Itinerary Portugal and Spain in Fourteen Days from Lisbon

The first day of our Itinerary Portugal and Spain in Fourteen Days from Lisbon will be dedicated entirely to visit Lisbon, devastated by the earthquake of 1755, the largest ever recorded in Europe, so it was necessary to design a new city with the first anti-seismic constructions, drawn with a set of straight and perpendicular streets organized around an axis the central part of Rua Augusta.
In these streets were given the names of the various crafts of the time and artisans of that time among them; cobblers, corraliros, of gold.

“Baixa de Lisboa” is also known for the monumentality of its buildings, which represent a new social order that values the merchant and financial class. To test the resilience of these buildings to a new earthquake used troops marching inside buildings.

Time to explore Belem and its monumental works such; the Tower of Belem, the Discoveries Monument, the Monastery of the Jeronimos that besides its beauty, provided the monks the way to make this wonder pastry called “Pastel de Belem”, impossible to miss it.

At the end of the day we will visit the “new” Lisbon nowadays called the “Park of Nations”, with its Oceanarium, the lovelly train station designed by the Spanish Callatrava, the extensive bridge Vasco da Gama and its modern buildings.

Overnight in Lisbon

Discover Sintra, once the summer retreat of Portuguese royalty. Stroll through its charming streets, try the famous Travesseiros and Queijadas at Piriquita, and choose to visit one or two iconic sites like Pena Palace, Quinta da Regaleira, or the Moorish Castle — each with its own unique style and history.

We’ll then head to Cabo da Roca, the westernmost point of mainland Europe, with stunning cliffs and ocean views — as described by Camões, “where the land ends and the sea begins.”

The tour continues to Cascais, a stylish coastal town, and nearby Estoril, home to Europe’s largest casino and wartime spy stories.
Return to Lisbon via the scenic coastal road with breathtaking views.

Overnight in Lisbon

On this travel day from Lisbon to the Algarve, we stop in Évora, a UNESCO World Heritage Site rich in Roman, Moorish, and Portuguese history. Highlights include the Roman Temple of Diana, the Cathedral, and the impressive Água de Prata Aqueduct, still visible in parts of the city center.

We’ll explore the narrow Moorish alleys, remnants of the 11th and 12th centuries, and learn how Évora became a cultural hub during the Portuguese Discoveries, home to royal patrons and artists.

A must-see is the Chapel of Bones, inside the Church of São Francisco, where the walls are lined with the bones of over 500 monks — a haunting and iconic symbol of the city.

To complete the experience, we may stop at a local winery to learn more about Alentejo’s celebrated wines, with a tasting included.

We then continue south, arriving in the Algarve, with a suggested overnight stay in Albufeira.

Overnight in Albufeira

On this day, we explore some of the most culturally rich cities in the Algarve.

We begin in Tavira, where we’ll visit the City Hall, the Islamic Museological Nucleus, and the Church of Misericórdia, a prime example of Renaissance architecture in the region.

Next is Faro, considered the Algarve’s historical heart. Within its ancient walls lies a mix of Roman, Moorish, and post-earthquake heritage — a city shaped by prosperity and destruction.

In Lagos, we confront the city’s complex past at the Slave Market Museum and enjoy its reputation for excellent gastronomy, particularly fresh fish. Weather permitting, we’ll also take a boat tour to the Ponta da Piedade caves, known for their stunning rock formations.

The day ends in Sagres, at the iconic Sagres Fortress, ordered by Prince Henry the Navigator. Inside, we’ll see old cannons, a 16th-century tower, the Church of Our Lady of Grace, and the mysterious wind rose — believed by some to date back to the prince’s nautical school, considered the first in the world.

Overnight in Albufeira

On this day, we say goodbye to the Algarve and head toward Andalusia, the Spanish region known for its flamenco rhythms and strong Arab influence.

Before crossing the border, we’ll visit Vilamoura, Portugal’s largest luxury resort complex. With its modern marina, five golf courses, tennis and diving clubs, high-end hotels, and vibrant nightlife, Vilamoura attracts luxury yachts from all over the world — starting with the Giralda sailboat of the Count of Barcelona in 1974.

We’ll also make a stop in Castro Marim, one of the Algarve’s oldest towns, valued since Roman times for its strategic location near the sea. Conquered from the Moors in 1242, it was later supported by Portuguese monarchs with privileges and charters that helped revive the town after the Christian reconquest.

After exploring these highlights, we continue our journey into southern Spain, beginning the Andalusian leg of our 14-day Portugal and Spain tour.

Overnight in Seville

Today we explore Seville, a vibrant Andalusian city known for its energy, heritage, and intense summer heat — often reaching up to 50°C.

We begin at the Seville Cathedral, originally a 12th-century mosque, now the largest Gothic cathedral in the world and the second-largest Catholic church in Spain. Nearby, we visit the Giralda Tower, once a minaret, now offering panoramic views of the city from over 100 meters high.

Next, we explore the Royal Alcázar, the oldest royal palace still in use in Europe and a UNESCO World Heritage Site. Still hosting members of the Spanish Royal Family and international guests, it blends Moorish and Christian architecture.

We’ll then relax at the stunning Plaza de España, featured in films like Star Wars and Lawrence of Arabia, before heading to the modern Metropol Parasol, an iconic wooden structure nicknamed “The Mushroom.”

To end the day in true Andalusian style, we recommend an authentic flamenco show.

Overnight in Seville

On this day of our 14-day Portugal and Spain itinerary, we leave Seville and head to Córdoba, a city deeply marked by Arab heritage.

We’ll visit the iconic Cathedral-Mosque of Córdoba, a stunning example of Islamic architecture converted into a Christian cathedral after the Reconquest. We’ll also cross the historic Roman Bridge, watched over by Saint Raphael, the city’s patron saint — so revered that nearly 20% of locals share his name.

Another highlight is the Alcázar of the Christian Monarchs, a fortress-palace that witnessed Roman, Moorish, and Christian rule.

Along the way, we stop in Baena, a lesser-known town with ancient roots, home to the ruins of a medieval castle, the Iberian Lion statue, and El Crismón, a remarkable Visigothic cross.

We end the day arriving in Granada, ready to explore one of Spain’s most enchanting cities.

Overnight in Granada

Granada is one of Andalusia’s true gems, with the Alhambra as its crown jewel — a magical 13th–14th century Moorish fortress later transformed into the stunning Nasrid Palace. After the Christian Reconquest, the mosque was converted into a church, blending Islamic and Christian influences in one of the most beautiful monuments in the world.

Beyond the Alhambra, Granada offers much more: the Albaicín neighborhood, with its whitewashed houses and panoramic views, and the vibrant Alcaicería Market, once a Moorish silk bazaar, now a maze of narrow alleys filled with North African-inspired goods.

The city flourished during the Renaissance, becoming a hub of art, culture, and lively nightlife — a perfect mix of history and energy.

Overnight in Granada

Despite its small size, Toledo has played a major role in Iberian history, preserving traces of Roman, Visigoth, and especially Moorish influence. From the 12th century, it became a political and religious hub for both Muslims and Christians, until its decline in the 16th century when King Philip II moved the capital to Madrid.

Highlights include a visit to the magnificent Toledo Cathedral and the Synagogue of Santa María la Blanca, a unique blend of cultures and architecture.

To recharge, don’t miss tasting the traditional marzipan (mazapán) — especially from Confeitaria Santo Tomé in Plaza Zocodover.

After our visit, we continue to Madrid, the final stop in our 14-day Portugal and Spain tour.

Overnight in Madrid

Madrid is one of Europe’s great capitals — rich in culture, architecture, and energy. One day may not be enough, but we’ve selected key highlights to make the most of your visit.

We start at Puerta del Sol, home to the famous bear and strawberry tree statue, one of the city’s most photographed landmarks. Then on to Plaza de Cibeles, a symbolic hub of Madrid, followed by a scenic walk up Paseo de Recoletos, lined with 19th-century palaces and charming gardens.

For art lovers, a visit to the world-renowned Prado Museum is highly recommended (tickets should be booked online in advance).

All of this — and more — can be adjusted to your interests in a tailor-made Madrid experience.

Overnight in Madrid

We begin the day in Ávila, one of the world’s most stunning walled cities and a UNESCO World Heritage Site. Before entering, we’ll stop at the “Mirador de los Cuatro Postes”, the best panoramic viewpoint to admire the medieval layout.

Founded by St. Teresa of Ávila, the city is known for its perfectly preserved walls, with 87 towers and 9 gates surrounding the historic center — a true testament to Spain’s medieval past.

Next, we head to Salamanca, a city that blends youth and tradition. Known for its university, one of the oldest in Europe, Salamanca also charms visitors with its golden-hued Villamayor stone architecture.

Highlights include:

• Casa de las Conchas

• The University Library

• The Old and New Cathedrals

• Palacio de la Salina

• The majestic Plaza Mayor, a baroque masterpiece with 88 arches and historical medallions

This day combines rich history, breathtaking architecture, and the vibrant energy of two of Spain’s most emblematic cities.

Overnight in Salamanca

We return to Portugal with a stop in Aveiro, often called the “Portuguese Venice” thanks to its charming canals. A Moliceiro boat ride is highly recommended to explore the city’s 3 km of waterways, once used for transporting seaweed (moliça) and salt — two pillars of Aveiro’s economy.

We’ll also visit the Aveiro Market, a striking iron-and-glass structure reminiscent of Eiffel’s style, and admire the city’s rich collection of catalogued Art Nouveau buildings, reflecting Aveiro’s former prosperity.

Our day continues in Costa Nova, famous for its colorful striped fishermen’s haystacks (palheiros). Originally simple warehouses built on stilts, many have been converted into summer homes, creating one of the most picturesque coastal settings in Portugal.

Overnight in Oporto

We begin our day in Avenida dos Aliados, the vibrant heart of Porto, surrounded by grand architecture and crowned by the impressive City Hall. From here, we visit the iconic Lello Bookstore, a must for literature lovers — especially fans of Harry Potter, as J.K. Rowling lived in Porto while beginning her first novel.

Next, we explore the stunning São Bento Train Station, where 20,000 hand-painted tiles depict Portugal’s history and culture. Nearby, we visit the Porto Cathedral, a Romanesque-Gothic monument with breathtaking views and Baroque additions by Nicolau Nasoni.

Then, we head to the Church of São Francisco, famous for its rich gilded woodwork — over 300 kg of gold dust — and its remarkable Tree of Jesse sculpture, a masterpiece of religious art.

We end the day across the river in Vila Nova de Gaia, where Port wine is aged in historic cellars. You’ll visit one of them, learn about the winemaking process, and of course, enjoy a tasting of this world-famous wine.

Overnight in Oporto

We leave Porto heading to Coimbra, where we begin with a visit to the stunning Joanine Library, one of Europe’s most spectacular Baroque libraries, located within Coimbra University. With its exotic woods, gold-leaf carvings, and painted ceilings, it is a true temple of knowledge.

We then explore Coimbra’s historic center, filled with medieval streets, artisan shops, and centuries-old buildings — a city where history and tradition remain very much alive.

Our next stop is Fátima, one of the world’s most important Marian pilgrimage sites. We visit the Chapel of the Apparitions, the Basilica of Our Lady of the Rosary, where the three shepherd children are buried, and the modern Basilica of the Holy Trinity.

From here, we return to Lisbon, marking the end of our 14-Day Private Tour through Portugal and Spain. We hope the journey has been as meaningful and memorable for you as it was for us to guide it.

Overnight in Lisbon