This was a conversation I’ve had with a few folks. Do you book in advance for where you sleep or wing it?

Well, in Nepal in spring and summer I think you can wing it. But in Europe, in peak season, in valleys where you need to ask the landowner to camp? When you’re tired after 30+km and 2,000m of elevation and it’s hot? No thanks.

We also couldn’t wing it on the Great Divide Trail; way too many days and nights passing through National Parks.

So we opted to book most of the way. Yes it sets a schedule, and it feels a bit structured. But heck we love spreadsheets, so no problem there. It does put pressure on us.

Pros of booking ahead
• Guaranteed place to sleep at the end of the day
• Less stress searching for accommodation while tired
• Saves phone battery and time on trail
• Avoids last-minute language barriers while calling (and doesn’t assume connectivity is available)
• Secures spots in popular huts and hostels that fill up early
• Easier to budget with accommodation costs known in advance
• Helps maintain a steady and realistic hiking pace

Cons of booking ahead
• Less flexibility to change distances, routes, or rest days
• Pressure to keep moving despite bad weather, fatigue, or injury
• Cancellation fees and rebooking can become complicated
• Requires significant planning before the trip
• Limits spontaneity and unexpected discoveries
• A disrupted schedule can affect multiple future bookings

There is no right answer to this. Some folks love winging it and complete their goal. Some folks like booking abead and reach their goal. But neither approach is perfect.

It’s just a compromise; everything in life is a compromise if you think about it.