Not Pre Booking Hotels for flexibility with weather on our upcoming trip in September?

We used to travel that way but with the advent of the internet that is long past. The best I can say is to keep an eye, about every two weeks, on the places you would like to stay (several in each location) and if they begin to fill up you had better grab a room when you can.

I think this has to do with your comfort level with how much risk you are willing to take and how truly flexible you can be.

I am thinking that as long as you had the accommodation for the next night nailed down the day prior and before you started your journey to the next location you should do okay. It might mean that you wouldn't get your first choice of hotel or even location, but you will certainly have more flexibility. I wouldn't feel comfortable traveling to a location and then starting to look for accommodation there. Too many memories of that sort of disaster as a child!

I’ve done it twice in the past and usually was able to find great accommodations through the TI at the railroad station or in the town. Often got nice discounted rates as well. Underutilized free resource.

Just a WAG on my part. Given the pent up demand for travel, this may not be a good year to try such a strategy out.

Sorry, but I wouldn’t travel anywhere in Europe this year without firm bookings. If Switzerland is anything like the U.K., people are so keen to get away after months of lockdowns that places are booked out and prices have risen. It depends how much risk you are happy to take. Check on websites for your chosen dates and locations to assess availability and monitor it.

The last time I attempted this on a journey was 2003! I would not be willing to risk it now. And trying to get a bed in a mountain hut without a reservation? Best of luck there.

Have you considered pre-booking cancellable/refundable accommodations but making changes along the way if you want/need to? A lot of places allow cancellation within 24/48 hours. Then if all else fails, you have somewhere to stay even if not where you necessarily wanted to be. I wouldn't chance going with no reservations.

I wouldn't want to speculate about a wait-and-see approach this fall even in places I've been to recently, which most definitely do not include Switzerland. I'd just point out that Swiss hotels are very expensive. If all the places in your preferred price bracket are booked up and you have to go upscale, it could be an expensive experience. Theoretically, that could happen: Maybe a lot of places haven't reopened. Maybe the Swiss are being very cautious and traveling at home this year. I certainly do not know.

I highly recommend that you play around with what's available at your possible destinations on booking.com. For example, for the nights of Sep 28 and 29, I see 7 to 12 places with rooms available in Appenzell, depending on how you define "in Appenzell". For two nights starting tomorrow, there are 8 or 9 Appenzell hotels with rooms available. So it doesn't look bad at the moment, but I'd be watching the Sep dates every few days to be sure the situation still looks OK. And of course check Lucerne as well. I don't know anything about booking mountain huts.

Thanks all! I decided to go ahead and book some places for now that I can cancel a few days beforehand, that way I have rooms, and if I want to or am able to change up the itinerary closer to the cancellation cut off I can. Thanks!