Winging it in the Alps?

I have winged it in the Swiss alps before and never had any trouble finding quality lodging - but this was always in shoulder season. Late July and early August are peak season. In fact, August 1 is a national holiday (Swiss 4th of July) so it could be a different story.

Personally, I think you'll be fine. As you say, there's always a B&B somewhere with availability. The challenge is finding it! Be sure to have a guidebook with a list of accomodations in areas you will likely want to visit.

I think it really depends on the size of the town. My sister-in-law who lived in England for several years traveled all over with her kids - never with reservations. She would just go straight to the TI when they got into town and the TI would find them something. I ALMOST always travel with reservations, but the one time I didn't I had no trouble finding a place (in June). Went to the TI and they had several recommendations. They even called the place to ensure they had a room available. As long as you are not too picky about where you end up you should be fine, however if you are planning on staying in a small village like Gimmelwald, Murren, Wengen or Lauterbrunnen you may run into trouble because there are limited options.

You are traveling on peak summer season, so beware of what other members might say about trips in June, or late August, for instance.

I think it is an inefficient and pointless travel strategy, but it is your trip, time and money - not mine.

Make it high-tech at least: get a decent international roaming plan, and bring a smartphone with Booking.com app (or other similar services, Booking is just the European leader at it) installed. When you are looking for accommodation, Booking will have inventory information for you. They got quite good at last-minute reservations, and hotels put more and more of their rooms over there. So instead of wandering around looking for a hotel on foot or driving around, you can stop, get your phone, and command a search of available properties in the vicinity.

That may work but it will take some effort at that time of the year. Since it is the brainchild of your children maybe it would be good if they are in charge of that part of the holiday - so they can't complain if they don't like where they end up.

Remember that you will be getting the left-overs that others who plan ahead haven't picked.

Be sure your car gets its Vignette. And driving in Italy has lots of ways to incur fines if you don't know the tricks. IDPs required for Italy.

I've "winged" it in Europe in high season and it can certainly be done. Just know that finding lodging for the next night can be time consuming and sometimes frustrating. You won't be able to be choosy and could end up in a very out-of-the-way, NOT convenient place. In some parts of Switzerland, towns can be few and far between. Do you know which part of Switzerland you will focus on? That might affect how you approach your trip. Some areas I wouldn't hesitate to travel this way...other areas I definitely would make reservations. Where do you plan to go?
That said, we've pulled into towns before and had good luck going straight to the tourist office for help booking a last-minute room...usually they can make a quick call and get you set up for the night. Booking.com is also a great way to see what's available as you move from place to place - that way you can see where you can get in for that night and just head in that direction...I don't know if I would want lodging availability dictating my itinerary though...that might be what you end up doing.

An alternative to "wing it" at the moment is to, at least, do it one night in advance. Meaning: you arrive at a pre-booked hotel one night, settle in, check weather forecast (reasonably accurate for next 24h nowadays) and other info, then make a reservation on Booking (or other app) for the next night. That way you always depart in the morning with a guaranteed bed in the evening. You enjoy your day without the need to lose time or worry about where to spend the night - and you "wing it" from a desk in your hotel room, not at some gas station or local tourist office.

I think that is a reasonable compromise.

If you are really keen on not pre-booking anything, at least take a look on Booking the morning you depart to have an idea of how plenty of scarce are rooms in the direction you are traveling and the price range. Searching Booking on their map function is very helpful for that. Browse the map and check availability in some locations.

If your kids are tech-savvy enough, you can outsource this task to them.

Hi Ontherun, honestly, I would never "wing it" but that's just me. July and August are busy vacation seasons and I'd rather get to a place and settle in rather than spend precious time searching for a room(s). It's your vacation. If you're feeling "lucky", go for it!

I love winging it. I had lots of success with it in Austria years ago.
I posted a similar query here a few years ago, regarding "winging it" in the Dolomites. We ended up making reservations ahead, but found out along the way that there was lots of availability (our plans changed and we didn't have any trouble switching to another Chalet).

So many of the ski-resort towns have excess accommodations in the summer that they never quite fill up. However I know some Swiss towns are very hot in summer, and wouldn't venture a guess about them.

I see you are traveling with two teenagers. I have had difficulty booking a "quad" or "family" room even in advance, since they are often not available or limited in number in many European hotels. Keep that in mind, unless you just plan on getting two separate rooms, in which case, may also be more difficult doing last minute than just finding one room for you and your spouse.