Old Friends, New Roads – TDA’s Incredible Cycling Community

Benjamin Levin is the Content Creator on the 2025 Olive Route Cycling Tour.

As I sat waiting for the introductory riders’ meeting to begin on TDA’s new Olive Route tour, I couldn’t help but notice how many riders were chatting away like old friends. I know from previous experience that on our cycling tours, people become fast friends and form strong bonds over the course of the ride but this time, it seemed like the connections were happening instantly.

As the meeting began and the group introduced themselves, I realized that most of them hadn’t just met. Many had ridden together on previous TDA tours. How special that here in Athens, about to embark on a two-and-a-half-month cycling adventure, they were reconnecting, sometimes for the third, fourth or even fifth time. As special as that seems, it’s not unusual on a TDA tour. Time and time again, riders return, especially for new tours, and reunite with a unique group of individuals who share a passion for cycling and adventure.

All smiles on the road

In 2025 and 2026, TDA is running five brand-new tours: Road of Empires, Olive Route, Island Hopping Japan, Tea Route, and Road to Valhalla. Five new tours in just two years is a major undertaking. Creating new routes, scouting, arranging accommodations – it’s no small task. So why do it when our tour catalogue is already so full?

Well, because our riders love these tours so much, they literally do them all. I’m not exaggerating. Here on the Olive Route, 17 of the 19 riders who started in Athens had done a TDA tour previously. Veteran rider Chris Willie has completed a staggering 16 TDA trips over the years. That kind of loyalty inspires us to keep imagining new journeys, giving returning riders new places to explore and new adventures to undertake. “It is really exciting to be the first rider on a new route. That is a very special thing,” Chris exclaimed. “Every day is literally like a present waiting to be opened. For me, and I think many other riders on TDA tours, every day is Christmas.”

Michele (Left), Brett, and Kaye (Brett and Kaye met on a TDA trip and are now partners!)

What keeps them coming back? One reason is, of course, the cycling. TDA runs trips through places other companies won’t – routes few cyclists ever get to ride. The Olive Route, however, passes through Greece, Italy, France, Spain and Portugal, passing through relatively well-known areas. These aren’t uncharted territories like the Namib Desert in Africa or the Pamir Highway in Central Asia. The second reason riders return so often is the group dynamic. On TDA tours, many riders become lifelong friends. We’ve seen cyclists arrive as total strangers and leave with tears in their eyes, bonded like family. Some have even met on a TDA tour and returned on the next one – married!

Daniela enjoying the flat tire troubles of her fellow riders!

When you bring together people who love cycling, adventure and pushing themselves, something magical happens. It creates an atmosphere where connection thrives. For many riders, that sense of camaraderie is just as important as the cycling itself. “I got hooked 10 years ago when I was a rookie.” Daniela Holme shared. “At first, I was like what have I got myself into, but the group truly inspired me… I have even stayed in touch with a couple of those people from 10 years ago. This is part of what is so special about TDA, and I am sure it [this trip] won’t be my last.”

Janice and Simon rolling out of Athens under the Acropolis’ watchful eye

If you’re reading this as someone who’s never done a TDA tour and you’re worried about being the outsider – don’t be. These groups are anything but exclusive. They are all built on a shared love of cycling, something you likely share, too.

Here on the Olive Route, first-time rider Matthew McGuinness admitted that during the opening meeting that he was nervous. “I was feeling like that because I had never done a tour like this, and I did not really know what I was getting into… it was a little daunting.” Now, just a few weeks in, it’s hard to imagine he hasn’t been doing this his whole life. When asked about that feeling he stated, “After that first day I was like ok hmm, and by the third day I was like, yeah, I want to do all of this… now I’m interested to see how I feel when it’s over.”

Matty and Kristen taking photos of the Olive trees

That sentiment, from Matty and so many others, is what keeps people coming back to TDA tours, and what motivates us to keep creating new experiences for our community. Whether you’ve been touring with us for as long as Chris has, or you are just beginning, like Matty, the essence of the journey is the same: cycling through spectacularly beautiful, culturally rich landscapes, alongside friends from all around the globe.

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