reservation-less trip?

I like to know where I’m going to lay my head down at night, but that’s just me. The one time we tried going with no reservations, we hit the weekend of the Brighton Festival in Brighton; and there were no rooms to be had. The TI Office found us a perectly nice, not expensive hotel in a town a bit down the road. We also had option B, which was to drive back to London, where we were living for the year. We also have friends, who in their salad days were doing a bicycle trip around England, with no reservations. One evening, they almost struck out. Place after place had no vacancy. It was getting dark and rain was threatening. They had visions of sleeping under a tree in a storm. Finally, one woman, who didn’t have an avaiable room, knew someone to call, who did. They’ve joined the always have reservations crowd.

I will point out that there is a pent up lust for travel since the pandemic struck, and June is high season. And yes, the internet has reconfigured the playing field. Otoh, it has also made it easier to ferret out places at the last minute. You’ll get lots of advice on both sides. In the end, you’ll just have to do what seems right to you.

Whereabouts do you plan to visit? June is popular for those wanting to get away before places get busy with school children so I wouldn’t risk not having anything booked if you want to stay in particularly popular locations such as the Cotswolds or Skye.

You may be able to find accommodation on the hoof, but it might not be the kind of place that you want. These days, there are few B&Bs that aren’t on Sawdays, TA, Booking.com, Airbnb or tourist board websites.

Most trips in the past 6 or 7 years have had all our lodging reserved before leaving the U.S., although a Scotland trip 8 years ago had half of our places reserved, where we knew where we wanted to stay, and worked our schedule around being there at the appointed time, and the other half reserved the day of arriving there. Isle of Skye needed a reservation so we’d be assured of a room, and we booked a B&B that still had space before our trip started. For other spots, we started calling when we decided where we were going to spend the night. By car, we determined midday where we’d stop that night.

This worked in Ireland/Northern Ireland in September/October 3 years ago, too, and 10 years ago in Ireland as well.

Not to put too fine a point on it, but you're 25 years older now. Circumstances that might have been tolerable then might be unbearable now.

I've already booked the hotels for my April 2022 trip to Italy, mainly because I anticipate a "land rush" on lodgings as the pandemic winds down. Of course it's possible; but personally I wouldn't risk it.

In all of my 250+ nights in Germany, I have found that you get better deals reserving in advance. The one or two times (3 or 4 separate nights, as I recall) I've tried getting rooms "on-the-fly", I was always able to find a place (those time I was traveling in low season, and most places were not booked), but the places I found on-the-fly were not as convenient or as economical as ones I could have had, had I booked in advance.

Our best experiences were at places I would have never found in a guide.

Of the 39 places where I stayed on my last 3 trips (8 weeks), one was found using an RS guide book and one was in one of his books, but I found it on my own. The other 37 places were not in Rick's guidebooks.

Now, Rick's guidebooks are not the most comprehensive guidebooks, he only features towns he has been to and likes. My travels have been to a lot of small towns he would never feature. I have learned to rely on town websites and Google Maps, and I almost always book in advance, to get the place I really want.

While we used to travel without reservations but now with better planning, we know where we’ll be and make advance reservations. Even with advance planning, we don’t always get our first hotel choice.

I think it is still doable but you would probably have to settle for whatever no one else wanted. Twenty five years ago everyone was in the same boat. Not today. People research lodging a lot just to get the best deal for their money.
Of course we can not anticipate what the tourist crowds will be like next year and what will be the demand for rooms.
Another thing to keep in mind is if there is a special event going on that will take all the rooms available.

I surrender...back to the spreadsheet method.

I feel for you. I loved my trips where I wasn't booked and had freedom of movement, but I fear those days are gone. Even if you travel in the off season, there are fewer places open and so you can still have trouble. Also, you had to be accepting of less than ideal accommodation. It wasn't always en suite or the room overlooks the beer garden etc.