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I’ll be honest — I came to bike travel a little later in life.
I was a hiker first. A wanderer. A “let’s see what’s down that side road” kind of traveler. Cycling felt… intimidating. Lycra-clad speed demons, endless hills, and the fear of being that person slowing everyone down.
Turns out, I couldn’t have been more wrong.
After diving into bike tours over the past few years — from Europe to Japan to Patagonia — I’ve learned that bike travel is one of the most immersive, confidence-building ways to explore a destination. And you absolutely do not need to be an elite cyclist to do it.
If you’ve ever thought, “A bike tour sounds amazing… but how do I even choose the right one?” — this is for you.
(And if you want the full behind-the-scenes conversation, I talk all about this in my Vacation Mavens Podcast interview, where I share my newbie cyclist lessons learned.)
First, Let’s Address the Biggest Fear: “Am I Fit Enough?”
This is the question everyone asks. I did too.
The truth is, bike tours exist across a huge spectrum. Some are designed for experienced cyclists chasing climbs and mileage. Others are designed for travelers who simply want to explore a destination differently.
The key is matching the tour to your comfort level — not someone else’s.
When I did my first cycling trip in Europe, I was nervous. Would I slow everyone down? Would the hills break me? Would I regret it? Would I be miserable? I really went into it with no biking experience.
Instead, I discovered something empowering: most bike tours aren’t races. They’re journeys.
I also discovered ebikes!
You stop for coffee. You stop for photos. You stop because there’s a cat sitting in the middle of the road looking at you.
And you realize — you belong there.
Guided vs. Self-Guided Bike Tours: Which Fits You Best?
This is the first big decision — and there’s no wrong answer.
Guided Bike Tours
Guided tours are especially great if you’re new to bike travel or want the reassurance of support vehicles and experienced leadership.
Guided tours are fantastic if you want:
- Built-in support and logistics handled
- Local insight from experienced guides
- A social experience with fellow travelers
- Peace of mind if something goes wrong
You also gain local insight you’d never get on your own. Guides know the stories behind the landscapes. They know where to stop for the best pastries. And they know when to tell you, “Don’t worry, this climb looks worse than it is.” You ride, explore, eat well, and sleep — someone else sweats the details.
Self-Guided Bike Tours
Self-guided tours are all about freedom. You still get route maps, luggage transfers, and support — but you ride independently. You choose when to start. When to stop. How long to linger over lunch.
It feels like an adventure — but with guardrails.
Self-guided trips are ideal if you:
- Love flexibility and independence
- Prefer riding at your own pace
- Enjoy navigating and choosing your own stops
- Still want luggage transfers and route support
- On a budget
Choose Destinations With Solid Bike Infrastructure
Not all destinations are created equal when it comes to cycling.
Some places embrace cycling with dedicated bike paths, quiet country roads, and drivers who expect to see cyclists.
Other places… do not.
When choosing a bike tour, look for destinations known for cycling infrastructure. Europe excels at this. Countries like Ireland, Portugal, France, Italy, and the Netherlands have incredible networks. Asian countries are further behind in their biking infrastructure and drivers are far less used to seeing cyclists on roads.
Before you book, research:
- Dedicated bike paths and trail networks
- Quiet backroads vs. highway riding
- Bike-friendly accommodations
- Local tour operators and support services
A great starting point is local tourism board websites — they often highlight their best cycling routes and bike-friendly regions.
💡 If a destination actively promotes cycling tourism, that’s a very good sign.
Match the Tour to Your Comfort Level
This is where many people go wrong — they overestimate what they’ll enjoy.
Before committing, look closely at:
- Daily distance (miles per day)
- Elevation gain (those hills add up!)
- Terrain (paved roads, gravel, mixed surfaces)
- Traffic levels
A 40-mile day on flat terrain feels very different than 40 miles with 4,000 feet of climbing. Be honest with yourself. A tour should challenge you just enough — not make you miserable by day three. It is your vacation after all!
Seriously… Consider an E-Bike
I’ll say it loud for the people in the back:
E-bikes are not cheating.
They are:
- Confidence-boosting
- Knee-saving
- Hill-flattening
- Game-changing for new cyclists
I’ve utilized ebikes in a number of destinations. Times when I knew I wasn’t in shape enough to enjoy myself on a regular bike, or times when I knew the terrain or weather was going to be too challenging. It allowed me to ride farther, explore deeper, and finish each day feeling energized instead of exhausted.
Now, I see e-bikes for what they truly are: enablers of adventure.
E-bikes open up destinations and itineraries that might otherwise feel out of reach — especially in hilly regions or on longer routes. Many tours now offer them, or allow you to switch mid-trip.
And guess what? You’re still pedaling. You’re still outside. You’re still exploring.
What to Look for in a Bike Tour Company
Not all bike tour companies are the same — and this is where doing a little homework pays off. Here’s what I look for when choosing a bike company to travel with:
Quality of Bikes
A well-maintained and fitting bike is the foundation of your experience.
Ask questions:
- What brands do they use?
- How old is the fleet?
- Are e-bikes available?
- Are bikes regularly serviced?
- If you are using an ebike, ask about the battery life.
- Do they carry extra batteries?
Don’t be afraid to call them. A good company will happily talk bikes.
Know Their Focus
Some companies are:
- Cycling-first (more miles, more intensity)
- Destination-first (culture, food, scenery, with cycling as the vehicle)
I personally prefer companies that prioritize exploration over intensity. Where cycling is the vehicle for discovery — not the goal itself. Choose the one that matches your travel style.
Ask About Flexibility
Important questions:
- Can you bring your own saddle, pedals, or bike computer?
- Can you switch to an e-bike mid-trip?
- Will they install personal gear for you?
These little things make a big difference.
Understand Terrain & Traffic
Find out:
- Backroads vs. highways
- Gravel vs. paved
- Typical traffic levels
If traffic stresses you out, say so — there are tours designed specifically to minimize it.
Evaluate Pre-Trip Support
Great companies often offer:
- Training tips or fitness guidance
- Pre-departure group calls
- Detailed route notes and packing lists
This support can make your first bike tour far less intimidating.
Group Size & Guide Setup
Ask:
- How many people per tour?
- Do guides ride with the group or drive support vehicles?
- Can you ride at your own pace, or must you stay together?
This affects everything from your daily enjoyment to how pressured (or relaxed) you feel.
Bike Travel Changed My Relationship With Fear
Cycling between state capitols in my Capitol to Capitol project has pushed me far outside my comfort zone.
There were days I doubted myself. Days I felt like an impostor. Days when traffic scared me.
But each mile built confidence. Not just as a cyclist — but as a person willing to try something new.
Bike travel reminded me that you don’t need to start as an expert. You just need to start.
Bike Tour Companies & Resources I Personally Recommend
These are companies and resources I trust — and travel with myself.
Bike Travel in the U.S.
Adventure Cycling Association
The Adventure Cycling Association based in Missoula, MT is an incredible resource for bike routes, maps, and bike-friendly trail systems across the U.S. This is definitely for more independent travel, but they do also run group tours. I’ve never taken one of their group tours, but I have used their maps and website for planning my own trips.
Bike Travel in Europe
Experience Plus Cycling Tours
Operating for over 50 years and perfect for all levels. I took my first trip with Experience Plus last summer and absolutely loved it. They are experts in Europe and especially Italy (where they started). One of my favorite things? You can ride at your own pace instead of staying in a tight group. Everyone starts when they want and simply follow the chalk arrows the guide lays down. This allows you a lot of freedom on a group tour!
In addition, they always include some additional cultural tours on their itineraries and the accomodations are high quality. They are definitely a destination focused company.
👉 Read about my Southern France biking trip with them last spring.
Ireland Walk Hike Bike
Ireland is a great place to cycle in – quiet roads, sweeping views, and lots os sheep. I run a lot of hiking tours in Ireland utilizing the local company Ireland Walk Hike Bike. They also have a large array of self-guided cycling tours. They arrange your accommodations each night. Your luggage will be transferred while you are out cycling. And they provide detailed maps and a GPS app to get you from place to place each day. Plus – even though it’s self-guided they offer the security of 24-hour telephone support.
Ottsworld readers get a discount! Use code OttsWorld2023 for 5% off their offerings – not good with other offers
Want to Ride With Me? Upcoming Cycling Tours
If you want to experience bike travel with me (and skip the learning curve), here’s what’s coming up:
Patagonia eBike Small Group Tour
Ride an e-bike across the Patagonian steppe and into the shadows of the Paine Massif, stay in remote ranches, meet seasoned baqueanos, spot guanacos and wild horses, and end every day closer to one of Earth’s most iconic parks. It’s more than a vacation—it’s a transformational adventure that challenges, inspires, and delivers a story you’ll remember forever.
Dates: November 1–7, 2026
Only 8 spots
Cost: $5,400 ($1,350 deposit)
Maine Capitol-to-Capitol Cycling Tour
This fall, I’m opening up something I usually do solo — my Capitol-to-Capitol Quest. Join me cycling from Augusta, Maine to Montpelier, Vermont during peak leaf-peeping season, when New England explodes in golds, reds, and fiery oranges. Quiet backroads, car-free trails, charming small towns, and a front-row seat to one of the most beautiful times of year in the U.S. Every detail is handled, local guides have our backs, and you get to be part of an epic story that connects generations, places, and people.
Dates: October 7-14, 2026
Cost: $3550 Max: 12 people
Shiminami Kaido Japan Cycling and adventure Tour
Coming November 2027.
Be sure to sign up for my tour newsletter to you can get the latest updates on these custom cycling tours.
A Final Thought
One thing I’ve learned over years of travel is that curiosity and movement go hand in hand.
Whether I’m hiking a rugged coastline, pedaling across a suspension bridge, or chasing cats through Japan’s backstreets, I’m reminded that exploration doesn’t have to be epic — it just has to be intentional.
If you’re curious about bike travel, you’re already halfway there.
The rest? You’ll figure out one pedal stroke at a time.
