Lisbon to Caceres, Madrid & Toledo - 5 Days

From £461£92 per day Save 25%

Who is this trip for

Age range

0 - 99

Start / End

  • Lisbon
  • Lisbon

Physical rating

2/5

Group size

1 - 50

Meals included

4

Highlights

  • Lisbon - cross into Spain and travel through the rural landscapes of Extremadura
  • Caceres - wander the UNESCO-listed old town and historic Plaza Mayor
  • Madrid - enjoy a guided city tour and explore the Spanish capital at leisure
  • Toledo - take in panoramic views and stroll through the medieval old town
  • Trujillo - visit the birthplace of Spanish conquistadors before returning to Lisbon

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Summary

Journey through the heart of the Iberian Peninsula as we travel from Lisbon to Madrid and back again. Along the way, we uncover the medieval allure of Caceres and the grand history of Trujillo, birthplace of conquistadors. In Madrid, we blend guided sightseeing with free time to explore its stately avenues, royal landmarks and buzzing neighbourhoods. A trip to Toledo offers a glimpse into Spain’s layered past, with its blend of Christian, Jewish and Moorish heritage. This five-day adventure captures the essence of Spain and Portugal in one seamless loop.

Itinerary

  • Day 1

    Lisbon to Caceres & Madrid

    We depart from Lisbon at 7:30 a.m. and head across the Spanish border to Caceres, where we have free time to explore the atmospheric Plaza Mayor and wander through the remarkably preserved medieval old town, recognized as a World Heritage Site. After lunch at our own pace, we continue to Madrid and settle in for the night.

    Please note: This tour is bi-lingual, and will be conducted in Spanish as well as in English. 

    Meeting Point: Hotel Lutecia Smart Design, Av. Frei Miguel Contreiras 52, 1749-086 Lisboa, Portugal at 7:30.

  • Day 2

    Madrid

    After breakfast, we get to know the Spanish capital on a guided morning tour, taking in key sights including grand boulevards, historic squares and notable landmarks. The afternoon is free to explore more at our own pace—perhaps browse the boutiques, relax in Retiro Park or visit one of Madrid’s many museums.

    Please note: A tour escort is not provided during the stay in Madrid. Madrid tours operate as part of a regular shared service

  • Day 3

    Madrid to Toledo to Madrid

    This morning we journey south to the ancient city of Toledo. From the Mirador del Valle, we enjoy panoramic views before heading into the old town on foot to discover its winding lanes and blend of Christian, Jewish and Moorish heritage. We return to Madrid with the afternoon free to continue exploring.

  • Day 4

    Madrid

    Today is completely at leisure. You might visit the Royal Palace, delve into the collections of the Prado or Reina Sofia, or enjoy an optional excursion to El Escorial, Avila or Segovia. In the evening, Madrid’s tapas bars and lively neighbourhoods are perfect for soaking up the local atmosphere.

  • Day 5

    Madrid to Trujillo to Lisbon

    After breakfast, we travel through the Extremadura region to Trujillo, birthplace of Spanish conquistadors. There’s time to explore the grand Plaza Mayor before continuing across the border into Portugal. We arrive back in Lisbon where our tour ends.

What's Included

  • Meals

    Breakfasts: 4, Lunches: 0, Dinners: 0

    Vegetarian options are available on all meals throughout the adventure.

    Vegetarian options available

  • Local Guide

    Guided

    This adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.

  • Wifi

    Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.

Dates & Prices

  • Aug 25

    from £498
  • Sep 25

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  • Oct 25

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  • Nov 25

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  • Dec 25

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  • Jan 26

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  • Feb 26

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  • Mar 26

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  • Apr 26

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  • May 26

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  • Jun 26

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  • Jul 26

    from £498
  • Aug 26

    from £498
  • Sep 26

    from £498
  • Oct 26

    from £498
  • Nov 26

    from £461
  • Dec 26

    from £461
  • Jan 27

    from £461
  • Feb 27

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  • Mar 27

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  • Save 25%
    Sat 1 Nov 2025 > Wed 5 Nov 2025Guaranteed Departure
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    Solo Room from +£202
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    Sat 8 Nov 2025 > Wed 12 Nov 2025Guaranteed Departure
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    Sat 15 Nov 2025 > Wed 19 Nov 2025Guaranteed Departure
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  • Save 25%
    Sat 22 Nov 2025 > Wed 26 Nov 2025Guaranteed Departure
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    Solo Room from +£202

Essential trip information

Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.

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