Inspiration for your own tailor-made trip
Spain – Madrid – Toledo – Salamanca – Segovia
100% customisable for you
Rise and shine, your getaway to Spain starts today. Head to the airport, whizz through security and relax in the lounge before your direct flight to Madrid, which takes around two and a half hours, with no time difference to adjust to.
On arrival, you’ll be privately transferred to your base in the city centre, a short walk from the Royal Palace and the Sabatini Gardens, where you’ll spend the first three nights. Madrid’s restaurants don’t really come alive until late evening, which, after a short flight and a day of anticipation, feels exactly right.
Today you’ll explore Madrid with a local resident who knows the city in a way guidebooks don’t: the neighbourhoods worth lingering in, the bars worth discovering and the version of the capital that takes a while to reach on your own. The morning shapes itself around your interests: art, food, architecture, football and beyond. Madrid has enough to feed most passions and a reasonable talent for creating new ones.
Priority passes for the Prado, Reina Sofia and Thyssen museums are already included and valid throughout your stay. The Prado alone warrants most of a day – Las Meninas and Goya’s Third of May – but the passes give you the freedom to return at your own pace rather than attempt everything at once.
For extra exploration, take an optional walking tour of Madrid through the lens of renowned director Almodovar and the streets, bars and corners that appear throughout his films, with a guide who knows both the city and the work.
This morning, your rail adventure begins. Board the train to Toledo, just half an hour south of Madrid and a city more than worth the short journey.
A private guide will take you through the old town, beginning with the cathedral, a masterpiece of Gothic and Spanish ornament built between the 13th and 15th centuries. Then, it’s on to the church of Santo Tome, home to El Greco’s vast and celebrated Burial of the Count of Orgaz, before visiting the 12th-century synagogue of Santa Maria la Blanca, whose Moorish arches and whitewashed interior speak to a more plural Spain than the one that eventually expelled it. Finally, the Alcazar, site of one of the Spanish Civil War’s most iconic sieges, is worth the visit alone.
You’ll be back in Madrid by evening – with, if the timing allows, a stop for marzipan, Toledo’s most unassuming export.
This morning, fuel up on a hearty breakfast before boarding the train to Salamanca. The journey usually takes around two and a half to three and a half hours, depending on the route and connections.
On arrival, Salamanca reveals itself as one of Spain’s most quietly brilliant cities, golden-stoned and built around the oldest university in the country. Settle yourself here for two nights, with accommodation that’s just a short walk from the cathedral.
This afternoon is yours to relax and discover – the Plaza Mayor is a natural starting point, and the jamon in Salamanca is hard to beat.
Wake up bright and early and begin the day exploring Salamanca by bike. Accompanied by a private guide, you’ll start in the outer neighbourhoods and pedal past the Tormes river before heading into the old city.
The Plaza Mayor anchors everything: it’s one of the finest squares in Spain and the kind of place where sitting down with a coffee feels like a cultural activity. From there, you’ll find the two cathedrals side by side – the old Romanesque one and the new Gothic one, which began in the 16th century at the height of Salamanca’s intellectual and economic confidence and wasn’t completed until 1733.
The Dominican convent of San Esteban, with its elaborate plateresque facade, and the Casa de las Conchas (decorated with as many scallop shells as there are days in the year) are both worth the short detour.
Round off your outing with a delicious dinner at a local spot recommended by your in-the-know Concierge.
Another day, another rail adventure. Board the train to Segovia (a little over an hour on a direct route) and base yourself for two nights in the historic centre.
The city announces itself before you’ve left the station – built on a rocky spur above the meeting point of two rivers, with the Alcazar jutting out like the prow of a ship and the Sierra de Guadarrama rising behind it. The Roman aqueduct, 2,000 years old and still standing without a drop of mortar, runs straight through the heart of the city and manages to look entirely at home there. Find your bearings this afternoon – with a setting like this, it won’t take long.
Spend today soaking in Segovia, a city best experienced slowly.
The aqueduct is the obvious starting point, with 166 arches of pale grey stone, both monumental and elegant; it’s the perfect spot for a photo. From here, continue on through the old town to the Gothic cathedral, begun in the mid-16th century and among the last of its kind built in Spain.
Finally, head to the Alcazar, which sits at the far end of the old town. It’s a fortified castle of turrets and pointed rooftops that looks less like a real building than the collective memory of what a castle should look like (and is, for the record, said to have inspired the animation of Walt Disney’s Snow White).
For those wanting the full story behind the stones, opt for a private guided tour of all three with a local expert.
Sadly, it’s time to wave goodbye to Segovia this morning as you take the train back to Madrid and check in for a final night in the city centre.
The afternoon is free for you to spend as you please: return to any museum left unfinished, wander through the streets of La Latina or Lavapies or enjoy a straightforward sit-down at a trendy bar with something cold.
This evening is all about immersing yourself in the culture. Head to the Corral de la Moreria for flamenco, one of the oldest tablaos (flamenco venues) in the country, founded in 1956 and just a short walk from the Royal Palace. Here, you’ll enjoy a captivating performance – a fitting way to celebrate your final evening in the capital.
This morning marks the final day of your rail adventure in Spain. Take a private transfer to the airport, breeze through security and fly directly back to London – at two and a half hours, it’s a short enough hop to make the journey home feel effortless.
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from checking you in for your flights to our network of local Concierges
