How to Plan a European Cycling Trip and Retirement Scouting Adventure in the Same Trip

Watching the Tour de France With Paul Has Become an Annual Event. Watching Paul Watch the Tour de France Is Half the Fun.

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Tour de France Mountain Stage. Photo by Mike Dot.

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From Watching the Tour de France to Planning a European Cycling Adventure

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Paul is wearing his t-shirt design. Photo by Wendy Stieg

Having a strong understanding of what I mean when I say “bucket list item” now makes sense. With that said, it should come as no surprise that we have had at least five iterations of the trip we have been planning. I think we are coming close to settling on the latest iteration of our trip. In September, La Vuelta is set, at least the start and end dates. The stages in the middle will be announced in late December 2026 or perhaps early January 2027. What does that have to do with our next decision? EVERYTHING.

One practical consideration when traveling through several European countries is staying connected along the way. Airalo offers travel eSIMs that can help you access mobile data abroad, whether you're navigating unfamiliar roads, checking travel plans or exploring a new destination.

Planning a Trip Around La Vuelta and Scouting Retirement Destinations

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Madrid street. Photo by Paul Lampe.

It is hard to plan around a literal moving target. But it also fits our style, which is keeping the trip loose enough that there is room for spontaneity. We want it planned enough that we can shift dates, but we also want to make a decision when good airfare pricing occurs. Our timeline and loose structure do both: allow us to find the best airfare and also give us room to shift as needed for La Vuelta. We have decided to also include a scouting trip in this plan, as those of you following us know our ultimate plan is to retire in Spain, most likely. But our minds are still open to France and Italy. So a new idea is to do La Vuelta and a scouting trip, then the Tour de France and a scouting trip, and finally Il Giro d’Italia and a scouting trip. So over the next three years, we will do that. We also know Portugal pretty well. I love planning around a sporting event. I think it brings a whole new level to what we are doing, not to mention blog fodder for me and a podcasting sportsman’s dream.

Spain has been on our retirement radar for some time, and this trip will give us another opportunity to explore what living there might actually look like. I wrote more about the possibilities in Have You Considered Spain for Retirement?

Rethinking Retirement: Building a Life Around Travel and Adventure

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Mountain biking in Colorado. Photo by Paul Lampe.

All of this is actually connected to our larger idea of how, when and where we plan to retire. We own a home in Montrose, Colorado, and it has proved to be a great investment so far. We have a lot of ideas for how to leverage this home, but we are not sure yet how we will do that. That demonstrates our loose grasp on our idea of retirement. We know we need to create an income source that can carry us through our retirement years. We are building this based on the adventurous life we have always lived and will continue to live.

As we continue exploring the possibility of living abroad, we're also thinking about the practical side of managing money internationally. Wise offers international money transfers and currency conversion, making it another resource worth researching as part of planning a life that might eventually take us overseas.

Our Spain and France Travel Itinerary: Barcelona, Girona and the Pyrenees

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The Spanish Pyrenees. Photo by Raoul du Plessis

What we are thinking now is our rough draft of our final overall plan: Fly into Barcelona, spend a few days in that incredible city, pick up a Siesta campervan, move on to Girona, a cycling capital of Spain, and get ready to head to Aragón, the French Pyrenees and back to Catalonia. We will also pepper in Tarragona, possibly a day in Valencia via train, plus a couple of days in Perpignan, France, for potential scouting ideas in France. Allowing ourselves to be open is the idea. Memories of our Portugal retirement idea come flooding back as I think this through.

France is also part of our bigger retirement conversation, especially as we consider the possibilities of living somewhere that puts travel and adventure within easy reach. I explored some of those considerations in How Retiring in France May Be Right for You.

Why Portugal Is Still Part of Our European Retirement Dream

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Algarve Coast, taken during a Portugal scout trip. Photo by Wendy Stieg

Portugal was something we grabbed onto fast and furious and found that we just couldn't do it yet. Portugal will always have a place in our hearts. It’s where we said our vows and where we first conceptualized this idea of a European retirement. This time we are taking about five years to decide, save money and build our business in order to be able to continue supporting ourselves. Weaving in our bucket list ideas of chasing European bike races gives us a great excuse to go to Spain, France and Italy, as well as have scouting trips.

Portugal continues to hold a special place in our hearts, but dreaming about living somewhere and understanding the realities are two different things. I explored those questions in Retiring in Portugal: Is It Still as Easy and Affordable as Ever?

In Closing

Wendy, Serro Summit, near Hwy. 50. Photo by Paul Lampe.

We are investing in ourselves, building a travel blog plus sports podcast business, woven together in order to realize the life of our dreams. A life that increases our thinking, experiences, language learning, and more. All designed around ways to increase longevity and adventure as we move into this next phase of our lives. Who doesn’t expect to find a way to have fun and adventure as the key important point of retirement? Paul rolls his eyes every time I mention money, except when he gets to spend it and have adventures. Doesn’t everyone plan retirement that way? If they don’t, maybe they should!

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Chasing adventures, one ride at a time. Photo by Paul Lampe.

We have a big update! Paul and I just booked flights from Montrose to Barcelona in September! The planning begins!

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Identifying Your Income Gap