Category: No Stupid Questions
A rolling series of answers to real rider questions, usually long, meandering and unfiltered. Want your burning question answered? Drop me a line here.
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No Stupid Questions: How To Deal With Racial Prejudice While Cycle Touring?
A reader writes: I’m sorry to be awkward but my question is about race. I’m planning to embark on a cross-Europe cycle tour this spring. I’ve read a lot of people’s blogs on similar journeys but I’ve noticed that they tend to be white travellers. As a North Indian looking guy with a very Southern English accent, I wondered if Islamophobia / anti immigrant sentiment was something I should worry about in Eastern Europe? I’d love some pointers to blogs I might have missed, as well — I understand if this might not be a topic you feel totally comfortable explaining.… Continue reading →
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No Stupid Questions: What’s The Best Route Planning & Campsite Finder App For Cycle Touring In The USA?
A reader writes: Are you familiar with [the Great American Rail Trail] at all? The route is currently about 55% off road and more complete in the east but there is an almost 1,000 [mile] gap through Montana and Wyoming. So my question is what app do you use when riding to find the best on-road [but] safe cycling conditions on the gap sections between trails? And do you have a favorite app to find accommodations: camping (preferred) or hotels on the route every few days? Thanks for the question! Let’s start with what might be called “dynamic” route planning for… Continue reading →
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No Stupid Questions: How To Plan Cycle Tours In Unusual Places (Like Jamaica)?
A reader writes: I am a new subscriber to your mailing list as I hope to get into travelling by bike. I was wondering if you have any insights about biking in Jamaica? While being there I will able to do both short and very long rides. So my questions are: Is it safe? Is Jamaica friendly to cyclists? I have a gravel bike and wondering what kind of wheels I may need in that country. Any route suggestions? Anything that you can provide I will greatly appreciate it. This is an interesting question for a couple of reasons. First,… Continue reading →
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No Stupid Questions: Can I Still Cycle Tour With An Enlarged Prostate?
A reader writes: I, like many men of my age, suffer from an enlarged prostate. When I was diagnosed with this a few years ago I asked if I could still cycle. Needless to say [the doctor] advised against it other than occasional short runs. Straight after diagnosis I bought suitable saddles (those with a significant cutaway to relieve pressure on the perineum – very common now) and reduced my cycling to a max of 2 hours once or twice a week. I had always worn padded shorts. I have a couple of friends that suffer this problem but they carry… Continue reading →
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No Stupid Questions: Cycling Across Land Borders, Custom Bike Builders, & Top 5 Things To Pack
A reader writes: I have an ambition to set off for Australia from Norwich in the UK in 2025 when I retire at the age of 67. I have never cycled more than 240 miles in a single multi-day ride. But I love being out on two wheels and am inspired by the stories and photos from bicycle travellers like yourself. I am an experienced traveller so am familiar with foreign lands but have the following questions for you, if you have the time. How best to prepare for and cross international land borders with a loaded bike? Firstly, thanks for… Continue reading →
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No Stupid Questions: How To Fly With Bike Boxes & Bags For Touring & Bikepacking?
A reader writes: Thanks for the question! The truth is that flying with a touring bike and gear is rarely simple, but it’s always possible… somehow! It sounds like you’ve got plenty of experience packing your bikes for flying already. But your concerns are more specific, so let’s get right into them right now. Continue reading →
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No Stupid Questions: How To Secure My Bike & Gear While Riding Across The USA?
A reader writes: My biggest question about touring is security for my bike. I’m riding across the US in 2025, with a friend. Maybe a U‑lock is enough because we can always leave one of us at the bikes, but what if we want to eat at a restaurant? Or have some beers at the end of the day in a bar? And what about all the bags and gear on the bike, even if the bike is secured? And what about trackers? Are they worth the money? Thanks for the question! Bike security on a cycle tour or bikepacking trip… Continue reading →










