I set out once to ride where fancy took me, an unstructured tour with neither route nor ambition.

I packed it in after three days. I enjoyed it but the purpose wasn't there. Not every ride has to be a challenge or have an ambition but, for me, there has to be a hint of both. Or at least a target, a destination.

So, how about you?

Do you set off with a song in your heart and just an apple in your pocket? Or do you research the route and all there may be to see along it?

How long before you set off do you begin the planning? Or don't you plan? If you don't, what has happened as a result?

I wish I were the sort of person who could set off on a whim, without a plan. I do not have that type of personality Indeed, I enjoy the routing part of tour planning. Some cyclists don't wish to be bothered with the organizational part, and they join  paid tour  as a result. Not me! This year on our return from Spain, we were scheming about our return before our plane had landed stateside.

Because we motel exclusively, and usually in tourist areas, I book rooms far in advance. The year we rode the Sierra Cascades, I called in October for a July booking in Yosemite. Too late. Most troublesome locations I book in Oct/Nov, for a June stay. I fill out the bookings by the New Year.

Other motel staying friends book a few days to a week at a time. That gives flexibility with direction of travel and weather. I can appreciate that. I like to know I have a pillow at night! Plus, rates are often cheaper if booked in advance before demand builds. 

There are many different methods of touring. We have toured as long as ten weeks, with advance bookings. Twice we've had to make big changes. Once when Jacinto's mother passed away, and we scrapped the entire tour. Once during COVID (who saw that coming?). We made small changes in Canada due to weather. All in all, we find the advance planning works best for us.

I've always thought it would be fun to wake up one morning, decide it would be a great day to start a bike tour, and just go for it.  I'll bet some people have done that, and maybe someday I will too.  For now, however, I kind of like to have an end point or turn-around point in mind.  Also, I like to plan a tentative route to get to that point.

I like to tour in non-touristy areas, so it's pretty easy not to worry about making reservations ahead of time, though I will occasionally reserve a room in inner-city hotels on busy weekends.  Carrying a tent gives me the ultimate flexibility though.

Anyway, on the spectrum of "winger" to "planner," I think I lean a little bit toward the "winger."  Too much planning takes away from the things that surprise the hell out of me while on the road.

I don't like to plan anything: No predetermined route before starting a tour, no planned duration, and no destination. And the very last thing I would ever do is buy plane tickets or do anything else that requires me to have any kind of deadline for finishing. I don't know how people can stand doing that.

I value spontaneity and surprise above almost everything else at this point.

Joy and I did a six-week tour in 2016 in which we abandoned the Great Divide Mountain Bike Route at the halfway point, when we woke up one morning and decided we were tired of the route. For the rest of the trip we did almost no planning  until we reached Canada. It was a lot more fun that the GDMBR itself, so that's how I've approached every bike tour since then.

I've done several tours like this, and they've all worked out fine. It makes stumbling upon some interesting site, event, or people in the middle of nowhere much more fun.

I lean strongly towards PLAN but try to be flexible while executing the plan. Serendipitous discovery is one of the joys of bicycle traveling.

I plan months in advance. Like Kelly I stay in motels and travel through resort areas that require advance reservation if you're not camping. I do miss the schedule flexibility of traveling without reservations when I was camping.

Most of my tours have a geographic or cultural theme that I research extensively before the tour. The theme usually dictates the route (connecting hot springs, waterfalls, covered bridges, gold rush towns, LDS temples, etc). My routes tend NOT to be straight. I'm almost always wandering, seldom trying to race across the map.

We need to know that we have a bed for the night but we usually only book two nights ahead so our tours have some structure.

I am a full-on planner. I actually enjoy planning as much as the tour itself. Like other planners, I stay indoors, either paid or hosted. This requires a much higher level of preparation then simply finding a wild camp for the night, though I understand that takes a bit of local planning, as well.

How much in advance I need to plan depends on the where and when of the tour. I just finished a tour in Northern Italy and Switzerland in July, a high time for tourism. I found places to stay in short supply and so booked well in advance. In April/May or September/October, I usually can be much more lax in my bookings, which provides all the flexibility I need/prefer in deciding where to stop.

One benefit of long-term planning is finding roads and routes that are both safer and more interesting. It often takes me a fair amount of research to decide on a route that makes me feel like it is one worth riding. I often write to warmshowers hosts with questions, as well as, local riding clubs and forums. This wouldn't be possible if I were deciding where to ride on the fly.

I read a lot of journals before a tour - does that qualify me as a planner?  

On the one hand we have a broad-brush route we try to follow (but usually end up changing to some extent) and on the other hand we seldom know where we will sleep the next day and often only know towards the end of a day where we will spend the night.

Essentially,  I like to know where I am going but am averse to schedules.

I've always thought it would be fun to wake up one morning, decide it would be a great day to start a bike tour, and just go for it. 

You should try it! There's something exhilarating about riding out of your driveway on a nice sunny morning and having no idea when  you'll be back home.

I like to tour in non-touristy areas, so it's pretty easy not to worry about making reservations ahead of time, though I will occasionally reserve a room in inner-city hotels on busy weekends.  Carrying a tent gives me the ultimate flexibility though.

Yes, those two things - touring in non-touristy areas, and carrying a tent - make "winging it" easy and enjoyable, in my experience.

I don't like camping, and in fact only do it occasionally, but carrying the camping gear removes so much pressure. Because sleeping in the tent is almost a last resort for me while touring, that means that when I do camp, it's often in an "unofficial" campground, like a tiny town's park. I've had enjoyable experiences meeting local people when I do that.

I think another thing that makes "winging it" a lot easier is touring on a mountain bike with big, tough tires and sealant-filled tubes. I can ride virtually every kind of surface, no matter how rough, on my Salsa Fargo. When I  used to tour on a touring bike, riding on rough gravel or dirt roads scared me - I was always afraid of getting a flat tire, or damaging the bike. Being able to ride on any kind of road or rough trail makes on-the-fly routing a lot easier, in my experience. 

One of the things I've always wondered about the approach of reserving lodging weeks (or even months!) in advance is: What do you do if there's a day with truly terrible weather, you have a major mechanical problem, or you have an injury or an illness and you need to take a day (or more) off? I guess you need to call all the places you've reserved and try to reschedule?

One negative thing about winging it, I guess, is that without having (and announcing) a definite destination and duration, it's easier for me to end the tour and go home earlier than perhaps I should, whereas if I tell everyone I'm riding, say, to the pacific ocean from Kentucky, I would feel more motivated to actually do that, and not wimp out and come home when the going gets tough - something that I have done at least once before.

I plan.  I plot.  I scheme and connive.  Hours go by as I tinker with possible routes between projected daily stopping points, looking to find interesting things along the way or just to ensure that I'm not setting myself up for a stretch that will exceed my drink-carrying capacity.  

Ride With GPS, my main planning tool, often selects routes that bypass towns in favor of small back roads, which is great except when it also means there aren't many places for replenishment and succor unless you deliberately choose them and route yourself accordingly.

Planning is, for me, an enjoyable part of the overall journey.  It adds to the experience, heightens my anticipation.  It's also, as others have mentioned, a way to ensure that I won't have to crawl under a bridge or occupy a park bench overnight.  

I observed to my dismay last summer how much seemingly open land Out West (in the U.S. of A.) is in fact separated from the public right-of-way by fences and No Trespassing and Private Property signs. Those things pretty well rule out "wild camping" for me because one of the unwritten rules to that game is that those signs need to be honored.  If someone specifically denies me access, I can't claim to be in the right if I take it anyhow.  And then there's the unsettling but very real-seeming possibility that they may have a "shoot first, don't ask questions" sort of attitude...

I recall reading, in one of your journals, of someone you met while you were out touring.  He was headed to whatever town, city, village, or hamlet lay in the direction the road ran, precisely and simply because the road passed in front of his home and that's where the road went.  

I'll never forget the description you gave, which included the memorable phrase that "his hair looked like it had been used to mop a barroom floor", and also that his "luggage" consisted solely of a trash bag in a cardboard box.  When you asked what he'd do in the event the box was ruined by rain- as it surely would be, and as was its probable fate if he spent enough time outdoors- you said he looked at you as if you were a simpleton.  "I'll find another box."

I doubt he was a compulsive, obsessive over-planner.