The Wellington Society Of Madrid

Unique Unforgettable Walking Tours in Madrid and Spain

Madrid may not be the home to Jack the Ripper, but it does have its share of history, legends, and tales of a darker sort. Beyond the vibrant streets and lively atmosphere, the city conceals narratives that delve into its mysterious past. We know where all the bodies are buried, where all the fights were fought, and where history was made. Moreover, our tours provide an immersive experience, offering a glimpse into the enigmatic side of Madrid.

In addition to uncovering the secrets of the city’s history, our tours also introduce you to the culinary delights it has to offer. Explore the best places for tapas and wine, both of which are seamlessly woven into the fabric of our guided experiences. Plus, when you take one of our tours, you automatically become a member of the Wellington Society of Madrid, granting you access to a myriad of associated benefits.

Given that we operate as a small but dedicated team, whether you join one of our Madrid walking tours, Hemingway tours, a museum tour, or embark on an excursion to Segovia, Toledo, or an extended visit to the battlefields of the Peninsular War, your guide will always be the Society’s Chairman, historian Stephen Drake-Jones.

Should you find yourself pondering the best choice of tours or in need of a personalized experience, feel free to reach out to the Chairman. We are always happy to assist, and you can conveniently contact us on WhatsApp if that better suits your preferences.

As you navigate through our website, you will discover a wealth of information awaiting your exploration.

See What Our Guests Are Saying

“Tony and I want to thank you for our fascinating stroll through the backstreets of Madrid punctuated by juicy historical stories, and wonderful watering holes. We will be sure to write a glowing review, and do more research on the history of Madrid. What a gem of a city it is, and so are you. Keep us posted on Don Ernesto.
All the best,” – Marnie and Tony

“Bill and I wanted to thank you for yesterday. We had a fabulous time and are still savoring every aspect of the tour. You made our Madrid time very special.” —Cheers! Patty

“We fell in love with the amazing city of Madrid, and that’s largely thanks to Stephen! After our Friday tour, we visited the Prado using his book as our guide — it was the perfect companion. Stephen’s passion for Madrid and its history made our visit so much more meaningful. Travel is about the people you meet, and we are so grateful to have met him. Highly recommend!” —Melanie and Jim

“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. With historical sites, wine and snacks along the way, it was as enjoyable as it was educational. His instant recall of dates is remarkable. Book a tour with Stephen — you won’t regret it!”— Mitchell

“My husband and I enjoyed a personal tour with the Chairman of the Wellington Society, Stephen Drake – Jones, last week. Stephen Drake was a marvalous tour guide and fascinating historian. During our afternoon, we walked and discussed Hemingway, the Bourbon’s and the Hapsburgs as well as other stops off of the beaten path. My only regret is that our tour was on our last day of our vacation. I can’t wait for the book….” –Sheryl B – Newington, NH

“Stephen Drake-Jones gave us a wonderfully personalized tour, combining two itineraries just for us. The highlight was at Cafe de Oriente — tapas, wine, and scandalous tales of Spanish royalty overlooking the Royal Palace! Charming, professional, and passionate, Stephen made us feel right at home. A perfect experience for history buffs and lovers of gossip, delivered in a great British accent!”— Lauren

“My husband and I spent a delightful afternoon with Stephen on Spanish Constitution Day. Starting with a Hemingway history lesson, we explored Madrid with tapas, wine, famous statues, and even a few murder sites — all brought to life by a gifted storyteller! Stephen showed us a side of Madrid no guidebook could capture. An absolute must for anyone visiting the city!”— CbusTravelGirl

“So glad my wife and I were able to begin our trip to Madrid with a delightful, informative and relaxed Sunday Stroll with Stephen Drake Jones! Stephen’s insights into the history, culture, food, wine, and everyday life of Madrid and Spain really enriched the rest of our visit. A few evenings after our stroll, we returned to one of the Tapas Bars we visited with Stephen and were greeted like old friends by the waiter! Don’t wait until the end of your visit to meet up with Stephen Drake Jones; the sooner the better!” —Brooks D

“My wife and I had a wonderful afternoon walking through the streets of Madrid discussing the history of the city with the Chairman. He even graciously customized our itinerary based on topics my wife and I were interested in.
I highly recommend this experience for history lovers. It’s incredibly rare to be able enjoy something like this alongside an actual historian…and the wines and tapas that go along with it are exceptional.” —Donald L – Dublin, OH

“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. Excellent choices of tapas stops and historical locations throughout. When we return to Madrid, we plan to do another tour — the Hemingway tour looks intriguing!” —Chris from Greensboro, NC

“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. To say he is an encyclopedia of knowledge about the history and culture of Madrid would be an understatement. The bars, restaurants, and shops he takes you to are mostly small family owned establishments that have been his friends for years. His stories at entertaining and humorous. I will see him again the next time I am in Madrid. I highly recommend purchasing his book!” —SteveInLA

“We didn’t know what to expect when we booked Stephen Drake-Jones, but our entire family — teens included — were pleasantly delighted! Stephen makes history fun and engaging, with anecdotes, illustrations, and plenty of good wine and food. These aren’t typical tours — they’re more like spending time with an old friend sharing vast knowledge over a great glass of wine. Highly recommend!”— Peter A

“Stephen is great. It felt like we were getting a tour of Madrid from a close friend. Stephen is very personable. We started with some wine and cheese at a bar/restaurant that was frequented by Hemingway. We enjoyed classic torta, pane and tapas along with a variety of Spanish wines.
Lots of interesting stops (original Mickey Mouse) and if I forget any details I can always read about because “It’s in the book” which Stephen recently released.” —Kelly C

“Don and I wanted to thank the Chairman again for our unforgettable time in Madrid and Toledo! His wealth of knowledge is truly priceless. The tapas tour, the Prado, and Toledo were all simply amazing — Stephen sparked such an interest in us that we returned to the Prado on our own! We hope our paths will cross again!” —Mary and Don

“Gail and I have been raving about our grand excursion through Madrid with Stephen ever since! His descriptions were vivid and clear — from the bombing site to the Hemingway photo at Cerveceria Alemana. He took us to places we’d never have found alone. The tapas, wine, and conversation were all superb. A great guide and simply a great guy!” —Dick and Gail

Need Help Finding Your Way?

To help you find your way around the city, try out our interactive map of some of Madrid 's more popular attractions. Of course, if you come on one of our singular tours, you will never be lost.
To see a larger version, just click on the square on the right below.

Family Friendly Pricing and Accessible Tours Available.

** We Love Solo Travellers **

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Your best choice for Madrid History, Hemingway, Museums, Fine Wine and Tapas, Toledo, Segovia, Wellington vs Napoleon!

All tours include tapas and beverages along with the most entertaining time you could imagine

First time coming to Madrid?

Join our entertaining and informative morning stroll or a visit to one of Madrid’s world renowned Museums or find out about Hemingway’s time in Madrid.. Want more? Browse through our tour pages or email about a package of tours. Once you take a tour, you become a member of the the Society with all of it’s valuable benefits.