Explore Madrid With Stephen Drake-Jones
Historian, Author, Storyteller and Founder of The Wellington Society of Madrid
There’s no shortage of walking tours in Madrid. What there is a shortage of is a society founded and still run by an actual historian who has spent several decades learning its history and unearthing the city’s blood, wine, and scandal — and who leads every single tour himself.
Most Madrid walking tour companies hand you off to whichever guide is free that day, often a rotating cast of a dozen or more, some reciting from the same script, herding a group of fifteen, twenty, sometimes thirty people down the same well-worn route. You get a guide. With the Wellington Society, you get Stephen Drake-Jones — historian, author, and Chairman of the Society — every time, on every tour.
Small by Design, Not by Accident
Our tours aren’t private — you may well be walking alongside another couple or two — but they’re never a crowd. Most groups are one or two couples, not a busload. That means:
- Stephen can actually answer your questions, not just field them
- The route bends toward what you’re curious about — Hemingway, the Bourbons, the Spanish Civil War, Wellington’s campaigns, or Madrid’s darker history of duels and executions
- You get a seat at the same small tapas bars and wine stops Stephen has frequented with the owners for years — not a tour-bus café with a fixed menu
- Nobody’s craning to hear over a crowd, and nobody’s rushing you along
It’s the difference between watching history from the back of a group, and having it told to you directly, over a glass of wine, by someone who’s spent his life chasing it down.
Of course, if a private tour is what you are looking for, we are here to help.
A Historian, Not a Script
Anyone can memorize dates and facades. Stephen has spent decades in the archives, the bars, and the backstreets, tracking down the stories that don’t make it into the guidebooks — where the bodies are buried, literally and figuratively, and where history was actually made. His instant recall, his eye for the telling anecdote, and his very British turn of phrase (“salubrious,” anyone?) have turned first-time visitors into repeat guests who come back for a second and third tour.
But facts alone don’t explain why guests leave saying it felt like spending the afternoon with an old friend rather than following a guide. Stephen is a natural raconteur — the kind of storyteller who turns a street corner into a scene and a footnote into a favorite story you’ll retell for years. Guests consistently remark that within the first ten minutes, it stops feeling like a tour at all.
What Guests Are Saying
“Stephen is great. It felt like we were getting a tour of Madrid from a close friend. Stephen is very personable… Lots of interesting stops (original Mickey Mouse) and if I forget any details I can always read about because ‘It’s in the book.’”
— Kelly C
“Mr. Drake-Jones brings real gravitas to the walking tour. His use of language is memorable — will we ever forget ‘salubrious’ or ‘chuffed’? His personal perspective on Madrid is far more engaging than a generic history lesson.”
— Chris, Greensboro, NC
“Stephen Drake-Jones gave us a wonderfully personalized tour, combining two itineraries just for us. The highlight was at Café de Oriente — tapas, wine, and scandalous tales of Spanish royalty overlooking the Royal Palace!”
— Lauren
“If I could give more than 5 stars, I would. I took three of Stephen’s tours while I was in Madrid and they were all amazing. The bars, restaurants, and shops he takes you to are mostly small family-owned establishments that have been his friends for years.”
— SteveInLA
“The ‘Bloody Madrid’ tour with Stephen was absolutely fantastic! His colorful anecdotes and knowledge of Madrid’s violent past brought history to life at every stop. His instant recall of dates is remarkable.”
— Mitchell
“Don and I wanted to thank the Chairman again for our unforgettable time in Madrid and Toledo! His wealth of knowledge is truly priceless — Stephen sparked such an interest in us that we returned to the Prado on our own!”
— Mary and Don
Every Tour Comes With Tapas, Wine, and Membership
Every Wellington Society tour weaves in stops at family-run tapas bars and wine spots that have been part of Stephen’s Madrid for years. And when you take a tour, you don’t just walk away with photos — you become a member of the Wellington Society of Madrid, with access to the benefits that come with it.
First Time Coming to Madrid?
Not sure where to start? That’s exactly what a first visit is for. Join the Chairman on an entertaining, informative morning stroll through the city center, take in one of Madrid’s world-renowned museums with a historian’s eye, or trace Hemingway’s footsteps through the bars and streets he loved. However you begin, you’ll leave with more than photos — you’ll leave a member of the Society, with all the benefits that come with it.
Explore With the Wellington Society
- Madrid Walking Tours — history, hidden hideaways, legends, and Madrid’s darker past
- Hemingway Tours — following Papa’s footsteps through the city he loved
- Museum Tours — the Prado and beyond, with context you won’t get from an audio guide
- Wine Tours — enjoy an afternoon learning about and sampling exquisite Spanish wines
- Toledo, Segovia & Beyond — full-day excursions beyond the city
- Battlefield Tours — the Peninsular War, on the ground where it happened
- Custom Tours — individualized to inspire
Ready to Stop Being a Number in a Crowd?
Family-friendly pricing. Accessible tours available. We love solo travellers.