What Ted Simon's "Jupiter's Travels" Gets Right About Long-Term Riding

A worn Triumph Tiger in the Moroccan dirt, 1973 — the exact kind of unglamorous, functional moment Simon captured, and the kind most Instagram travel feeds still crop out today.

⚡ Problem-Solver Card

Who this solves for: Riders planning their first overland trip of 3+ months. Also restless souls who own a bike and a copy of Jupiter's Travels they've never finished.

When to use this advice: When you're overpacked, over-insured, and overthinking. Or when you're convinced you need a $25,000 adventure bike to start.

Estimated effort: 3/5 — unlearning modern gear obsession takes longer than learning to patch a tube.

Cost range: $50 (just the book) to $6,500 (a running bike, basic tools, and six months of cheap camping).

Risk level: Medium — higher if you ignore Simon's real lesson about loneliness.

Time saved: About two years of gear research and three unnecessary credit card bills.

Why This Problem Ruins Trips (And Why Most Advice Fails)

I pulled into a petrol station outside Tiznit, southern Morocco, on the fourth day of what was supposed to be an eighteen-month loop through West Africa. My 2019 BMW 850GS had 1,400 miles on the odometer, three panniers stuffed with dry bags, a tank bag big enough to hold a small dog, and a GPS unit that had already frozen twice in the heat. A local rider on a 1974 Yamaha 250 glanced at my bike, then at my face, and said something in Arabic that his friend translated as: "You look like you're moving your whole house."

He wasn't wrong. I had a camping stove I'd never lit, a first-aid kit with thirty-seven items and no knowledge of how to use most of them, and three different charging cables for devices that all used the same port. I was wearing a $900 Klim jacket that made me look like a Power Ranger and sweat like a dairy cow. The Yamaha rider wore sandals, a button-down shirt, and a helmet that looked like it had been painted with house enamel.

He'd been on the road for two years. I lasted four months before I flew home and sold the BMW.

That's when I finally read Ted Simon's Jupiter's Travels — the book every long-distance rider mentions but half of them haven't actually finished. I'd bought a copy three years earlier. It sat on a shelf, spine unbroken, because I assumed a 1979 account of a four-year, 63,000-mile ride on a Triumph Tiger was too dated to teach me anything about modern long-term touring.

I was spectacularly wrong.

Most adventure-riding advice today comes from Instagram reels, sponsored YouTubers, and gear reviews that use the word "bombproof" every third sentence. The root problem is not a lack of information — it's an excess of it, and almost all of it is about stuff. How to pack it. Waterproof it. Charge it. Insure it. Mount it securely to a frame that already weighs more than a Honda Civic from 1993.

What Simon understood, and what most modern guides miss, is that long-term touring is not a gear problem. It's a psychological endurance problem disguised as a logistics problem. The Yamaha rider in Tiznit didn't have better equipment. He had better relationship with uncertainty.

The Step-by-Step Solution

1. Stop Buying Gear. Start Buying Miles.

Simon rode a 1973 Triumph Tiger 500 that broke down roughly every 1,200 miles. He rebuilt the top end on a dirt floor in the Sudan using a borrowed wrench and a rock as a hammer. He did not have a satellite communicator, a heated seat, or a collapsible titanium spork. What he had was a willingness to sit still in a place he didn't understand until it started to make sense.

Here's the uncomfortable truth: the modern motorcycle is mechanically more reliable than Simon's was, but the rider is mentally less resilient. We've engineered the breakdowns out of the bike and designed them into the human. We panic when the phone dies. We cancel trips because the forecast shows three days of rain. We spend six hours researching tire pressure monitoring systems instead of riding to the county line and back.

Action: Before you buy another farkle, ride a 1,000-mile weekend on the bike you already own. Sleep in a tent you've pitched before. Eat food from a gas station. If that feels miserable, no amount of carbon fiber luggage will fix it. The discomfort is the point. Simon understood that the boredom, the heat, the monotony of straight roads — these are the actual curriculum of long-term travel. Gear is just the paper you write the answers on.

✅ Pro Tip From Someone Who's Been There

Take a notebook, not a phone. Simon wrote Jupiter's Travels in longhand on paper he bought in stationery shops across four continents. You don't need to publish a book — but writing by hand after a day of riding forces you to process what actually happened, not what would make a good caption. I started doing this in a $2 spiral notebook in Colombia. Eighteen months later, I had six filled notebooks and zero regret about the photos I didn't take.

2. The Speed Trap: Why Going Slow Is the Only Real Cheat Code

Simon averaged maybe 200 miles a day. Not because his bike was slow — because he stopped. He stopped for tea with strangers. He stopped to watch a man fix a fence. He stopped because a road looked interesting and he had no pressing appointment anywhere. Modern long-distance riders brag about 700-mile days like it's a competitive sport. I've done 800 miles in a day. You know what I remember? The pain in my wrists and the fact that I ate a gas station hot dog in Kansas. That's it. One hot dog. Seven hundred miles of America, compressed into a single mediocre sausage.

The practical fix: Set a hard cap of 250 miles per day for the first two weeks of any long trip. If you're feeling strong, you can push it to 300. But you have to stop for at least 45 minutes at every third fuel station — not to rest the bike, but to talk to whoever's there. Simon's entire book is a record of conversations with strangers. That doesn't happen at 80 mph with earplugs in and a GPS voice telling you to turn left in 500 meters.

I tested this on a ride from Bogotá to Medellín. First day: 200 miles. I ended up eating dinner with a retired coffee farmer who showed me how to roast beans on a comal. Second day: I tried 350 miles to "make up time." I ate a sad arepa alone in a bus station. Simon doesn't mention a single bus station arepa in four years of travel. That's not a coincidence.

3. The Loneliness Nobody Talks About

This is the part of long-term riding that all the glossy magazines skip. Simon didn't. He wrote honestly about the crushing isolation that hits somewhere around month five — the moment when every new road looks the same, every conversation starts with "Where are you from?" and you'd trade your entire trip for one night on a familiar couch with a person who knows your name without asking.

I hit this wall in San Cristóbal de las Casas, Mexico. I'd been on the road fourteen weeks. I sat on my bike outside a hostel and cried for twenty minutes. Not sad crying. Angry crying. I had no reason to be upset. I was in a beautiful place, doing a thing I'd planned for years. And I wanted to go home so badly I could taste it.

Simon solved this not by pushing through but by leaning into the slow rhythm of solitude. He wrote that he learned to "inhabit the present moment like a room." He didn't fight the silence — he let it become the background texture of his days. The modern solution is to call home, scroll Instagram, or message friends. Those things help for about twelve minutes. The real fix is harder and slower: you have to make peace with being alone with your own brain for hours at a time.

What worked for me: I started a daily ritual of writing down three things I noticed that day that I couldn't post online. A crack in a wall that looked like a map of Madagascar. The exact sound of a particular bird at dusk. The way a certain old man adjusted his hat before speaking. After two weeks of this, the loneliness didn't disappear, but it stopped being the main event. It became background noise — and eventually, something I actually valued.

4. Your Bike Is a Tool, Not a Personality

Simon's Triumph Tiger was unremarkable. It was a middleweight British single that leaked oil and vibrated bolts loose. He didn't name it. He didn't refer to it with anthropomorphic pronouns. It was a machine that carried him, and when it broke, he fixed it. The modern adventure-riding culture acts like the bike is a character in the story. It's not. It's the punctuation.

I spent my first long trip fussing over my BMW. I washed it in rivers. I worried about scratches. I checked the chain tension every morning like I was performing a medical procedure. Meanwhile, the local riders I met in rural Mexico treated their bikes like bicycles — they used them, abused them, repaired them with wire and zip ties, and never once photographed them against a sunset.

The practical truth: The best long-distance bike is the one you already own, paid off, and understand how to fix with basic tools. Simon's Triumph cost him about $300 in 1973. Adjusted for inflation, that's roughly $2,100. You can buy a perfectly capable used motorcycle for that today — a Suzuki DR650, a Kawasaki KLR650, a Honda XR650L. It won't have cornering ABS or a quickshifter. It won't impress anyone at a coffee shop. But it will get you to the other side of the world, provided you bring the one piece of equipment that Simon had and no amount of money can buy: patience with your own company.

⚠️ Real Traveler Mistake

I spent $2,300 on a satellite messenger, solar panel, and backup battery bank before leaving for South America. By month three, I had lost the charger for the solar panel, the satellite messenger had a cracked screen, and I was paying $8 a day to charge my phone at hostel desks. Simon carried a notebook and used payphones. The lesson: complexity is fragile. The simpler your power and communication setup, the less it will break. A $30 power bank and a universal USB cable will survive more than a $600 solar kit ever will.

Pro Tips From Someone Who's Been There

These aren't from a magazine. They're from the roadside, the hostel patio, the mechanic's dirt floor.

1. Carry a physical road atlas. Simon used paper maps because he had no choice. I use one now by choice. When my phone died in the Atacama Desert — battery drained by cold and GPS use — I unfolded a paper map and found a route in thirty seconds. The road hadn't changed in forty years. The map hadn't changed either. Paper doesn't have a battery.
2. Learn to patch a tube before you leave. Simon did this on the side of a road in Algeria with a tire iron and a bucket of water. I've done it in a muddy field in Bolivia. Tubeless tires are common now, but not everywhere. If you're going to remote areas — and if you're going long-term, you will — the skill of vulcanizing a rubber patch is worth more than any premium roadside assistance plan.
3. Pack one book, not a Kindle. Simon carried a copy of War and Peace for two years. I carried a paperback of Cormac McCarthy's The Road — dark, I know, but appropriate. A physical book runs out of battery exactly never, and when you finish it, you swap it with another traveler. That exchange — handing a book to a stranger in a hostel in Peru — is a small human moment that a Kindle can't replicate.
4. Learn fifty words of the local language before you cross the border. Simon didn't speak Arabic when he entered North Africa. He learned it by being wrong in public. But even fifty words — hello, goodbye, please, thank you, how much, where is a mechanic — change the entire texture of a trip. Locals in rural Iran remembered Simon because he tried to speak their language, badly. Fifty years later, that same principle works exactly the same way.
5. Plan for the post-trip crash. Simon wrote that returning home was harder than leaving. He was right. After my South America trip, I spent three months feeling like I'd been unplugged from a life-support system. The fix: schedule a small project — a week of hiking, a visit to a friend in another city, even just a weekend bike camping trip — within two weeks of coming home. Don't go from four continents to a cubicle in forty-eight hours. Your brain needs a decompression chamber.

Common Mistakes Travelers Make With This Issue

I've made all of these. You don't have to.

Mistake 1: Overplanning the route. Simon didn't have Google Maps. He had a general direction and a lot of curiosity. I've met riders who plan every overnight stop for six months in advance. That's not adventure — that's parcel delivery. Leave gaps of three to five days with nothing scheduled. Let the road decide.

Mistake 2: Carrying too much clothing. Simon traveled with two sets of clothes and washed one while wearing the other. I left for Morocco with eight T-shirts. After three weeks, I was using the extras as rags. You need: one riding outfit, one off-bike outfit, one set of rain gear, one jacket for cold mornings. Everything else is ballast.

Mistake 3: Ignoring your body's signals. Simon wrote about a period of weeks when he felt "hollow" — he kept riding, thinking the road would fix it. It didn't. He had to stop, rest, and eat properly. I pushed through a knee injury for 1,200 miles in Colombia because I didn't want to lose time. I lost three weeks instead. Pain is not a weakness. It's a message. Listen to it.

Mistake 4: Comparing your trip to someone else's Instagram. Simon had no social media. He didn't know what other travelers were doing. He rode his own ride, literally. The single most corrosive thing for long-term morale is seeing someone else's highlight reel while you're sitting in a laundromat in a dusty town. Uninstall the apps. Your trip is your trip. The only person you need to impress is the one who'll read your notebook in ten years.

Your Quick-Action Checklist

Before you turn this article into a bookmark you never act on, take these steps. Each takes under thirty minutes.

• ✅ Buy or borrow Jupiter's Travels. Read Part One before you touch a spreadsheet or a gear list.
• ✅ Ride a 200-mile day with zero technology. No phone. No GPS. No music. Just you, the road, and whatever you see. If it feels unbearable, practice it in shorter doses until it doesn't.
• ✅ Empty your luggage. Lay everything you planned to carry on a tarp. Remove half of it. Then remove half of what remains.
• ✅ Practice one mechanical skill. Adjust your chain. Change a tire. Clean your air filter. Do it twice.
• ✅ Write down three places you want to visit that have no cell reception. Simon's best moments happened where nobody could reach him.
• ✅ Book a cheap room for your first night. Don't start a long trip already exhausted from sleeping in an airport.

Frequently Asked Questions

Q: Is "Jupiter's Travels" still relevant for modern motorcycle touring?

Yes — because the book is not about motorcycles but about how to live with uncertainty, boredom, and solitude for months at a time, which no amount of modern technology has solved or will solve.

Q: What's the biggest difference between Ted Simon's approach and modern adventure riding?

Simon treated the journey as a series of human encounters, not a logistics challenge — he spent more time drinking tea with strangers than adjusting his luggage, while modern riders often do the opposite.

Q: What bike did Ted Simon ride and can I still use something similar today?

He rode a 1973 Triumph Tiger 500, a 500cc single-cylinder that cost about $300 — and yes, a modern Suzuki DR650 or Kawasaki KLR650 follows the exact same philosophy: simple, air-cooled, fixable with basic tools.

Q: How many miles per day did Ted Simon average on his world tour?

He averaged around 150-200 miles per day, often less, because he stopped frequently to talk to locals, write in his notebook, or wait out a mechanical issue — a pace most modern riders would consider "wasting time."

Q: What is the single most useful skill for long-term motorcycle travel that Simon demonstrates?

The ability to sit alone in a foreign place without distraction and feel neither panic nor boredom — a skill he practiced for four years and that no GPS, satellite messenger, or adventure jacket can teach you.

Final Word: You've Got This

I won't tell you to quit your job, sell your house, and ride to Ushuaia. That's someone else's fantasy. What I will tell you is this: if you've got a running bike, a basic tool kit, and the willingness to be uncomfortable for longer than feels reasonable, you already have more than Ted Simon had when he left London in 1973.

He didn't have a plan. He had a direction, a cheap motorcycle, and a stubborn belief that the road would provide. It did. Not always in the way he expected — he got sick, he got robbed, he got lonely as hell — but it provided enough. Enough encounters. Enough stories. Enough material to write a book that still matters fifty years later.

Your trip doesn't have to be four years or 63,000 miles. It could be two months across your own country. It could be a single summer in the mountains. The scale doesn't matter. What matters is that you start, that you go slow enough to actually see where you are, and that you come back with something more useful than a gas station receipt and a phone full of photos you'll never look at.

Simon's final line in Jupiter's Travels is: "There is no end to the journey." He meant it as a hopeful statement, not a bleak one. There's always another road. Another conversation. Another morning when you wake up in a place you never expected to be and realize you're exactly where you should be.

So read the book. Then go ride. Not because you have to — because you already know you want to.

📌 Save this guide. Share it with the one friend who's been talking about riding around the world for five years. And when you get back — not if — come tell me what you learned that wasn't in any book.