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Madrid and Lisbon - Evora - Beja: Chauffeured Collection

11 to 16+ Nights from $1,552*
* Sample price: priced within the past 7 days for a 3/3/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 11 night sample itinerary includes:

  • Flight into Madrid and out of Lisbon
  • Hotel for 3 nights in Madrid
  • Flight from Madrid to Lisbon
  • Hotel for 2 nights in Lisbon
  • Transfer from Hotel in Lisbon to Hotel in Lisbon to Hotel in Evora via Palmela and Almendres Cromlech
  • Hotel for 2 nights in Evora
  • Transfer from Hotel in Evora to Hotel in Beja via Castle of Portel
  • Hotel for 2 nights in Beja
  • Transfer from Hotel in Beja to Hotel in Lisbon via Alcacer do Sal and Cape Espichel
  • Hotel for 2 nights in Lisbon

Embark on an enriching journey, linking the capitals of Spain and Portugal!. Combine Madrid (artistic and energetic Spanish capital) and after, Portugal's ancient capital soul in Lisbon. Continue to The Alentejo Region with stays at Evora (UNESCO World Heritage city with Roman and medieval history at its core) and Beja (historic hub of the Baixo Alentejo, known for its regional culture and tradition); until get back Lisbon, to finish enjoy what the portuguese capital has to offer. The route is defined by iconic stops: the panoramic vistas of Palmela, the ancient stones of the Almendres Cromlech, the Castle of Portel, key historic port of Alcacer do Sal and the dramatic Atlantic cliff of Cape Espichel; all of them, with refined ease.

What Makes Tripmasters Vacation Packages Different?
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Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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Flexible Itinerary

  • Madrid

    about
  • Lisbon

    about
  • Evora

    about
  • Beja

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  • Lisbon

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Portugal
Spain

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Trip Summary

  • Madrid
    Madrid

    In the last few years, Madrid has gained the reputation of being one of Europe's most active and attractive cities for its nightlife and cultural activities. Capital of Spain since 1562, Madrid's museums host, among others, Dalis, Miros and Picasso's Guernica. Madrid is a city of great contrasts: the Old City, the Madrid of the Hapsburgs, the Royal Palace, the Puerta de Alcala, the Retiro Park. At night, the city changes gears with its famous Madrid nightlife. The city's endless energy is hard to resist, and its sociable style invites you to jump right in.

    Visit Palacio Real, Plaza Mayor, Prado Museum, Puerta del Sol, Puerta de Alcala, Plaza de Cibeles, Gran Via, Madrid Cathedral, Thyssen-Bornemisza and Reina Sofia Museums and so much more!

  • Lisbon
    Lisbon

    Lisbon, a dazzling city stretching along the Tagus river, makes an enchanting European capital. Its nucleus, an ancient fortress, is now circled by neighborhoods drenched with medieval charm. Handcrafts - from embroidery to leatherwork - are peddled right on the streets. At night, yellow electric tramcars continue to wind their way up and down the hills to the sound of traditional Fado songs. Ample opportunities exist for seeing popular celebrations, for shopping, and for enjoying the nightlife along the riverbank.

    Visit Alfama, Baixa and Chiado, Se de Lisboa, Sao Roque Church, Mosteiro dos Jeronimos, Torre de Belem, Discoveries Monument, Museu Nacional dos Coches, Parque das Nacos, Elevador de Santa Justa, Tram 28 and so much more!

  • Evora
    Evora

    Evora is the main city in the Alentejo region of Portugal. Boasting a rich history which spans 5,000 years, Evora is known for its agricultural importance as well, as olive groves and wineries thrive just outside the city center. Evora's long and storied history was recognized by UNESCO in 1986, when the organization named the entire historic center of Evora a World Heritage Site. Evora is also a key academic city in Portugal: It is home to one of the county's most famous universities.

    Explore the University of Evora, Cathedral of Evora, Roman Temple, Roman Baths, Praca do Giraldo, Royal Palace, Igreja de Santo Antao, Igreja da Misericordia, Chapel of Bones, and so much more!

  • Beja
    Beja

    Beja, situated on a hill high above the Alentejo's Golden Plains, boasts a history that stretches back to the time of the Celts. Romans knew Beja as 'Pax Julia', a prime trading outpost connected by road to Lisbon, Merida, Santarem and Braga. One of modern-day Portugal's most dynamic regional capitals, Beja has grown to become a haven for artists, sculptors, writers, and restaurateurs.

    Explore Beja Castle, Beja Cathedral, Igreja de Santo Amaro, Igreja da Misericordia, Igreja de Santa Maria, Ermida de Santo Andre, Porta de Evora, Praca da Republica, Praca de Touros de Beja, Memorial al-Mu`tamid, and so much more!

  • Lisbon
    Lisbon

    Lisbon, a dazzling city stretching along the Tagus river, makes an enchanting European capital. Its nucleus, an ancient fortress, is now circled by neighborhoods drenched with medieval charm. Handcrafts - from embroidery to leatherwork - are peddled right on the streets. At night, yellow electric tramcars continue to wind their way up and down the hills to the sound of traditional Fado songs. Ample opportunities exist for seeing popular celebrations, for shopping, and for enjoying the nightlife along the riverbank.

    Visit Alfama, Baixa and Chiado, Se de Lisboa, Sao Roque Church, Mosteiro dos Jeronimos, Torre de Belem, Discoveries Monument, Museu Nacional dos Coches, Parque das Nacos, Elevador de Santa Justa, Tram 28 and so much more!

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