Madrid, Segovia and Toledo Express: Discover Spain’s Heritage
Madrid, Segovia and Toledo Express: Discover Spain’s Heritage
The trip in a nutshell
This is a trip designed and realised entirely by an experienced WeRoad Travel Coordinator. The Coordinator takes care of the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. Via WeRoad website you can book the trip and manage it in your personal area, just like any other WeRoad.
Discover the heart of Spain on an unforgettable journey through Madrid and its most iconic heritage cities. This 5-day adventure blends vibrant city life, cultural richness, and centuries-old history, perfect for curious travelers eager to explore beyond the ordinary. We begin in Madrid, Spain’s lively capital, where grand boulevards, world-renowned museums, and buzzing tapas bars set the tone for an authentic Spanish experience. From there, we venture to Toledo, a stunning hilltop city known as the “City of Three Cultures,” where medieval architecture and narrow cobblestone streets tell stories of harmony and heritage.
Next, we explore Segovia, a city straight out of a fairytale. Marvel at its soaring Roman aqueduct, wander through the historic Jewish quarter, and admire the Alcázar, a castle that seems plucked from a storybook. With time to enjoy both guided visits and free moments to roam, you'll experience these places like a true traverler, not just a tourist. This isn’t just a trip, it’s a journey into the soul of Spain. Designed for young adults who want to connect, explore, and experience culture firsthand, this itinerary offers a perfect mix of history, adventure, and community.
Ready to say ¡Vamos!
Travel mood
Physical effort
Intermediate. This itinerary is relatively easy-going and any extra sports or activities are entirely optional. There is walking and/or hiking involved so pack comfortable shoes!
Entry requirements
Please visit your country's official government website to find out the necessary requirements for entering the country of destination.
Arrival and departure
This trip starts and ends in Madrid. On the first day of the trip, aim to arrive 6 pm - on the last day you are free to leave whenever!
What's included
Accomodation
WOW experience: guided tour through the streets of Toledo, a UNESCO heritage site
Train tickets to Toledo
Bus tickets to Segovia
Welcome Drink
- Travel Coordinator services
- Free cancellation with 100% refund up to 31 days before departure
Itinerary
Arrival in Madrid
A Royal Walk Through Madrid
Arrival in Madrid, Spain’s electric capital, where vibrant culture, grand architecture, and buzzing nightlife await. After checking in at the hotel, we’ll meet our Travel Coordinator and fellow travelers for a brief welcome session.
We'll start the trip toasting with the Welcome Drink, followed by an optional tapas crawl, a the perfect way to ease into Spanish life, one bite and glass of wine at a time. Afterward, we might head into the lively streets of Malasaña, one of Madrid’s most iconic neighborhoods known for its alternative bars and retro energy. a holdover from the city’s countercultural movement in the ‘70s and ‘80s.
Included: Welcome Drink, accommodation
Money pot: n/a
Not included: meals
Toledo: A City of Three Cultures
Travelling to where Christian, Jewish, and Muslim legacies intertwine
This morning we head to Toledo, a UNESCO World Heritage Site where Christian, Muslim, and Jewish cultures have left a lasting mark. Surrounded by ancient walls, this hilltop city is a maze of cobbled streets and stunning viewpoints. We explore iconic landmarks, from the Gothic cathedral to El Greco’s masterpieces, and uncover stories from centuries past. A guided tour will help us dive deeper into Toledo’s layered history.
In the late afternoon, we return to Madrid for some well-earned rest… but not for too long! The evening brings us to Plaza Mayor for more amazing food, followed by a walk through Lavapiés and La Latina, two of the city’s most lively neighborhoods. Tapas, music, and good company close out a memorable day.
Included: train tickets, guided tour, accommodation, breakfast
Money pot: tips
Not included: meals
A Royal Walk Through Madrid
Art, Icons & Sunset Magic
We start our morning by diving into the art and soul of Madrid with a visit to the Reina Sofía Museum, home to masterpieces like Picasso’s Guernica, a haunting symbol of modern art. For those eager for more, the Prado Museum awaits just nearby, a sanctuary of classic European art.
Not an art buff? No problem, explore the quirky stalls of El Rastro, one of the largest and most colorful street markets in Europe (open on Sundays), or browse the boutiques around Chueca and Gran Vía.
Later in the day, we regroup to admire Madrid’s regal side. the Royal Palace, Almudena Cathedral, and a guided walk through Plaza Mayor. We’ll take our time, stopping for photos, churros, or even a cheeky vermouth. The day wraps up with free time to relax or join an optional flamenco show or dinner with the group.
Included: accommodation, breakfast
Money pot: entrance tickets, transport
Not included: meals
Segovia’s Fairytale Charms
Castles, Cathedrals & an Aqueduct That Defies Time
Today we take one last day trip, and trust us, it's worth it. We're off to Segovia, a city that looks like it was plucked straight out of a fairy tale. Known for its dramatic Alcázar castle, Gothic cathedral, and one of the best-preserved Roman aqueducts in the world, Segovia will have you staring up in awe more than once.
After arriving, we'll start with the Aqueduct of Segovia, an architectural marvel built without mortar that still stands strong after 2,000 years. Then, we'll wind our way through the historic center, stopping at quaint squares and charming corners until we reach the Segovia Cathedral, perched elegantly above the city.
In the afternoon, back to Madrid for the last night!
Included: accommodation, breakfast, transport tickets to Segovia
Money pot: tips
Not included: meals
Departure Day
Farewell, Madrid
As our unforgettable journey comes to a close, we gather for one final breakfast together. It’s time to reflect on the incredible moments we’ve shared, from cultural discoveries to spontaneous fun. With hearts full of memories, we say our goodbyes to Spain.
Included: breakfast
Money pot: n/a
Not included: n/a

The travel coordinators
Our travel coordinators are chosen because they are people like you. Not only are they the best travel buddy you could hope for, but they're trained professionals guaranteed to show you a travel experience like never before
Available dates
FAQs – Frequently Asked Questions
Round-trip flights are not included in any of our trips because we like to give you autonomy and flexibility: you can choose the airline you want to fly with, the departure airport that suits you best, and how many and which stops you want to make.
Since flights are not included, you also have more flexibility with your travel dates: if possible, you can arrive at your destination a few days earlier or return home a bit later – or even continue independently to a nearby destination!
This is the question of all questions, and here’s the answer, broken down into points!
The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator.
It is used to streamline paymentsfor extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
It is typically collected on the first day of the trip in local currency, although at times, the Travel Coordinator may ask for it to be paid before departure.
You’ll find the amount of the money pot on the website under the section ‘What’s included in the money pot’ – how do you get there? Look for ‘What’s included’, scroll down to ‘Money pot? Click here’, and you’ll find the details.
The amount varies depending on the destination chosen.
It is used exclusively for group expenses that ALL participants decide to take part in.
It is estimated based on the experiences of other groups but can vary depending on the needs of the group itself. As such, the Travel Coordinator may need to increase the amount during the trip.
If not all of the money pot is used, the difference will be returned to all participants at the end of the trip in equal amounts.
The Money Pot also covers the Travel Coordinator’s share of the activities included in the money pot, except for those activities that are free for the Travel Coordinator.
If you pay in advance part of the money pot before the trip for certain non-refundable optional activities, unfortunately, the amount cannot be refunded in case of trip cancellation.
We offer several payment methods to meet all needs:
1. Credit or debit card from Visa, Mastercard, or American Express.
2. Installment payments for certain countries only
If you choose the deposit and balance option, you can pay the balance from your MyWeRoad Personal Area via bank transfer.
Anyone who books a WeRoad trip has the option to cancel or modify the trip – including both the dates and the destination – free of charge up to 31 days before departure. In case of cancellation, you will receive a 100% refund of the WeRoad trip price. If you make a change, a price adjustment will be applied to the new trip chosen – meaning, if the new trip is cheaper, we will refund the difference; if it’s more expensive, you will need to pay the difference.
If you’ve purchased the Flexible Cancellation Option (which you can add in the first step of the booking process), you can request a cancellation or trip change until 8 days before departure. In case of cancellation, you’ll receive a 100% refund of the WeRoad trip price, minus the cost of the Flexible Cancellation option.
How to request a cancellation or change to your trip? Send us an email at [email protected] or a WhatsApp on +447716573700. Please share the booking reference for the trip you want to cancel or change, and, in case of a change, the new trip you would like to join.
In general, we always choose local accommodations, avoiding large hotel chains, because we love to experience the culture of the place and, whenever possible, contribute to the local economy. Typically, our accommodations are hotels, apartments, guesthouses, and hostels run by local entrepreneurs, with the same standard maintained across all trips in the same destination.
For our Collection trips, which are our premium category, the accommodations are always 4 or 5-star or carefully selected boutique hotels.
The list of accommodations for your trip will be shared with you by your Travel Coordinator between 5 and 3 days before departure, along with other useful details for your adventure!
If you're wondering why WeRoad trips have a money pot, we’re assuming you already know what it is. If not, or if you have any doubts, we invite you to read all the information here!
Let’s quickly recap: The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator. It’s used to speed up payments for extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
But let’s get to the point: why the money pot? First of all: it gives us a lot of flexibility. In all WeRoad trips you will have a bunch of Must See/Must Do activities already included - these are experiences, places or activities that simply cannot be missed! Any extra activities is decided by the group, why? Because each group is unique and may have particular wants or desires and the Money Pot allows each group to customise their trip to make it perfect for their requirements!
It also helps us speed up payments – imagine being in the subway in New York City, one by one purchasing the ticket...a nightmare right? Thanks to the Money Pot, the Travel Coordinator can simply purchase the tickets for everyone making the entire processes smoother! Any leftover money will be returned at the end of the trip and split equally amongst all participants.
In some destinations, buying goods or services on site is more economical as you are able to negotiate the price - places like Morocco, or South East Asia, bargaining is part of the culture. As such, our Travel Coordinators will be able to secure the best deal for all participants.
The amount of the money pot is specified in each trip – look for this button
which will take you to a detailed breakdown for each trip, like this:
WeRoad is not authorised to provide this information due to privacy reasons.
However, there is a solution - you can connect with your travel buddies by joining our Facebook group. Look for a post related to your trip, or ask the group admins for help in connecting with your future travel companions!
If a Travel Coordinator has already been assigned to the trip you're interested in, you can easily find their introduction post in the group via the website: in the tour list, click on 'Ask the coordinator', or in the trip details page, in the coordinator section, click on 'Ask [coordinator's name] for information on this trip in our Facebook group'. For both cases, see the screenshots below!
Tour List
Trip details page
In all our groups, the Travel Coordinator and participants speak English – knowing how to speak and understand English is therefore a fundamental requirement to participate in our trips.
On average the groups are made up of 6-15 people, with a minimum of 3/4 participants and a maximum of 15.
All our travellers are in theirs 20s, 30s and 40s. If you're very curios to know the age range of the group for a tour you're interested in, you can contact us by WhatsApp at +447716573700
Regarding the male-female ratio, this is not guaranteed and varies trip by trip.
Yes! If you're curious, you can take a sneak peek at the group before booking – although, in our opinion, that kind of spoils the surprise! You’ll find the info in the ‘Group’ section for each trip on the departures page, showing how many WeRoaders have already booked. Click the little arrow and you’ll even see their gender and ages – but hey, that’s exclusive info, so we’ll ask you to log in or sign up to see that!
You can spot this info in the screenshots below:
desktop (insert screen)
mobile (insert screen)
Yes, in all our trips you will share a room with other same-sex travellers, and the bathroom will either be private or shared only with fellow participants of the trip. The rooms we select can be doubles, triples, quadruples, or multi-bed (up to 8 people in exceptional cases), depending on the destination and availability.
There are never dorms with people outside the WeRoad group, except in certain cases for local experiences, which are specifically mentioned in the itinerary or communicated before booking. These typically involve specific nights in unique accommodations like tents, homestays, or camping, offering a more adventurous travel experience in exchange for some comfort.
During the booking process, you can also choose to opt for a mixed room: in this case, if needed, only those who have agreed to this option may share a room with travellers of a different sex. If you are booking for multiple people together and select this option, the room will not be exclusive to your group but may be shared with other travellers in the group.
The WeRoad Travel Coordinator is an experienced and skilled traveller and will be the perfect companion for your trip. They will be available for any eventuality and will manage all the logistical aspects of the itinerary (transports, timings, accommodations, meeting points, etc.), so you can enjoy the trip without any worries!
You will have the chance to get to know them when the WhatsApp group is created approximately 2 weeks before departure - this will be the moment to ask any pre-departure questions and get to know the rest of the group! If the trip you are interested in already has a Travel Coordinator assigned, you can contact them before booking – their details will be specified in the schedule or on the trip page, or you can search for their name here. After booking, you will find their contact details in your Personal Area, under ‘Bookings and Trips’ > ‘Your Upcoming Trips’ > ‘Trip Details’.
When you set off on a WeRoad trip, you’re officially a WeRoader – and as we often say, 'Once a WeRoader, always a WeRoader'. This means that once you’re part of the community, a little piece of WeRoad will always stay with you, even if you no longer travel with us.
But you’re not just a WeRoader during your trips, far from it! The community is alive and active all year round: you can stay in touch by following and interacting on our social media channels, like the Facebook group or the Instagram profile. We can also meet up for a dinner or a trek together at one of the events organised by our coordinators around the world!