A circular tour around the ancient Roman province of Lusitania, this trip will show you the similarities and contrasts between two regions with a common past.

From charming and vintage Lisboa passing through the lesser-known gems of the Alto Alentejo into Spain, enjoy the amazing Roman vestiges in the Portuguese city of Évora and neighbouring Spanish Mérida, once the provincial capital Emerita Augusta.

Once in Spain, take the opportunity to discover its least known province – Extremadura – with an immense wealth of truly unique experiences – historical, natural and gastronomical.

Explore the Sierra de Gredos and Salamanca and their splendid valleys before “jumping” into the Serra da Estrela mountains. End your trip by the sea in the spectacular Atlantic beaches of the Portuguese coast.

The full route takes fourteen days but you can do as little, or as much, as you like.

  • Tour Highlights:
  • Vibrant and vintage Lisboa
  • Roman vestiges in Évora and Mérida
  • Trujillo´s multicultural heritage and Monfrague National Park
  • Valleys of Ambroz & Jerte – true beauties of nature
  • Serra da Estrela, Portugal’s highest
  • World Heritage Estremadura – Batalha, Alcobaça & Tomar
  • Spectacular Atlantic beaches
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£1550 p/p

* Indicative mid-season price for 14 nights (including car hire – flights not included) in our suggested hotels.

Full details (PDF)

Day 1 & 2 – Lisboa & around

  • Hop on a tram and explore Portugal’s exciting capital
  • Rossio square and train station
  • Skip out to Sintra, and the beaches of Cascais & Aldeia do Meco
  • Bar hop in Bairro Alto, dine in style in Chiado
  • Mosteiro dos Jerónimos – a Manueline delight
Accommodation options

Day 3, 4 & 5 – Alto Alentejo

  • World Heritage Évora, Roman ruins, medieval walls
  • Alentejo wines, Portugal’s finest
  • Hilltop fortress towns of Monsaraz, Marvão and Castelo Vide
  • Pottery towns among the vines El Corval and Redondo
  • “Marble towns” of Vila Viçosa and Estremoz
  • World Heritage Elvas with its magnificent Roman aqueduct
Accommodation options

Day 6, 7 & 8 – Central Extremadura

  • Monfrague National Park – a bird-watcher’s paradise with buzzards, vultures and black stork
  • Historic Cáceres & Trujillo with its imposing castle
  • Take a pilgrimage to Guadalupe
  • 2nd century Roman bridge at Alcántara
  • Excellent local cheese and game dishes
Accommodation options

Day 9 & 10 – Northern Extremadura

  • Explore the high Sierras of Gredos and Salamanca
  • Lose yourself in the Jewish Quarter of Hervás
  • Valle del Jerte cherry trees by the million – a real treat in Spring!
  • Visit Candelario & Béjar – two true beauties
  • Plasencia – key staging point on the Via de Plata
Accommodation options

Day 11 & 12 – Serra da Estrela

  • Walking, cycling, kayaking and much more in the Serra da Estrela Nature Park
  • Visit the Burel Wool factory in Manteigas
  • Scale the Torre peak – Portugal’s highest
  • Manteigas and Sabugueiro – charming mountain villages
  • Rich Jewish heritage and historic castle of Belmonte
Accommodation options

Day 13 & 14 – Estremadura, Portugal

  • The magnificent monasteries of Batalha and Alcobaça
  • Saõ Martinho do Porto a little pearl set on a string of surf washed Atlantic beaches
  • The Convent at Tomar, delightful city of the Templars
  • Sierras de Aire y Candeeiros Nature Park – riddled with caves
  • Medieval Óbidos with its famous white houses
Accommodation options

The itinerary includes the following:

  • Accommodation in our listed hotels – 2 sharing 1 std. double ensuite, B&B
  • Economy 4dr car hire
  • Regional guide book
  • Personal Travel App including highlights, weather forecast and restaurant suggestions for all areas en-route
  • Instructions to find all accommodation


Not included:

  • Flights – but we are able to advise
  • One-way car hire charges, where applicable (see your quote email)
  • The following car hire extras – these can be added at pick-up point
    • extra driver
    • Portuguese toll device (we highly recommend to take this service)
    • child seats
    • GPS
  • Garage parking where applicable (mostly city stops) – please ask us about parking charges

Getting there

Fly directly to Lisboa / Lisbon and hire a car – the best options are:

From London Gatwick: Easyjet or TAP Portugal or BA
From London Stansted: Ryanair
From London Heathrow: BA or TAP Portugal
From Luton: Easyjet or Wizzair
From Edinburgh: Easyjet or Ryanair
From Manchester: Ryanair, Easyjet or TAP Portugal
From Bristol: Easyjet
From Dublin: Ryanair, TAP or Aer Lingus

Or fly directly to Porto / Oporto and hire a car – the best options are:

From London Gatwick: TAP Portugal or Easyjet
From London Stansted: Ryanair
From Manchester: Easyjet, Ryanair or TAP
From Birmingham: Ryanair
From Luton: Easyjet
From Briston: Easyjet
From Dublin: Ryanair or TAP

You can also fly via Madrid starting in the Spanish side of the route. Several direct flights from UK. Please ask for advice.

PLEASE NOTE some flights are seasonal.

NB: Flights are not included


Getting around

As part of your package we will include a hire car. Normally we include a 4 door economy class car but please let us know if you would like something different.

AITO reviews

New route for 2022

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