Lisbon to Caceres, Madrid & Toledo
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.
For a detailed itinerary and information about visas, money, weather and more.
Tour Overview
Duration
5 daysHotel Rating
3 star hotelsStarts
LisbonEnds
LisbonMinimum age
No minimum ageMaximum age
No max ageArrival Transfer
NoDeparture Transfer
NoTour Guide
Escorted by a bi-lingual tour leader with local guides for some sightseeing (tour is conducted in English & Spanish)Countries
Spain, PortugalMeals included
Breakfast: 4Passengers
$645.00
$400.00
Tour Style
Group Size
Min 1 / Max 50
Trip Type
Large Coach Tours
Range
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip. Our Budget tours offer incredible experiences at a great price. As well as guided sightseeing (depending on the Tour Inclusions), there's free time to explore independently or take part in optional excursions so you can focus on doing just the things that suit you.
Guiding Style
This tour is led by a dedicated tour guide or tour leader who stays with you throughout the entire journey. From start to finish, they manage logistics, offer insights at every stop, and are on hand to assist with anything you need. You may also enjoy sightseeing with local expert guides, as per the Inclusions. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Tour Guide
Escorted by a bi-lingual tour leader with local guides for some sightseeing (tour is conducted in English & Spanish)Group Size
Min 1 / Max 50Tranportation
N/ALanguage
EnglishLanguage
EnglishRange
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip. Our Budget tours offer incredible experiences at a great price. As well as guided sightseeing (depending on the Tour Inclusions), there's free time to explore independently or take part in optional excursions so you can focus on doing just the things that suit you.
Guiding Style
This tour is led by a dedicated tour guide or tour leader who stays with you throughout the entire journey. From start to finish, they manage logistics, offer insights at every stop, and are on hand to assist with anything you need. You may also enjoy sightseeing with local expert guides, as per the Inclusions. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Trip Type
Large Coach ToursTour Highlights
Included
Not Included
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.
Tour Reviews
Extras and add-ons
If you'd like to add extras or add-ons to your booking, you can do this easily during checkout. Just review the available options and select any additional services or upgrades you'd like before completing your purchase.
Hotels
The hotels listed below are examples which we frequently use on this tour. Alternative hotels of a similar standard may be used instead.
Prices & Dates
All departure dates are guaranteed. Prices shown are per person travelling. 'Double/Twin' prices per person apply when there are 2 people travelling, sharing a room. 'Triple' prices per person apply when there are 3 people travelling, sharing a room. The 'Single' price applies for solo travellers who require their own room or for anyone else who would like the privacy of their own room. Room sharing is not available on this tour.
Can't find a date that works for you?
Dates for 2027 haven't been released yet.
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