Madrid and the Heritage Cities

Madrid – Segovia – Ávila – Salamanca – Cáceres – Toledo - IC4

Madrid and Inland Fly-drive
14 Nights From £2,300
Food tours
Heritage tours
Wine tours
Tour Highlights
  • UNESCO World Heritage Sites

  • Madrid – Spain’s lively, artistic capital

  • Ávila, Salamanca & Toledo

  • Roman Mérida & Segovia’s aqueduct

  • Ribera del Duero wine one of many here

  • Cáceres – a living museum

  • Dehesa landscapes & delicious Jamón Ibérico

  • Sierra de Madrid, Sierra de Gredos, Sierra de Francia & Guadarrama

Feefo logo
14 Nights From £2,300
Enquire Now

Overview

World heritage will be your travelling companion throughout this magnificent trip. Starting in Spain´s vibrant, cultural capital, and without straying too far from it, you will discover five fascinating cities, each with the status of World Heritage City, where the evidence of a great past can be found everywhere.

Tour Highlights
  • UNESCO World Heritage Sites

  • Madrid – Spain’s lively, artistic capital

  • Ávila, Salamanca & Toledo

  • Roman Mérida & Segovia’s aqueduct

  • Ribera del Duero wine one of many here

  • Cáceres – a living museum

  • Dehesa landscapes & delicious Jamón Ibérico

  • Sierra de Madrid, Sierra de Gredos, Sierra de Francia & Guadarrama

Monumental cathedrals, royal palaces, historic universities and truly awe-inspiring Roman remains have survived over the centuries to tell us epic stories of Conquistadores and Kings and illustrious characters from Romans to the Inquisition .

But it is not all about those ‘old stones’. The immense mountain Sierras of Castilla and the enchanting ‘dehesa’ landscape of Extremadura offer some of Europe’s best bird-watching and star gazing opportunities and you’ll discover a rich living culture and excellent regional gastronomy with wines to match at each stop along the way.

The full route takes two weeks but you can do as little, or as much, as you like.

Holiday Code: IC4


Itinerary

Day 1 to 3– Madrid

  • Capital of Spain – one of Europe´s largest

  • Golden Triangle of Art – Prado, Reina Sofia & Thyssen Bornemisza Museum

  • Puerta de Alcalá, Royal Palace, Almudena Cathedral…

  • World-class galleries, theatres, cultural centres & events

  • Distinctive atmosphere in each barrio; lively bars & restaurants

  • Royal Monastery of San Lorenzo de El Escorial

Day 1 to 3 – Madrid

Day 4 & 5– Segovia & Sierra de Guadarrama

  • 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 4 & 5 – Segovia & Sierra de Guadarrama

Day 6 & 7– Ávila & Sierra de Gredos

  • Ávila with its magnificent walls, a World Heritage Site

  • Gredos mountains rising to 2500m at Pico Almanzór

  • Astronomy & stargazing in this Dark-Sky location

  • Trekking, climbing, birdwatching, horseriding…

  • Walk the Puerto del Pico Roman way

Day 6 & 7 – Ávila & Sierra de Gredos

Day 8 to 10– 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 8 to 10 – Salamanca

Day 11 & 12– 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 11 & 12 – Cáceres

Day 13 & 14– 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 13 & 14 – Toledo

& why not?

  • Add a stop in historic Valladolid - once the capital of Spain - now a capital of wine

  • Visit Europe's largest concentration of Romanesque in Zamora

  • Head south to Córdoba - incredible Moorish Heritage

  • Ask about superior rooms 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 circular itinerary, this route is best enjoyed flying into Madrid as it is very well connected with the UK.

It is also the best destination airport for intercontinental connections. There are several options for customers coming from EEUU, Australia, etc.    

See your flight options in the table below or contact us for help and advice if you don’t see your nearest airport here:

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.


Reviews


Related Tours

14 Nights From £2,300
Enquire Now

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...

Image

Stay Updated

Get exclusive deals, travel tips, and destination inspiration delivered directly to your inbox.

NO SPAM - UNSUBSCRIBE ANYTIME

Why choose Caminos

Image
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!

Image
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.

Image
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.