Madrid, Segovia and Toledo Express: Discover Spain’s Heritage




This is a WeRoadX
A trip designed and created entirely by an experienced WeRoad Travel Coordinator.
This is a trip designed and created entirely by an experienced WeRoad Travel Coordinator. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.
Group info
Expected WeRoaders: 8
Itinerary
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!


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.

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.

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.

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!

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.
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
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
What's not included
- Food and beverages when not specified
- All the extras you'll be able to fit in your backpack
- Anything not mentioned in the "What's included" section
Money pot
- Coordinator's money pot share
- All extra activities that each member of the group agree on doing and the coordinator's fee as well
Additional info
Four nights nights in a twin bed rooms with bathroom
- Private Room Option Show all details
Why WeRoad
Small groups, on average 11 people
Free cancellation included (deposit refunded as a gift card)
Book with a £/€100 deposit
Find your flight
For this trip, we recommend arriving and departing from these airports.
FAQs – Frequently Asked Questions
About this trip
This trip starts at Madrid. On the first day, we meet at 18:00.
This trip ends at Madrid. On the last day, you are free to leave anytime from the morning onward, so you can arrange your flights as you prefer!On the first day, aim to arrive at 6 p.m. On the last day, you’re free to leave whenever you want!
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!
For this itinerary, you can choose the type of luggage you prefer – we always recommend a backpack, but you can also travel with a duffel bag, a holdall, or (it breaks our heart to say it) a cabin trolley case or a checked suitcase, as long as it’s moderate in size. Our Travel Coordinator will suggest the ideal luggage before departure in the WhatsApp group!
About Spain
If you are a UK citizen, to find out the entry requirements for Spain, you can check this informational page from our partner Sherpa. If you need a visa, you can apply for it through Sherpa. If you are not a UK citizen, you can still use Sherpa by changing the nationality in the 'Passport' section.
Before traveling, always remember to check the government website of your country of origin for updates on the entry requirements for Spain – you wouldn’t want to stay home due to a bureaucratic detail!
- UK residents: review the FCDO Travel Advice.
- US residents: consult the US Department of State Travel Advice.
- Other residents: refer to your government or local consulate's travel advice.
Spain mainly operates on Central European Time (CET), which is UTC+1. During daylight saving time, from the last Sunday in March to the last Sunday in October, it switches to Central European Summer Time (CEST), which is UTC+2.
If it is 12pm in the UK, it will be 1pm in Spain during CET and 2pm during CEST.
Keep in mind that the Canary Islands follow Western European Time (WET), which is UTC+0, and Western European Summer Time (WEST), which is UTC+1 during daylight saving time.
Spain uses the Euro (EUR) as its currency. The daily exchange rate can vary, but as a rough guide:
- 1 GBP is about 1.15 EUR
- 1 USD is about 0.95 EUR
- 1 EUR is roughly 1 EUR
You can exchange currency at banks, exchange bureaus, and some hotels. It's also convenient to withdraw Euros directly from ATMs using your debit or credit card.
In Spain you can pay using cash, credit cards, or debit cards. Most places accept major credit cards like Visa and Mastercard. It's a good idea to have some cash on hand for smaller businesses, markets, or in rural areas where card payments might not be accepted.
ATMs are widely available for withdrawing cash if needed. Keep in mind that American Express may not be accepted everywhere, so it's better to have an alternative card as a backup.
Tipping in Spain is not mandatory, but it is appreciated for good service.
- In restaurants, it is common to leave a small tip of around 5 to 10 percent of the bill.
- In cafes and bars, you can leave some small change.
- For taxis, rounding up to the nearest euro is a nice gesture.
- Hotel staff, like bellhops and housekeepers, also appreciate a small tip for their services.
Remember, tipping is not expected but always welcomed.
In Spain, the internet is generally reliable and Wi-Fi is widely available in most urban areas, hotels, cafes, and restaurants. If you're traveling from Europe or the Schengen area, you can use roaming services, which means you won't need to buy a local SIM card for data use. However, if you're coming from outside Europe and want to ensure a stable connection, consider buying a local SIM or an e-SIM data plan. Popular providers include:
- Movistar
- Vodafone
- Orange
Wi-Fi is usually free in public places, but speeds can vary, so having mobile data as a backup is a good idea.
In Spain, the primary language spoken is Spanish, also known as Castilian. However, you might also encounter regional languages like Catalan, Galician, and Basque. Here are some useful Spanish expressions you might hear or use:
- Hello - Hola
- Thank you - Gracias
- Please - Por favor
- Excuse me - Perdón
- How much is it? - ¿Cuánto cuesta?
Being familiar with these can make your interactions smoother and more enjoyable.
In Spain, you'll find Type C and Type F plugs. The voltage is 230V and the frequency is 50Hz. If you're coming from a country that uses different plug types, like the UK or the USA, it's a good idea to bring a universal adapter to ensure your devices can be charged without any issues.
The main religion in Spain is Roman Catholicism. Catholic traditions play a significant role in Spanish culture, and many public holidays are religious, such as Easter and Christmas. Major celebrations like Semana Santa (Holy Week) feature processions and events throughout the country. While the majority identify as Catholic, Spain is quite secular, and other religions are practiced as well. Dress is generally casual, but if visiting religious sites, it's respectful to cover shoulders and knees.
Spain offers a diverse climate, so packing wisely will ensure you're prepared for any adventure.
Here's what you should include in your backpack for Spain:
-
Clothing
Lightweight shirts and shorts for hot days
Long pants and a light jacket for cooler evenings
Swimwear for the beaches
A scarf or shawl for visiting religious sites -
Shoes
Comfortable walking shoes for city exploration
Sandals or flip-flops for the beach
Dress shoes if you plan on dining out -
Accessories and Technology
Sunglasses and a hat to protect from the sun
A reusable water bottle
A power bank and smartphone
A universal adapter for charging electronics -
Toiletries and Medication
- Sunscreen and lip balm
- Basic toiletries like toothbrush, toothpaste, and deodorant
- Common travel medication like ibuprofen, antihistamines, and motion sickness tablets
Spain's weather can vary greatly depending on the region, so here's a quick breakdown:
- Northern Spain: Expect cooler, wetter weather, especially in regions like Galicia and the Basque Country. Summers are mild, with temperatures around 20-25°C.
- Central Spain: In cities like Madrid, summers are hot and dry, often reaching 30-40°C. Winters can be chilly with temperatures around 5-10°C.
- Southern Spain: Areas like Andalusia enjoy hot summers, with temperatures often above 30°C. Winters are mild, around 10-15°C.
- Coastal Areas: The Mediterranean coast, including Barcelona, has warm, dry summers and mild, wet winters.
For the best weather, consider visiting in spring (April to June) or fall (September to October).
About WeRoad
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 fit every need:
1. Credit or prepaid card (Visa, Mastercard, American Express);
2. Instalment payment with Scalapay up to €4,999 (only available with the “Full trip payment” option – not available with the “Deposit and balance” option; pay in 3 instalments up to €1,200 or in 4 instalments over €1,200);
3. PayPal (for selected destinations);
4. Revolut Pay to pay even faster straight from your Revolut account;
5. Welfare credit – BEFORE BOOKING, reach out to us at [email protected].
If you choose the deposit and balance option, you’ll also be able to pay the balance via bank transfer from your Personal Area.
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. (Deposits will be refunded in the form of a gift card valid for 365 days from issue date.) 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. Deposits will be refunded in the form of a gift card valid for 365 days from issue date.
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:
Even if we don't know the flights of all WeRoaders, there are several ways to find out which flights your travel companions have purchased.
1. Each WeRoader has the ability to communicate their flight details after booking within their personal area so that other travel companions can see the details anonymously. Enter your booking and you will find this section:
[Screenshot]
2. If you want to find out before booking, instead, you can contact us and we will support you in your search or you can ask your travel companions for direct information by joining our Facebook group 'WeRoad... let's get to know each other before leaving! (official)' – (here is the extended link: https://www.facebook.com/groups/weroadit) look for a post associated with your trip, or ask the group administrators for help in getting in touch with your future adventure companions!
If the coordinator has already been assigned to the trip you are interested in, you can easily find his/her presentation post in the group through the site: in the shift list click on 'Ask the coordinator', or in the trip tab, in the coordinator section, click on 'Ask [coordinator name] about this shift in our Facebook group'. For both cases, see the screenshots below!
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On our group trips, the Travel Coordinator and participants speak English – knowing how to speak and understand English is therefore a fundamental requirement to participate in WeRoad.com trips.
On average, groups consist of 12 people, with a minimum of 3-4 participants and a maximum of 18-20 in exceptional cases.
The average age varies depending on the age range indicated for each trip: for 25-35 year-olds, it's usually in their 30s, and for 35+ year-olds, it's around 40. However, if you'd like to know the average age of a group, contact us via WhatsApp at 3484231163.
Regarding the gender mix, there's no guarantee that the group will be balanced, as it all depends on you and on when and what you book! We can, however, reveal a detail: many women book well in advance, while many men often arrive a bit last minute!
Want to know the specific composition of your group? Find out how here.
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!
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’.
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.
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!