The Toledo Run

Northern Spain to Toledo via the Heritage Cities of Castilla y León - IC5

Madrid and Inland Fly-drive or Ferry-drive
14 Nights From £2,150
Classic car tours
Food tours
Motorbike tours
Heritage tours
Wine tours
Tour Highlights
  • World Heritage at every stop!

  • Cathedrals of Burgos and León

  • Salamanca – oldest university city in Spain

  • Ávila's walls and Segovia’s aqueduct

  • Wines of Ribera del Duero, Toro, Rioja or Rueda

  • Historic Cáceres and Trujillo; Roman Mérida

  • Toledo ‘City of the three cultures’

  • Birdwatching in Monfrague Nature Park

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14 Nights From £2,150
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Overview

Discover the immensely rich heritage and awesome landscapes of inland Spain.

Tour Highlights
  • World Heritage at every stop!

  • Cathedrals of Burgos and León

  • Salamanca – oldest university city in Spain

  • Ávila's walls and Segovia’s aqueduct

  • Wines of Ribera del Duero, Toro, Rioja or Rueda

  • Historic Cáceres and Trujillo; Roman Mérida

  • Toledo ‘City of the three cultures’

  • Birdwatching in Monfrague Nature Park

Cruise to Spain by ferry or take the short flight down and explore the immense mountain Sierras of Castille and the enchanting  ‘dehesa’ of Extremadura, with landscapes and wildlife not to be found anywhere else in Europe.

This unique tour takes in monumental cathedrals, royal palaces, historic universities and awe-inspiring Roman remains – and so much more besides…

You’ll discover a rich living culture and excellent regional gastronomy with wines to match at each stop along the way and a friendly welcome wherever you go.

Holiday Code: IC5


Itinerary

Day 1 & 2- León

  • Crossroads of Camino de Santiago and Via de Plata

  • Cathedral of Santa Maria – beautiful stained glass

  • Tapas in ‘la Zona Humeda’ in Leon old-town

  • The true Holy Grail? In the Colegiata de San Isidoro

  • Lovely Astorga with its Gaudi palace

Day 1 & 2 - León

Day 3 & 4- Salamanca

  • Salamanca – truly monumental university city

  • Toro, Rueda & Sierra de Salamanca wines

  • Delicious jamon from Guijuelo

  • Historic Tordesillas, Toro & Zamora

  • Cruise on the river in the Arribes del Duero

  • Sierra de Francia & villages of Las Batuecas

Day 3 & 4 - Salamanca

Day 5 & 6- Cáceres

  • Old Town of Cáceres – UNESCO World Heritage Centre

  • Monfrague National Park – a lesser known gem

  • Trujillo with its imposing castle

  • Take a pilgrimage to Guadalupe

  • 2nd century Roman bridge at Alcántara

  • Excellent local cheese and game dishes

Day 5 & 6 - Cáceres

Day 7 & 8– Toledo

  • Churches, synagogues & mosques – The City of the Three Cultures

  • Cathedral of Toledo – 13th Century´s Gothic masterpiece

  • Ancient Alcázar – Toledo´s Army Museum

  • Old Town & Jewish Quarter

  • Toledo´s walls – from the Romans to the Christian Reconquest

  • El Greco “The Greek” Museum – life and work of the painter

Day 7 & 8 – Toledo

Day 9 & 10- Segovia

  • Segovia – World Heritage Site – Roman Aquaduct, Moorish Alcazar, Cathedral and large Jewish Quarter.

  • Sierra de Guadarrama National Park

  • Sepúlveda & Hoces del Duratón Nature Park

  • Medieval Pedraza & Cuellar

  • La Granja de San Ildelfonso – the Spanish Versailles

Day 9 & 10 - Segovia

Day 11 & 12- Burgos

  • Essential stop on the Camino de Santiago

  • Truly awesome cathedral, recently restored

  • The city of El Cid Campeador

  • Bustling old town; lively bars & restaurants

  • Spain’s best lamb & delicious black pudding

  • Atapuerca & the Museum of Human Evolution

Day 11 & 12 - Burgos


& why not?

  • Include a stop in Madrid

  • or Ávila, known for its impressive wall

  • Extend your trip by adding a few extra days for longer stays

  • Ask about superior rooms, better cabins or a larger rental car

  • or more economical options if you're on a budget...

  • Call us to talk through all the options - we'd love to hear from you!

& why not?


Map


What's Included

  • Accommodation in our listed hotels – 2 sharing 1 standard double ensuite, B&B (unless specified)

  • Economy 4-door car hire (talk to us about upgrades)

  • or ferry crossings with Brittany Ferries (vehicle + 4 berth outside cabin, exclusive use)

  • Guide book to Spain

  • Personal Travel App including highlights, weather forecast and restaurant suggestions for all areas en-route

  • Instructions to find all accommodation

What's Excluded

  • 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, child seats, GPS

  • Garage parking where applicable (mostly city stops) – please ask us about parking charges

  • Local tourist taxes (where applicable)


Travel Details

Getting There

A premier circular route, this itinerary has excellent access by air and sea.

Plus most UK and international airports to Madrid – please ask for more information (also see our Madrid and the Heritage Cities Tour - IC4).

See your flight options in the table below:

PLEASE NOTE Flights are not included and some flights are seasonal.

Ferry: If you wish to bring your own car, classic car or motorbike we can include the ferry crossings as part of the package - see timetables below:


Flight Options

Choose your preferred UK airport and then select from possible destinations to see airline providers.

Getting Around

For passengers travelling by air we will include a hire car as part of the package. Normally we include a 4 door economy class car but please let us know if you would like something different.

For those coming on the ferry you will use your own vehicle but in either case we will provide full instructions to arrive at each hotel, complete with GPS, as well as a map of the area.


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Our Expert Touch

Our team of experts have over 35 years travel expertise in Spain & Portugal.

You’ll receive friendly, personal service from start to finish of the booking process.

Call and speak to Andy, Leonor or Antonio about your dream holiday in Spain & Portugal...

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Why choose Caminos

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About us

With 40+ years’ experience designing holidays in Spain & Portugal, our friendly, expert team offers personal service from booking to your return. While away, you’ll have ground support from local agents.

Every trip is tailored to your budget and needs.

Call us - we’d love to hear from you!

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About our tours

Discover authentic Spain & Portugal, far from tourist crowds. Stay in charming, trusted places — from castles and palaces to rural guesthouses and Paradores.

Your pack includes maps, guidebook, and touring tips. Plus, our Vamos travel app keeps all your documents and guides in one place.

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Peace of Mind

We’ve been a fully bonded UK tour operator since 1985, so your money and holiday are protected.


We’re also members of AITO (Association of Independent Tour Operators) — the hallmark of trusted, specialist holidays. Independent dispute resolution means you always travel with confidence.