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 p.p.

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Tour Highlights
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14 Nights From £2,150 p.p

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Overview

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

Tour Highlights

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



Travel Details

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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

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!

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.

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.