I’ll be honest with you…
Most cyclists don’t have a fitness problem.
They have a travel problem.
Not because they don’t want to go.
But because every time they start thinking about it, it turns into a lot.
Where would I even ride?
How do I get my bike there?
Is it safe?
Am I ready for that kind of trip?
So the idea just… sits there.
And you end up riding the same local routes, telling yourself maybe next year.
I know that feeling.
I lived in it for a long time.
Until one day, something shifted.
The Shift
I stopped asking if I was ready.
And started asking where I wanted to go.
That one question changed everything.
Because once you start thinking like a traveler, not just a cyclist, the world opens up in a completely different way.
Why I Put This Together
Yes, there’s a giveaway.
You can win a $1,500 bike tour.
But that’s not really the point.
The point is to give you a starting moment.
Something that nudges you out of the “maybe someday” phase and into actually doing it.
Because once you take that first trip, everything changes.
If You Win, Here’s What That Could Look Like
These aren’t random trips I found online.
I’ve ridden with every one of these operators. Different countries, different styles, different levels…
…and every single one left a mark on me in a different way.
Cycle Caribbean (Jamaica / Dominican Republic)
Jennifer Hilton and her team run one of the most unique cycling experiences I’ve ever seen. They literally coordinate with local authorities—police escorts, ambulance, full support—so you’re riding together as a group across Jamaican roads and you feel completely taken care of. Add in all-inclusive stays and the energy of the group… it honestly feels like a challenging reggae party peloton. You’re working hard, but you’re also having a really good time.
Terra Nova Bike Tours (Germany / France)
I rode around Lake Constance with them—on an e-bike, which was a first for me. And I get it now. You’re not just pushing through miles… you actually have time to stop, explore, and take in the culture. We’d roll into these small towns, sit at cafés, wander a bit—it felt more like traveling by bike than just riding through places.
Comova Cycling (Northern California, USA)
This one surprised me. You stay at their cabin, which is fully set up for cyclists—bike wash station, gear drying setup, all the little things you don’t realize you need until you have them. Then you head out into Sonoma… trees, climbs that hit double digits, and suddenly you’re on the coast passing through this old Russian fortress I didn’t even know existed. It’s a mix of nature, history, and “why are these hills so hard?” 😂
Pura Vida Cycling (Costa Rica)
I’m just going to say it… this one was psychotic (in the best way). This is a strong rider’s playground. I ended up riding with people who were basically top 1% Ironman level, and I was just trying to survive 😂 But they were so fun, so welcoming. It’s intense, it’s humid, it’s real training. And what I loved most—he brings used cycling gear to local riders, and you actually ride with locals the whole time. And they are STRONG.
Colombia Cycling (Medellín Region)
Tomas and his team might offer some of the best service I’ve experienced, period. I never once felt out of place, even riding with stronger cyclists. They really take care of you. And if you time it right, you can combine the trip with a gran fondo—which you absolutely should do. That’s when you really understand Colombia’s cycling culture… you’re not watching it, you’re in it.
Santander Cycling (Colombia)
Santander is one of those places that just stays with you. Big mountain energy everywhere. You’ve got climbs like Picacho and Zapatoca, and then the Chicamocha Canyon—which is massive. The views are unreal. I loved it so much I’ve genuinely thought about living there for a bit. It’s that kind of place.
Escapar Cycling (Spain)
David and his wife run this, and their place in Ontinyent is stunning—a full-on mansion surrounded by that “Valencian Tuscany” vibe. Quiet roads, beautiful towns like Bocairent, and if you’re into triathlon, there’s even an Olympic-sized pool at the house. He’s got a full fleet of bikes too. It’s one of those places where you ride hard… and then just enjoy life really well after.
Greek Cycle Holidays (Greece)
Steve used to be a professional chef in high-end hotels… so yes, every ride ends with incredible Greek food. That alone is worth it 😂 He has a villa in Evia and runs tours across different regions like the Peloponnese, Thessaloniki, and Crete. It’s that perfect mix of coastal riding, history, and meals you’ll still be thinking about later.
Off Beat Pedals (India)
Sujith and Francis are an incredible duo. Kerala completely surprised me—it’s lush, it’s peaceful, and culturally rich in a way that’s hard to explain until you’re there. This region is where so many spices come from, and you feel that history. And they don’t just do Kerala—they run trips in the Himalayas, Rajasthan, New Delhi… all over India. It’s the kind of experience that pulls you out of your comfort zone and expands you fast.
I didn’t just “enjoy” these trips.
They shifted how I see the world, how I travel, and honestly… how I ride.
And that’s why I’m so confident putting this in front of you.
Because whichever one you choose…
it’s not just going to be a ride.
What Usually Stops People
It’s not the cycling.
It’s everything around it.
The planning.
The logistics.
The uncertainty.
The question of whether you’re the “type” of cyclist who does trips like this.
That’s where most people stop.
Not because they can’t do it—but because it feels like too much to figure out alone.
What We Do Differently
Cycle Travel Club was built to remove that friction.
Not by selling you a random trip, but by giving you access to trusted operators, real routes, and a community of people doing the same thing.
So instead of guessing your way through it, you’re stepping into something that’s already been vetted and experienced.
How the Giveaway Works
You can enter here:
https://cycle-travel-club.kit.com/biketourgiveawaynew
There are a few ways to enter:
- Join the newsletter
- Join as a Basic member
- Join as a VIP member
Each step increases your chances.
Not just randomly, but intentionally.
Because the more you lean into this lifestyle, the more opportunities open up.
Why This Matters Right Now
Travel is changing.
People are taking fewer trips, but making them count more.
Experiences are starting to matter more than convenience.
Cycling fits into that shift naturally.
You move slower.
You see more.
You connect with places in a way that’s hard to replicate any other way.
This Is Your Moment
You don’t need to be faster.
You don’t need to be more experienced.
You don’t need to have everything figured out.
You just need a starting point.
If this is something you’ve been thinking about—even a little—this might be it.
Enter the Giveaway
https://cycle-travel-club.kit.com/biketourgiveawaynew
And even if you don’t win, I hope this gets you one step closer to taking that trip you’ve been putting off.
Because once you do it once…
It’s hard to go back.
