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.
We Tour, But We Never Bore
Stephen, we are leaving Madrid tomorrow and want to say how much we enjoyed our tour on Friday. We went to the Prado today, book in hand, and enjoyed using the Prado chapter as a guide! We have fallen in love with the amazing city of Madrid.
As we said, travel is also about the people we meet, and we are so happy to have met you. By sharing your passion for this city and it’s history, our visit has been much more meaningful. We are so grateful for the time spent and stories shared.
I will be eagerly checking your website for the Don Ernesto book. Our hope is you and your daughters have a wonderful time creating it!
All the best,
Melanie and Jim
I had a fantastic time on the “Bloody Madrid” tour. Stephen was an excellent tour guide and had colorful anecdotes for just about everything. Little did I know Madrid had such a violent past. But boy did I find out! Stephen had planned around 9-10 historical stops along the tour, in addition to 3-4 stops for wine and snacks (a well-earned break from the blazing summer sun!). He brought his own materials with him and was open to questions at all time. I previously did the self-guided tour at the Royal Palace but didn’t really understand much historical context. Stephen really helped piece it all together. Side note – the Chairman’s instant recall of dates is incredible! He was able to recite when a certain event occurred, down to the minute, off the top of his head. Also, he has a wide network of connections in Madrid/Spain, so definitely ask him for some advice. He was able to recommend me a taxi driver in Toledo who spoke English, which really saved my bacon!
Overall, definitely recommend taking a tour with Stephen. It’s a great time, you actually learn a lot, get to drink a lot of good wine, and his recommendations/knowledge are impeccable.
Highlight: seeing the bullet/shrapnel holes from the Morral Affair still preserved even over 100 years later. Cool!
I can’t wait for the book….
Sheryl B – Newington, NH
My boyfriend and I had a wonderful personalized tour with the President of the Wellington Society, Stephen Drake-Jones. Per our request, he did a combination of his “Morning Stroll” and “Old Madrid Underground” tours. He brought the city to life with anecdotes about important Spanish figures. We took the tour on our first day in Madrid and it really enhanced our entire visit. He showed us Roman ruins, the grounds of the Royal Palace, the Plaza Mayor, Mercado de San Miguel, and many other stops along the way. My favorite stop was at the swanky Cafe de Oriente overlooking the Royal Palace where Stephen treated us to some tapas and wine while teaching us about the sordid affairs of the Kings & Queens of Spain. He brought along books and photos to help orient us to the city and put faces to names. We went to the Prado Museum after our tour and sought out some of the key portraits that Stephen had taught us about. He was absolutely charming and made us feel at home in a city we only visited for a few days. He was very responsive via email and professional. I forgot to email him to let him know when we got to Spain and he still showed up at the designated place on time and ready. It was a rainy day, but that didn’t slow him down. Would highly recommend this tour to history buffs and lovers of gossip told in a great British accent. The highlight of our trip!
The afternoon progressed with tapas, wine, famous (and not as famous) statues, more tapas, more wine, Mickey Mouse’s precursor, murder sites… all explained by a gifted storyteller. Stephen is a wealth of knowledge and the best kind of teacher/guide. He made sure we were following along, answered all of our questions, and showed us a picture of Madrid we would never have gotten from a guide book.
I’d recommend to anyone an afternoon stroll with Stephen. Cheers!
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 gravitas to the walking tour and I very much enjoyed his use of language (will we ever forget “salubrious” or “chuffed”? No, we will not.) As he states at the beginning of the tour, this is Madrid from his point of view and we found that to be more personable than a generic history lesson. His choices of places to stop for tapas and drinks and historical locations were excellent. When we return to Madrid we plan to do another tour with him if possible (the Hemingway tour looks intriguing.) Thank you for a fun outing!
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!
We didn’t know what to expect when we booked Stephen Drake-Jones, but our entire family, teens included, were pleasantly delighted. Stephen made history, fun and engaging, complete with personal anecdotes, illustrations, and plenty of good wine and food.
We did a “morning stroll“ of Madrid, and the next day traveled to Toledo with Stephen. These are not energetic excursions, nor are they “tours“ in the usual sense. Rather, they are more like spending time with an old friend who loves to impart his vast knowledge of history over a good glass of wine or two.
Yes, he’s quirky and a little eccentric, but in the best kind of way. We can’t recommend him enough.
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.
Don and I wanted to thank you again for the time spent with us in Madrid and Toledo! Having you share your wealth of knowledge with us was priceless. The tapas tour, the Prado and the time in Toledo were all simply amazing. We walked around Toledo for another half a day on Thursday and then Don requested that we return to Madrid and go back to the Prado. You sparked such an interest in both of us. We so enjoyed our second visit, but wished you were with us.
We wish you all the best and we hope that our paths will cross again one day!
Mary and Don
Gail and I have been talking, between ourselves and to others we meet, about our grand excursion through parts of Madrid with you last Saturday. We thoroughly enjoyed your clear descriptions, including the bombing site, your laying of the wreath, the Hemingway picture in the Cerveceria Alemana, and Santa Anna, your favorite square. You took us to places we never would have seen on our own, like St. Nicholas Church. The tapas were delicious, the wine cold and good, and the conversation — because of you — lively, informed, engaging and cordial. You are, we think, a great guide, and simply a great guy. We are lucky to have been in your company.
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.
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.