elvas, visiting the impressive Senhor da Graça fortress - one of the strongholds of the Elvas defensive structures, while also walking this historic town.  Dinner will be at a quaint and typical Alentejo restaurant in the Elvas area.

We will have a free morning to relax. At noon we will head to a wine tasting followed by lunch at one of the Michelin Star recommended restaurants where you will enjoy a typical meal, surrounded by the Portuguese appreciation for bullfighting.

Feeling lighter and energized after lunch, we will then drive to Marvão, an enchanted, thousand-year-old small village founded by a Muslim rebel as the capital for his own kingdom. From there, hopefully, we will be able to capture one of the most incredible sunsets in Portugal, while enjoying evening cocktails & dinner.

We will start our day by visiting Campo Maior arriving at one of the most impressive cellars in the European wine landscape, created by architect Siza Vieira (winner of the Pritzker Prize - architecture’s Nobel) to have a wine tasting and picnic. After our wine tasting and lunch, we will head to Juromenha, not only to appreciate a fortress blown away by Napoleon's armies, but also to experience a boat ride/tour through the Alqueva dam (if weather & river conditions allow us) to end up at one of the most beautiful villages in the country: Monsaraz. We will end our final day in Portugal having a quaint casual dinner among a lemon tree garden, right beside a Muslim wall. We will be able to recap all the flavors and highlights of this southern Portuguese tour.

Lisbon Airport & back in the USA. Until Next Time, Obrigado!